Life update: I’m moving to San Francisco this week! My full-time job at BCG starts in a few weeks, so it was time to get a spot in the City, get settled, and start my new grad life.

I learned a ton during the process of finding roommates/apartment, and wanted to pass along that wisdom (plus for my own posterity’s sake). So, here I am sharing that story and all the lessons here. Enjoy!

Finding Roommates

First off, roommates. I knew I wanted to have them, the more, the merrier. The few times I’ve lived alone (I’m looking at you, Paris), I’ve felt quite lonely, which I absolutely wanted to avoid again. Plus, I loved the idea of having a very social apartment with several friends, and liked the fact that more roommates = cheaper rent. So roommates it was.

I didn’t personally know anyone moving to SF when I was looking to (early Jan 2026), but after a few calls in November, I managed to convince my friend from UCLA, Alex, to move up with me. He was working a fully remote software job at home, and I basically told him he should full-send it to SF. He eventually agreed.

1 down, 2 to do. I was still hoping to find a few more roommates to fill a 4-bedroom, so we decided to bite the bullet and look for roommates through Facebook.

I’d heard people finding great success (very nice!) looking for roommates in Facebook housing groups (e.g., here, here, and here), but I was still very skeptical that it’d actually work. Nevertheless, Alex cooked up a nice little blurb for us, I found some photos, and I posted it in a few different SF Facebook groups I found:

Hey everyone! My friend Alex and I are looking for roommates to join us in signing a lease for a 3-4 bedroom apartment. We’re aiming for an early January move-in.

The Vision: We are looking to create a household that is motivated and ambitious (entrepreneurial mindsets are a huge plus), but definitely social. We want a place where we can host friends, have people over for dinner/drinks, and actually hang out with our roommates rather than just coexist.

About Me: I grew up in the Bay Area, and am super excited to move to SF! I work in management consulting and just finished backpacking the Pacific Crest Trail this past summer. I love reading science fiction, cycling, and going on side quests.

About Alex: Alex is moving to SF from San Diego to try out a new city! He works in Software Engineering, is super social, and loves going out. He’s big on sports and the outdoors; you’ll usually find him surfing, backpacking, or hiking on the weekends. Insta @alexwest.coconut

The Logistics:

• Budget: $1,500 - $1,800 per person.

• Location: We are targeting the Marina, Russian Hill, North Beach, Nob Hill, or Chinatown/FiDi areas.

• Status: I’ve already toured a few solid options, so we have leads ready to go; we just need the right crew to sign with us!

If you think you’d be a good fit, shoot me a DM with a bit about yourself!

I was super excited to see who’d respond and… crickets. I was honestly very bummed for 2 days, until I realized that on Facebook, DM requests are a few clicks away from Messenger, so I was actually looking in the wrong place. What a terrible UI. Once I took a look at my DM requests, I found over 20 people asking to be roommates! Wow! This was even better than I’d imagined!

Alex and I were super excited about this, and I quickly made a bunch of group chats for Alex and me to schedule roommate interviews for the following few days. We’d call over FaceTime, get to know the people a bit, get a vibe check, and Alex would ask them about cleanliness. Everyone obviously said they were clean, but one person was in his current apartment at the time; I asked to see his kitchen, and it was FILTHY 🤮. There was also that one person who was moving to SF to start working the exact job my friend had just quit because of its toxic work culture. I laughed so hard.

The first guy we interviewed, James, was an absolute legend and we loved him immediately. Alex and I brought him into our roommate group right away, then added him to all the group chats to join us in interviewing potential fourth roommates. There were a few that weren’t fits, some that were ok but not great (I figured that since we had lots of interest, we should keep interviewing until we found someone we LOVED), and eventually chatted with Tucker, one of James’s friends of a friend from college. He was fantastic, we loved him, and brought him on to round out the elite roommate group.

Now all we needed was an apartment.

Touring Apartments

I pretty much exclusively looked on Zillow for apartments, and was very happy with how that turned out; I didn’t want to worry about scammy apartments on Craigslist and liked that you could apply for the places directly through the platform (you pay a $35 fee to apply to an unlimited number of units for a month). I was looking toward the end of 2025 so there weren’t a ton of new listings, but I ended up touring about 8 places all across North San Francisco and was happy with what was out there.

Funny enough, I was the only one in our roommate group who was actually living near SF at the time (Alex was living in SoCal, James and Tucker out of state), so it was up to me to do all the tours.

I actually… loved it? I thought it’d be quite monotonous to tour tons of places myself, but I really enjoyed checking out a bunch of different apartments (including a super cool penthouse suite in the Tenderloin which we ended up not going with… because it’s in the Tenderloin), meeting landlords, perfecting my parallel parking, and seeing what’s out there. I’ve never toured apartments before (only lived in the dorms and co-op, baby!) and have to say that I felt VERY grown up doing so now.

The flow was basically this: we’d find an apartment listing we liked on Zillow, and I’d DM the landlord to schedule a tour ASAP. I’d then go on a tour of the place, meet the landlord, and take a detailed video of the apartment to upload to YouTube and share with the roommates. We had a giant shared Apple Note with all of the different places I was touring, where we all left notes/thoughts about each spot, and applied for the ones we were interested in. I ended up inviting a lot of friends to the Apple Note (touring was actually super fun, as I’d never done it before), and I loved seeing everyone’s comments trickle in as I toured more and more places. Here’s a bit of what the formatting looked like:

Apartment #1: 946 Jones St, Unit 6

• (Price)

• 900 square feet (quite small)

• 3 bedrooms + 2 bathrooms + living room + in-unit laundry

• Great free on-street parking

• Lower Nob Hill Neighborhood

• (YouTube link)

• https://www.zillow.com/homedetails/946-Jones-St-6-San-Francisco-CA-94109/2080529430_zpid/?utm_campaign=zillowwebmessage&utm_medium=referral&utm_source=txtshare

• (alex) seems like that room would have to be a living room bc otherwise no common space really + doesn’t look ideal to live in there

• (Note: Alex, James, and I applied for, and got a lease for, this unit while we were looking for a fourth roommate, and decided to keep looking even because it was a bit small for us and we wanted a fourth roommate anyway)

Apartment #2: 1406 Post St

• (Price)

• 4 bedrooms + 2 bathrooms + living room + really nice patio (!!) + in-unit laundry

• 1350 square feet

• Great free on-street parking

• Japantown Neighborhood

• (YouTube link)

• https://www.zillow.com/homedetails/1862-Page-St-2-San-Francisco-CA-94117/2062403074_zpid/

• (alex) lol loving the quality filming content, i rly like this one, i feel like it’s more homey if the living room and kitchen are connected but like not a big deal

Apartment #3: 1458 Hayes St

• (Price)

• 4b2b in the panhandle, onsite but no in unit. Beautiful and quite large

• Shared laundry

• 2000 square feet

• (YouTube link)

• https://www.trulia.com/home/1458-hayes-st-san-francisco-ca-94117-2091498964

(I didn’t include the actual YouTube links for privacy reasons)

Now just imagine 10 such listings, and you basically have the Apple Note we shared.

As you’d expect, there are a ton of questions you should ask/information you should find out during an apartment tour. A lot of these are basic apartment-touring steps, so if you’ve toured places before and know how this works (translation: you’re an adult), you’re probably like, “Duh”.

But! I didn’t know any of this stuff before starting to tour apartments, so I’m sharing it here in the hopes it’ll help you, too. Thanks to my dad, friend Sanketh, and Uncle Gemini for explaining all this to me.

This is not a full list, but a great place to start:

• When was the last time things were repaired and painted? Walls, floors, heating, plumbing, electricity

• Any problems with heating/electricity/water/plumbing previously? Who do we call if things break?

• Are all appliances working?

• How much is immediately due upon execution of the lease?

• Do we pay for electricity, gas, Internet, water, and garbage?

• Why did the last people move out?

• Is this unit under rent control?

• How does signing the lease work? Each roommate pays separately, or just one pays for everyone? Is a 6-month lease negotiable, or is the default a one-year term? (Usually leases are one-year and convert to a month-to-month, meaning that you commit to the lease for a year, and from there you commit monthly and can move out after each one with sufficient notice)

• Is subletting allowed?

• Is renter’s insurance required? How much coverage do you need?

• Is there an on-site property manager? Who do I contact for issues?

• Has the building ever had pest issues (roaches, mice, bedbugs)? What’s the pest control policy?

• Is there any history of mold or water damage?

• Is this unit under San Francisco rent control? (Units in SF built before June 1979 typically are)

• What security features does the building have (cameras, secure entry, lighting)?

• Test the water pressure by running the sink and shower

Especially important for a 4-bedroom shared situation:

• What is the guest policy? Are there restrictions on overnight visitors?

• Can I add or change roommates during the lease?

• Is subletting allowed if someone needs to leave early?

• Is renters’ insurance required?

• What are the rules about decorating—can I paint walls or hang pictures?

• Are there quiet hours?

• What is the parking situation? Is there assigned parking, and how much does it cost?

• Are there any planned renovations that might cause noise or disruption? (HUGELY IMPORTANT TO KNOW UP FRONT)

We ended up securing a spot in Nob Hill and are moving in this week. It’s a mile from work, and I can commute by foot, bus, or CABLE CAR! Lfg!

Roommate Agreement / Splitting Rent

Since this is properly a big boy apartment and not a simple college student den (translation: three dudes crammed into a small room in the UCLA co-op), we (specifically Alex) wanted to make a formal roommate agreement prior to moving in so that should shit hit the fan, the wall would stay clean (wow, I’m proud of that line).

My philosophy around roommate agreements is like with a prenup: you should have one, so then you don’t need it. Being explicit and upfront about the rules and expectations before starting a legally significant relationship (e.g., getting married, or being roommates with multi-thousand-dollar rent commitments) makes sure that everyone’s on the same page from the get-go… which is just a generally good thing to do. It’s nice to go into a boxing match knowing that the balls are off-limits, so then you don’t need to guard your crown jewels.

The roommate agreement is honestly quite simple, and should cover only a few basic things, namely: financial stuff (who pays what rent split, so that in the case someone doesn’t pay it’s easier to get the money back), cleaning/chore obligations, shared spaces, guest policy, conflict resolution, and what’s the process for someone moving out early.

We decided that the rent should be split based on which room each person lived in because the rooms in our apartment weren’t all the same size. Also, 2 of them were on the street side, and the other 2 on the garden side (those get direct sunlight). Alex found this amazing website called “Divide Your Rent Fairly” where you input the total rent and the room square footage, and using a round-by-round auctioning system, the website determines the fair rent breakdowns for each room and who’d live where. Pretty nuts tbh, and super fun to do over FaceTime.

Alex then whipped up a quick, legally-binding document for free using DocuSeal (actually such a cool open-source service), we 4 roommates all signed it electronically, and received the final, signed-by-everyone copy by email for our personal records. Check out the template Alex made for reference here.

Just upload that into DocuSeal, assign the appropriate signature spot for each roommate, and you’re all set!

Renter’s Insurance

You’re not legally required to have renters’ insurance in California, but if your landlord requires it, then you need to have it. My landlord required it, so I needed to have it.

Basically, renters’ insurance exists so that if the house burns down, you and the landlord can get money for all the things you lost. After doing a (quite long) search for all the different renters’ insurance platforms, I found that Lemonade was the best bet. Their target market is young professionals, so it’s super cheap, very user-friendly, and any leftover profits are sent to your charity of choice. I chose a reforestation charity because more trees = less problems. Trees are great. Check out Lemonade here. My renters’ insurance costs only $26/month.

(Transparency Time: The Lemonade links above are with my personal referral code, which gives me a small bonus each time it’s used. If you want the generic link without my referral code, click here.)

Random Notes:

• In California, security deposits are typically capped, so watch out for exceptionally large deposits of more than one month’s rent. In SF, the legal maximum deposit is one month’s rent

• The latest our lease could start was one month after my tour of the apartment, which I found to be quite fair and reasonable. I imagine this is mostly an SF thing because the market moves so fast here, but good to know if you’re looking to move here soon

• I was looking into rent reporting services to improve my credit score, but decided against it. My credit score is sufficiently high that reporting rent payments wouldn’t improve it; rather, it’d decrease it because the reporting counts as opening another line of credit, which decreases your score. Reporting rent only makes sense if you have a limited credit history or your score’s below ~650. If you’re interested in doing this, Self was the best free option I found that reports to all three bureaus

• In San Francisco, rent-controlled units are capped at 1.4% annual increases through February 2026

And so we conclude our apartment-hunting saga! Thanks for tuning in, and if you’re in SF/moving there soon, reach out! I’d love to meet up.

Currently enjoying a nice Nespresso,
Dennis :)

Dennis’s Picks:

• This was a fantastic piece by Morgan Housel, describing the history of the US economy since WW2

• I loved this essay about the state of the average college student today in the age of AI. Recommended by my friend Alexandra (hi!)

• There’s this one dude at UCLA, Jenson Wong, who writes some fantastic stuff about technical product design. His articles on designing forms and buttons were extremely interesting and fun!

One of my favorite family traditions is how my family does New Year’s Resolutions: we all come together for the holidays, and have a giant feast on New Year’s Eve before staying up to midnight.

At dinner, we all take turns going around the table, sharing what accomplishments we had that year, checking in on that year’s goals/resolutions, and sharing our goals/resolutions for the year ahead. My mom diligently writes these all down in a specific notebook, then takes it out the following year for New Year’s Eve once again. This notebook now has many years of resolutions inside.

I love this tradition for a number of reasons: it encourages you to be grateful and proud of how the year went, and starts you off on the right foot for next year. It’s super important to look back and reflect on the previous year’s achievements; it often surprises me how much I got done, and it gives me a reason to celebrate. They say you overestimate how much you can do in one day and underestimate how much you can do in a year, and looking back on the year’s accomplishments is a perfect example of this in practice. Sometimes when I’m feeling down or like I’m not doing too much with my life, I remember that I’ve actually done quite a lot and feel better.

Regarding goals, my view is the more ambitious, the better. My goals are across a variety of dimensions (athletic, personal, relationships, travel, professional, etc.), and I rarely succeed in all of them. I’ve found that having more ambitious goals means you fail more often, but that in the process you accomplish and learn more than you would’ve otherwise. If your bucket list has 10 things and you do all 10, woo-hoo; even better, have 100 things on your bucket list and when you accomplish only 50, that’s still a helluva lot better than just 10. The key is not taking that failure personally and seeing every setback as an opportunity to grow. Definitely easier said than done, and something I’m constantly working on.

Ultimately, the goal should be to fail more, and fail better. As James Clear writes:

In my early 20s, I wrote a list of ambitious things I wanted to do in life. Go bungee jumping. Create a movie. Start a business. That sort of thing. I did a few of them, but not most.

Looking back, however, that list was incredibly valuable because it taught me the usefulness of chasing bold ideas, even if they never materialize. The dreams that didn’t happen changed shape and led me down other interesting paths.

The important thing isn’t to achieve all your dreams, but to keep dreaming. Your desires change as you learn and grow. Old dreams will spawn new dreams. And eventually, one of these newer, more refined visions will find their moment and become reality.

And without further ado, my 2025 accomplishments:

2025 Accomplishments:

• Skied every Ikon resort in California

• Found my own tutoring gigs, making $60+/hour

• Became a board director for the UCLA Co-op

• Curated an art gallery in said co-op, and hosted a grand opening with ~50 guests

• Went to every UCLA sorority’s brunch, then ranked them

• Led an unbelievably fun trip to Morro Bay with my friend Dylan through the Excursion Club

• Graduated from UCLA

• Traveled all over the UK and Ireland in April (Killarney for the win)

• Backpacked 2650 miles from Mexico to Canada along the Pacific Crest Trail with my girlfriend. Greatest adventure of my life (so far)

• Did my first work stay in Hawaii

• Interviewed for a bunch of AI startups in SF

• Didn’t succeed in any of the interviews (lol… more on this in a future blog)

• Toured 8 SF apartments, found 3 roommates, signed a lease in Nob Hill starting January 8th (More on this in a future blog, too!)

• Didn’t completely run out of money (a huge win)

2025 Goals/Resolutions:

Here are the goals I had for 2025 and how they turned out. There were 8 in total, and I managed to finish 6 of them. Not too shabby!

1. Hike the Pacific Crest Trail (PCT) ✅

   • This was an extremely ambitious goal for me, and I’m beyond proud that I went on this grand adventure and walked from the California/Mexico border to the Washington/Canada one. You can read the overview of the trip here, and all about it on my travel blog, Adventure with Dennis!

     

2. Read 50 books ✅

   • This is a standing goal for me every year. This year I read 70 books… click the footnote to see the full list and my recommendations! →1 ←

     

3. Visit 10 National Parks ✅

   • Another standing goal for me each year. This year, I visited 13 National Parks: Grand Teton, Haleakalā (twice), Killarney (in Ireland, with my friend Federico), Yorkshire Dales (with my girlfriend and her friend, Libby), Loch Lomond and the Trossachs (on a Scottish Highlands solo trip), Sequoia, Kings Canyon, Yosemite, Lassen, Crater Lake, Mt. Rainier, North Cascades, and Everglades. 7 of them (Sequoia —> North Cascades) I hiked through on the PCT

4. Graduate from UCLA ✅

   • Lfg. Super proud of this one, what an epic adventure that one was!

5. Increase the number of weak ties I have ✅

   • This basically means to expand my professional and personal network in the goal of increasing unexpected, downstream opportunities. This sorta happened, but I’m looking to be more intentional about it this year

6. Run 2 more marathons ✅

   • I ran the LA Marathon in 4:44:58 and the Southampton Marathon in 3:59:51. 💪

7. Reach 1,000 Interosity subscribers ❌

   • No luck with this one. I currently have a few hundred and was writing well at the beginning of the year, but spent most of April onward writing my travel blog while in the UK and on the PCT. Thanks for being here anyway!

8. Intramural Champion ❌

   • Epic fail here. Probably my biggest disappointment at UCLA was not winning an intramural sport, which I tried so so SO hard to do. I must’ve played 30 different IM sports across my 10 quarters at UCLA, and made it to the finals of cornhole with my friend Nolan once. The other team brought their own bags and cooked us in the finale… still a bit salty about that one

     

2026 Goals:

These are fixed things/events you want to make happen. A good framework for setting good goals is SMART: specific, measurable, attainable, relevant, and timely; the best goals tick off all of these traits. Here are mine for 2026:

1. Beat my sister and girlfriend in the Escape from Alcatraz Triathlon that we’re racing in June (overall and in every discipline)

   • The three of us are competing in the Escape from Alcatraz Triathlon this year, where you swim 1.5 miles in the open SF Bay, bike 20 miles across the peninsula, and finish with a punishing 8-mile run. The goal is to beat their times in each discipline (swim, bike, and run) and the overall time

2. Win the Holiday Fun Run outright

   • The Holiday Fun Run is the local December race in my hometown, and I’ve been racing in it for at least 15 years. This year, I won my age group and got 4th place overall; the goal for 2026 is to win 1st place outright

3. Bench 225 lbs

   • This one is the most ambitious goal, and mostly stems from the fact that Jack Raines, my writing hero, once wrote that “every self-respecting man should be able to bench 225 lbs at least once in their life.” My brother and I have recently been on quite the weightlifting grind, which, for those of you who know me, is extremely unusual. But! I benched 135 lbs yesterday, and I (possibly, almost certainly, naively) think that increasing that by 90 lbs in one year is totally doable. Stay tuned

4. Publish an app on the Apple AppStore

   • I’m currently working on one, the goal is to have it published by March :)

5. Backpack 10 nights

   • I’ve grown to love backpacking after doing the entire Pacific Crest Trail in 2025, and while doing something like that, extreme is not in the picture this year, I definitely want to keep up the outdoorsiness and get in at least 10 nights in 2026. Summer JMT hike? Tahoe Rim Trail? Who knows!

6. Read 50 books

   • A standing goal for every year. Please text/email/call/comment any recommendations you have!!!

2026 Resolutions:

These are broader than specific goals, and highlight more general trends/improvements I’m focusing on this year. There are 3 of them:

1. Increase sense of fashion/style

   1. My current fashion style mostly involves pants/shorts + Hokas + hoodie. Now that I’m moving to SF and am generally becoming an adult, that needs to change. Fortunately my girlfriend is quite motivated in this department. Lol

2. Become more fit/have a more toned upper body

   1. This goes hand in hand with the “Bench 225 lbs” goal, and stems from the fact that I have (very) fit legs from tons of cycling… and not that up top. Looking to change that in 2026

3. Buy food when I need it/focus on nutrition and dietary health

   1. This one’s a huge one for me, and comes from the fact that I (for some reason) am quite frugal with spending more money on better-quality food. When I interned at Kraft Heinz after my sophomore year, I’d eat 20 McNuggets for lunch because McDonald’s had a $5-for-20-McNuggets deal every lunchtime, and I wanted to save money. Needless to say, I started feeling quite shitty in the afternoons, and eventually bit the bullet and started spending $5/day more on lunch… it’s crazy how much my afternoon thinking, clarity, and energy levels improved after that. I’ll be really focusing on this one now that I’m on a BCG salary and my SF apartment is literally a block from Trader Joe’s

So there you have it! My New Year’s Resolutions for 2026! Stay tuned for the 2026 Year in Review next January to see how it all turned out. Thanks so much again for reading, and please share your goals/resolutions below; I’d love to stay in touch and hold each other accountable this year.

Let’s have a fantastic one :)

Dennis’s Picks:

• I absolutely loved Gurwinder’s 26 Useful Concepts for 2026. Below are my favorites:

• Google’s 2025 Year in Search. I’ve always loved these yearly recaps, and 2025’s did not disappoint

• The quote, “Investments in your 20s pay off for the rest of your life, whether they are good investments or bad ones.”

• I generally think that Substack Notes are a plague to society (why host short-form posts when the entire point of your platform is to have long-form essays and increase attention span, not reduce it??? Keep that stuff on Twitter), but sometimes a gem like this pops up that makes me momentarily forget how much I dislike Notes

• I really enjoy the blog Unplugged Traveler, where the author goes on international trips without any devices or planning and figures it all of on the fly, then writes about it at home. Her recent piece about travel coincidences was great

• I have absolutely no idea where I found this article about gooning, but it was crazy (plus my first time hearing of the word). Enter at your own risk

Background

Strava, for those who don’t know, is a platform where you can track your rides, runs, swims (any exercise, really), and share these activities with friends. Other Strava users can then look at your activities and give you “kudos”… basically the Facebook equivalent for athletes. A main feature of Strava is its GPS tracking, meaning that after your activity, you can see exactly where you went on a nicely-rendered map. Knowing this, some athletes go as far as to run/ride/swim/ski/whatever in a specific pattern in the real world, creating a beautiful design when looking at the GPS route afterward. This is Strava art.

I’ve been using Strava since the start of high school, but I first heard about Strava art a few years ago when one of my UCLA cycling teammates, Max, biked a turkey-shaped route in San Francisco on Thanksgiving. Besides being a 60-mile-long turkey, the amazing thing was that the route did, in fact, look just like a turkey:

For some reason, a few days ago when I was pondering the rapidly approaching holiday season, I remembered this festive bike ride, and decided to go ride some Strava art myself. So, I found a neighborhood a few miles away from mine that had a somewhat-regular street grid, drew out a route that would spell “HoHoHo”, got on my bike, and set off.

It failed miserably:

Besides the letters being a lot more smushed together on the final map than I’d anticipated, I mistakenly biked an extra road, spelling “HoHodo”. Bruh moment.

Once I got home, I called my friend Sanketh to tell him about the ride, and proceeded to spend a few minutes looking at some Strava art examples online. It turns out that there are a ton of fantastic routes people have created (each one MUCH better than mine), including some “HoHoHo” designs that actually spelled… “HoHoHo”. A few examples:

I figured there had to be some design tools out there that helped create Strava art, looked into a few different options, but eventually decided to have a go at making my own website to help me out. I’d been hearing all about vibe coding for the past few months, and figured this would be a great project to try out vibe coding with.

Vibe coding, for those that don’t know, is the process of creating some programmable product with an AI tool that’s sufficiently advanced so that you don’t actually need to… know how to code. Rather, you just use normal English to direct the AI programmer to do exactly what you want, and then it goes and does it. Plus, I’d recently listened to my friend Cole’s podcast interview of a professional vibe coder (who calls vibe coding “hyper-engineering”), so naturally I was itching to do some kind of project at home. So vibe coding a Strava art website, it was.

Game time

My go-to tool for this kind of development is Cursor, which I’d previously used to reformat my resume using LaTeX. I’d heard about Cursor from my sister… who just so happens to work there. I tried it out for a few small projects, loved it, and used it for this one, too.

For the layperson, Cursor is basically an all-in-one AI-powered coding assistant that can do pretty much any coding task you ask of it. Any task, at least, that I can think of asking it to do. It has a friendly interface, fantastic tools, and the cheeky line “Planning next moves” when the coding agent is deciding what to do.

This was the initial query to the agent:

Create a React-based web application for creating GPS art routes for Strava. It should allow users to click on a map to create routes, upload images to trace over, snap routes to roads, and export as GPX files. Upload the files to GitHub and host the website under GitHub Pages.

(GitHub is a free code storage and running service, and GitHub Pages is GitHub’s free website hosting service. Lit. If you don’t know what any of this means, ask Uncle Gemini)

After making the query, the agent went ahead and did all that I asked insanely quickly and pretty much perfectly. I gave a number of follow-up commands (re-format this, make the footnotes that, add this feature, remove this unnecessary one), and after about 2ish hours of decent focus, I was able to create a nicely polished website. Check it out!

Its features include:

• You can click on the map to drop points, which are then linked together into a route

• You can upload a PNG file, which is then transparently overlayed onto the map for you to trace

• You can draw directly onto the map, which is then converted into the closest approximated route based on the available roads

• You can enable “Snap to Roads”, which makes sure the different points you drop are actually connected via real roads and don’t go through building/train tracks/water/obstacles

• Plus, it looks great with nice UI :)

To top it all off, I used the website to create a much better route than my initial “HoHoHo” attempt, and biked an 8-mile snowman with my dad and brother on Christmas. Take that, Santa! 🧑‍🎄

Ultimately, it seems that powerful AI tools have replaced nearly all the prerequisites to making most basic programmable things, making your imagination the only limit to what you can build. Lfg

Some lessons learned/notes:

• The better you prompt and the more details you include, the better the final result will be. This so-called “prompt engineering” actually makes a huge difference, so knowing what you want and what can be made is a huge +. The takeaway there is to use lots of great products to see what greatness looks like… and then copy the shit out of that for your own projects

• Open source mapping software is a gift to the world. The Open Street Maps map that I used, and the free road-snapping algorithm, meant that I didn’t need to invent anything, but rather piece together existing services for the website. Plus, I used the free app Organic Maps to upload the .GPX file to my phone and then followed it on the bike ride

• Opus 4.5 is by far the best model to use on Cursor. Yes, it burns through credits like they’re made of paper, but I’d rather pay more for something that works than less for something that doesn’t. So, Opus does all the major work, and Cursor’s in-house Composer 1 (which is way cheaper and faster) does all the tune-ups (editing footnotes, reformatting buttons, adding text, etc.)

• Cursor’s Auto mode sucks. I started with Auto, it wasn’t working, and I was getting ready to give up. I then switched to Opus at my sister’s recommendation, and it magically started working (see above)

• For a $20/month Cursor subscription and a free GitHub account, you can pretty much create any intermediate-level-or-above programmable thing you can think of. Strava art website? Check. Personal website? Check. LaTeX resume formatter? Check. Meditation app? Yessir. My next project is a much more ambitious long-distance backpacking app, which I’ll write more about when things get up and running

• There are three great existing websites for creating Strava art, all of which are much better than mine, two of which are free. Check out my website, but check out the others, too! RouteSketcher and RouteDoodle were the free ones

Resources:

• My Strava art website

• Public GitHub repo

• Cursor (students get one free year of Pro!)

Dennis’s Picks:

• I quite enjoy “xx things I learned by xx years old” lists, and this one has been one of my favorites. I found it from one of Jack Raines’s articles, who himself is a fantastic writer and the inspiration for this blog

• I recently read the book “Private Equity” and loved it. It’s a personal memoir of the former sole assistant to a top hedge fund manager, and chronicles her insane life and work commitments on the job. Fascinating read, and makes me want to go into finance even less than I already did lol. I’ve been on quite the memoir kick for the last few months, and this one was one of my favorites

• The website GPTZero. You paste in text, and it tells you which parts, if any, have been written by AI. I’ve found it to be very accurate, making it quite eye-opening when you realize something you thought someone actually wrote was, in fact, written by Uncle Gemini

I wrote a very in-depth guide for writing and formatting your resume about a year ago (including free templates!), which I recommend checking out here!

A few weeks ago, I started applying for a few start-up jobs in SF (this is an entire separate story), so it was time for the time-honored tradition of updating my resume before I actually sent it over to companies for review.

Unfortunately, now that I’ve graduated from UCLA, I no longer have access to my beloved free Microsoft 365 subscription, which sucks because without the subscription I can’t update my Word-document-formatted resume, which sucks because that meant I couldn’t add to my resume the delightful fact that I’d thru-hiked the Pacific Crest Trail this summer. Not good.

Fortunately for me, around this time I called my dear friend Nathan to virtually play a game of Blokus (my favorite board game). I met him online months ago when I was looking for some Blokus strategy articles to improve my playing, stumbled upon his blog (one of the only good resources on the topic), emailed him to connect, and the rest is history. We started playing Blokus online regularly, and he’s a good friend to this day.

So back to the regularly scheduled tale. I met with Nathan to play Blokus (he cooked me), told him about my resume dilemma (me not wanting to fork over money for my own Microsoft 365 subscription), and after a long conversation of which I’ll spare you the details, he basically said something along the lines of “why don’t you just make your resume in LaTeX.”

I’d heard of LaTeX1 but had never used it before, and after a little digging around I found out the following things, in about this order:

1. LaTeX is a programming language that turns code into PDFs (it’s also great for writing math formulas, but fortunately I don’t need to do that)

2. LaTeX is fantastic at making resumes because of its perfect formatting and simple layout

3. It’s free, forever

4. Lit

So, I found myself pulling up my ~favorite~ AI researching tool, Perplexity2, made a game plan to convert my existing PDF resume into LaTeX so I could edit it, pulled up my ~favorite~ AI-integrated coding environment, Cursor, and was all ready to go.

And… it turned out great! The entire resume is now just 159 lines of code (including comments), which I can edit at any time, for free, forever. Not bad!3

It looks like this:

(This can definitely be overwhelming if you’ve never coded before, but don’t worry, I describe how to read it clearly later on!)

\documentclass[10pt]{article} % sets font size to 10pt, don't change

% textbf{...} bolds everything inside the brackets
% textit{...} italicizes everything inside the brackets
% \hfill right-aligns all the text after

% Packages, don't change the below 5 lines
\usepackage[margin=0.5in]{geometry} % sets margins to 0.5in
\usepackage[hidelinks]{hyperref} % adds hyperlinks to the document
\usepackage{titlesec} % allows for custom section formatting
\usepackage{enumitem} % allows for custom list formatting
\usepackage{xcolor} % allows for custom colors

% Sets color shades for section titles
\definecolor{darkblue}{RGB}{0, 51, 102}

% Formatting for section titles, don't change
\titleformat{\section}{\large\bfseries\color{darkblue}}{}{0em}{}[\titlerule]
\titlespacing{\section}{0pt}{10pt}{5pt}

% Removes default paragraph indentation, don't change
\setlength{\parindent}{0pt}

% Custom formatting for job entries (see example of this below)
% #1 is the company name
% #2 is the job title (e.g. Product Manager Intern, Marketing Lead, etc.)
% #3 is the location (e.g. Los Angeles, CA; Seattle, WA; Chicago, IL; etc.)
% #4 is the date (e.g. Jan 2023 -- Mar 2025; Jun 2024 -- Aug 2024; etc.)
\newcommand{\jobtitle}[4]{
    \textbf{#1} \textbar\ \textit{#2} \textbar\ #3 \hfill \textbf{#4}
}

% Custom formatting for job descriptions
% Creates a new bullet-point list environment with no separation between items and a left margin of 0.25in
\newcommand{\jobdesc}[1]{
    \begin{itemize}[nosep, leftmargin=0.25in]
        #1
    \end{itemize}
}

% Removes page numbers from the document
\pagestyle{empty}

% Start of the actual document!!
\begin{document}

% Header section
\begin{center}
    \textbf{\Large Dennis Gavrilenko} \\
    (xxx) xxx-xxxx \textbar\ \href{mailto:dennisg009@gmail.com}{dennisg009@gmail.com} \textbar\ \href{http://www.linkedin.com/in/dennis-gavrilenko}{linkedin.com/in/dennis-gavrilenko} \textbar\ \href{http://www.interosity.co}{interosity.co}
\end{center}

% Education section
\section{EDUCATION}

\textbf{University of California, Los Angeles (UCLA)} \textbar\ Los Angeles, CA \hfill \textbf{Sep 2021 -- Mar 2025} \\
B.A. in Business Economics, Minor in Data Science Engineering \textbar\ GPA: 3.7/4.0, Dean’s Honor List \textbar\ SAT: 1580, ACT: 35 \\
\textit{Relevant Coursework: Natural Language Processing, Computer Vision, Data Science, Intro to ML, Econometrics, \\ Programming in R, Intro to Computer Science I/II, Linear Algebra, Probability Theory, Calculus I/II/III, Intro Accounting}

\vspace{5pt}

\textbf{Sciences Po} \textbar\ Paris, France \hfill \textbf{Aug 2023 -- Dec 2023} \\
\textit{Semester Exchange: International Trade \& Finance, Labor Economics, Corporate Governance, French Imperial History}

% Professional Experience section
\section{PROFESSIONAL EXPERIENCE}

\jobtitle{UCLA Undergraduate Admission}{Campus Tour Guide}{Los Angeles, CA}{Jan 2023 -- Mar 2025}
\jobdesc{
    \item Provided in-depth, informative, 90-minute tours of the UCLA campus to 2000+ guests (prospective/admitted students).
    \item Showed everyone how wonderful and amazing UCLA is and encouraged thousands of students to pursue higher education.
}

 % Dennis was here!

\vspace{3pt}

\jobtitle{Boston Consulting Group (BCG)}{Summer Associate}{Seattle, WA}{Jun 2024 -- Aug 2024}
\jobdesc{
    \item Recommended strategies for a major US family foundation’s board to reduce staff tensions and streamline operations.
    \item Interviewed 20+ executives, board members, industry leaders to identify best operations practices to address pain points.
    \item Led an extensive analysis of 40+ major US cities to identify the best location for an upcoming headquarters move.
    \item Conducted a peer benchmarking analysis to identify client’s weak points in OpEx, grantmaking efficiency, and impact.
}

\vspace{3pt}

\jobtitle{The Kraft Heinz Company}{Product Manager Intern}{Chicago, IL}{Jun 2023 -- Aug 2023}
\jobdesc{
    \item Helped build four data-driven dashboards for digital supply chain team while managing 15+ stakeholder interests.
    \item Created an interactive visualization model with Excel pivot tables, decreasing unordered customer inventory by 20\%.
    \item Coordinated product development with 10+ data engineers and UX designers to align product vision with business goals.
}

\vspace{3pt}

\jobtitle{Amazon Prime Gaming}{Product Consultant}{Los Angeles, CA}{Apr 2023 -- Jun 2023}
\jobdesc{
    \item Developed a product roadmap and designed 5+ high-fidelity mock-ups in Figma for Amazon Prime Gaming’s website.
    \item Created two strategies to gamify UX with weekly website prizes, increasing user retention by 25\% and signups by 10\%.
}

\vspace{3pt}

\jobtitle{kommu}{Product Manager Intern}{Los Angeles, CA}{Mar 2023 -- Jun 2023}
\jobdesc{
    \item Planned technical feature set and designed 20+ high-fidelity mock-ups in Figma for a startup’s new web portal login.
    \item Analyzed 200+ users’ data to determine top growing markets, recommended three new marketing strategies for Q3, Q4.
}

\vspace{3pt}

\jobtitle{Hussle}{Marketing Lead}{Los Angeles, CA}{Aug 2022 -- Dec 2022}
\jobdesc{
    \item Collaborated with development and customer success teams to create two new app features based on user feedback.
    \item Directed all marketing operations, created \$3000 marketing budget, distributed 1000+ flyers, organized 3 outreach efforts.
}

\vspace{3pt}

\jobtitle{First Republic Bank}{Lending Services Intern}{San Francisco, CA}{Jun 2022 -- Sep 2022}
\jobdesc{
    \item Digitized paper housing records system to simplify documentation access and increase loan closing team’s efficiency.
    \item Built Excel dashboard with pivot tables and VBA to analyze 100+ intern surveys, recommended 3 areas for improvement.
    \item Continuously communicated, implemented changing needs for 40+ stakeholders, including 2 managers and 35+ clients.
}

% Leadership and Volunteer section
\section{LEADERSHIP AND VOLUNTEER EXPERIENCE}

\jobtitle{The Bruin Group Consulting}{Project Manager, Senior Consultant}{Los Angeles, CA}{Jan 2022 -- Mar 2025}
\jobdesc{
    \item Led a 10-week, 5-person project to create growth strategies to increase a startup carpooling service’s user base by 300\%.
    \item Created a developer marketing strategy and implementation timeline for a startup’s SaaS and API products.
}

\vspace{3pt}

\jobtitle{Boy Scouts of America}{Senior Patrol Leader, Quartermaster}{Antioch, CA}{Feb 2014 -- Sep 2021}
\jobdesc{
    \item Led my troop of 20+ Scouts on extended camping trips, earned 51 merit badges, advanced 10+ younger Scouts’ ranks.
    \item Participated in several city clean-ups, Christmas tree pickups while volunteering hundreds of community service hours.
    \item Volunteered in 13 Eagle Scout Projects, earned 2 Eagle Scout Mentor pins, National Youth Leadership Training.
}

% Skills and Interests section
\section{SKILLS AND INTERESTS}

\textbf{Programming Skills:} Data Analysis (Python, R, SQL, VBA, Excel, PowerPoint), Project Management (Jira, Notion, Agile Development, Scrum), Product Marketing (User Research, A/B Testing, Setting KPIs), Java, C++.

\vspace{3pt}

\textbf{Languages:} Fluent in English and Russian, learning French so that I can talk to the Parisian baker in my neighborhood.

\vspace{3pt}

\textbf{Achievements:} Backpacked the Pacific Crest Trail (2025), Eagle Scout, LA Marathon finisher (2023, 2024), SF Marathon finisher (2024), climbed highest volcano in CA (Mt. Shasta) twice, curated art gallery in LA, WayUp Top 100 Intern (2023).

\vspace{3pt}

\textbf{Interests:} Growing ghost peppers, reading science fiction novels, juggling, poker, geology, raising chickens, postcards, \\ Roman archaeology, playing the accordion, long-distance cycling, blogging on Substack, Blokus, hitchhiking, regular hiking.

\end{document}

Phew, we made it to the end.

To turn this code block into a resume, simply copy all the code, go to the website Overleaf (a free LaTeX renderer), paste the code into the editor, compile it, and boom! It’s my resume! Sick! (You can also just look at the PDF version below lol, but it’s cool to see the code compile into a full resume)

Dennis Gavrilenko Resume

90.5KB ∙ PDF file

Download

Download

At this point, if you’ve taken a coding class before and can read the LaTeX document pretty easily, you’re pretty much set. Just use my code as a template for yours, edit as needed, and have yourself a resume that you can edit for free, forever! If you’re even more tech-savvy and code regularly, you can edit the LaTeX in your coding environment of choice (Cursor for me) and commit any changes to GitHub with git, and now you can see all the resume edits you make over time. This way, you can revert any bad changes, but even better you can see your resume changes and grows over time. Pretty neat, and something I wish I started tracking earlier in college as I completed internships and joined new clubs. If you have no idea what those last 2 sentences mean, don’t worry and pretend you never read them.

If you haven’t coded before, don’t worry! Throughout the code, I’ve included a ton of comments for you to read and better understand what’s happening; in LaTeX, the commenting characters are percents (“%”), so every time you read after a percent symbol, the comment isn’t actually code, but rather descriptions of the code to describe to human readers what’s happening there. You’ll see plenty of %s in the code, so read what they say for more helpful context! Comments that say “don’t change”… shouldn’t be changed; sections without them should be updated with your info!

Play around with changing different parts of my template resume in Overleaf, and see what those changes do to the final PDF rendering. Once you’re comfortable with how coding in LaTeX works, go ahead and change all the information to be yours, and enjoy your resume! If you’re having trouble or have any questions, just respond to this email or text me, I’d love to help.

Well, that’s all for me. Enjoy the template code, good luck with making your resume, and have a generally slay day!

Best,
Dennis :)

Dennis’s Picks:

I’m really excited to get back into including Dennis’s Picks at the end of my Interosity pieces, which are basically my favorite other media I’ve been reading/watching/listening to recently. I’ll try to include 3-5 of my favorites since the last article, both as a way to share cool things with you and to create an archive of what I was learning at this particular moment in time.

• I really enjoyed Robin Guo’s piece, Life is Poker, Not Chess, where he describes how all of your decisions, especially those related to your career, are more analogous to poker than chess because they deal with incomplete information with uncertain probabilities. Highly recommend

• This promotional video for a startup called Poke. I haven’t even used the product, but boy does that video remind me of studying abroad in Paris ❤️

• The Acquired podcast. Holy shit, they’re good. Fantastic, long-form episodes that are deep dives into different business histories. All their episodes are great, but my favorites are Costco, Trader Joe’s, and the Google saga. Amazing amazing amazing, I could listen to David Rosenthal all day

• The Lumineers. Wonderful band, wonderful music. Melancholy and meaningful and delightful, all in one

3

To top it all off, I did this entire resume-transcription-in-LaTeX project at my girlfriend’s house while I was home alone with her anxious dog, and generally had a tremendous time screen sharing my laptop to their TV while petting the aforementioned anxious dog. Anxiety cured, resume built. 💪

I was on a walk with my friend Justin this morning when we started talking about jobs. He’s applying to a few at the moment, so naturally we were sharing stories about our recruiting experiences throughout college. It was a good time, and a pleasant walk down memory lane.

Back in college, I was very involved in a professional consulting club, and spent a ton of time during my freshman and sophomore years recruiting for different internships, jobs, and clubs. It was a twisting journey full of countless dead ends, failures, and funny lessons, but by the end I had finished recruiting earlier and was able to really enjoy my last two years at UCLA. (Highly recommend doing it this way, rather than the other way around)

Once a junior, I started sharing these lessons with my mentees in the consulting club, and eventually was inspired to start this blog to share them with even more people. I figured that all of the hard-earned recruiting lessons I’d learned were probably applicable to everyone who was looking for a job… so basically everyone. I’d write blogs here on Substack, post about them on LinkedIn, and then magically more people would start reading them.

And by far the most common question I’d get was “Dennis, how do I get a job/internship” or “Dennis, how do you write such funny LinkedIn posts” (just kidding, that rarely happened), to which I’d generally respond with this:

1. Getting an internship is super important to getting a full-time job after graduation, since you’re likely to get a full-time job offer if you did well in the internship

2. The more experience you have, the easier it’ll be to get more experience (since you’ve demonstrated your skills and abilities before)

3. Logically, the first internship will be the hardest to get

4. Therefore, apply to a shit ton of internships when starting out and try to get something, anything really. I started calling this the “spray and pray” strategy, since you’d be “spraying” your resume everywhere and “praying” it’d stick somewhere. I’ve written about my professional journey before, but long story short, I applied for 50 internships during my freshman year at UCLA (all at First Republic Bank, where I got one interview in Lending Services and ended up there the following summer), about 100 internships my sophomore year (and got significantly more offers, ~10), and only to a handful my junior year at top consulting firms. I ended up with an offer from BCG Seattle

Crucially, when spam-applying to all these summer internships, you’d ideally tailor your resume to highlight experiences most relevant to that job. And since resumes are usually read by an automated grading machine (a so-called “Applicant Tracking System”, or ATS) before ever being looked at by a recruiter, having a well-formatted resume full of target keywords that matched the job listing was vital to getting that first interview.

Back in my day (about 3 years ago), I had to do this all manually: I’d spend hours scouring job listings, changing verbs from “led” to “spearheaded” to “masterminded” (and etc.) depending on the particular listing, then applying to dozens of jobs with these custom resumes. As you can imagine, this would take forever.

But on this walk with Justin today, we discussed how it would probably be super easy to do this with AI. Of course. EVERYTHING WITH AI!!! (preferably with the word “agentic”)

Quickly, we hammered out the steps on how to do this:

1. Upload my resume, LinkedIn profile, this blog, and my travel blog to ChatGPT’s custom GPT maker

2. Give it extremely detailed instructions on what to do (tailor my resume, I have the exact wording below)

3. Create the GPT

4. Once created, simply give it the link to a job listing, and it’d automatically edit the bullet points for each of my experiences to best fit the provided listing

5. Celebrate

Sounds pretty doable. Fortunately, I wasn’t doing too much right when I got home, and figured that this project wouldn’t really take that long. Maybe 15-20 minutes to create the GPT and fine-tune it to output the correct stuff, and then I’d be pretty much set. Plus, I’d get a nice blog post out of it. (hello!)

So I did that, and it worked great. Check it out here!

Important notes and lessons learned from this mini-project, which are listed below in no particular order:

• The custom GPT can’t actually create the Word document or the PDF itself, only the text (despite saying that it could and then making me wait while it “generated” nothing). It can create the tailored bullet points, but I still had to input them into my resume template in Word. (For tips on this, check out my resume guide!)

• It took a bit of follow-up questions to fine-tune the output to what I was looking for, since the GPT creation interface didn’t seem to understand my simple directions to keep the section headers exactly the same. I’m used to using Perplexity for my projects, and that never hallucinates, so this experience kinda reminded me why I stick with my preferred AI tool lol. At the moment, however, you can only create these custom GPTs with ChatGPT easily

• Some job listings block AI crawlers, so for those, I couldn’t just give the GPT model the job listing link. For these, I simply copy-pasted the text of the job listing and that worked perfectly fine for creating the tailored bullet points

• It’s crazy how much time and mental energy this saved. Obviously, write your own initial bullet points to make sure they’re truthful and accurate, but once you have those the GPT can tailor them as needed. It’s crazy how many hours this would’ve saved me if this were around in 2022

Below is the exact text I used to customize the GPT:

Hey there! I’d like to create a custom GPT that tailors my resume to job descriptions with ATS-optimized formatting. Here are your instructions below, and I’ll also add some references for you to use. These are the current resume in PDF form, my LinkedIn account, and my personal and professional blogs. I’ve written a resume guide on my professional blog that I’d like you to reference as well.

(Resume attached)

LinkedIn: https://www.linkedin.com/in/dennis-gavrilenko/

Professional blog: https://www.interosity.co

Professional blog resume guide: https://www.interosity.co/p/resumes-101?r=tbrbl

Personal blog: https://www.adventurewithdennis.com/

ROLE: You are an expert resume writer, ATS optimization specialist, and recruiter.

TASK: When the user provides a job posting, analyze it and create a tailored resume.

PROCESS:

1. Analyze the job description for key skills, keywords, and qualifications

2. Reference the user’s uploaded resume and LinkedIn profile

3. Create a new resume version that:

   1. Highlights relevant experience matching the job requirements

   2. Incorporates high-impact keywords from the job description

   3. Maintains the user’s original formatting style and structure

   4. Ensures ATS compatibility (single-column, no tables, clear formatting)

   5. Uses action verbs and quantifiable results where applicable

4. Present the tailored resume in both PDF and Word format

CONSTRAINTS:

1. Only use truthful information from the provided documents

2. Maintain consistency with original experience and achievements

3. Flag any gaps between job requirements and background with [MISSING SKILL/EXPERIENCE]

4. Format should be ATS-friendly (avoid images, complex formatting, special characters)

1. What in the world is this email?

2. Who the hell is Dennis Gavrilenko?!

After a moment’s thought, you may think a third thing:

1. Oh wait, that dude? I completely forgot that he even existed.

Well folks, welcome back to Interosity! It’s been a long 6 months since the last article back in April, but I’ve been up to a lot of exciting things since then and am excited to share them with y’all.

For starters, I graduated from UCLA back in March. That’s right, diploma secured! Four fantastic years of college finally wrapped up this year, and I honestly couldn’t be more proud and happy with how those four years went. I got especially cooked academically by the end (meaning all desire to do classwork plummeted off the deepest, darkest cliff imaginable), and I spent most of my time the last quarter hanging out with friends, exploring UCLA’s campus, ranking the deliciousness of every sorority’s brunch, hosting Blokus board game nights, curating an art gallery in my hallway, and just generally enjoying being a college senior. 11/10 recommend.

Then, after a wonderfully relaxing week-long spring break in Hawaii with my family, I flew to the UK for a month-long trip around the British Isles. I’ve for some reason had a lifelong fascination with British culture and just the Isles in general, and it’d been a dream of mine for ages to do a big trip there. Fortunately, a few of my study abroad friends from Paris (Ben, Emma, Joe!) were either finishing up their bachelor’s degree or completing a master’s in the UK, and combined with my Scottish roommate Finlay’s family/friends in Edinburgh and my Italian friend Federico, I had plenty of people to travel with and visit all over. It was a phenomenal April.

After that, I flew back home to California, relaxed for about 3 days, and then promptly flew to San Diego with my girlfriend to start a 143-day thru-hike of the Pacific Crest Trail, a 2650-mile-long backpacking trail from Mexico to Canada through California, Oregon, and Washington. It was unimaginably beautiful, crazy hard, and fantastically fun. I could spend all day writing about the UK trip and the absolute adventure that was the PCT, but that would take too… oh wait, I have! All that’s on my personal travel blog, which you can check out here. (I like to keep my personal travels and more general essays separated between that blog and this one so they don’t dilute each other)

After coming back from backpacking for 5 months, I spent another week relaxing at home before flying (again) to Hawaii (again with my girlfriend), this time to do a 10-day work stay on someone’s farm. Unbelievable experience, cannot recommend enough. I also became a pro hitchhiker.

And now, I’m back home more permanently! I have two more months of free time before I start working full-time in January at BCG SF, and I’m honestly loving the time off. I wake up every morning with coffee and hours of reading, and then work on fun side projects all day; I’m learning to play the accordion, and just started working on an app idea I was brainstorming during my thru-hike. I also get to play with my brother every day, which is an absolute highlight (he’s building a PC at the moment and selling lots of stuff on eBay… to fund the build).

So that’s it for now! Stay tuned these next few months for some more essays I’ve been drafting recently, and stay curious. Happy Trails!

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You’re probably thinking, “Dennis, this happens to me every single week, what’s the big deal”, but I guess I’m just not as well-traveled as you are. For me, it was quite the unusual experience.

We had a big decision to make between two wonderful options. On the one hand, we could order the “Tasty Deal for 2”1, which featured a 12” medium pizza and a regular side. Or, we could order the “Treat Yo’self”, a 14” pizza and a regular side.

We were torn. Both were great choices, and we were struggling to decide.

Enter the random number generator.

During my freshman year at UCLA, one of my suitemates2 was a guy named Simon — devilishly handsome, extraordinarily clever, and hailing from Boston. And he had a lot of interesting habits and tricks that I found quite interesting.

Besides loving In-n-Out and consistently taking handwritten notes on reams and reams of paper, he used a random number generator to outsource all minor decision-making from his life.

The idea was quite simple. Every day, there are a ton of little decisions that you need to make — things like what outfit to wear, where to eat, or whether you should study here or there. Spending the time to make one of these minor decisions isn’t that big of an issue, but if you spend your entire day addressing these little problems, you’re left with no time or mental energy to deal with the major things.

I saw Simon do this all the time — anytime he needed to make a minor decision where he had no preference between the outcomes, he’d open his phone app, create interval ranges for the different options, and click the random number generator. I quickly adopted this strategy too, and together we decided many minor things randomly (such as which dining hall to have lunch at, or who was more attractive3).

Let me give you an example of how this might work:

Let’s say you want to get dinner with your friend, but neither of you prefers the two proposed options. Rather than spend time debating where to go, you say that if the generator results below 50, you go to the first option; above 50, the second. You spin the generator and go to that place for dinner. If there are three options, you can make the interval ranges 1-33, 34-66, and 67-99. And so on, creating as many intervals for as many options as you have4.

You don’t even need to have a random number generator app for this5 — you can just use your phone stopwatch: Open the clock app, start the stopwatch, look away, wait a few seconds before stopping, and use the millisecond’s place as your random number.

And when you use this method to make a minor decision, one of two things happens, both of which are good:

1. You find that you actually don’t have a preference between the different options, so the generator removes unnecessary cognitive load from your brain.

2. You feel slightly disappointed by the outcome of the generator, indicating that you actually want to do one of the other options. Then you go do that, and all doubt in your mind is removed as to what you actually want to do.

Which brings us back to 4 Star Pizza.

Federico and I set up two intervals for the two options, and lo and behold, the random number generator produced 49. We ordered the Tasty Deal for 2, destroyed the delicious pizza, and went about the rest of our evening. Crisis averted!

Best,
Dennis

Dennis’s Picks:

• I was talking to my roommate a few weeks ago at UCLA about how complicated subjects like to use simple terminology, and simple subjects like to use complicated terminology. It seems that academics want to seem smart and fancy, but that’s already achieved if you study something hard like physics. If you study something less crazy like sociology, the terminology becomes extra complex for no reason. Reminds me of LinkedIn too, lol. I read a very good article on a similar topic about students’ writing here.

• I just finished reading the Remembrance of Earth’s Past trilogy, one of my favorite sci-fi series ever. You’ve probably heard of the first book, The Three-Body Problem, but the others are just as good, if not better. Can’t recommend the series enough!

• I love Jack Raines’s piece on why should travel more when young. I’ve read it at least 10 times over the years, and most recently with Federico while in Dublin. Please read it as soon as you can!

The store didn’t have the exact brand she had at home, so I got another Italian one that I thought she’d like. I bought the bag of whole beans, then asked the clerk at the counter where I could grind them since I didn’t see a grinder in the aisle.

The clerk looked at me like I was crazy and asked: “Why in the world would there be a coffee grinder in the store?”

At its most basic form, an axiom is any statement from which others can be logically derived. Throughout math and philosophy, plenty of these axioms are used to build all other propositions, most of which we intuitively grasp and don’t even think about.

From the axiom (a + 0 = a), for example, you can prove any valid statement of addition. Using it and through some very convoluted (but valid) steps, you could eventually even get to (1 + 2 + 3 + 4 + 5 + 6 + 7 + 8 + 9 + 10) = (7 + 8 + 9 + 10 + 11 + 1 + 2 + 7). I know you didn’t read all that. Both equal 55.

But math and logic aren’t the only domains to which these axioms can be applied. As funny as it is, the coffee incident made me ponder this idea deeply, and I’ve decided to call my proposition the axioms of existence.

These axioms are not the basis for fancy mathematical manipulation, but rather are the building blocks of our world, ones on which we build our experience of living. These axioms are completely informed by our environment and surroundings, and we never really question them. They’re just there. The sky is blue. Green means go. Red means stop.

Of course the store has a coffee grinder. Why wouldn’t it?

And so when we’re faced with challenges to these axioms, we like to describe them as “culture shocks”. We feel disoriented in a new place, and feel strange in a foreign land filled with different attitudes and another way of life. It’s the classic experience of any American traveling in the UK: “That’s so funny, they drive on the left side of the road!” We call our families about it, tell our friends back home, and forget about it not too much later.

But sometimes, something new is not merely a “culture shock” — it is so profound, so unexpected, that you find that an axiom of your existence, one that you never even consciously thought about, is dramatically interrogated and found to not be universally true.

As funny as it is, the coffee anecdote I shared above was one such example — the idea that a store could sell whole coffee beans without a grinder was not just strange, but unfathomable. It forced me into an unexpected adventure around northeast London (which I won’t go into here), and shook me to my core.

These axioms are not just confined to coffee and their grinders (or lack thereof) — you could imagine visiting a friend in a place where the bathrooms had no toilet paper. After a traumatizing visit to the loo, you ask your friend why there weren’t any of the precious squares, and in a confused tone they ask you why you didn’t bring your own. In their world, everyone brings their own toilet paper when they go for a much-needed #2.

This situation would not just be a culture shock and a reason to buy new underwear — it would be a profound and very strange experience, one where an axiom of your existence (that all bathrooms provide toilet paper) was found to not be true at all. And I hope that that axiom, for one, is never questioned.

The axioms of existence, eh? What an interesting thought!

Best,
Dennis

P.S. No, I didn’t hear the term “axioms of existence” from anywhere before. As far as I know, this was coined right here on Interosity!

P.P.S. I know my description of an axiom is an oversimplification of the idea. Math students, please don’t kill me. (I’m looking at you, Nathan)

And quite recently, a very fun side effect has emerged: the creation of DennisGPT!

Not too long ago, I learned that you can make a custom GPT through ChatGPT.

Basically, this means that you can create your own model to do something you’d like, and all you need is a sufficient amount of training data to do so. I found out about this GPT-creation thing from my friend Nathan, who’s building one for UCLA Admissions to share with college applicants.

The general idea was that if you could feed this GPT all the available information about UCLA undergraduate admissions, it could create a custom chatbot that’s best suited to answering questions from prospective and current applicants. He fed in all the data he could find on UCLA’s website about admissions and different academic departments, and I provided the tour guide script (all 37 pages!) for further refinement. This was a cool project, and something I was happy to contribute to.

But I was curious about just how well this GPT-creation thing worked, so I decided to try and create one myself. I fed in all of my blog articles (all ~80 of them between Interosity and Adventure with Dennis), and asked it to create a model that copied my writing style.

Boom! Just like that, DennisGPT is born!

And the crazy thing is, since I had a sufficiently large training corpus (translation: I’ve written lots of articles), the model was pretty good at emulating my style. We’re talking random anecdotes everywhere (albeit hallucinated), floating conjunctions all over the place, and a complete disregard for normal formatting or citation standards.

Sound familiar? That’s me!

Funnily enough, I didn’t find many uses for DennisGPT, besides copy-pasting stuff and having it rewrite as if I wrote it myself. And there wasn’t any reason to do that, except for the completely hypothetical situation of my friend sending me his CS homework and DennisGPT going to town on it before I submitted it (enough said on that topic).

But the thing is, while DennisGPT can write like me, it can’t think like me. It can’t create anything new, and is stuck with rewriting existing work. It’s not me.

It’s a shadow of me.

At the start, I shared many benefits to writing, one of which is that it forces me to think critically. And that’s because writing well is actually really fucking hard.

Writing a good article involves consolidating a vast amount of information, coming up with a thoughtful analysis, and making it interesting to your audience. Gurwinder explains just why this is so hard: “Writing requires you to filter out bad information because you have a duty to your readers to not be full of shit.”

And writing without being full of shit is really, really hard to do.

But it’s also incredibly rewarding, and there are few things like it. The feeling I get when I read through a polished article draft is best described as the feeling you get when you’ve been debugging your code for hours, and it finally works.

Like a legend! Like the best that’s ever lived!

Dare I even say… godlike?

For an example of this writing process, let’s just look at how I wrote my most recent article, “Some thoughts on the encroachment of AI”. During the course of the piece, I share a few different anecdotes, each from a different place:

• An intro about AI phone calls, which I read on someone else’s Substack (I forget exactly whose)

• An anecdote about AI image creation, which I read about on LinkedIn

• Harry Dry’s YouTube video analysis from his wonderful marketing newsletter

• Another anecdote about my writing class and my professor’s grading

• One more anecdote about keeping all handwritten notes I receive

Taking those different things and making an Interosity article out of them required me to sit there and ponder how to make it flow together well, which again, is really fucking hard. As Paul Graham says, “The easy, conversational tone of good writing comes only on the eighth rewrite.”

This conversational tone is something that I’ve gotten much better at in the months since I started writing (rereading some of my earliest articles makes me cringe), and something I’m extremely proud of. And unless DennisGPT can somehow download the entirety of my brain (unlikely), it’ll never be able to write these original pieces like I do.

Jack Raines describes this best:

The problem with taking an AI-first approach to tasks is that it robs you of everything that you would have gained by doing the work yourself.

I don’t write to simply generate a 1,200 word output. I consider writing to be an extension of my curiosity, and the writing process itself is what turns a rough idea into a finished product. I begin with a vague idea based on some observation of the world, and I put that on paper. As I’m writing that idea, two distant synapses in my brain connect, bridging seemingly-unrelated ideas. Maybe an anecdote from my time playing football relates to risk-taking in financial markets. Maybe a conversation I had at the bar the previous weekend sends me in a new direction entirely. As I continue down this path, the story evolves until it hardly resembles the original idea. Writing is a metamorphosis that turns vague abstractions into novel ideas, but you have to go through the writing process to connect the various points along the way.

Source: “The Purpose of Things Isn't to Stop Doing Things.”

And that’s basically how all of my articles are written. lol

Long story short, I’ve never written any blog post with DennisGPT, and never will. Because at the end of the day, DennisGPT is no match for Dennis himself.

Best,

Dennis 1.0 (me) :)

P.S. I was telling my friend Alex about my DennisGPT creation, and he told me that he wished he had an AlexGPT equivalent. The funny thing is, I had recommended that he start writing when he studied abroad in Barcelona, but he “didn’t have the time” and wished that ChatGPT could write the blogs for him. That means that unfortunately, he doesn’t have any training data to create an AlexGPT with, since you can’t train a model of your writing style with writing that ChatGPT wrote itself. Lol 🤦

You’re understandably distraught, so you call your friend in a panic. You vent with them about how frustrated you are about the situation, and scream at yourself for your mistake. Your friend is wonderful, listens patiently to your ranting, and comforts you over the phone. You eventually feel better, and hang up.

You then get a notification, “Thank you for testing out our new AI phone calling system. We’d appreciate your feedback!” Your friend, in fact, wasn’t on the phone with you at all, but were rather replaced with an AI that sounded and spoke just like them.

You’re obviously horrified. But why? Why is some part of our human nature repulsed by this fictional scenario?

We’re living through a pretty crazy time right now — the dawn of the AI age. As dramatic as it sounds, it’s a huge deal, and future generations will undoubtedly look back at us and wonder how we lived without it. It’s on the level of the printing press or the Internet in terms of its potential impact, so the world is naturally in a state of extreme flux as everyone is figuring out what to do. For me at least, it feels like the Wild West — exciting, but scary.

It’s actually crazy! AI can write fully functional essays and, in theory, complete all of my college-upper-division coding projects (not that I’d know). And just this past week, OpenAI released 4o Image Generation, the best image creator to date. Here’s an example of two pictures that I uploaded to ChatGPT, which I then made in Cubism and Studio Ghibli versions:

This is amazing!

But while this model is a true testament to the ingenuity of human engineering, its art has a fundamental limit — the simple fact that humans didn’t make it. AI did. Humans value human effort, and value things that we ourselves have put blood, sweat, and tears into. It’s why Studio Ghibli founder Hayao Miyazaki said that “whoever creates this stuff has no idea what pain is whatsoever.” There’s a fundamental need for human suffering and effort to be in an artwork, and we feel empty and disdainful without it.

Harry Dry, a marketing professional, describes this phenomenon in an analysis of what makes YouTube videos successful:

2/ What do these four YouTube videos have in common?

Take a moment to think.

The answer: They all signal the effort in making them.

- $21,000 spent on a plane ticket

- A few hours making a pretty mind map

- More than a few hours watching football to find 16 freekicks

- One trip to the supermarket to buy two packets of crisps

Your conscious mind probably didn't notice. But your subconscious mind did. All four videos got twenty times more views than the channel average.

The technical term is “costly signaling theory”.

“The significance we attach to something is felt in direct proportion to the expense with which it is communicated.”

“But it's just two packets of crisps”, I hear you cry! Yes, that is all it takes. Here's the same thumbnail without one trip to the supermarket.

If you still don't understand, read this screenshot!

This is exactly why my professor would much rather have me submit a poor paper that I wrote than a world-class paper written by ChatGPT. The first one gets a C. But the other gets an F and is reported to the dean for cheating.

These days, it’s the fact that you went and did it that matters, not necessarily the final output. Obviously, the goal is to have your work be as good as possible, but not at the expense of sacrificing the fact that you wrote it yourself. For the same reason, I’ve saved every single handwritten note that my little brother or girlfriend has ever given to me — because I value and appreciate the effort that went into writing them.

And it’s why the hypothetical phone call at the beginning is so repulsive to us — we value knowing that there’s a human on the other side, whether it’s an artwork, a piece of writing, or a simple phone call. It doesn’t matter if they say much, because there’s simply a magical connection that happens between people, regardless of the time or distance involved. It’s what makes human interaction so beautiful, and what makes life so exciting.

Maybe one day when AI becomes sentient, we’ll appreciate their artwork and writing more. But as long as they remain machines at their most basic level, we’re left to appreciate our humanity. 🤖

Best,

Dennis :)

P.S. Brooke, the opening may or may not have been inspired by you! 📚

Besides taking a natural language processing course to finish up my data engineering minor and a Soviet cinema class just for fun, the last class I needed to graduate with my Business Economics degree was Eng Comp 131B — writing for business and social policy.

And it was quite enjoyable — the professor was very nice and chill, my classmates were all graduating seniors, too, and we laughed a ton together each week. It was a nice combination of being relatively fun and interesting, not that much work, and in the late morning, meaning I found myself looking forward to attending class.

Long story short, the class was designed to teach students the different writing “items” (I couldn’t think of a better word lol) that one might encounter in the process of entering or living in the business world.

In lecture, our professor shared how to create these different items and all the elements that go into it, followed by a student presentation regarding a chapter of the professional development book we read in tandem. In order, these different assignments were:

• Professional email and memo

• Executive summary

• Resume

• Cover letter

• Opinion editorial (I was EXTREMELY proud of mine!)

• Non-profit grant proposal

• Final group presentation on a real company’s PR crisis

These assignments were quite interesting, and I did enjoy the runway we had in scope and material we could cover — any relevant topic was fair game for our work, and it was cool to see the different subjects my peers and I chose for each assignment. Plus, the conversations and group discussions we had in that class were quite fun, and dare I say even therapeutic.

The final thing to note about my professor is that she’s very particular about her formatting and proper citations, which I particularly struggled with throughout the entire course (lol). If you’ve read any of my articles before, you know I throw standard formatting out the window pretty much immediately, so a big part of the course was me learning to suck it up and format the way she wanted. She also kept insisting that there was no way that AI could properly cite in APA, but I learned pretty quickly that Perplexity is, in fact, quite good at doing so.

But that’s beside the point.

And so similar to when I shared my application responses to get into my upper-division economics research class, I figured I’d share my thoughts on the class and all the work I created for it for the following reasons:

1. It’s a great addition to my writing archive/portfolio, and something for me to look back on and read fondly later.

2. I love writing, and want to share my work with more people in the hopes of sharing wisdom in an entertaining fashion.

Alright, that’s enough of me talking. Let’s do this thing!

I just had the unfathomably amazing realization I can directly embed file attachments into my Substack articles, so reading my work for the class literally couldn’t be any easier. WOW THIS IS AMAZING!

Here is my final portfolio of work, which includes my email, memo, executive summary, resume (check out my in-depth guide on resumes here), cover letter, opinion editorial, and non-profit grant proposal. I’m particularly proud of my op-ed, so much so that I’m actually going to paste it into this article just for your enjoyment!

Dennis Gavrilenko Eng Comp 131b Final Portfolio

1.19MB ∙ PDF file

Download

Download

My opinion editorial:

UCLA Must Lead the AI Education Revolution by Providing ChatGPT Edu to All Students

As a UCLA student juggling coursework, internship applications, and many extracurricular commitments, I’ve experienced firsthand the transformative power of AI tools like ChatGPT, Claude, and Perplexity. These tools save countless hours each week, helping me debug code, find sources for writing projects, tailor study materials, and provide detailed tutoring on specific topics.

And yet, while peers at institutions like the entire California State University (CSU) system, UPenn’s Wharton School of Business, and Arizona State University (ASU) receive free access to these AI tools, UCLA students pay out of pocket for them or risk falling behind. This reflects a missed opportunity for UCLA to continue its leadership in the AI space, and it’s time to take the next logical step: provide free ChatGPT Edu for all UCLA students to teach responsible AI use, maintain academic competitiveness, and prepare Bruins for an increasingly AI-driven workforce.

---

UCLA has a long history of using technology in its education—the Internet was created on our campus, CLICC rents laptops to students, and many software services are provided for all students, to name a few. Our free access to these services, which include the full Adobe Creative Suite, Microsoft 365, and Canva Pro, greatly enhances our educational experience and is crucial for our professional and creative pursuits.

Crucially, these initiatives reflect a clear philosophy of UCLA: when students have equal access to resources, innovation thrives. But currently, UCLA risks ending this equal access, as ChatGPT Plus is only available to those who can afford a $20/month subscription. These subscriptions operate on a Freemium model, where a free base model is available with a limited selection of models and queries per day. Plus subscriptions, for individuals, and Enterprise and Edu subscriptions, for organizations, allow unlimited queries, better models, file attachments, and Web Search for its users.

Fortunately, UCLA has already demonstrated its focus on AI integration—in 2024, UCLA hired the first Chief Data and AI Officer in the UC system, Chris Mattmann, formerly the Chief Technology and Innovation Officer at NASA JPL, to lead the effort to adopt AI on campus. That same year, UCLA bought a limited number of ChatGPT Enterprise accounts, and invited students and faculty to apply for accounts to explore AI applications in research and coursework.

While these programs are a great start, they remain limited in their scope—only a few selected students received Enterprise accounts, leaving most Bruins to buy their own subscriptions or remain dependent on free, more limited models. This lies in stark contrast with the CSU’s system-wide ChatGPT Edu rollout earlier this month, which provided 460,000 students with frontier AI tools for coding, data analysis, and personalized tutoring. The entire CSU system has nearly ten times the number of students as UCLA, showing us that a similar rollout at UCLA is very possible.

---

When adopting AI in education, there is a very natural concern: that AI tools not only encourage cheating, but also inhibit students’ learning. But banning these tools is not the answer—teaching students to use them correctly is.

UCLA’s role is to teach its students how to use AI ethically and responsibly to prepare them for an increasingly AI-focused job market. At Wharton, MBA students are provided free ChatGPT Edu access and take mandatory training modules on AI ethics and citation practices. Across the CSU, students have access to the AI Commons, which provides free AI training, tools, and certifications in prompt engineering and data privacy. UCLA should adopt this model too, requiring first-year students to take a class on AI ethics and responsible use.

These peer universities prove that campus-wide AI access is both feasible and transformative. At ASU, ChatGPT Edu assists in 400+ projects, from simulating medical patients for nursing students to automating grant proposal drafts. The CSU system provides the best example of ChatGPT Edu’s potential—they created an advisory board with dozens of leading tech companies, including Microsoft, Meta, Nvidia, and OpenAI, to identify AI skills needed in the California workforce to teach their students. At a university where nearly half of students are low-income and 30% are first-generation, this free AI access is especially powerful.

UCLA stands at a crossroads, and it’s time to embrace the future of AI use in education. Our students are now entering a world where AI skills are becoming more and more important, and it’s UCLA’s job to prepare them for that. As Deanna Needell, a UCLA mathematics professor and executive director of the UCLA Institute for Digital Research and Education, remarked, “AI has drastically changed the world and will continue to do so. As educators, we need to make sure our students have the best chance of helping this change be a positive one.”

It’s time to give our students equal access to AI tools, and let innovation thrive on campus.

Here are the presentation slides for my in-class discussion on our professional development book:

Dennis Gavrilenko Eng Comp 131b Presentation, The Ripple Effect

1.19MB ∙ PDF file

Download

Download

And last but certainly not least, here’s the final project I did with my two groupmates, Miles and Jane. The PR crisis we focused on PG&E’s involvement in the 2018 Camp and 2021 Dixie Fires, and I couldn’t be more proud of our work!

Eng Comp 131b Report Draft (jane, Dennis, Miles)

6.62MB ∙ PDF file

Download

Download

Eng Comp 131b Presentation (jane, Miles, Dennis)

8.27MB ∙ PDF file

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Download

That’s all for now folks. See y’all soon, and best of luck if you’re taking the class yourself!

Best,
Dennis :)

I had just eaten a wonderful pizza from Blaze Pizza, and was feeling up for a delicious dessert. Fortunately, there’s a UCLA Store location right nearby, so I pulled up with Josie and bought myself a Lindor chocolate.

An interesting thing then happened, which I documented in a LinkedIn post around that time:

Today, I was buying a Lindor chocolate at the UCLA bomb shelter when the cashier ringed me up for 99 cents.

Shocked, I asked if she had the right price, since they used to be 55 cents. She responded that they recently increased some prices, but that she’d double check just in case.

Turns out they were 55 cents, and she accidentally chose the wrong item. Result?

44 cents saved! The importance of self advocacy cannot be overstated.

— My own LinkedIn post, June 2024

It was a funny experience at the moment, and it made me chuckle that the LinkedIn post got ~10,000 impressions over a few weeks.

But this chucklesome moment and experience became relevant to me quite recently. And by quite recently, I mean about two days ago.

Let me explain.

Over the last few weeks, I’ve been tutoring a local high schooler in pre-calculus. I saw a listing for the position in UCLA’s student newspaper (I’ve written much more about this here), and have been tutoring the student whenever their mom reached out to me as needed.

The first time this happened, the rate was $40/hour. The second time, I was expecting the same rate, but was paid $45 for a job well done. Nice!

And this past week, they reached out again to schedule two more hours. I happily agreed, but since I’m graduating from UCLA in three weeks, I figured I’d ask for a higher rate since my time is much more limited and valuable to me. Worst-case scenario, they’d just pay me $45/hour again. Not too bad!

So I found myself sending this email:

Hello Naz,

[scheduling stuff]

Also, I was wondering if we could increase the tutoring rate to $50/hour. I'm graduating from UCLA in three weeks, so my time is much more limited and valuable to me. Thanks so much!

Best,
Dennis

And to my surprise, this response came just a few minutes later!

Hi Dennis, thank you for getting back to me. I will pay you $60.00. Tomorrow at 5 pm works. Also, are you available on Tuesday as well? She needs two sessions anytime after 3 PM would work. Matisse is very happy with you and I appreciate your services. Hope you had a great weekend!

WHOA! That was even better than I had expected, this is crazy!

And when the tutoring session had ended, I was paid $65 for a job well done again. I was honestly blown away, and felt great the rest of the day.

The lessons from these experiences are twofold:

1. If you consistently show up and do great work, others will notice and reciprocate. This is a great way to build strong relationships, and keep yourself proud of your work.

2. The importance of self-advocacy cannot be overstated. This was true for the Lindor chocolate, and for the tutoring. They say that closed mouths don’t get fed, and that’s so true in many aspects of life!

That’s all for me now, folks. Until next time 💪

Best,
Dennis :)

Dennis’s Picks:

• I just finished reading the book Land of Big Numbers, and it was one of my favorites in a long time. It’s a collection of beautifully written short stories about Chinese culture and experiences, and I finished it in one amazing afternoon.

• I really enjoyed this article from Nat Eliason, who wrote about the importance of exploration and self-discovery. My favorite quote from the piece: “You can explore and try new things with a certain lightness. It doesn’t need to work out right away, or in the way you want it to, and you don’t need to justify the exploration at the start. By exploring you are discovering the ways in which the exploration can justify itself. So try things, experiment, explore. You never know how the various threads will tie together later.”

What struck me the most about this incident was not that the tiles were intentionally placed — it’s easy to imagine such thoughtful things on such a great campus — but that in all my time here, I’ve never noticed it.

I must’ve gone to that bathroom in Ackerman at least 100 times (it’s the closest one to the tour guide office, where I work) in my 4 years on campus, and I literally had never even realized that those silly blue tiles made something special.

I found myself pondering this incident all day, and specifically was wondering how this could have happened. How, despite me being at UCLA for all this time, had I never noticed the little beauty of the tiles?

Modern humans have a very interesting predicament — we no longer have to be bored. Before modern technology, we had to sit in our boredom, or at least talk to the person next to us.

Now, we can just whip out our phones to distract ourselves whenever we please.

Have an extra minute? Take out your phone to check your texts.

Friend running a bit late? Go on TikTok.

Walking to class? Listen to music or a podcast.

And while each individual instance of this happening is not a problem per se (and well-earned leisure time is, in fact, a great thing), it’s not good when it becomes our default way of dealing with boredom.

And this aversion to boredom makes perfect sense. Being bored is, well… boring.

But the unfortunate thing is, being bored is quite the good thing. When bored, your mind has to find ways to entertain itself, and you end up with some interesting thoughts as a result. When I sit or walk with nothing to do, I find myself thinking about new Interosity posts, my upcoming travels, or even how I’m going to go drink a cup of coffee soon (yum).

Crucially, this boredom is where we can allow our thoughts to marinate and become something truly great. It’s just like a soup that’s left to simmer — sitting with your thoughts while bored is when you often cook up something truly special (like that line I just wrote).

Reflecting on what happened with the tiles, I realized that I never noticed them before because I was always distracted by something else — either listening to music, calling someone, or rushing to meet my tour group on time. I never took the energy to be there slowly and intentionally, and missed this cool thing in front of me as a result. Now, I’ve told all the tour guides about this tiles thing, and a few of them even thought that it was really cool, too.

And so for the last few days, I decided to try out this boredom thing and see what happens. I’ve been walking to class and around campus without listening to music, and what an epic result! I’ve found a profound increase in the amount of spontaneous ideas I’ve had, and have felt so much more creative as a result.

It’s actually wild. Just this week, I came up with 5 new Interosity article ideas, and I’m super duper excited to share them with y’all soon.

And it showed me a really important insight — the reason that I get so many good ideas walking around campus without music, or even while taking a shower, is because it’s often one of the few times a day when I’m not distracted and let my mind wander.

The solution isn’t to take more walks, or even to take more showers, but rather to spend more time letting our minds be bored and free.

Best,
Dennis :)

My favorite part about my many excursions with Finlay is the many conversations we have while exploring, and yesterday was no different. We chatted and discussed many a thing on our way up to the top of the mountain, and it was a tremendous time through and through.

And it was during one of these chats that I pinpointed a very interesting phenomenon I’d been experiencing recently — that of the secretary problem — and one I wanted to share with you here.

The secretary problem is a famous math problem that deals with optimization and decision-making. I first heard about it from my dad, and it goes something like this:

Imagine an administrator who wants to hire the best secretary out of n rankable applicants for a position. The applicants are interviewed one by one in random order. A decision about each particular applicant is to be made immediately after the interview. Once rejected, an applicant cannot be recalled. During the interview, the administrator gains information sufficient to rank the applicant among all applicants interviewed so far, but is unaware of the quality of yet unseen applicants. (so the interviewer can tell how strong an applicant is based only on the strength of previous applicants they interviewed)

The question is about the optimal strategy (stopping rule) to maximize the probability of selecting the best applicant. If the decision can be deferred to the end, this can be solved by the simple maximum selection algorithm of tracking the running maximum (and who achieved it), and selecting the overall maximum at the end. The difficulty is that the decision must be made immediately.

Secretary problem, Wikipedia

Long story short, you need to pick the best applicant out of a large group, but the catch is that you don’t know how strong everyone in that group is.

Ultimately, the secretary problem boils down to the predicament that if you pick an applicant too early, you miss out on all the other, potentially better, applicants later on. But if you wait too long, you may have incorrectly rejected all the best applicants earlier and can now never go back.

Fortunately for us, there is a solution! The secretary problem is a solved one:

The optimal stopping rule prescribes always rejecting the first ∼n/e (where n is the number of applicants and e is Euler’s number, roughly 2.718) applicants that are interviewed, and then stopping at the first applicant who is better than every applicant interviewed so far (or continuing to the last applicant if this never occurs)

Secretary problem, Wikipedia

For the layperson, that means that you should spend roughly the first 1/3 of your time exploring and establishing a baseline, and then pick the first thing that is better than that baseline you’ve set. When you do this, you optimize your chances of finding the best option, and always find a great one regardless.

What’s so good about the secretary problem is that it’s not just a math problem, but a great strategy for finding the best things to do with our time. It tells us to spend some time exploring and seeing what’s out there, before eventually committing to something that we enjoy or value based on the baseline we’ve set for ourselves.

This is very useful — here are a few college student examples:

• Explore a bunch of different clubs before committing more time to one or two (and maybe even serving in an officer position)

• Go on a bunch of different dates to find out what you value in a partner, then commit

• Spend a lot of time at different social events and parties to meet new people, and then mostly hang out with your close friends once you find them

• Try out different restaurants around town, then mostly go to the ones you like most

Of course, we always want to keep exploring somewhat (who knows what great things you can find!), but once we find what we enjoy, we should spend most of our time on those things.

And this is exactly what I realized was happening to me while hiking with Finlay: I had already set my baseline of friends, and would much rather spend my last few weeks at UCLA with people I knew well than go out and meet more people. Since I’m graduating (so!) soon, I prioritize spending time with the close friends I already have rather than making new ones.

The subconscious calculation is that in my (very) limited time left, I’m much better off with those I already know than investing in new friendships. On the other hand, when I first started at UCLA and didn’t know anyone, there was much more of a focus on going out and meeting people, since there was no baseline there at all. Similarly, once I graduate and go on my month-long trip around the British Isles, I’ll be doing a lot more exploration rather than optimizing since I’ll be traveling and not knowing anyone.

Remember to keep exploring, and enjoy the things that you find. Spend ~1/3 of your time on exploring and ~2/3 on optimizing and deepening — let the secretary problem strike again!

Best,
Dennis :)

Dennis’s Picks:

• I read this wonderful article yesterday, 40 Thoughts on Turning 40, full of great stories and life advice. Highly recommend!

• On my hike yesterday with Finlay, I saw this funny sign warning passers-by of falling pinecones. lol

Lebron and I DMed back and forth on LinkedIn for a bit, and had a lovely call yesterday. We discussed my many LinkedIn posts, my consulting recruiting experiences, and his undergrad journey at Rice.

In particular, he was wondering whether he should stay in the few business classes he enrolled in this quarter, or drop them and do something else. He’d already finished up his major, and was looking to fill up his time before he graduates this fall semester.

I asked him why he’s taking those business classes, and it turns out, he figured he might as well get a third major in business because he wasn’t sure what to do with his extra time. Plus, “it’d look good on his resume”.

This made me quite concerned, and we proceeded to chat for another 15 minutes about this particular predicament of his. I was quite worried that he was filling his time for no reason, and that he’d regret not doing something more meaningful during his last year of undergrad.

I ended up recommending that he explore all the different buildings at Rice instead, and we had a super exciting and fun chat about my similar exploration at UCLA. (much more on this in a future post, don’t worry!)

And so here we are now, after a day of pondering Lebron’s situation. I wanted to explore my idea of following default paths here, and shared some thoughts I had about it recently.

Let’s do this darn thing!

Throughout most of my schooling experience, I had one main goal: go to college. And ideally, go to a good one.

And while this process of getting into a top college was quite hard, at the end of the day, it was quite simple. I needed to get good grades, play some sports, volunteer, become an Eagle Scout, write some sappy essays, and I was all set.

These steps were very hard to accomplish, but the path itself was very clear.

And somewhere along the way, I realized that I actually didn’t have any clue about what I wanted to do with my life. I took a few law classes in high school and really enjoyed my economics classes, so I decided to apply for business and economics programs at a few different universities. I told myself that “I’ll figure it out in college”, and called it a day.

And after many conversations with many different people, I’ve realized that I’m definitely not alone in this thinking.

When we don’t understand what we actually want to do in our lives, we settle for the default societal path. We figure we’ll decide what to do later, and hope for the best. So we do all of these things we knew we should do: get the good grades, play the sports, do the volunteering, write the essays, etc.

And then something crazy happens — we get into these great schools we’ve worked so hard for, and we suddenly have no idea what to do. All of the clear structure we’ve had in our lives (get into a good college) is gone, and we have to figure out ourselves what to do.

From personal experience and observation, I’ve found that when this happens, a few curious things occur.

First, you have an existential crisis, and you kinda wonder how in the world you’ll move forward. This is the classic fresh-in-college experience, and most of the people I’ve spoken to about this have felt this crisis feeling many times.

And crucially after that, two main things can happen:

1. You take the time to figure out what you want to do in your life. You explore different things, try out the different options, and start to narrow down on what you actually find fulfilling. This sounds easy, but in reality is actually quite hard and uncomfortable.

2. You choose another default path to go down to delay this self-exploration. You still don’t know what you want to do with your life, but you again convince yourself that “you’ll figure it out later”.

And it’s crazy how many times I’ve seen this latter option play out so many times at UCLA. In my particular niche at UCLA (the business world), this ends up manifesting itself by a ton of students pursuing investment banking and consulting without knowing what these fields actually are and why they actually want to pursue them. (this is especially true of some pre-med and pre-law peers I’ve met)

The logic used to justify these careers is that they give you a lot of optionality after working them, they pay well, and they’re very prestigious. The word “exit opportunities” is thrown around, and students convince themselves that once they’re in those roles, they’ll figure out what they want to do with their lives.

This sounds exactly like college admissions. But instead of following the steps to get into a great college, students are now following the steps to get into a great career. And this is pretty much exactly what happened to me.

I’m often asked why I joined The Bruin Group (TBG), expecting some grand response about how it aligned with my professional goals and all that. The reality is that all of my peers were applying to these business clubs, I didn’t want to be left behind, and so I applied to all of them, too.

TBG was the only club I got into, and it just so happened to be a consulting club.

And when everyone in TBG started recruiting for consulting internships and talking about how great they were, it was only natural that I did the same thing, too. It became very hard to rationalize doing something different than everyone around me. If everyone was recruiting for consulting and I didn’t too, wasn’t I going to be left behind?

I ended up getting a top offer, and I felt super duper proud of myself. But curiously, this feeling of pride only lasted a few days. After that, I found myself simply feeling relieved that I was done with internship recruiting.

At the end of the day, there’s nothing wrong with the default path, or clear career paths in general. If they didn’t exist, society would struggle as its young people had to each figure out, from complete scratch, what to do with themselves.

The important thing is to intentionally choose where you’re going. From the people I’ve met and talked to over the years, the happiest and most fulfilled ones were those who consciously chose to do what they were doing. They felt that they decided their own future.

Those who slid into their lives, not really thinking intentionally about what they wanted to do, ended up seeming quite unhappy. They seemed to be discontent with their careers and ultimately, their lives. I’ve been there before myself, and felt this lack of satisfaction in life. The scariest thing about being there was not that I disliked where I was, but I began to feel indifferent about it. I began to feel, at times, like a spectator in my own life. And let me tell you, that’s not a good place to be.

I encourage you to really consider what you’re doing with your time. We only get to live once, and it’s crucial that we make the most of it. I’ve spent the last few months doing a lot more exploration, and I’ve grown and learned so much during this time. And I’m more excited for the future than ever before.

Are you intentionally doing what you’re doing now, or are you just following what those around you are doing? Are you blindly walking through your own life, not knowing what you’re doing? Are you spending all of your effort climbing up a mountain, without even stopping to see if that’s where you want to go?

Are you an excellent sheep?

Just know that it’s never too late to open your eyes and make your own path and that the sooner you start, the better. You don’t want to be the person who looks back on their life with regret, trust me.

Good luck!

Best,
Dennis :)

Dennis’s Picks:

• I was exploring Bunche Hall with my friend Ariv last week, and found this hilarious comic on one of the professor’s office door:

Student: Can I borrow a pencil?

Teacher: I don't know. Can you?

Student: Yes. I might add that colloquial irregularities occur frequently in any language. Since you and the rest of our present company understood perfectly my intended meaning, being particular about the distinctions between "can" and "may" is purely pedantic and arguably pretentious.

Teacher: True, colloquialism and the judicious interpretation of context help us communicate with nuance, range, and efficiency. And yet, as your teacher, my job is to teach you to think about language with care and rigor. Understanding the shades of difference between one word and another, and to think carefully about what you want to say, will give you greater power and versatility in your speech and writing.

Student: Point taken. May I have a pencil?

Teacher: No, you may not. We do not have pencils since the state cut funding for education again this year.

And that goal was to get into a good college.

At the end of the day, while the goal may have been hard to achieve, the steps to do so were quite clear: get high grades, play sports, join clubs, volunteer, start a charity, and write some banger admissions essays.

And for many students (myself definitely included), we figured that we’d figure out what to do with our lives once we got to college. “I’m not too sure what I want to do with my life right now”, we tell ourselves. “But once I get to college, I’ll find out.”

This leads us to work very hard in high school to get into an amazing university (like UCLA), but as soon as we arrive there, we find ourselves to be completely lost. All of a sudden, the goal we’ve had our entire lives—to get into a great college—is gone, leaving a feeling of profound emptiness and existential dread in its place.

I felt this feeling like crazy during the first quarter of my freshman year, and I had some crazy mental health issues at the time as a result. But fortunately (and something I’m extremely grateful for to this day), my family and my roommates Gilbert and Matthew were there for me during the entire time, and made sure that I came out on the other side.

It was about a month into my first quarter at UCLA that I was truly struggling—I was completely burnt out from being in NROTC (the Naval Reserve Officer Training Corps, which I was in at the time), struggling in all of my classes (I went from online covid high school to in-person UCLA quarter system classes), and to top it all off, was struggling through a long-distance relationship with my high school girlfriend who went to a different school.

In the midst of all of this, my 18th birthday happened, and my roommate Matthew wrote me one of the kindest notes I’ve ever received.

I wanted to share this with you, my dear reader, as it has helped me through many dark times over the years. I truly hope it can do the same for you.

Best,
Dennis :)

September 30, 2021

Dennis,

Happy birthday! I wanted to write you this using my handwriting, but I'm afraid my writings are not legible. So bear with my typing. I want to let you know that you are the perfect roommate to me. Your cheerfulness and extraversion perfectly balances out my gloom and introversion. You also have an awesome capacity for bringing people together. Within a week, we already have a cohort of six with you, Simon, Sam, Q, Gilbert, and me. This is something that l've rarely experienced in my life, and I'm glad you made that possible.

But recently, I noticed you are having some life troubles that's been eating away at you: uncertainty about the future, stress from work, homesickness, relationship troubles, feeling left behind by your peers, and constant self-doubt. Many of these have troubled me greatly as well. Though, I cannot speak on them because I do not have the wisdom to advise you. So, beyond the physical gifts [a very interesting novel on economics], I want to impart some words from someone wiser than me. They may not solve your issues at hand, but they—for me at least—can provide the strength to suffer through this difficult time and restore your will:

“… if at this moment you and I, and all our companions, were not aboard these ships, in the midst of the sea, in this unknown solitude, in a condition as uncertain and risky as you please; what other situation in life would we find ourselves in? What would we be doing? How would we be spending these days? Do you think, more happily? Or would we not rather be in some greater trouble or anxiety, or else full of boredom? ...Even if we gain no other benefit from this voyage, it seems to me that it is most profitable to us, in that for a while it keeps us free of boredom, renders life dear to us, and makes us value many things that we would not otherwise take into account." (Giacomo Leopardi)

This is the situation that I like to imagine you and I are in—on a voyage, sailing far, facing violent storms and colossal waves. But these tribulations are never grounds to remain ashore because in our troubles and anxieties, we encounter the gravitas and exhilaration of life. However, that still doesn't rob our sufferings of their reality; if you need to cry, shout, or talk, do so freely. It's only human.

Ultimately, I know you have within you the strength to see this journey through. If you ever stumble (which everyone does), I'll be there to support you. And if I do, I hope you could do the same for me. I'm glad to have you aboard this enterprise. We will accomplish great things.

Best wishes to you,

Matthew

And so when the opportunity came to apply to its Board of Directors, I was intrigued. I had previously lived in a co-op in Seattle during my summer internship, and was curious to see how the much larger one at UCLA worked. How does it govern? What does its Board actually do?

So I found myself in the quite unexpected predicament of considering whether or not I should apply to the Board.

On the one hand, it seemed like a great way to get more involved in the co-op, make some extra money, and acquire another funny story to tell: “Back in my day, I was a Board Director at the UCLA Co-op, lol”

Yet being on the Board would mean committing some of my precious, last-quarter-at-UCLA-before-I-graduate time and mental energy to this endeavor. Was that trade-off worth it?

Naturally, I consulted my roommate Finlay on this decision, a common occurrence. We chatted about it for a bit, and I found myself considering what I’d regret more: Applying for a Board position, getting it, and locking in some of my precious senior year time? Or not applying at all and wishing that I had?

When I looked at it like that way, it was clear to me that I should apply. I did, and ended up getting the role.

Hooray!

This experience reinforced an idea I’d been thinking about for quite some time: Regret is a tremendously interesting thing, and often, our regrets are misinformed.

Let me explain.

Regret involves looking back at our past selves, and wishing that the course of action we took was different. Here are a few personal examples:

• “Damn, I really should’ve asked that girl for her number”

• “I should’ve called my grandma more before she passed”

• “Eating that prickly pear cactus at Morro Bay was a terrible idea, why didn’t I see those tiny spikes on it” —> I subsequently spent the next 4 hours picking these tiny spikes out of my fingers, lips, and tongue 🙃

Interestingly, we regret inaction more than action, meaning that we regret not doing something more than doing something. Failed attempts are usually considered learning experiences (so-called “taking an L”), whereas failing to attempt causes much regret after the fact. In these cases, you realize that you undersold yourself, that somehow your mind confused lack of effort for inability.

But we are often too hard on our past ourselves. We judge retroactively with the information we presently have, and hindsight is always 20/20.

With the benefit of this hindsight, of course, there are likely many things that you’d change if you could go back, but that’s usually because you now have some information that you didn’t have then. This new information, subsequently, makes the past decision clearly a wrong one.

At the end of the day, this is unfair to your past self. If you make the best decision you can at the time with the information you have, you can’t regret that action — you did the best you could. Plus, if you’re happy with where you are in life now, you can’t regret any past decisions.

All of them, the good and the bad, led right to where you are now.

This naturally begs the question, how can you make the best decisions? For that, let’s look at Jeff Bezos.

Before he founded Amazon, Bezos was working at a top hedge fund in New York City. At the time, he was curious about this new thing called the Internet, and was considering leaving his cushy job in New York to move across the country selling books online.

He wasn’t sure what to do, so he imagined that he was 80 years old and looking back on his life. What would he regret more? Leaving his nice job to take a big risk, or never making that risk at all?

For Bezos, it was clear to him that he’d much more regret never trying, so he packed up his things, drove to Seattle, and the rest is history. He remarks, “If you can project yourself to age 80 and think, ‘What will I think at that time’, it helps you get away from the daily pieces of confusion.”

Thus, the “regret minimization framework” is born! To help make the best decisions, look at each option and think about how much you’d regret not doing it in the future. Pick the one that minimizes the regret, and you’re all set.

This is surprisingly easy, and helps makes these difficult questions seem much simpler.

When I looked at applying for the Co-op’s Board of Directors, it was clear to me that I’d much more regret not doing so. When I was thinking about whether or to study abroad, it was clear that I’d much more regret not going to Paris than missing a quarter of social life at UCLA. There are so many more examples, and this strategy of minimizing regrets has served me tremendously well.

So what’s the point of all this?

First, to make the best decisions, think about to your future self and look back on what you’d regret more. Then, pick the option that minimizes your regrets the most.

Remember that regrets from inaction are much stronger than those from action. Doing something risky and failing is much better than never taking the risk and wishing you had afterward. The risk of failure is often much worse than it seems. If you sit down and really think about how bad the outcome of a decision can be, you realize that it’s not actually that catastrophic.

Yet we often sell ourselves short. As Judy-Maie Zhu writes,

The majority of people do not follow up after a failed interview, the majority of people can not handle beyond a few failures, a few cold shoulders. And the majority of people are willing to accept the world as it is presented to us; neatly wrapped with a big bow and unable to be tampered with. “That’s just how the world works”, we begin to say as we sound more and more like the adults we so wondered about as children. The moment you start poking and prodding, however, the bow unravels and the pristine wrapping paper is realized to have a gaps and flaws and room for you to poke your finger in. What you may find inside said box, Schrödinger may argue, is a world of infinite possibilities — only given to those who have the courage to poke at things.

“Cold emails, cold calls… cold shoulder?”

So keep poking, and go take those risks. You have some regrets to minimize!

Best,
Dennis :)

P.S. After all this, I’ve realized that I don’t regret eating that cactus in Morro Bay. Now I know not to do that again!

Dennis’s Picks:

• The article Mechanisms too simple for humans to design. The idea is that humans have an extremely hard time replicating nature not because it’s so complex, but because it’s so simple. A tremendously interesting read!

• This piece about the pleasure of the journey of creation. A tremendously helpful reminder, especially when I feel like banging my head against the wall when my writing doesn’t seem to be coming together.

• Happy 1-year anniversary, Brooke! Going on that backpacking trip to Santa Barbara is something I’ll never regret ❤️

The Daily Bruin is UCLA’s student newspaper, and prints three editions each week to distribute at different locations around campus. The stories are often interesting, and feature updates about campus events, reporting on sports games, and diverse opinion pieces from students on campus.

But the greatest part of this newspaper is its games section — specifically, the sudoku. These tri-weekly puzzles are a vital part of my student experience, and I have religiously solved each and every one of them in the hundreds of newspapers printed during my four years at UCLA.

It was during one of these sudoku-solving sessions that I noticed an interesting thing. An advertisement was on the page, right next to my beloved game:

Looking for a UCLA student to tutor my granddaughter in math and English. Prior experienced preferred but not necessary, flexible on the scheduling. Please contact [contact info] if interested.

(Or something along those lines. I never did save that ad, only the solved sudoku.)

But the important thing is that I was a UCLA student, and figured that I’d happily tutor this person’s granddaughter for some extra money. I called the family, set up a time for the first tutoring session, and was all ready to go. Then came the ultimate question: “How much do you charge?”

Surprisingly, I hadn’t expected this at all, figuring the family would offer a flat rate in a take-it-or-leave-it situation. I thought for a bit, and decided to be ambitious. After all, we could always negotiate down, right?

“$50/hour”, I responded, fully expecting a scoff and a harsh counteroffer.

“Would you be able to do $45?”, came the quick reply.

There was only one answer to that question, and the answer was yes. I started tutoring the granddaughter weekly for the rest of the quarter, with great success (she ended up getting the highest grade in her math class).

And then a month later, another opportunity fell out of the sky: in a UCLA parent’s group chat, someone was looking for a tutor for their child. My mom told me about this, and I quickly set up a call with them, too.

This time, when the conversation reached payment, I had a benchmark rate and figured there was no reason not to reach for an even higher one. I told them I was tutoring another student for $60/hour, which was eventually negotiated down to $55.

Holy shit. I realized I was onto something.

Quickly, I realized that tutoring was not the only place to make this kind of money. In an Econ Department newsletter earlier this month, I read the following beautiful words:

“One of our alumni (PhD in Economics) is looking to hire a student to do bibliographic research on a retired UCLA professor. The student should have good writing skills, knowledge of Google Scholar, JSTOR, and other bibliographic research techniques. Please send a transcript, resume, and a paragraph or two explaining your qualifications to [email]. This is a one-to-two-week position and will be paid.”

— Econ Department newsletter, January 17th, 2025

Opportunities like that don’t often fall from the sky, so I immediately sent an email (with this blog as a writing sample!) to schedule a meeting. It went well, and the ultimate question came again. I figured that bibliographical work wouldn’t be as intensive as tutoring (and much easier to learn), so I initially asked for $30-$40/hour.

Right away, he agreed to $30/hour for the first week, and $40/hour for the second based on performance. Now that’s what I’m talking about!

And so I found myself in quite the crazy situation: in just a few months, I had independently found three opportunities for “intellectual service work” (what I call anything where you trade your time for mental brainpower) that easily charged $40+/hour. And I’m not alone: some friends regularly tutor high schoolers for $60+/hour, finding their own clients online through personal networks and family connections.

This begs the question: How is this possible? And most importantly, why are these students (including myself) able to charge so much?

The answer, it turns out, is quite simple: UCLA students have a combination of unique traits, and folks are willing to pay a lot of money to access it. And over the course of my four years at UCLA, I’ve learned what they are:

1. UCLA students are generally smart, with a broad understanding of many things.

2. UCLA students are usually very good at something. Very likely, that’s how they got into such a good school in the first place.

3. And most importantly, UCLA students can learn new things very quickly.

These traits are carefully filtered for by the admissions committee for the school, and combined with the near-infinite amount of academic and professional resources, makes UCLA a truly special place.

This explains why companies spend time recruiting UCLA students, since the admissions committee already filtered only great candidates into the school. And it’s exactly why students can charge so much for their time: folks understand that UCLA students know a lot of things, and can apply it well, too.

(This is exactly what makes UCLA such a special place for me. My favorite part is not the classroom education, but the vast network of brilliant peers and professors you instantly get access to.)

At this point, you’re probably thinking something like this:

“So Dennis, how do I get these jobs? What are the main takeaways?”

Well, there are a few:

1. To charge high rates for intellectual service work, you obviously need to find some in the first place. The best way to do this is to broaden the number of avenues in which you can learn about this work — join online forums for your school, department newsletter, start a professional blog to expand your network 😁, and actually read the school newspaper ads. There’s a ton of great jobs there!

2. Don’t sell yourself short. It’s far better to set your hourly rate higher than the final amount, and then negotiate down. Start off too low, and you have no wiggle room at all.

3. When negotiating your hourly rate, remember that the initial price you propose greatly affects the final rate. The two things to remember here are 1) Use a range to convey your rate ($40-$50 an hour, for example) to anchor the other party to the lower end of that range, and 2) Expect the other party to negotiate down your initial suggestion. In the case of my tutoring, the final rate was $5 lower than my initial offer. The optimal way to do this negotiation is discussed in the book Never Split the Difference, which I recommend highly.

4. Remember that time is your most precious asset. Trade your time and mental power wisely — you won’t get it back!

And lastly, remember that great opportunities come from strange places, and often fall from the sky. Countless people must’ve read the same tutoring ad in The Daily Bruin and seen the same job listing in the Econ Department newsletter, yet it was I who jumped on the opportunity first and made the most of it.

Or maybe the ultimate lesson is to do more sudokus. After all, who knows what good can come from it?

Best,
Dennis :)

Dennis’s Picks:

• This absolutely amazing piece about the dangers of short-form content and dopamine addiction. Gurwinder’s writing is some of the finest I’ve ever read.

• The following quote: “The reason people get good ideas in the shower is because it’s the only time during the day when most people are away from screens long enough to think. The lesson is not to take more showers, but to take more time to think clearly.” The times when I don’t have my phone are my most productive, and every digital detox I’ve ever had has been truly amazing. Those notifications can wait, trust me!

• This hidden secret that my friend Ariv and I found while exploring Murphy Hall. If you’re at UCLA, go find it on the first floor!

• For many more tips on negotiation, read Never Split the Difference by Chris Voss. Or, read the highlights here.

I’m so excited to share the work of Cole Hume, a recent graduate of UCLA, first-year Associate at Boston Consulting Group (BCG), and an all-around wonderful dude.

When I first met Cole last year, we were eating tacos together on a bright, sunny UCLA day. He had just come back from a semester-long study abroad program in Yokohama, Japan, and was finishing up his last two quarters of college. I had reached out to him because he had previously interned at BCG, and as someone working there that upcoming summer, I had a ton of questions to ask.

What struck me the most about Cole was his curiosity. He studied Computer Science and Philosophy, a combination that taught him to think both critically and analytically. I was quite blown away by how well-spoken he was, his confidence, and the wisdom he shared with me then. I’m honored to call him a friend, and can’t wait to see what he does these next few years.

Below, Cole shares his experiences with his first “mini retirement”, an 8-month break between his graduation from UCLA last June to starting his full-time job at BCG this month.

This time has been a creative explosion for Cole — he’s started his own newsletter (if you like Interosity, you’ll love Cole’s newsletter, please subscribe), learned audio engineering, written several original songs, traveled to Japan to visit his study abroad family, and earned his real estate license.

And without further ado, here’s Cole!

Retirement at 23

In his book The 4-hour Workweek, Tim Ferriss begs people to test retirement before they are old and beautiful, and insists you’ll learn some life-changing lessons by doing so.

You’ll get a better feel for whether decades of boring work or office drama are really worth it, just for the ability to sit on the sand with a White Claw every day at 65.

And, he bets that you’ll discover three things:

1. Retirement is boring, especially if you are a doer.

2. Exchanging youthful energy and joy for a safe retirement is a bad deal.

3. Real wealth is control of one’s time and mobility, money is merely an instrument.

Tim is extreme by most standards. Here is what led him to his first retirement.

Seeing his Princeton peers normalize 100-hour/week investment banking jobs — trading vitality and meaning for Nobu dinners and chronic stress — contributed to suicidal ideations. He went to pick up a book on suicide at his local library, his final step of research, but was forced to reconsider his deadly plan due to a phone call from his mom.

Tim had applied to check out the book under his family’s home address. So his mother called him with confusion when she received a note from the library saying “the suicide book is ready for pick up.” This conversation with his mom stopped him in his tracks.

After graduation, Tim was rejected by consulting and tech firms but eventually landed a sales gig. He optimized his role to do it in half the time and get off early.

Corporate higher-ups did not value this. They valued perceived effort more than his actual output.

He wanted freedom and fulfillment, which his 9-5 did not deliver, so he sprinted towards the fences to start his entrepreneurial journey. To help motivate his new path, he developed an anti-vision — a vision of the future that meant he truly failed. And what did it look like?

A fat man driving a red Ferrari.

This symbolized trading health and meaning for status and hedonism.

But once he started “entrepreneuring,” the devil wore a new dress.

A dress he had sewn.

Fulfillment and freedom did not come as he worked 90+ hours/week to try to make his startup supplement business generate continuous income. He realized his methods were unsustainable so, despite fearing the crumbling of his business, he took a break.

He retired — for a bit.

When he returned, he realized his internet supplement business thrived without him. The monthly revenue barely diminished. The fires he was putting out daily would have burnt out themselves and never needed a power hose to spray them for 14 hours a day.

Okay, this is my blog, not Tim’s. So, I’ll stop engaging you by regurgitating his story and ideas. But there are some lessons from his story that weave into my last 10 months. In this article, I share the three main lessons learned from my “mini-retirement #1.”

I might be the most tenured Incoming BCG Associate on Earth.

For 18 months, that read as my LinkedIn headline because BCG gave me an option for when I wanted to return.

As a “recovering Type A”, I had to fight my inclination to choose the earliest possible return date. Starting early would keep me ahead, right? That would keep me on the path of prestige and building career capital?

And the most difficult question: Am I seriously going to forego $60,000 to have free time from June to December?

But I realized that would be living in fear. It would have been me saying that I am confident I cannot fill the time with as instrumentally valuable and meaningful moments as that which a firm assigns.

So, I took my first mini-retirement. 10 months with total control of my calendar from when I graduated in March.

And holy shit. It was one of the best decisions I have ever made.

What follows are three of the most important lessons from my last 10 months. They might not resonate at all with you and that is okay. We might be wired a bit differently. But I’m sure a few of you would have had a very similar experience to me.

1. You are born a million men, and you die as one.

College can be a self-limiting community. Frequently, your major becomes your core identity. There is little expectation or normalization of the “renaissance man” — the person who dabbles in art, engineering, athletics, and more.

Specialization is often praised. The seemingly smartest kids in a major jockey for a prestigious job, making you feel stupid to not also pursue that job. You must choose an identity quickly or you will not make sense to others. And it feels good to make sense to others.

Quickly, you form communities surrounding the identities you decided when you were 18 years old. These communities become your continuous feedback loop as to who you are, and leaving those communities would be damn disorienting.

But leaving them is extremely empowering if you are comfortable greeting a world that does not have any idea of who the hell you are.

Living in Yokohama, Japan for 5 months during my study abroad was my first experience of radically new environments. And it shifted me. It shined a light on what was truly important and what was important because others thought so. I didn’t focus on just classes — my time was filled with poetry, music, language learning, exercise, and meditation.

This most recent mini-retirement was my second experience of creating time and space away from communities. But this time, I had no exams or external objectives. I largely spent time away from my familiar communities by living in my childhood home in San Diego.

This time, I not only figured out the fiction that I had believed because others believed them. I figured out the fictions that used to be true because I had believed them — my self-limiting or self-defining beliefs.

I think people with ambition and a desire to grow and introspect should try to step away from their communities or typical daily races.

This makes it much easier to learn that:

Nearly everything can be learned or done given enough time, energy, and a little intelligence. You are an artist, technician, socialite, creative, athlete, and entrepreneur. But until you have time and space, you may never realize these identities and never know which ones are the most crucial to the person you want to be on your deathbed.

I have wonderfully supportive friends, but if I had to consistently see them as I was creating content, outputting original music, networking like a hardo, getting my real estate license, and so many other silly things, I would feel friction from being unconventional.

Many of these unconventional things have informed my habits and identities and I have never felt more true to myself. You are born a million humans, and yes, you will die as one, but try to die as one who is satisfyingly, honestly you by creating time and space for yourself to learn who the hell you are.

2. I can’t sit on the beach without wishing I had a surfboard.

I am not a surfer. At least I do not look like one when I attempt to conquer a rising wave that instead feeds me to the ocean floor.

Yet, I would not enjoy resting on the sand all day as a beautiful ocean taunts me with a challenge. I will never enjoy a white claw on a beach for back-to-back-to-back days. It is just not in my nature. And that is okay.

In many crowds, you will be judged for continuing to try and do things. Untamed ambition is looked down upon. But, frequently those crowds have not found the arenas where actualized ambition is what it means to feel alive.

I believe rest is often sought by those who haven’t seen effort rewarded—whether in education, relationships, or personal growth. Rest has its time and place, but if your work leaves you begging for it, take note. It may signal that your effort isn’t being effectively rewarded.

When I created time and space, I naturally felt the urge to create value. This reassured me that I don’t need to fear failure if I leave a job; I will always strive to build something valuable for myself or the world.

My mini-retirement taught me that if given time and space, I will give a satisfying effort. An effort that delivers much more satisfaction than a simple paycheck could.

Thankfully, I can’t sit on the beach without wishing I had a surfboard.

3. Community is the most important ingredient in my recipe for happiness.

Yes, communities can limit you. They can trap you in a role you didn’t choose, but they’re also what gives your life so much more meaning. Growth is something you largely do alone, but joy comes from sharing it and allowing your growth to better others’ lives.

The people you love — who love you no matter what you do — make all your effort to become a more compassionate and capable person even more worth it.

A life well-lived is not one in isolation. I isolated a lot the past couple months and every time I stepped back into a community, I felt a sense of awe and joy of how lucky we are to have one another.

Yes, there are moments in life where isolation is the vehicle for introspection. But, I am beyond grateful and see it as my life mission to develop and grow not just for me, but to more effectively have a loving impact on others’ lives. For me, that is true fulfillment—being able to say, “I had a loving impact.”

My next mini-retirement likely does not need as much isolation.

In Closing

There will be another mini-retirement in my 20s, maybe several.

Your paycheck matters of course, but there are so many ways to make money out there and if you save, invest effectively, and live below your means during said retirement, it is extremely doable. Not to mention, you will probably start building something potentially profitable if you create all that time and space and you have similar energy to me.

I am excited to embark upon my next chapter of intense professional growth at BCG and play more of the games of life. However, as I step into what many call “the real world,” I hope to never use the expression “well, in the real world” to justify long stretches of unfulfillment, a lack of play, or a lack of love.

If you appreciated any of this, I share financial, professional, and life insights in my newsletter and podcast Young, Smart, & Battling Broke. Please connect with me on LinkedIn as well! Love meeting new, brilliant people.

Beyond grateful to Dennis for sharing my piece here. I am hopeful he can take a mini-retirement after graduation. The world should watch the hell out for what he does with that much time mixed with his unreal, wonderful energy.

As always, smile at strangers and trust your curiosity :)

Besides being a tremendous time, full of great views and stunning terrain, it was also a great chance for my cousin and I to catch up. Eventually, he started asking me some questions about the English language (he’s improving his level of fluency after moving to the US a few years ago), and we started discussing the specific differences between similarly meaning words.

I didn’t think much of it, until I realized that this stuff is actually extremely complex.

For example, what’s the difference between build, assemble, and construct? They’re all quite close to each, but they aren’t all pure synonyms. You could build a road, but you wouldn’t really assemble one. After some thought, I decided that building means creating something new, whereas assembling is building something with a finite set of pieces.

Like Legos, or Ikea furniture. You could assemble those!

And what about the context around when you’d use “almost”, “around”, and “about” regarding time? “It’s almost 2 pm” is slightly different to, “It’s about 2 pm”. One means that it’s before 2 and soon to be 2 pm; the other is an approximation of the fact that it is, roughly speaking, 2 pm.

And other various things like that.

This conversation with my cousin made me realize that languages are actually much more complex than we’d think, and that it’s honestly quite miraculous our brains can understand these things so quickly. As fluent speakers of a language, we know these contextual differences from a lifetime of practice, yet I never really appreciated how hard that was up this hike with my cousin.

It reminded me of when I first started learning French.

I was at the Alliance Française in Chicago in preparation for my upcoming study-abroad semester (Episodes 1-29) in Paris, and our instructor, Geoff (pronounced “Jeff”), was highlighting how strange languages can be.

He asked everyone in the room how they’d order a coffee at a café. Taking turns, my classmates and I shared our different ordering phrases:

“Coffee, please”

“Let me get a coffee”

“Can I have a coffee”

“I’d like a coffee”

“May I please get a coffee”

And so on.

As fluent speakers of English, we all understood that these phrases convey the same idea (a desire to order coffee), but they all use slightly different wording to do so. Someone who is just starting out learning a language may not know all these versions, and subsequently be confused when standing in line at the cafe.

So what was the point of all this? Was there some grand theme, major takeaway, monumental understanding of the universe achieved?

Not really. Maybe it’s that we should appreciate just how crazy cool our communication with each other is. Maybe I just thought it was tremendously interesting, and wanted to share it with you all.

Or maybe this is all just to tell you that you wouldn’t really assemble a road — you’d build it.

Best,
Dennis :)

My favorite linguistic blunder came from a conversation I had with a Parisian friend a few years ago. After asking them if they wanted to hang out later in the evening, they promptly replied, “Why would we go hang ourselves?”

Any linguistic blunders you’d like to share? Please comment them, I’d love to see!