My Twenties
I’m writing from a cafe (BUNA) in Mexico City. I’m sitting out from the Xochimilco excursion because I’ve tweaked my ankle in the last few days. It’s kind of nice taking it easy after a pretty packed week.
The coffee is delicious, the light comes in beautifully through the open doors. The breeze fills the room and it’s so peaceful watching people walk by with their dogs on these tree lined streets.
In moments like these I feel like I’m coming up for air. It’s so easy and normal to be constantly inundated with distractions and tasks and reminders. Feels nice to completely disconnect.
There are periods in my life where I slow everything down and remember to completely zone out. I hope this upcoming year is full of this.
For the next few pages, I’m going to go year by year to remember / record what happened during my twenties.
2014 & 2015 / Sophomore Year / Dark Days / 20 Years Old
This was my second year in college. My first year had gone ok. I had a few gripes. Having a roommate that went home every weekend to study leaving me a bit lonely (shoutout Vidush—it worked out for him as he went on to grad school at Stanford and a job at Google for the last few years). I also held major gripes about the gender ratio of my freshman floor. I’d imagined college to be a promised land where I’d meet so many people and eventually get a girlfriend. But neither of those things really happened.
My sophomore year was when I hoped to turn it all around. I started the year living with Will T, Brandon and Bill in Martinez.
TLDR this year turned into major depression. I was lonely, unsure of what I was doing with my life. I’d more or less tanked my GPA. I remember thinking life was like a treadmill and I had already messed up and was constantly playing catch up.
Besides Will, I either begrudgingly accepted or actively disliked my roommates and didn’t have the social circle I’d imagined having.
I ended up going to church more often—enticed by the promise of a good social circle and free food. This worked out ok until pressure to “be a good Christian” amped up and I felt coerced instead of enticed.
I had a big crush on a girl in the class above me. Andrea L. We’d met in church and ended up taking the same Astronomy class together. We had an assignment to study stars. She borrowed her sister’s car and offered to give me a ride up the hill to see the stars. As we sat together driving up listening to John Mayer I couldn’t help but think she was absolutely into me. BUT! I was afraid and a bit depressed and said nothing. We drove up, saw the stars, drove down and never dated. Not making a move here was one of my bigger regrets in college, for sure.
Years later Will T came for lunch at my office and dropped the news she’d gotten engaged (actually to another dude at our church!). I sat slightly dazed for a few minutes and I think this was a formative moment in resolving to not let opportunities pass me so easily.
This year I also ended up meeting Chaitanya (along with his roommates Sanjeev and Vivek). Chai ended up being a close friend that I continue to see to this day.
I also had a somewhat disappointing summer internship at a wedding startup (think Airbnb for wedding venues). This was absolutely a step up from my previous summer of data entry (transitioning to web development the last half of the summer) but I was disillusioned with the concept of work. The idea of trading all this time… for what?
One huge highlight (in hindsight) was getting into music production. I’d developed insomnia due to all the stress and stayed up most nights til 4am. During this time I’d walk around the apartment complex like a ghoul waiting to fall asleep. One night I started toying around on my cello playing / composing small melodies. Eventually I wondered if I could make these into real songs and eventually found my way into music production.
2015 & 2016 / Junior Year / The Golden Year / 21 Years Old
The previous year I’d sat with Chai, Sanjeev and Vivek talking about what we’d do the following semester. Harry had mentioned taking an acting class (I think) and on a whim I decided to do that too.
Acting turned out to be incredibly fun. I met a greater variety of people compared to my usual computer science classes. I developed a small crush on a girl named Sophia who was two years above me and looked vaguely like my first crush. After classes ended we were walking together and I asked her to my friend’s party on a whim. She agreed to go with me and…. I did nothing again lmao. Baby steps, I suppose.
A highlight of this year was going to India for a study abroad program (for just a week). Traveling to Visakhapatnam and Hyderabad, making a long term friend in Rosie, getting E Coli. All pretty memorable.
After that trip (and honestly the food poisoning) a lot of things started to click. Immediately after the trip, for whatever reason, I kicked my habits of bingeing tv and watching porn. Maybe I’d been reading a lot of the NoFap subreddit and gotten inspired. I spent a lot of time reading more and hanging out with friends instead of with my devices.
In the immediate aftermath of the food poisoning, I cleaned up my diet too, focusing more on low carb, high protein. I remember making some—in hindsight—disgusting foods. Slow cooking shredded chicken and beans and just eating a mound of that to stay in line with my diet. One memorable night of cooking spaghetti squash with Rosie (and Amy?). I also remember getting mad at Chai for not following my diet instructions (after he’d asked me for advice). A silly episode of arguing in the bread aisle of the grocery store because he wanted to eat more carbs despite me telling him to stop. The diet also led to more exercise. I became a lot more active (and energetic).
This year was a golden year in artistic pursuits as well. One of my most memorable moments was in a Shakespeare class. I’d been assigned Sonnet 66—a Shakespearean sonnet of lamenting at the sorry state of the world. In true Woody fashion, I started off cautiously. More stating / reciting the sonnet instead of actually acting it. On paper, I didn’t want to “overact” it. I thought melodrama here was unnecessary and I’d play it cool and straight. But that didn’t fly. My acting teacher (Chris H—probably the best teacher I’ve had in my life) had me repeat it over and over until I actually felt and performed the emotion. Once I actually performed it, I felt like the floodgates had opened. This is what it felt like to act. To feel the words on the page instead of just reading them. To feel and show emotion instead of fearing how the emotions would be interpreted. What a feeling.
The next few months felt amazing as an actor. I felt like I could do no wrong. And the acting absolutely helped me open up as a person. I never knew why but Chris kept giving me romantic roles. I ended up doing a lot of kiss scenes. At that point a kissless virgin, I was amused and happy to play these roles.
That year I also developed a huge crush on Mimi. I’d first seen her the previous year when I’d gone to the Theater department building to sign up for acting auditions. I’d seen this cute brunette girl and thought nothing much of it besides—wow she’s pretty.
Fast forward a year—we ended up in the same Shakespeare class. In hindsight, I was uncharacteristically bold pursuing her. Our school allowed student led electives and Mimi taught an elective on Shakespeare that semester. I joined wanting to get closer to her. We went in a circle introducing ourselves and what character we identified as. She said she identified as Juliet. When it got to my turn, I looked at her and said I identified as Romeo… good job young Woody.
One day after class, I suggested we go to the bookstore to pick up reading material for our next scenes. She, Michelle and I ended up going together. I remember wishing it was just the two of us so I could talk to her one on one. Luckily Michelle picked up on that and excused herself early so she could go home. As Mimi and I walked back towards campus—each block we passed felt like sand falling through the hour glass. I knew I wanted to ask her out but didn’t know what to say. Finally I turned to her and said I had something to say to her. With trembling lips (truly shocked that I was that affected) I confessed that I’d had a crush on her and wanted to take her out. She said yes!
The next few weeks were emotionally volatile. This was the first girl I’d ever asked out and the first girl I’d ever go on a date with. We had our first date on the grass in front of the student union. I thought it’d gone relatively well and she agreed to go on another date with me. But each time I tried to schedule something she kept saying she was sick. At a certain point I thought she was toying with me and stopped pursuing her.
I think that’s one of my greatest weaknesses (and strengths). The unwillingness to go for broke. To lay it all on the line. I’d been so into this girl, but after just a couple of rescheduled dates, I moved on instead of seeing it through to the end. If I sense that it’s a losing game I won’t even try. This isn’t to say the outcome would have been that different, but I wonder how different of a person I’d be today or how things would have changed if I’d tried a bit harder.
Over the next few years, Mimi and I kept in touch. I remember being pleasantly surprised when she reached out to me years later (2019) when I was living in New York. At that point, I was again too rigid. She’d send voice notes and selfies but I felt too insecure to respond in kind. We ended up reconnecting in London a few years ago (2022) and even kissing but I think at that point it was too little too late.
A couple months after Mimi, I met my first girlfriend Quincy at a dinner for scholarship students. In hindsight, we weren’t a great couple. We had so little in common. But I was pleasantly surprised that she asked me out and I was intrigued that she was blond and pretty and in a sorority and I was pretty inexperienced in dating overall, so it felt like a huge win when we started dating and I wanted to lock that down. We didn’t date long and I dragged out the breakup instead of ripping off the bandaid so I have some regrets there.
Besides getting fit and dating, this year I also declared my major. I was actually kind of late to declare. Most students got it done by Sophomore year but my GPA wasn’t high enough. I had one final chance—my algorithms class. I needed to get at least an A- to reach the GPA requirement to declare. This semester I studied my ass off (and actually enjoyed algorithms). With my best efforts, I eked out an A- and hit the base requirement of a 3.0 to delcare my major. Now that I was officially a Computer Science major, my meal ticket was printed. I spent most of my time afterwards focusing more on acting than my CS courses.
This year my social life bloomed as well. I clicked well with my housemates (Chai, Vidush, Tyler). We’d spend hours playing board games (shoutout Coup) and hosting other friends (Amy, Sanjeev, Rosie, Sam). Between my social life, love life, academic success, and artistic pursuits, everything felt right in the world.
2016 & 2017 / Senior Year / 22 Years Old
A tumultuous year. The summer after my Junior year I interned at a food reservation company in San Francisco. I moved out to Noe Valley to join a house of four as the fourth roommate.
I fell off hard this summer. I felt so lonely being away from my Berkeley friends. I didn’t have much of a social life. The concept of work felt so restrictive / daunting. The idea of spending 8+ hours in a building sitting at a computer and the idea that this would be my life for the next few decades were deeply unsettling.
In my loneliness and disillusionment, I fell off. Stopped working out. Spent days inside home alone. Filled my days with TV and porn. Undid a lot of progress that I felt I’d made in my golden year.
One highlight this Summer was meeting Will W as fellow interns. Our friendship continues strong to this day, though he’s currently in Taiwan.
The disappointment followed me in my return to school. I continued my acting classes and usual activities but I felt like something was missing. It felt like I was waiting for Real Life to start. For us to graduate and move into the real world.
We hung out less as a friend group. My housemates fought more this year.
I may be forgetting something but in hindsight, this year felt like purgatory.
One memorable incident happened right before graduation. I tried to repeat a party trick of sabering a champagne bottle with a kitchen knife. The bottle exploded and a glass shard shredded my thumb. I ended up in the ER and got stitches as well as surgery the next day.
2018 / Young Working Professional / 23 Years Old
Also a bit of a dull year. This year I started my first full time job as a software engineer at a bank. The bank management was convinced we had to invest in higher tech so I was placed on an internal tools team that worked on developing a chatbot for a robot that would live in our IT bar.
What this meant mostly was writing countless if statements anticipating what kinds of questions people would ask the robot.
This also meant a very lax working schedule. Getting into the office around 10, leaving at 4pm.
I lived with Chai this year and our friendship became a bit strained. Living and working at the same office just a couple blocks from our apartment, having mostly the same friend group, we ended up spending so much time together. I wanted more space and time alone.
Though I felt mostly lost, there were some good things to come out of this year. I became much better friends with Andrew L. When we first met I thought he was uptight and didn’t like me much. But that year in San Francisco, we hung out a lot. I also became pretty good friends with Tony from work.
One evening I caught up with Will W and Kelvin at Fang. We hadn’t seen each other for months and we went round in a circle catching up on our lives. When it got to my turn, I realized I didn’t have much to update. It had been months! And yet nothing of note had happened to me.
Around that time I decided to leave my job and explore living in a different city.
I spent a good 2-3 months studying Leetcode and landed a job at a food delivery company in NYC.
2019 / New Jork / 24 Years Old
I started the year with a fresh move to New York City. In contrast to the dull year I had before, I was excited to explore a new city—one of the greatest cities in the world.
I resolved to make tons of new friends, do tons of new things, build the exciting new life that I wanted to live… But work got in the way.
That ended up being one of the most stressful jobs of my career. Partly due to not having much experience from my job before, party due to passive aggressively feuding with my manager.
I learned a lot that year. A major lesson was to ask for help. I had a deep pride that I could help myself and didn’t need to ask for help. But instead of flailing alone I should have reached out. In my defense, it wasn’t an easy team to ask for help. Others were pretty stressed due to deadlines and team culture.
I ended that year with an ultimatum from my manager—find a new team or leave the company. I definitely considered the latter many nights. But ultimately switched to a different team.
One upside to this year was reconnecting with Sherry. Harry’s old crush from Summer camp years ago that I saw on Tinder and decided to reach out to. We came pretty good friends.
I also did make a lot of friends at work. Probably the side effect of working in the trenches together but we spent a lot of time together. Jess W, Daniel L, Justin, Naveed, Chris, Chynna. Unfortunately I no longer speak to any of these people… I could chalk it up to having been just work friends but who knows.
I kept up with some music production. I did a couple open mics this year, but mostly work got in the way.
I also dated Aydan pretty soon after I got to the city. A classic situationship that went on / off / on through the year. In hindsight, I regret keeping her at arm’s length. Despite it being a situationship I wish I’d made more effort to connect with her. I don’t think we took any photos together. I fell into the classic NYC male pattern of 1. wanting to date around as much as possible 2. thinking I could probably do better.
2020 / Pandemmy / 25 Years Old
Everyone—me included—was so excited for 2020. Then the pandemic hit.
Books will probably be written about the pandemic experience. For me, it was pretty uneventful.
I switched teams at work and work got so much better. Worked for one of my favorite bosses of all time and got a promotion. I never grew to love the work but found contentment and satisfaction in building stuff.
I split my time between NYC and California. I did a lot of edibles. I gained a good amount of weight.
I dated Cara for a bit. But ended things with the idea of potentially going back to California for the pandemic.
Mostly an uneventful year.
Could I have done things differently? Maybe. Some people had amazing times during the pandemic. Or they used that time getting pretty ripped. Or found the love of their life. Or learned a new skill.
But back then, things were stressful. Not knowing when or how the pandemic would end. Looking back it’s actually an insane thing to go through and I’m surprised I spent so much time alone.
2021 / Recovery / 26 Years Old
I started this year feeling socially stunted. Didn’t know how to interact with people. I spent the first few months socializing post pandemic.
Also not the most eventful year. But there were some highlights.
I did a cross country train trip with Harry. I remember marveling at how beautiful the USA was in some of its most remote parts. I also remember taking a number of edibles and sleeping uncomfortably with a mask on the train.
I did a solo trip through Portugal and London. Portugal was beautiful and I made some friends there. In London I reconnected with Mimi.
Will and Kelvin moved to New York and I spent much more time with them.
2022 / Growth / 27 Years Old
At this point, roughly two years out of the pandemic, I wanted to do more with my life. I’d moved to NYC for a reason! And yet, due to the pandemic I hadn’t done much.
I wanted to be an artist. I wanted to make music. I wanted to act. So why was I sitting with my thumb up my ass doing nothing?
This year I threw everything at the wall hoping something would stick. I did everything
Joined a choir
Started playing volleyball
Got a physical trainer
Started doing improv
Joined a sewing class
Got back into making music (and released song songs, finally)
Maybe it was pent up energy from the pandemic, but I wanted desperately to live! To feel like I was living to the best of my abilities.
It was not easy. I remember having a slight breakdown after choir feeling I’d been a fool. That despite having joined, I hadn’t done as much as I could have. Purposely sidelining myself instead of trying my best. I felt like New York was a blender, squeezing energy and emotions out of me til I was a husk. I remember Chaitya and Saad being there for me as I vented.
But things got better. And in hindsight I’m so grateful and proud to have pushed myself outside of my comfort zone in these different ways.
My love life was a bit lackluster. I had a crush on a friendquaintance Linda and actually tried to take her on a date. We had a first date that I thought went well but when I asked her for a second, she declined. We talked about staying friends but at some point I got ghosted and was too prideful to double text. Not sure if things would have made a difference either way? About a year later she replied to one of my IG stories but I was dating someone and decided not to respond.
I did a trip to Edinburgh and to London again where I saw Mimi. We met in a park and caught up. As we were leaving she made a joke about being too heavy, and I made a joke about being able to lift her. She leapt into my arms (surprisingly with her face facing me and her legs wrapped around me). What choice did I have but to kiss her? After all those years it felt like vindication(?) but it was also a bit underwhelming. Maybe because we were both sleep deprived or maybe the timing was wrong. We met up the following day but nothing more came out of it.
2023 / Continued Growth / 28 Years Old
It may be recency bias but 2023 felt like a big year.
I started that year dating Aastha, who’d asked me out at the end of 2022. I was flattered and thought I should give it a try but ultimately wasn’t interested. Maybe it’s because I’ve heard time and time again from my parents that the guy should chase the girl and the girl should be chased, but it didn’t stick.
Pretty soon after that I got interested in Christina and tried to make that work but that also didn’t stick :’). The good news was I was actually trying instead of sitting on the sidelines. The whole sidelining idea really stuck with me. The bad news was maybe I gave up too early? If I was so interested, why not go on a limb. Wait to see how things turned out instead of giving up and ending things so early?
I went on a number of dates that season but ultimately met Karin, who I ended up dating for almost nine months. This was a weird relationship. I thought she was super cute and tried my best to keep seeing her. She was hard to get but ultimately came around but kept me at arm’s length knowing she’d likely leave the country at the end of the year.
She did tell me a couple months in that she’d be leaving and gave me a window to end things but it was hard to end things then so we kept seeing each other.
Outside of dating, I focused on my health. Eating much better (thanks to my company’s stocked salad bar), continued seeing my trainer, took up boxing.
I started doing musical improv.
I also started a new job at a music streaming company.
2024 / Where Next / 29 Years Old
Having done a whole recap on this past year, I don’t have too much to add on.
I started the year pretty fresh from the breakup. A couple months later I went to Sweden for work where I developed a random and strong crush on someone I met there. But she lived in Europe and I was here and ultimately it led to nothing. I did try to follow up but I think I’m not the greatest at flirting, also not the best at sustaining conversation over text.
In the months to follow I went on a couple dates but nothing serious. I met Tara in August and we burned intensely for a few months but ultimately couldn’t sustain the flame. As of now I feel ok about it and hope there isn’t too much pain there (especially when I return to NYC).
The other notable achievement was releasing MORE SONGS! My current magnum opus Waltzin—a song that I listen to and marvel that I was able to make it more or less by myself.
I tried to leave NYC for LA but ended up coming back to NYC. Life is not so straightforward.
I also started going to therapy on a weekly basis. That’s been an interesting sometimes useful, sometimes frustrating experience.
Reflections
It’s interesting to see my past decade laid out like this. It feels like it passed by so quickly. It feels simultaneously like a lot has happened and not much has happened.
I look back on the earlier part of the decade with fondness and nostalgia. Less so on the latter part. I wonder if that’s because time makes memories look better over time or those years really just were better.
In any case, I’ve had a pretty happy and content life. I’m blessed with an amazing family, pretty great friends, good hobbies, and a decent love life so far.
I’ve been described and considered myself a restless person. This is a double edged sword. It’s a tether that keeps me chasing after the unknown, a driving force that reminds me to become a better person despite countless failures. But it also keeps me from appreciating what I have at the present. Scanning the horizon for something better instead of looking directly at what’s in front of me.
I started this decade pretty unsure of myself. Then I found myself as thing clicked into place—acting, health, social life, self esteem. Then, I lost myself for a bit—disillusionment with work life, pandemic. Now I’m somewhere in the middle.
Life will always swing back and forth. Consistency is the hardest thing to achieve in either direction (well maybe it’s easier to consistently let yourself go).
I find myself rushing towards the unknown future while lamenting the pace at which life passes by me. What a pothole.
At times I throw my hands up in exasperation, feeling like I’m treading water but getting nowhere. Then I realize that I know exactly what I need to do to improve my life (get less addicted to the distractions of the world, be healthier, focus on relationships, focus on my interests, don’t be afraid to reach out, don’t be afraid to go out of your comfort zone). But then I realize it’s not easy to juggle everything. That it’s easy to forget the truths you know and fall down to your base.
But ultimately, slowing down and reflecting PROBABLY is a silver bullet. Carving out that time to think about what you want and where you are in your life and where you want to head to.
Embracing the quiet instead of floating aimlessly in the noise.
My Takeaways
Reach failure. Go out on a limb.
I’ve been so afraid of failure without admitting or realizing it at times. So afraid of the embarrassment and ridicule of true rejection that I stop myself from the edge. But I’m curious what that looks like. To push yourself to the point of failure, to see if you can burst through to the other side.
I have such a strong instinct to avoid going over the edge. This is useful in most cases, but counterproductive when it comes to going over the edge towards good things.
My therapist might ask what is a good thing vs what is a bad thing. But generally, you know. Drugs, crime, etc. BAD!!! Going out of your comfort zone, reaching out towards people you want in your life, instilling better habits, etc. GOOD!!!
Why overcomplicate your life?
See everything as a potential opportunity. Anything could happen but nothing will happen if you close yourself off.
The best times of my life have coincided with a feeling of openness towards the world. Easier said than done. It takes a degree of security and self esteem to convince yourself to open up to the world. The conviction that you will be ok doing this and if shit hits the fan, you will still be ok.
But this seems to be the point (or one of the points) of living—connecting with the world and other people and growing.
Environment and the people you’re with matter a lot.
Don’t sit on the sidelines
In my past decade, I’ve felt the most shame and regret in putting myself on the sideline due to fear or embarrassment or self preservation. Please please please live your life! The time you have will be gone in an instant (even as I write this myself I know this in my head but not as much in my heart).
Try your best but don’t judge others when they don’t (or can’t)
One of my greatest faults is how restrictive I can be to other people. I have a high bar of expectations because I expect a lot out of myself.
BUT! This gets in the way sometimes. I should give chances and be graceful towards others.
I think this stems from insecurity. The idea that I have to surround myself with the best people to get ahead in life, so when people fall short of my expectations, that reflects on me.
If I truly were living at the best of my abilities, I’m pretty sure I’d feel this judgement less.
Feels good to get it out on paper. Not sure of what’s to come but in this moment I want
To move to LA and build a life to last here
Really put in effort to stay in touch with friends
Focus on my health and diet. Transition to eating more whole foods (meat, fish, vegetables, fruit) and cut down on the carbs.
Open up to the world
Spend time on the things I truly want to do instead of spending too much time on time wasters