Every year, I make a point to sit down and write a reflective piece. The idea came from my friend Marshall—he started doing this either in college or just after he graduated.
He’d put together a document that captured the lessons learned from the year and offered advice to his future self. When he first told me about it, I thought it was a cool, introspective thing to do, and I decided to give it a shot. I’ve now adopted the tradition, adding my own spin to it, and I do it around my birthday every year.
Each of these pieces is framed around the transition from one age to the next—like 24 to 25 or 25 to 26. It’s a milestone reflection, designed to track my progress and help me acknowledge how far I’ve come. It also serves as a way to encourage myself to make better decisions, to keep improving with every year.
I’ve been doing this since I turned 23, right after college, and it’s become a ritual that I look forward to. What I’ve found is that while the years fly by, having this practice allows me to see the lessons that emerge from each year.
The original format was pretty straightforward—just lessons learned from the year. But as I kept doing this, I started to tweak it, adding categories to analyze my progress in different areas of life. That idea came, in part, from a perk I had at Bird. They offered us four free professional coaching sessions, which helped me understand these “life categories” more deeply. It’s something I’ve written about before—treating your life like a business you’re consulting for, setting annual goals, and making a clear plan.
So now, my yearly write-up is split into two sections. The first is a reflection on life categories, and the second is a list of lessons to me to (hopefully) carry-forward into 29.
Reflecting on the year of 28
These are the categories I write about as reflect on the year:
Summary of the Year
Lifestyle
Work
Wealth
Travel
People (both new people I’ve met and updates on relationships with the ones I know and love)
Love/Dating (there’s always some emotional component worth reflecting on)
I was going to copy-and-paste my writing into this post, but I realize that most of my writing would be redacted, so I’ll leave you with the categories and write from a high-level about my reflections on the year.
This past year, from 27 to 28, has felt like a significant leap.
I joked with my friend Grace that 28 was much more “well-rounded” than 27—like the number itself just feels solid. And maybe it’s the mental shift of being closer to 30, but you start to notice certain things. Your early 20s make you feel invincible, like you can fall off a cliff and get right back up. But as you approach 30, you notice how health—both mental and physical—becomes something you need to protect. It’s not drastic, but you see how the little things can turn into bigger issues if left unchecked.
Overall, this past year—my 28th—was a really good one. It was full of growth, even with the inevitable sense that time is moving faster and faster. The biggest highlight would be going from a rather aimless sabbatical when I was 27 to starting a company and feeling more driven and focused than I have in a long time.
Work is a very big part if not the biggest part of my identity, so it’s no wonder why 27 was a bit of a confusing and hard time for me. I think there are three things that helped me figure out my career situation:
The invitation from my now-cofounder to team up and build a company.
The gradual trial-period of working together and understanding how we complement each other.
Overcoming my own doubts and insecurities I’ve accumulated about when and what it would take for me to create a startup.
There’s no perfect medicine for how I found myself out of the career confusion, except to take the advice that my friend Alex Moller once told me. To paraphrase, if you don’t know what to do, sometimes you just need to wait long enough for it to become obvious. Eventually, it became more obvious to me that the opportunity to work with Kiet, my cofounder, was a great option. I couldn’t tell you with 100% certainty that it would work out, and we both went through some challenges in the business, but it feels like we are working to create our own luck with our company, and each decision we make gets us luckier.
Outside of work, I became more at-home in NYC, more certain about where I like to spend time and when, and more confident in my own instinct. I also realized that when you’re in a city like NYC, there are not many situations that you’ll regret going to.
I continued to go to the gym almost daily and started to occasionally swim. It’s very satisfying to have the full body soreness a day after a good swim session, but it does take some extra prioritization to add into my routine.
Lessons for 29
Do not twist the knife.
A psychologist gave a TED talk about "emotional first aid" and it has some incredibly powerful takeaways. How to practice emotional first aid | Guy Winch | TED - YouTube
The key idea here is that if you're already in pain, or something happens, you will not benefit from mulling over it too intensely. The example Guy Winch uses is that if you had a physical injury you wouldn't continue hurting yourself, so why do you do that with your ideas in your head?
For me this was a lesson I digested when someone I cared about stopped following me on a social app – and it really ruined my morning when I found out! Then I had to pause and thing well it's not useful for me to wallow in the pain of that realization.
If someone blocks or unfollows you don't overthink it.
If someone wronged you, don't mull on it.
Take good care of your ears –
For those of you that have chatted with me in the past year in any loud environment, you've probably heard me something along the lines of "huh" or "say that again?" because I was wearing an earplug. I damaged the hearing abilities in my right ear while I was in Mexico City last year.
I got a hearing test recently (for $500!) and was relieved to find out that my hearing was perfect. Sadly though, the cause of the pain in my ear in loud environments is entirely unknown to the doctor.
Nevertheless, Apple just announced that their AirPod Pro 2's can let you do a clinical grade hearing test later this Fall. For only $250, I highly highly recommend you upgrade your headphones to them so that you can take a test for yourself and protect your hearing.
Know what activities you love and make time for them. I didn't do this enough this year, and it continues to be something I find hard to prioritize. Maybe it’s being a bit burnt out of “activation energy” at the end of the day / week.
This quote from Joe Rogan:
New York will demand your attention – If you don't control your attention, you will be caught up in tons of activities and experiences that you may or may not want to opt-in to. It’s almost like you need to control the wave of information and FOMO.
Many things in life will decay if you don't invest in them (flexibility, fitness, friendships, health).
Go to the dentist frequently – get in the routine of visiting the dentist. A clean polished smile is a huge boost in confidence, especially when most of your workday is just sitting on calls staring at yourself and your colleagues through a screen.
Even in people's late 20s there is an immense amount of insecurity in the world
You would think that by later 20s people would probably have reached a level of self-maturity that would let them exude confidence and live their best life, but you couldn't be further from the truth.
Because there is still a lot of insecurity in the world, most of the decision-making people make are fueled by that insecurity.
Insecurity bleeds its way into all aspects of someone’s life – no category is immune. It’s been surprising to see how much of business is influenced by insecurities.
Stability in decisions is underrated. The tendency to react to things is a negative trait of being human.
Your ego is likely looking to stir up insecurity and chaos in decision making – if you make a practice of fighting it and being patient, you won’t suffer from as much stress.
The buses where you live aren't that bad.
The G train in Greenpoint was down this summer for a few months and the options were either to walk to the next train station or to take a bus. While the buses were crowded then as they were the only option, most of the time I’ve ridden a bus in NYC (and LA) they had plenty of room.
I've found that riding public transportation comes down to the classic marshmallow test. If you just wait a couple of minutes, you very likely can get on a bus going exactly the direction you want for just a few dollars. And going on a bus can be nice – you get a full cell connection during the whole ride, unlike on the subway.
Even better, if you're thinking about taking an uber or a taxi, you'll save a good amount of money by doing a multi-modal trip (half bus, half taxi)
Having a ritual of a tv show is a great way to connect with friends during the winter and is a great thing to look forward to. Find something to watch on a Friday night, order a pizza, and go out afterwards.
All professional tasks involving other humans come down to reminding other humans.
If you haven't sent three emails to someone in a row, you haven't earned the right to try a different tactic or think your outreach was a failure.
Even when your emails fall-flat, there are still other ways to get in front of someone.
Measuring people by the amount of money they have or make is a horrible horrible horrible indicator of anything about a person.
I've met people who are phenomenally wealthy and horrendously awkward to be around. They exude insecurity and make you wonder why the world rewarded them with wealth.
I've met people who don't know where their next paycheck is coming from and are infinitely cool. They exude confidence and make you question what ways you haven't been true to yourself.
Anecdotally, when you have less money, you tend to have more authentic experiences. People who are wealthy sometimes try to create the same level of serendipity, but the affordable fringe is where culture and innovation comes from. The stories of lavish vacations and retreats are
Writing a newsletter is a great way to step away and reflect. It doesn't have to be perfect – it's nice just to get ideas out into the world. In fact, most of the challenge of creating something is battling your perfection of how you may be perceived by sharing it with the world.
We all could do a bit better about putting something out into the world and just moving on.
Rick Rubin talks about how sharing your art with the world is the great achievement, not what happens after it.
For many of you that thought about writing a newsletter, I’d encourage you to do so. Don’t overthink the title of it, or what you’ll say, just say something and share it with the world. My best friend Grace continues to write weekly ever since starting her own newsletter, and she says it’s not only been the most consistent thing she has ever done, but it’s also extremely rewarding.
Read a real book. Perhaps try going back to buying physical copies. My phone has been a bit of a life-suck lately, and while the Libby app is so great for getting free digital books and audiobooks, it is still so easy to get distracted.
The entire world is unqualified for their jobs until they eventually become qualified through failures that are specific to their roles and industries. If you want to succeed or make a career change, you must be prepared to suffer through the failures. But eventually, if you’re passionate about what you’re doing, you’ll make it far enough down the path that you’ll wonder why you ever doubted yourself in the first place.
Along the lines of failures in business categories, each industry has its own culture of operating. Cross-pollinating these cultures could be really helpful, but the usual single-track-career that most people are on prevents this.
If social media makes you feel bad about yourself for whatever reason, shut it down. Set a daily time limit of 1 minute and get away from it. The notifications constantly popping up to pull you back in are treacherous for your focus and self-esteem.
One of the biggest challenges with fitness is just keeping it entertaining. You know what you need to do, but it can be boring to do it again and again week after week. I think the secret is to just make sure you attack each workout with intensity – focus on each part of your body participating and make a conscious effort to “drive” intensity to that muscle group.
People will demonstrate how badly they want something through their actions and “energy”. It doesn’t hurt to want to invest in something or someone, but eventually if you find yourself over-investing in something with no “return”, you may want to reevaluate why.
I’m not sure how many of these “X going on Y” posts I’ll declassify but I’d love to hear from you if any of these lessons resonated.