Happy new year! This is my third annual review in which I look back on how the last 365 days turned out for me across a number of areas. I'll follow the same structure as last year's review, mostly because I don’t see any reason to tweak things. If it ain’t broke, don’t fix it. These three questions will serve as prompts:

  • What went well this year?
  • What didn't go well this year?
  • What did I learn?

Before we dive into the review itself, let's get the humble-bragging portion of this post out of the way. Keep in mind the disclaimer that lists like this always look more glamorous than they actually are:

  • Started a new full-time role as a product manager at Metabase
  • Spent the Summer of Love in NYC celebrating things reopening
  • Got rid of a bunch of stuff and went all-in on being a digital nomad
  • Traveled to some new places including New Orleans, Denver, Mexico City, Tulum, Cancun, and Playa del Carmen
  • Completed 4 Reforge courses on product and growth
  • Sent out 30 newsletter issues of Oversimplified
  • Published 33 new blog posts
  • Read 12 books

What went well?

🛠 Leveling up in product management

Throughout the course of my career, I’ve been slowly inching closer and closer to product management. It’s fun to connect the dots looking backward: I started out as a data scientist serving as a “right hand man” to PMs at Squarespace. Then I joined Hugo as employee #8 to focus on growth, which started out with a marketing tilt but quickly shifted towards product. Then around 6 months ago, I had the chance to go all-in and join Metabase as a product manager. I’m loving it so far.

That’s a fun narrative, but there’s also a lot of learning that has been (and still is) taking place. Part of committing to a new domain is learning the territory: What problems are you trying to solve? What situations do you need to be prepared for? What tools are in your toolkit? How do you interface with an organization? When it comes to product management, there’s a whole lot of territory to cover! I’ve made great progress though experience and mentorship, as well as a bunch of reading and learning online, including some Reforge courses that were helpful.

❤️ Spending time with those I care about

Despite the pandemic, working a bunch, and traveling more than ever, I feel as if I spent a lot more meaningful time with those that I care about this year. Particularly this fall, I had the chance to make some amazing memories with my girlfriend, family, and friends that I’ll cherish for a long time. After the shutdowns in 2020, calling this is a breath of fresh air would be a massive understatement.

🌏 Going full digital nomad

In August, I finally took the plunge and did something that I’ve wanted to do since I was in college: Skip the annual lease, sell a bunch of my stuff, and start living the “digital nomad” life. It’s been a bit of a blur since then, in the best way. Some positive effects I expected, like getting more minimalistic and interacting with other cultures. Others were a surprise, like learning a ton about the role that environment plays in fulfillment.

That last point felt kind of profound to me. It’s easy to get into the swing of things in one environment and forget what parts of it you do and don’t like. It’s just the way that things are. I’ve done this a dozen times before. But when you’re changing your environment completely every few weeks (housing, landscape, culture, neighborhood grocery store, etc.) you can much more easily detect which things give you energy vs. which detract from it. Up to this point, I’ve been bouncing around the following places on a semi-monthly basis. More to come:

  • New Orleans
  • Denver
  • New York
  • Washington D.C.
  • Mexico City
  • Playa del Carmen
  • Tulum

What didn’t go well?

⏳ Making time for learning and personal projects

While I did a great job spending time on my career and meaningful relationships, I didn’t do as well putting time aside for my personal learning and growth. If I’m being honest, this has been triggering a lot of guilt and dissatisfaction over this past year.

This perception could be wrong but I feel like I never used to have issues like this: I wrote on more days than not, read on a daily basis, and hacked away on side projects when I wanted to. As you get older, more stuff falls on your plate. That’s only going to continue. Ultimately, it’s about how I prioritize my time, and I want to do a hell of a lot better.

✅ Maintaining routine

You never like to see a repeat from last year’s post, but hey, routine is hard! Especially when you throw in frequent travel and adapting to the schedule of a product manager.

On travel specifically, I feel like it’s made me realize the importance of routine even more. I’m just flat-out happier when I have my morning routine to provide structure to my day, especially when so many other things are in flux. This has been getting better lately, but there’s still a long road ahead. Here’s to avoiding the “hat trick” and righting this before next year’s post.

🤕 Staying at full health

I would not have expected this to be here at the start of last year! I don’t usually get sick all that often. I’ve never broken a bone or had any serious injury. I sprained my knee once in middle school, but that’s pretty much the extent of it. I’ve been super lucky to this point, and still am, but definitely hit more than a few road bumps this year.

Physically, I suffered some version of a bulged disc while deadlifting towards the beginning of the year, which has lingered since. It’s been a hassle, but it is on the come-up as of late, since I finally pulled the trigger and started physical therapy. More generally, I’ve just been getting sick a ton, including a fairly rough encounter with COVID and what I think was the flu. I’m mostly attributing this to constant travel, which isn’t stopping any time soon. More vitamins and hand-washing I suppose.

What did I learn?

✨ Where my fulfillment stems from

It takes a while to learn what things truly fulfill us. It’s complex stuff and there are false positives everywhere. By no means do I have all the answers, but I did learn a lot about myself this year. I attribute a lot of these learnings to a combination of travel and consistent therapy.

As I alluded to before, there’s something about frequently changing your environment that triggers some interesting reflection. All this is to say, these are the things that I’m being more intentional about next year:

  • Relationships: This one is a bit of a no brainer. Life is better when you spend time with people you care about.
  • Thinking: Sitting down at a desk with no distractions and thinking. Just an empty text editor, some idea, and eventually some words to go with.
  • Travel: There are few more energizing things for me than arriving in a totally new place and walking around by myself just taking it in.
  • Hobbies: It’s easy to forget about this one as your career expands to take up more of your headspace. But I've realized it's a big one for me: I like having something on the side I’m trying to improve at.
  • Fitness: This ties into the previous point, but deserves its own bullet. Every day is better when you take time to work up a sweat.


📚 Books I read

I read 12 non-technical books last year. Not as many as I would like as I kind of got away from my nightly habit for a while. We’ll do better in 2022 but for now, here’s the full list in chronological order from first to last:

📝 Blog posts I wrote

I wrote 33 new blog posts. This is less than the 45 I shipped last year but still pretty damn good. I always feel like I’m failing to write and then it all adds up at the end of the year. The really cool thing is I could put out a lot more here than I do now. I just need to show up more. Here’s the list:

📬 Newsletter issues I sent

I sent out 30 issues of Oversimplified this past year. This is easily the lowest mark that I’ve had since I started the initial version of this newsletter some six years ago. I don’t have a ton of good excuses — It just got away from me as career and life stuff ramped up. I’m going to do better with this, as I really do enjoy it. Here’s the archive:

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