I don’t normally write year in review posts, but I want to start 2024 off right, so I’m doing this to close a few chapters and start some new ones.


A great year at Figma

Following my unexpected exits from Basecamp and Twitter in 2021 and 2022, I was adrift about work, and uncertain whether I still had the energy to care about tech anymore. My professional identity was so tied up with those companies that I had to rediscover who I want to be.

I’m in my 40s, I’ve been doing this for quite a while, can I still hack it? Is there such a thing as a great second act? Should I even bother trying to have one?

I joined Figma with the hope that it would rekindle my spirit, working on a beloved creative tool with a ridiculously smart group of people.

I’m happy to say that’s how it worked out. 2023 wasn’t an easy year for Figma by any means, with huge launches and conferences to coordinate, the challenges of internal growth, and the major ups and downs of the Adobe acquisition. But the team has so much heart and enthusiasm that it spills over into everything we’re doing, and it turns out that’s all I really need from a job at this point.

I had the good fortune to work on Variables, Dev Mode, and a bunch of other big and small things we shipped in 2023. It was tough to pull off, but so amazing seeing all of this hard work land successfully. I felt incredibly lucky to be a part of it.

Finding my way as a manager

I’ve been managing teams for almost 5 years, but most of those years were clouded in some type of existential turmoil—ranging from shipping a new product amidst big public controversies, surviving the uncertainty of the pandemic and forced remote work, facing difficult social and political reckonings, trying to remain calm during the strange hostile takeover of a social media company, and riding the rollercoaster of the tech industry’s excesses and instability.

Moving into management is never easy, but doing this in 2019-2022 was a trial by fire on Extreme mode.

In 2023, I was finally able to breathe a little, focus on who am I as a manager, and get better at a lot of practical and philosophical things. In many ways I still feel like a complete newbie, but I think that’s probably just the reality of the job. Every day is always a fresh challenge you haven’t seen before.

I’m also lucky to have a super supportive crew of peer managers at Figma, which is something I never had in previous roles. I can’t emphasize enough how important this is—management is lonely, and you need people in your corner.

Side project progress

In February, we launched Weather Machine, an API service built on a complete rewrite of our tech stack that powers Hello Weather. This didn’t take off as we had hoped (more on that in the lowlights), but shipping this was a big achievement.

We also made a ton of progress on a complete ground-up rewrite of Hello Weather for iOS, which has been SO MUCH WORK. omg.

At this rate we’ll either launch the new app in 2024, or die trying. But this has been a great adventure as well, forcing me to get proficient with SwiftUI. I’ve done most of the front-end work for the app, and it’s been fun to work on, except for about a dozen things that are maddeningly hard to achieve with SwiftUI in its current form.

Personal stuff

I went to New York for a week, visited San Francisco multiple times, drove the California coast from SF to LA, and spent a few perfect days as a tourist in my home city of Chicago. I love all of these places, and it was such a treat to see them.

We managed to nab tickets to one of Taylor Swift’s concerts at Soldier Field, saw the last Dead & Company shows at Wrigley Field, and Bonnie Raitt at the Chicago Theatre.

Here’s my playlist from 2023.

I enjoyed Build by Tony Fadell, Department of Speculation by Jenny Offill, and Design as Art by Bruno Munari.

This was the year of The Bear and Doctor Who.

We survived, and tried to thrive. It wasn’t an easy year, but we’re still standing, so that’s a highlight?


Work/life balance

I haven’t figured out how to do management full-time while still nurturing my intrinsic need to keep creating and designing things myself. The side projects are nice, but they take a ton of time and effort, and it’s basically like having two different jobs. The net result is not nearly enough free time, and feeling pressure to be constantly productive, which isn’t healthy.

Side project survival

Similarly, we were disappointed that Weather Machine didn’t have more success out of the gate. Hello Weather is still a net-negative financial endeavor, in that it pays for itself but it doesn’t pay for us to work on it (we essentially donate our time, and take occasional small payments when we can.) Our hope was that an API product could round this out, but alas, not yet.

Meetings and gap time

I’m an “introvert in denial,” and the problem with remote design management is that you usually spend most of your waking hours talking to people on Zoom. I enjoy this, but it’s also very taxing, and I haven’t nailed the balance yet. Need to block out more gaps in the schedule.

Losing my voice

With so much going on, I haven’t had nearly enough time for reflection, writing, longform reading, and the creative play/exploration that I miss doing. I also spent a lot of effort trying to rebuild my networks on Mastodon and Threads, since I divorced myself from using Twitter earlier this year.


It was a tough one for our family, with multiple bouts of Covid, and one of our kids being hospitalized with pneumonia, among various other issues. Glad we made it through.

Personal goals for 2024

I always overcommit to things, so this is it. Posting here for accountability!

  • Shipping Hello Weather.
  • Much more writing and sharing. Getting back to blogging, newslettering, and podcasting. (Longer term stretch goal: writing a book!)
  • A little refresh for this website.
  • Less social media, more books.
  • Being more present.

Happy new year, friends. Hope you have a healthy and joyful 2024.