I haven’t shared a yearly reflection since 2018. Given 2023 is the year I rediscovered a joy for writing online, it makes sense to restart the habit. I always enjoy reading recaps from others.
2023 was full of ups and downs. Professionally, my time at Ness ended, I joined Paytient, and I grew significantly as a product manager. Personally, our oldest started kindergarten. My wife and I also experienced our first 13+ hour roadtrip with three boys under five. It was an experience.
Here’s a recap of the big themes from the year.
Ness and Paytient
At the start of 2023, we were just beginning to onboard our first cardholders at Ness. Energy was high. We all believed in the bright future ahead. Fast forward to July and the team had to make the difficult choice to layoff a significant portion of the staff. Even more unfortunate, Ness completely shutdown in November.
I spent a lot of time reflecting on my two years at Ness. We had grand ambitions for making healthy more accessible, and I continue to be incredibly proud of what we accomplished. As Derek shared on LinkedIn, sometimes you swing big and miss. Ness was a transformative experience for me personally. I learned about the fintech ecosystem, gained more exposure into healthcare, grew as a product manager, and had the opportunity to work alongside an incredible roster of teammates.
After Ness, I spent several months figuring out my next step. I detailed my job search in a blog post. It was an emotional rollercoaster, but I ultimately believe I found the perfect fit at Paytient. It’s the ideal blend of healthcare and fintech with a very talented, mission-oriented team and a bright future ahead (we’re hiring!).
Books
I’ll close out 2023 having completed 37 books. Compared to previous years, I read more fiction—about a 50/50 split. Previously, I viewed fiction as a waste of time. Between the intensity of working at Ness and the all-consuming aspects of the job search, I grew to really enjoy the mental escape provided by books like Tomorrow and Tomorrow and Tomorrow and Anxious People (two of my favorites).
On the product front, I’d recommend Continuous Discovery Habits and Shape Up. The former shaped how I think about product discovery. The latter challenged many commonly accepted Product-y ideas around velocity and execution.
More broadly, Where Does It Hurt? was a fascinating read as I dive more into healthcare. Tunnel 29 was an eye-opening account of digging a tunnel beneath the Berlin Wall. The level of bravery is truly hard to fathom.
Other Reading
2023 was also the year where I tried to bring some structure and organization to my online reading. I started my subscription to Reader and invested in a note-taking system in Obsidian. In terms of habits, I scaled down how much I read and scaled up the intensity.
Regarding volume, I was heavily influenced by Oliver Burkeman’s post, Treat your to-read pile like a river, not a bucket. In short, bookmark items liberally but choose what you read judiciously. There’s no point in trying to clear your “reading inbox.” There’s an infinite amount of content to read. My Reader backlog has 20 items in it right now (and growing). Previously, I would have tried to read everything. Now, I’ll read 2-4 items per week in detail.
On the intensity front, I set aside two 30-minute sessions per week for reading and digesting articles I find online. This is manageable enough even with a full-time role and extensive family commitments. When possible, I now try to read thematically during a given month (November was around AI, for example). Once I read something, I try to incorporate it into my existing knowledge bank in Obsidian.
This combination—reading fewer items with more reflection per item—has helped more than I would have previously thought. Reading is now more enjoyable, and I don’t feel the overwhelm of an exploding queue.
Writing
Inspired largely by Tom Critchlow, I started writing online again in 2023. I don’t have grand ambitions for how this evolves. I mainly write to organize my thoughts. My recent post on Business Maps is a great example. That idea had been bouncing around in my head for several weeks. It felt good to get it out on paper.
Looking ahead to 2024, I want to keep the weekly writing habit. I already have a few topics in mind (one: how to gain context quickly when joining a new company). I also want to strike a balance between sharing short ideas (aka riffs), longer posts, and notes.
Personal
Our family had an amazing year. We spent a week in Broken Bow, Oklahoma and made several trips to visit family. Mostly, my wife and I grew more accustomed to juggling all of the demands that come with raising three boys. It’s wonderful (and stressful at times) watching them grow up. In particular, it was eye-opening watching our oldest start kindergarten. There’s something about the preschool to kindergarten transition that makes you appreciate the younger years.
On the fitness front, I was largely in maintenance mode. I still do CrossFit in our garage gym five days per week. The biggest shift has been moving my workout times from ~lunch to 5 am. It’s been an adjustment! I won’t say I love the early morning workouts, but it has been helpful freeing up time in my day.
Goals for 2024
Recently, I haven’t set any sort of yearly goals. Instead, I have a longer-term vision for my life and career. I then lay out semester plans that increment towards that future. I do think it’s helpful to have a scorecard of sorts though so I’ll take a stab at laying out some focus areas for 2024.
Publish regularly. For years, I wrote at least one post a week. Then, I went through a dry spell before picking it back up. When I’m actively writing, I have more ideas and generally feel more inspired. 2023 was the year I fell back in love with writing online and transitioned from Substack back to my personal domain. In 2024, I want to continue that trend – aiming for 40+ posts including 5 longer form pieces that I’m proud of.
Make time and space for a new hobby. We’ve been busy having our three boys so neither my wife nor I have really had time for hobbies. It feels like this is starting to change ever so slightly. I’m looking forward to diving in on a hobby that’s completely separate from work. Eventually, I’d love to do this hobby with the kids as a shared experience. Right now, I’m set up to go hunting in 2024 for the first time, and I’m looking forward to it.
Grow professionally. I have a handful of professional goals that don’t necessarily fit in a public list, mostly because they’re inherently specific to my work at Paytient. As a general success metric, at the end of 2024, I want to feel like I contributed meaningfully in terms of work delivered and grew as a product manager. This happens through reading and learning but committing to improving at the craft.
Deepen my knowledge of the healthcare industry. In an upcoming post, I’ll dive further into this topic, but I’m all in on healthcare. I’d like to devote the rest of my career to making “healthy” more accessible for everyone. There are several areas I’m keen to explore further – one being how people pay for healthcare (aka Paytient!). I have a lot of learning to do in this area. I’m excited to read more, meet other like-minded individuals, and build my mental map.
Connect with other like-minded individuals. Speaking of connection, one positive outcome from my job hunt was an renewed appreciation for “networking.” I know that word has tricky connotations and feels somewhat icky. I have a post in my mind tentatively titled “Small n networking” that describes my approach. In a nutshell, I met some fascinating people this year, and I want to do it again next year. Meetups, 1:1 coffee chats, cold outreach – all of it. It’s not about expanding my network; it’s more about growing through learning from others.
That’s it from me in 2023. Wishing you all a Merry Christmas and a very happy New Year! See you in 2024.