2019 has come to an end. What a year! This year was possibly my biggest for personal growth.


I’ve been in a long-term relationship for almost seven years, and each year is better than the last. This year I proposed to Shelby and am now engaged! While I made the decision at the beginning of 2019, it took me a full year to figure out how I wanted to do it and execute. It wasn’t the original plan, but I proposed on New Year’s Eve - and that turned out to be great way to end the decade.

I moved from Intercom to Affirm in June. While Intercom was a great place to work, I was ready for something different and a new space. Leaving marketing tech SaaS for fintech and payments has been a lot of fun and is a completely different world. Lots of new learnings, perspectives, and challenges.

I covered this in-depth when I wrote My Top Books of 2019. Most notable is the shift from audiobooks to actual reading and a large volume increase. I challenged myself with long titles and found many new perspectives. Maintaining this will be a priority in 2020 because it’s amazing how much knowledge I can amass.

Habit Tracking
I built a rigorous system to track my own habits and help me develop new ones. I enjoyed building the tooling, and now it’s an easy system to maintain. The primary benefit is being able to see the actual progress I’m making. Among other habits, I’ve been able to improve my sleep, email efficiency, and reading frequency.

Journal Keeping
Along with habit tracking, I write a one-line statement to recap the day’s highlights. It has helped me understand what I value and it’s fun to go back and review.

Intermittent Fasting
I’m not overweight and have no need to fast, but I’ve appreciated the mental challenge of fasting each day. I skip breakfast and eat a larger lunch, and when I break my fast, I enjoy the meal more. Material impacts such as weight or energy have been about the same.

In May, I challenged myself to go a month without drinking. There wasn’t much of a need because I have always been a below-average drinker, but I wanted to experiment. I found complete sobriety to be easy but didn’t think I needed to have such an extreme rule. I wrote out my own policy for alcohol and have adhered to it since. I realized that I value mental clarity, so casual drinking has lost its point to me.

When I lived in SF, I biked daily to commute but would regularly get out for exercise too. When I moved to Oakland, I stopped commuting by bike and my exercise frequency diminished. I rode over 2000 miles in 2016 but less than 200 in 2018. I made an effort to ride more in 2019 and ended the year at 1200 miles. Some highlights were beating my personal record for the most popular climb in Oakland and riding Highway 1 to Santa Cruz.

Similar to biking, I upped my overall fitness regiment too. For years, I’ve been going to the gym once a week to maintain a baseline strength level. This year, I went more often and forced myself to do more difficult workouts. I also started using.

I’ve always admired friends who write and publish on the Internet. Having thought about this off and on for years, I made a serious effort this fall. I rebuilt my website and wrote 83 posts in the last few months. It’s difficult to keep up, but I enjoy the structured thinking exercise. It’s helped me logically form deeper opinions and I also use it to retain what I learn in books. While not the primary goal, I expect there will also be professional merits to keeping it up.

Watched Friends Start Companies
Some of my close friends started companies this year. I am so excited to see them make the leap, but it’s also bittersweet to not have a pursuit of my own. I had the opportunity to join some, but none felt like the right move. I am being patient, and I know I’ll get there again - but the time feels like it could be soon. I want to explore a couple concepts in 2020, they might be interesting… 🙃

Less Personal Travel
After a ton of travel in 2017 and 2018, I was a little burnt out and questioning its value. Unless travel has a purpose, it is a short-term indulgence that has little merit. I still went on trips in 2019, but I tried to have a reason for it such as to learn or develop a relationship. If the reason is learning, I think that it has to be specific so that a purpose is clear.

Took My Mom on a Trip
Until I was an adult, it was always my parents that took me on trips. This year marked the fist time that I took one of my parents on a trip. I took my mom to Boston and realized how little one-on-one time I spend with her. Related to the thread of purposeful travel, this was a great time to deepen our relationship and made me think about gifting time.

One of my 2019 themes was relationships and an actionable goal was to host a dinner at my house each month. We only hosted seven and I explained the challenges when I wrote about the lessons I learned. Regardless, they were a lot of fun and I’m planning to continue dinners in 2020.

Another first for me, I volunteered for my first nonprofit, Affirm Cares. So far the work has been easy to manage and rewarding.

My life isn’t as serious as I make it look. 2019 was also filled with a lot of memorable experiences. Here are some highlights from each season:

Top Memories