Life Update: Post-Forward

Reflections, funemployment, and what comes next

I announced in mid-October that I was leaving my full-time job for a period of funemployment. Some have reached out wondering how I'm feeling, how I decided to make the leap, and what I'm going to do next. Things have slowly been taking shape, so I thought I'd reflect and share a bit of my journey with you.

Forward

I spent three years working at Forward, first as an engineer and then as a product manager. Microsoft (my prior job) was drinking from a sprinkler, while Forward was a firehose. It was the most rewarding, impactful, intellectually stimulating, and stressful experience of my life so far. I'm proud of what we built together in that time.

Engineer

It was my first real software engineering job. I did "data science" coding for my job, had completed a bootcamp and side projects in my free time, and done plenty of hours on Leetcode before the interview. I think I was likely just “good enough” technically, and they primarily hired me because I was a good culture fit, and believed in the mission. Thank goodness I had a well-structured onboarding (shoutout to Charles), and could compensate for a low y-intercept with a pretty steep slope. I contributed new features to our internal EMR, helped get our first dermatoscope prototype off the ground, and ended up as tech lead for the new version of our bodyscanner, which is a person-sized kiosk (link to a demo video from an older ad) that automatically collects biometric data from members before their visit. With just a small team, we took care of industrial design and hardware, sensor integration and validation, and tied it together with a compelling UX. It was a ton of work, and more often than not I got home after 10PM, but I loved it. If I'm having impact, learning, enjoying the work, and teaming up with great people, long hours are more rewarding than tiring.

Installing an early prototype. An awkward but satisfying moment.

My goal as an engineer was to be able to build and understand technology, so in the future I can prototype anything I need, speak the language, and work effectively with engineers. It's also a profound education in problem solving, creating systems, and managing complexity, which is useful across all domains. I thought this would take at least two years, but after just one I realized I was already where I wanted to be. I wanted to play a bigger role in shaping our products to make our members happier and healthier, and help the business succeed, so I asked to switch into PM.

Product Manager

I'm grateful they were supportive of this job change. As the second product manager at the company, it was a role with real responsibility. I think they were receptive because I was coming from engineering, I was dedicated to the company, and I learned quickly. I also did 50/50 eng/PM for about six months to prove myself. Much of this time it was more like 80/80; for a while I was doing a weekly all-nighter (literally up until dawn) to get through everything on my plate. I saw this as a pivotal time in my life -- it’s not easy to transition to PM -- and I was willing to go through a brick wall to make it happen.

I helped ship quite a lot in the following two years. Improvements to the safety, usability and efficiency of our EMR, overhauling our genetics product, and upgrading our member-facing automated symptom triage and prescription flows stand out as proud moments. During COVID, we came together as I'd never seen before - working nights and weekends for months to adapt our product to the remote world, while providing members with top-quality information, testing and care. I was happy living at the intersection of research, clinical practice and technology, and combining them into great products our members loved. Few places are sufficiently "full stack" to flex all of these muscles at once. I really enjoyed the work and am proud of what we created.

Departure

So, why did I leave? The short answer is that I stopped looking forward to coming in to work on Monday morning. For nearly my entire tenure, I truly loved working there. When that stopped being true, I decided that life is too short.

The longer answer is, I approached my time at Forward with a burnout mentality, eventually I ran out of steam, and cracks started to show. As a cyclist, I like to approach other areas of life as an endurance sport, working hard and testing my limits. I knew the number of hours I was putting in was unsustainable, but I had plenty of energy to give, and I was okay with taking some real time off to recover on the other end. In the meantime, the mentality was to go as hard as you can, learn and move as fast as possible, take little time for vacation (~2-3 weeks over the last two years), and hope for the best. I made more progress, and lasted longer, than expected. It turns out it's energizing to work towards an important mission, work with a great, supportive team, and make tangible progress towards your goals.

The interesting thing is, I didn't just burn out and stop wanting to work; starting about a month into COVID, my performance just slowly deteriorated. As I got more tired, and overburdened with too many secondary responsibilities (in hindsight I wasn't very good at saying no), I wasn't as prepared for meetings, was less emotionally grounded and empathetic with coworkers, and was playing catch-up where I would normally have been on top of things. PMs always need to look a few steps ahead: where could this go wrong, how could this break, and where are we going. Keeping many balls in the air requires rest and focus.

I was gutted by my next perf review. I knew there were some areas to work on, but on balance I had grown a ton and had a real impact on the company. The message I got was loud and clear: fix these things now, or you're fired. Initially I felt so much shame. How could I have been blind how severe these issues were? I must have screwed up royally for whatever I did to offset all of the good from the last year.

After many conversations with my manager and others, it became clear that my performance wasn't "mostly bad"; I was 90% there and there were a couple key areas to work on, as I intuitively felt to be true. I'm a bit of a junkie for getting direct feedback, and am always excited to improve; in the weeks after the review I had already made real progress. But independent of the feedback, the way the process was handled just made me feel awful. I felt like we could have worked on a solution in real-time, as a team, but instead a case was built up, and a gun was held to my head to fix it. After grinding for the company for so long, this killed the passionate flame I kept burning for the company. Burnout came when I no longer felt appreciated.

My friends and family often asked why I worked so hard. After all, I was working more than some of my friends who were running their own companies. It certainly wasn't for the money. It was because I loved the work and I believed in the mission (and still do). Once I stopped loving the work, and I felt the mission could still be reached without me (the PM and design team was bigger now and gaps could be filled), I no longer had a good answer. So I decided to call it there.

I'm not sharing this to make anyone look bad, or to elicit sympathy. This is my story, and I'm sure others involved have theirs. I'm focusing on how I felt, which was the core reason for leaving. I know and accept that everyone involved had good intentions and was doing their best, and don't have any hard feelings. Human relationships are difficult, especially when people are working hard, and so much passion and identity is involved. I wish the team the best and will continue to spread the word that Forward is doing great things.

Isn’t it scary to actually pull the trigger? I'm in a privileged position. I have enough savings to live without working for a while. I have enough skills to get another job when needed. I feel (perhaps irrationally) optimistic that immigration concerns will work out. Yes, there’s a pandemic, but the tech world is doing fine, and will emerge stronger than ever. We work so hard in life to have the freedom to do whatever we want, and many of us stay in jobs we dislike anyways. I think life's too short, and there will always be other opportunities around the corner.

Rest

My first priority was to release all of the stress I had accumulated over the last three years. It's kind of funny to create a plan to rest. Step 1: sleep in. Step 2: do whatever you want. I spent some quality time with Emily (including a couple weeks in Mexico), I rode my bike, took photos, meditated, hiked, hung out with housemates, and read broadly.

Hiking in desolation wilderness with Emily and some of my great housemates. Right to left: Me (haircut needed), Emily, Taha, Lisa, AJ. Regarding the lack of masks: we’re all in the same household!

It's interesting how you only realize the burden you've been carrying when it's no longer there, like the hum of a refrigerator suddenly stopping, creating a deeper silence. It took time. A torrent of massive todo lists, backlog grooming, "bonus" projects, and frustrated internal chatter all slowly faded to the background, and a lightness and joy took its place. I still have productive days, but when it comes from a place of excitement, it gives energy and feels like play.

It's bad to always rest, or to always be stressed, but together there is greater satisfaction and growth. Like an athlete, it's important to break down and build back up stronger than before. But in life, rest is also important to ask whether you want to keep lifting weights at all. It has been just over two months, and my mind is clear, I'm relaxed and happy, and I'm feeling ready to return to a more productive state of existence.

What's Next

I've always wanted to start a company, and I figure this is a great time to give it a shot. I've built up good experience and skills, and I have few personal obligations demanding my time. It's scary, but my recent feelings of inadequacy are slowly being displaced by confidence. I know I have a lot to offer, and there are so many important problems to solve, so why not?

My high-level plan has three main stages:

1. Wandering: Go wide in looking at latest technology developments and problems that interest me. Explore interesting fundamental technologies.

2. Walking: Focus on one general area, more deeply understand and validate the relevant problems. Think of possible angles of attack and MVPs to test. Find people to work with.

3. Running: Build and test MVPs, solidify the team, raise some money, and go full speed ahead.

I'm still in the Wandering phase. Writing helps me consolidate what I've learned, and meet people with similar interests. I've gone to conferences for CRISPR and AI Drug Discovery research, read a lot of research papers, talked to builders and investors in mental health, edtech and pharma, read way too much Financial Times and The Economist, and am nearly done with my "NLP Specialization" on Coursera.

I'm told by those who have tried similar things before that it's a trap to commit to an idea too early, or too late. I want to proceed step by step, but boldly. I'll start Walking in January, when I'll be starting the On Deck founder fellowship. Hopefully I'll be ready for the Running phase by May.

Home for my 14 day quarantine, near Georgian Bay in Ontario.

As I write this from quarantine in Canada, I'm feeling reflective and happy. I'm grateful for the last chapter, having a chance to build some badass, good-for-the-world technology with some of the smartest people I've ever met. I'm grateful for the support structures (Emily, my co-living community, and my family) that helped me through the transition. And I'm fired up to see what's next.