Ever since I asked “What’s the point?” in a moribund business school lecture, I’ve been interested in healthcare.

No matter what my skillset has been since then, I’ve always wanted to apply myself toward healthcare. Coming down with a life-threatening chronic illness only gave me more vested interest. Over the last 10 years, I’ve tried to become a health practitioner, gone to public health and public policy school, consulted doctors, founded health startups, and more recently helped clients build their healthcare apps. The only thing that seems unchanged through all this time is my passion for healthcare.

Of all those opportunities above, the “one that got away” was a startup, MyPatientMatch (MPM). The blank canvas it offered was the culmination of my hopes and dreams. All my pent up anger toward healthcare regulations and inefficiencies, lack of research, and lack of patient-centered care fueled me for 2 years. I was a hellbent warrior with boundless physical and creative energy, and going that hard at the same problems every day was almost an out-of-body experience.

But you’ve heard entrepreneurs say you shouldn’t let your startup become your identity? It’s for good reason. The Tasmanian force of nature that I was did not translate into company success and because of this I spent my last year with the company in a pretty dark place. If it were a non-healthcare startup, I likely would’ve left much earlier. When you care deeply about something, have more domain experience in that thing than anything else, commit every day of 2 years to this thing, and still end up not really moving the needle, it’s impossible to not feel like failure incarnate when it’s over. Just to fully capture how emotionally devastating this was, I even stopped talking to the patients that used to be my tribe, because of how they reminded me of my shortcomings.

After I left MPM, I decided not to do another healthcare startup. That’s when I got started with freelancing for digital agencies and soon after founded my own agency in Topflight. Although my original motivation for starting my own agency was more about rebounding financially (e.g. “Time for steady paycheck after not taking a dime for 2 years”) and emotionally (e.g. “Let’s work on something I have zero emotional attachment to”), over time it’s actually become a place of constructive rehabilitation to get back to where I belong.

Initially I outright avoided healthcare clients, but I slowly found the courage to ease my way back in. Recently I’ve been helping some well-funded entities like university researchers and hospitals improve their digital strategy and mobile app experiences, and this experience has made me realize that working with high-caliber clients allows me to do with them what I failed to do on my own.

That stagnant needle that we couldn’t move with MPM, was now starting to wiggle. Redemption: 1, Ego: 0.

There are still times when I want to leave healthcare altogether. When a lead from a large hospital ghosts me or turns down a project after I invest weeks into scoping the perfect app, or when I fail to help a healthcare client get enough users or hit their engagement metrics, these failures affect me 10x more than when I’m dealing with non-healthcare projects. One time, I almost managed a million-dollar budget for a company that co-created Blue Button, but ultimately couldn’t meet their demands due to my chronic illness. It was the sort of day where I felt like Icarus for flying too close to my dream project. But I learned to accept that the hurt will keep on coming as long as I care deeply about the results. The point is to be ok with this, don’t get too high, and don’t get too low.

When I look back at the last 10 years, I feel blessed that I’m still working in healthcare and I still want to be here. Everything I’m doing now has something to do with previous hardships. If we didn’t run out of money during year 2 of MPM, thus forcing me to learn to code, I probably wouldn’t be building healthcare apps with my team now. Thus, I’ve gained a more spiritual view of my place in time: I believe I am where I’m supposed to be (roughly illustrated below), and that nothing happens according to my plan. The only keys to moving forward are always choosing the harder project, facing each day with a little more bravery than fear, and reminding myself that there will be many more failures in the business of moving needles. But oh is it ever sweet when we move them.