Burning Out and Finding Stability

Earlier this year, I experienced my first panic attack. It was easily the worst experience of my life. I’d like to think that I’m a mentally strong person, especially after being independent for so long, but this broke me. The perfect storm of uncertainty, pressure, and overwhelming responsibility led me to completely spiral out of control and transformed me into a fragile, easily-triggered version of myself. I found a way through it, but even months later, I’m still recovering.

My first burnout happened in 2014. I was a full-time freelancer and naively said yes to every job that came my way. Back then, I viewed tight deadlines as a challenge—a great story on top of a great portfolio piece. This time, however, I took on too much work. For two months straight, I worked all day, all night, and every weekend. I crashed each night, then woke up and did it again. After crawling across the finish line, I felt mentally and physically defeated. I needed a break, but I also needed to recognize that I actually have limits.

After taking a proper vacation, I extended my time off to build Cushion—a freelancing tool that could help me avoid burnouts by visually forecasting my schedule and income. I desperately needed an app like this, so I designed it specifically for myself. With Cushion’s help, I was able to establish a comfortable balance between freelancing and working on Cushion itself. I absolutely loved this rhythm—freelance for one month, so I could afford to spend two months on Cushion. Instead of seeing time as money, I saw money as time. How much time could a freelance gig buy me, so I could keep working on Cushion.

Eventually, Cushion became my full-time job. Working on my own product day-to-day and supporting myself with its income was the bootstrapper’s dream. I always pictured myself reaching this point, then maintaining it until I retired—riding into the sunset. As time went on, however, I felt like I was limiting myself and Cushion. Wearing every hat meant wearing only one hat at a time. When I was designing, I wasn’t coding. When I worked on the front-end, I wasn’t working on the backend. Cushion had so much potential and I didn’t want to hold it back, so I hired Larry—a much better backend dev than me. By taking a giant weight off my shoulders, we were able to make progress in parallel, and I could focus on what I’m actually good at—design and front-end. With Larry, we were able to ship twice as fast and launch features that I only dreamed about. At the same time, our costs snowballed overnight. I was completely new to paying salaries, employer taxes, healthcare contributions, and workers comp. My comfortable rhythm instantly became a free fall.

For several years, we were able to make it work, but this past year was especially hard. Instead of the one month freelancing, two months on Cushion, I freelanced three days a week to support both of us, then worked on Cushion every other waking moment. I also cut my salary to the lowest I could legally pay myself, in order to keep payroll low. It was really difficult at first, but then we found stability with a longterm client who got us through the year. Going into 2019, I finally felt like we were on the right path. We had a few ideas that could take Cushion to the next level and enough of a financial “cushion” to lead us into summer. Then January happened.

When you run your own business, tax season hits hard—especially when there are surprises. I remember the moment I learned how much we owed. I remember how the numbness that I typically have for news like this was completely gone. I remember the thick skin that I developed from years of freelancing becoming a thin paper shell. I found myself spiraling. Our 7-month cushion instantly became less than two. To make matters worse, we under-budgeted and over-promised on our latest client gig, which would only buy us two extra months for at least six months of work. I felt mentally paralyzed. For weeks, I’d wake up in a panic around 3am and just lie there—my mind spinning—until I got out of bed hours later. During the day, I felt tightness in my chest and couldn’t fully breathe. My body was in a constant state of agitation.

I tried everything to calm myself down. I switched from coffee to tea. I tried rhodiola drops and CBD. I started meditating and using breathing apps. I went to acupuncture and took sleep aids at night. I spent as much time as I could with friends to distract myself from the thoughts that would cause me to spiral. Some things helped, but most of them didn’t because I was still in the same situation—running out of time, running out of money, while people relied on me to come through. Then, on Cushion’s 5-year anniversary, I experienced my first panic attack.

I like to think that our bodies can communicate with us in their own way. This panic attack was my body screaming at me to eject from anything causing the stress and anxiety in my life. I needed stability now. I can vividly recall my body taking the wheel and instantly knowing what to do, as if I were hypnotized at the snap of my own fingers. No one could’ve convinced me otherwise because nothing was worth what I was going through. As soon as my health was at stake, there was no longer a decision.

Over the next couple weeks, I took several steps towards a healthier, more stable life—no matter how drastic the changes. I told our freelance client that we couldn’t finish what we were hired to do, regardless of how humiliating it was to admit. We gave the remaining money back and apologized for throwing a giant wrench in their plans. I told Larry how unhealthy I felt and that I needed a break from the month-to-month sprint. Larry already knew because he could visibly see it on me, and he was ready for a change, too. I told a few friends what I was going through and that I needed to find stability. At first, it felt embarrassing, as if I failed or gave up, but a close friend of mine reminded me that after exhausting myself by sprinting uphill for so many years, I deserve to run downhill for once.

Several weeks later, I found stability—by joining Stripe. It’s still shocking to think about, but I know, without a shadow of a doubt, that it was the right decision—for my own sustainability. I need to be able to work without worrying where the money is coming from. I need to be able to switch off at night and actually enjoy weekends. I need to be able to take real time off without being the sole person on-call. Coming off the most nightmarish time of my life, Stripe has been the comforting environment that I’ve so desperately needed.

With Stripe’s history of hiring founders, they know exactly what I’ve been going through and were incredibly supportive throughout the process. They understand that Cushion is a big part of me, so I’m still able to run it as the longterm side project that it started as. My work environment isn’t changing either—I’ll continue to work out of the comfort of own my studio space in Brooklyn. The most exciting part, considering my freelance work, is that I’m joining the legendary Site team to work on, which couldn’t have been a better fit for me. For years, I’ve marveled at the quality of work that comes out of Stripe, and now I get to be a part of it.

Note: If you overwork yourself and feel like you’re burning out, stop what you’re doing and find stability—whatever you’re working on isn’t worth your health. Don’t feel the need to “hustle” because some people glorify it. Doing good work while living a healthy life is much more respectable.