Failure is not failing

Since a young age I’ve tried many different things. I’ve experimented, pivoted, tested, and pushed my way through a variety of skills, tasks, and learnings.

Throughout that time I’ve failed time and again. Projects fell apart, my technical abilities came short of the mark, and endeavors I worked toward didn’t meet my expectations.

That’s not all as bad as it seems.

In those failures I found learnings, I took away insights that helped me improve, and tweaked a few things here and there to do better the next time.

At one company a failure on my part cost the team five figures in lost revenue. I found the error, called it out to the team, and helped set in plan a way to never repeat that mistake. I will forever be grateful to leadership for supporting me, helping navigate the chaos, and trusting in me to keep learning and growing.

Growing comfortable with failure is critical in growing at all. Learning from a mistake allows us to improve and push forward. Fear of failure, fear of things falling apart leads to paralysis.

I’ve been incredibly privileged to have one main area of my life—riddled with wonderful and challenging failures—turn into something that became a career. As a designer I found companies and people willing to pay me for my design abilities. It was enough to cover the bills, and pushed me in the direction of learning more.

When I started fiddling around with websites, learning how to code, and messing with FTP, I found that tended to pay the bills even better.

Stepping into sales roles was terrifying, but it meant I had more ability to steer the project in a direction that could be successful. I tried out illustration, project management, product management, and then headed more toward product design.

When I tell the story of my career up to this point it sounds like a linear path from success to success. This isn’t even close to reality. There were times I felt lost, times I thought I should give up and walk away from the entire path I’d fallen into.

But I kept failing and learning, and somehow the thing I was becoming good at managed to pay the bills.

Now, years later, my career has fallen into a field ever growing and rewarding curiosity and continued failure.

Another element of all this has been the people around me. I haven’t pulled myself up by some imaginary bootstraps. True, I put in the effort and kept trying year after year. But I was also supported and helped by countless individuals who wanted to see me succeed, saw value in my attempts, and value in me. That, combined with my sometimes foolhardy desire to keep trying, has lent toward a wonderful, chaotic, and failure ridden life.

The next step I’m looking toward, apart from what I expect to be a lifetime of continued learnings, is if there’s a way to reduce the direct relationship between time and money, and if there’s a way to build on that with all the skills I’ve assembled.

I’m not sure if there’s an answer here. After all—while stumbling through this career path—I haven’t found it yet. But I’m ok with the not knowing, I’m ok with something that might require continued play, curiosity, and growth.

This is different, I hope, than the hustle culture of Silicon Valley that so many of us are familiar know. In my pursuits I’m replacing the brute force of time with curiosity and play. Instead of burning every waking hour I’m stepping back and thinking about where I want to go, where I want to improve, and what I’ll fail at next.

What I hope to tell my children, and what I share with anyone interested in listening, is a life worth living requires such a messy mix of characteristic.

Sometimes you just need to put energy toward a thing and see where it goes. Sometimes you need to stop and pull back, re-evaluate and be willing to close the door. Sometimes you just need to have a winning attitude, roll with the punches, and see where things go. Sometimes you need to say no to abuse, stand up for yourself, and face the results of your actions.

There’s no single answer to navigating success and failure, but the thing that’s kept me going is following what’s fun and interesting, what’s helpful to others and brings joy to people’s lives.

A day spent tinkering and finding answers, amidst failure, is a day that I’ll happily keep repeating.