Cultivating failure
Why it matters and how to make our failures work for us.
Reading time: 5 minutes
This post is a bit different from what I typically write, so I hope you’ll find it useful. I’ve been thinking about failure a lot lately.
First, some context: I’m working on a collection of short stories that I’d like to publish someday. Plus, I love literature, but I’ve never had the opportunity to study it. So, I applied to four of the most competitive MFA programs in creative writing and got rejected by all.
In the startup world, we talk a lot about failing fast and failing often, but almost no one talks about cultivating failure in our careers and in our lives.
Who doesn’t want that perfect resume—ex-Apple, ex-Zoom, ex-Figma, ex-[your favorite brand]—on our LinkedIn profile? When we see such profiles, it’s natural to think that this person has made the perfect, right decision at every step of their career. How brilliant!
Maybe.
Maybe they had some luck.
Maybe they had someone who gave them good advice at the right time.
Maybe they knew the right people at the right places.
Whatever it may be, thinking this way is not helpful to us. In fact, it hurts us and keeps us small.
I recently attended Guy Kawasaki’s (evangelist for Apple and Canva, author of 13 books) talk about his latest book, Think Remarkable, and one particular point he made stayed with me:
Make decisions RIGHT.
He talked about the time he passed on the opportunity to work for Apple again during the iPhone years and Yahoo during its heyday. Don’t we all have stories like this? I’m the genius who passed on the opportunity to be a core member of the Amazon Prime team in 2006 🤦🏽♀️.
Sometimes, we make poor decisions. We stumble, we make mistakes, and botch things up.
But whatever choice we make, Kawasaki tells us, we have the option of making it right. Making it work for us. We can commit to our choice and give it our all. When it doesn’t pan out, we can pivot. We can make a different choice when another opportunity comes along.
What does cultivating failure mean?
Angela Duckworth, a renowned psychologist, has extensively researched the concept of grit. She defines it as a unique blend of passion and perseverance for long-term goals. In her work, she emphasizes that grit is a significant predictor of success, often more so than intelligence or talent.
When we fail at something that really matters to us, and we double down and do not quit, it grows grit. I’ve been thinking about how we might apply this to our careers.
Feed our passion: Like me, you might have a particular aspect of your work life that deeply pulls you. For me, it’s storytelling and narrative. When we find this, it feels like falling in love—exciting, terrifying, daunting. I object to using the word “calling” as I get seized up in terror, but whatever we call it, IT chooses us rather than the other way around. When we find this, however scary it may be, let’s feed this passion. Let’s take the risk that others might not. When we feed our passion, it will eventually—and I firmly believe this— feed us.
Repetition: We learn by doing. By repetition and by making mistakes. Nothing can replace 10,000 hours of practice. So when we don’t get that promotion or that raise or that rejection letter (as in my case), let’s not just change jobs for a better title or simply give up. It may feel good in the short term, but it won’t serve us in the long run. Remember The Peter Principle? We all rise to the level of our incompetence. If we chase success without growing our capability (not just functional skill), then we are only hastening our ceiling.
Beyond us: If all we can think about is our promotions, raises, accolades, and praises, then we are constantly looking outside of ourselves for validation and approval. The world may occasionally notice us and bestow its benevolence, but then it moves on. What then? We collapse into ourselves. We feel unworthy. We think uncharitable thoughts towards our more successful peers. But if we look for a greater purpose beyond personal gain (service, contribution, making something that gives you great joy) and anchor in that, then we don’t get tossed about when the world forgets about us (which it will eventually anyway).
Reflection: When I botch things up, be it in my functional area, with my bosses, or in my interpersonal relationships, I would either (a) beat myself up or (b) blame the other party. Over the years, I’ve learned to be more kind to myself. Poor, silly, bumbling, clueless me. How did I get myself into this situation? Did I make some assumption that I should not have? Did I respond from a place of insecurity, ego, or fear? Reflection, I found, grows my grit muscle. The next time something similar happens, that muscle will remember. Now I have a choice of how to respond. I don’t know who said this (the Internet says it was the Greek philosopher Epictetus, and who am I to question the Internet) — “It’s not what happens to you, but how you react to it that matters.”
Reframe: Failure turns into grit by reframing. Yup, the annoying glass-half-full person speaking here. That doesn’t mean I don’t whine. I do. I routinely have “wine and whine” sessions with friends. But then, once that’s done, I try not to wallow. I try to walk the steps of my failure again and reframe it. Often it looks like this: “Ok, that super sucked. I bunged it up. But I learned something. This is just a little hitch in my very long growth journey.” Revisit. Revise. Reframe. Keep going.
Growth mindset: There are so many definitions of growth mindset (just Google or chatGPT it). But the bottom line is that fixed mindsets are not curious, not open to change, not open to being challenged, and not open to learning. A growth mindset is the exact opposite. Cultivating this openness is a constant, ongoing work for me.
I’ll end with a quote from one of my favorite writers, George Saunders:
“Don’t be afraid to be confused. Try to remain permanently confused. Anything is possible. Stay open, forever, so open it hurts, and then open up some more.”
What about you? What were your recent failures? Share them here and lighten your burden.