Permission to Screw Up

I’m currently reading this book by Kristen Hadeed:

I’m not finished with the book yet. So far, the book really has nothing to do with being an artist. And at the same time, the book has SO MUCH to do with being an artist.

When she was in college, Kristen Hadeed accidentally started her own, now very successful cleaning company, Student Maid. This book details the many ways in which she royally screwed up as her company grew—and how those very failures are what led to the company’s explosive growth.

I’m very slowly working my way through this book. It’s not a long read, but it’s taking me a very long time to get through it. Why? Because I’m a perfectionist (there, I said it), and reading the many detailed analogies of her failures gives me more than a little anxiety. I normally like to set aside at least 30-40 minutes to read each night right before bed. I can’t do that with this book, because I literally cannot relax while reading it.

This has given me cause to reflect (ding!) on my perfectionism, especially as related to my own business that I started in college—i.e. being a professional musician. Nathaniel Sullivan, Inc. (I’m not actually incorporated.)

Ms. Hadeed’s primary thesis seems to be that by leaning into the possibility of failure and embracing the challenge of fixing one’s own screw-ups when they inevitably occur, growth and innovation are cultivated. A secondary, more understated thesis that I’m picking up on is that, as a leader, you foster empathy and understanding for those in your managerial care by getting your own hands dirty and owning your own mistakes.

As an artist, I am my own leader, manager, and employee. And as a perfectionist, I seem to check Seth Godin’s box of being my own worst boss:

If you had a manager that talked to you the way you talked to you, you’d quit….If an organization developed its employees as poorly as you are developing yourself, it would soon go under.

Reading this book has encouraged me to not only own my mistakes and failures, but to actively seek out opportunities to facilitate failure. Not to purposefully fail—I’m not going to start missing appointments on purpose or waiting till the last minute to prepare for an audition or anything—but rather to remove myself from the safety net of perfectionism. To purposefully place myself in uncomfortable situations where failure is more than an anomaly, and more like a probability. And then, when those failures occur, to own the failures and to offer myself the opportunity to grow in the process of fixing them.

As an artist, that’s how I’ll do the good work. By giving myself permission to screw up.