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How to Fail

For the last eleven years, I’ve served as a part-time ACT/SAT verbal tutor while working in and out of the entertainment industry. Tutoring kids all over L.A. helped me pay down some substantial graduate student loans (don't worry, the irony's not lost on me), and I’ve enjoyed it.

Helping teenagers with grammar and reading reminded me of my favorite times in adolescence. My dad or half-brother would help me prep for my math or French finals beneath the Japanese juniper tree on our front patio on warm spring days, and we'd have fun. Tutoring also revealed to me that I genuinely like helping people get from point A to point B (hence the pivot to life coaching).

In tutoring more than one hundred students, I’ve learned more about learning, and I’ve learned more about failing. Having been part of Big Test for quite some time, I


can see how our schooling system sets us up to think so negatively about failure.

I wish it were different.

Of course, people should learn the basics (i.e., the difference between independent and dependent clauses, how to read/glean information quickly from something you don’t care about, etc). But with so much riding on getting the right answers during our formative years, we begin to condition ourselves into believing that if we don’t always get our desired results, we must’ve failed. We begin to repeat the message that if we continue to color in the lines and do what we’re supposed to do, obeying what I call “the silent rules we all agree to” in society, we’ll succeed.

And yet, when so many adults go through the motions of life perfectly, they still end up feeling so incomplete. Lacking.

Failure is (and always will be) a part of life. Especially if you pursue something creative. And I don't believe that it's a bad thing.

Here's why:

  1. Failure means that you showed up. Stepping up to the plate and trying something new means you didn’t stay in your comfort zone. You took a risk. It would’ve been way easier to do nothing and avoid that still small voice guiding you to do something new and different. The effort needs to be applauded.

  2. Failure is an action, not an identity. "Separating the problem from the person" is one of my new favorite expressions because it creates distance between the supposed failure from the identity of the person. We humans have a tendency to “overown” our mistakes; we believe that one failed action points to an overall identity as a failure. But that’s not necessarily true; it’s only when that one action is repeated that it can become part of an identity. (And if you think about it, that’s pretty rare. People generally stop repeating the same failed action when they see that it doesn’t work).

  3. Failure presents an opportunity for learning (If you look for it). As Jerry Seinfeld once said, “Pain is knowledge rushing in to fill a gap. When you stub your toe on the foot of the bed, that was a gap in knowledge. And the pain is a lot of information really quick.” Whenever I’ve reviewed not-so-great results with my tutoring students, I’ve tried to see their mistakes as messengers from areas of knowledge that need to be improved. If we go back to the Seinfeld example, not only can you learn about failure as it pertains to that particular situation, but you can use that knowledge to assess similar yet unfamiliar situations (i.e., another bed in, say, a hotel room). Failure can provide you with knowledge that helps you in the future.

  4. How can the circumstances still serve? Back in ‘18, I was up for a job at WB that I didn’t get. Had I gotten that job, I look at my life in retrospect and see a different, “Sliding Doors” version that I don’t recognize. I see so many job, learning, and friendship opportunities that I would’ve missed out on. Not getting that job served me because they gave the life that I was meant to have. I'm grateful for that.

How about you? What are your thoughts on failure? Feel free to share them below.


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