Permission to Fail, or the Best Gift I Ever Gave Myself

A couple of weeks ago, I bumped into a woman on LinkedIn. We connected, got to chatting, and we realized that we had much in common. As it turns out, Shira Miller is writing a book about thriving in turbulent times. Considering that I’ve spent the past several years surviving and finding new paths forward, she thought I might be a good person to talk to on this subject. Shira sent me three questions to ponder. And yes, overachiever that I am, I answered all three, but it was this question that made me stop and think:

How can we learn to trust ourselves?

Hmmm, how can we?

In the beginning…

Despite the fact that I’ve been coaching for years, Ad Meliora Coaching (my practice) is relatively new. I launched in the autumn of 2019; however, because of a long-planned trip to Tanzania in January of 2020, this really meant that Ad Meliora Coaching got going from a business perspective in February of 2020. So yes, I essentially started my own business just as a global pandemic hit its stride.

Oy vey. And I’m not even Jewish! Could my timing have been more off?

I did the only thing that could do: I started. In the beginning, I did some really stupid stuff like approach people on LinkedIn about coaching, neglected to use coaching contracts, and did my “billing” via email. And as you might expect, I cratered pretty hard. I was chastised by people on LinkedIn, I got burned by a few clients, and for several months I had no idea if I was making any money or not. (News flash: I was not.) If I could make the wrong move, I did. Here are some things the voices in my head said to me:

• If you screw this up, we won’t have any money and we’ll never be able to retire. Your stupidity could take down everything you and Joel have worked for! You should just go get a job.

• you’redoingitwrongyou’redoingitwrongyou’redoingitwrongyou’redoingitwrongyou’redoingitwrongyou’redoingitwrongyou’redoingitwrong

• You need to work a lot harder. You’re not doing nearly enough. Stop being stupid and do this right.

If you think that is fun to read, try listening to those klaxon warnings on repeat. I’d been expecting perfection, expecting that I could build something from nothing in the middle of a global pandemic, expecting instant success. None of this was realistic. So, I sat my sad, bewildered self down, and I took a good, hard look at what I was doing. As an agile coach, so many of the practices that I have with teams come home with me as well. That got me to thinking about retrospectives. During a team’s retrospective, I generally ask three questions:

• What are we doing well?

• What isn’t working for us?

• Where can we experiment?

To my thinking, not much was going well, pretty much everything wasn’t working, so that left me with experimentation.

The experiment I chose? Failure. I gave myself permission to fail.

The Gift of Failure

Yes, it’s okay for me to fail. I failed in the past, I’m certain that I’m doing something right now that will fail, and I’ll fail in the future. And do you know what? That’s okay. I’m doing so many things this year that I’ve never done or even thought to try (sales, marketing, building and launching my own product) that it would be ridiculous for me to think that I’m going to do everything right the first time. I couldn’t walk or ride a bike the first time that I tried, but I practiced until I was able to do so. So, I fail, but I fail forward. I take a hard, objective look at what I’ve done, noting what worked, what sort of worked, and what didn’t even get off the ground. I ask for feedback from people that know more than me.

And what happens? I get better, I improve, and things move forward. I build trust with myself because I don’t expect perfection on the first try. By giving myself permission to fail, I give myself grace, I grant myself trust.

Permission to fail is a deep breath, a confession. Permission to fail is the covenant I build with myself. By making failure something to be accepted, I learn to trust myself to overcome that failure. I trust myself to survive failure because I’ve done it before. I trust myself to learn from my experiments, from my mistakes. I trust myself to do better the next time. I trust myself to get up.

By giving myself permission to fail, I’m also trusting myself that one day I’ll succeed beyond my wildest dreams. There is that Glennon Doyle quote, “The braver I am, the luckier I get.” That is me. I do all kinds of stuff now that I never ever foresaw that I would do, and a bunch of it scares me half to death. But I do it anyway. Because I’ve done and survived other things that scare me, I know that I can do the next terrifying thing and more than likely I’ll live through that. I might like it, and at the very least, I’ll learn from the experience.

Giving myself permission to experiment, to fail, was the kindest of gifts. That simple act removed pressure and opened doors. It also helped me to see that while there is seldom a good time for anything, now is the perfect time to build trust.

The image used for the title of this blog post was captured by Linda Nickell. Connect with her on Instagram as @coznlinda.