My brother Kevin posed this question to me recently on an Untapt work trip. It’s a question he uses often in his counseling practice, and it’s one we’d all do well to reflect upon.

As I did so, I came up with two “collections” of answers. One collection I’ll call, “How I’ve historically related to failure” and the other, “How I’m learning to relate to failure.”

Historically? My Type 3 Enneagram profile summarizes it well: “You can smell failure from a mile away and you run in the other direction.” When I’m operating out of this mindset, I’m constantly running analyses on my likelihood of success and only taking on projects where I feel confident in my ability to control outcomes. 

There are some benefits to this approach:

• Racking up lots of W’s (albeit in an artificially-constructed game)

• Looking impressive in the eyes of others

• Avoiding the negative emotions related to failure (anxiety, shame, embarrassment, etc.)

But there are some serious downsides as well:

• Lower ceiling for what you can accomplish

• Fewer opportunities for both skill and character growth 

• Increased likelihood you’ll die with regrets

It was that last one that really got me. I didn’t want to get to the end of my “successful” life and think, “Gosh, what might have happened if I had done this or tried that?” 

I decided I’d rather take a few more “losses” if it means I get to die with fewer “What if’s?”

In this new and improved relationship with failure, there are only two ways I can lose:

1. If I let fear keep me from trying something

2. If I fail to learn from an experience 

It took me a while to get here. And I still revert back to my old relationship with failure every now and then. But for the most part, I feel like I’ve crossed the threshold. And what I’ve found on the other side is a tremendous amount of energy and freedom. 

It’s like a cheat code for life. When you’re no longer afraid to fail, you become like the poker player with the biggest stack. You’re able and willing to take more risks…which, in turn, allows you to win more hands. When you’re free to fail, you’re also free to flourish like never before. 

At least that's been my experience. But I'd love to hear from you:

• How has your relationship with failure evolved over the years? 

• What is one thing you would do if you knew you couldn’t fail?

• What resources have been helpful to you on this topic?

I'm genuinely interested to hear your thoughts. One of the biggest reasons I'm excited to start this newsletter is to learn from you all. Drop me a reply to keep the conversation going.