Fail Hard & Often

by | Jul 23, 2025 | 40 to 40, Mindset | 0 comments

T-15 Days to August 7th

Themes are beginning to emerge through these stories and the conversations surrounding them.

We all want to live better lives.

Most of us are scared to try.

We’re scared of rejection. We’re scared of the painstaking effort it will take to make progress. But most of all, we’re scared of failure.

It’s been common rhetoric since I was a kid (and I haven’t seen evidence that it’s changed) that failure is a bad thing. That success lives in a state of duality—if you’re not succeeding you’re failing. No in-between, no grey area, no margin for learning.

This mentality is drilled into us especially hard in the workplace. Where failure isn’t only frowned upon, it’s often met with repercussions.

Failure, without a shadow of a doubt, is the best way we get to learn and grow.

Failure is a signal that we’re trying things that are hard, that we’re expanding our mindsets, and that we’re engaging the brain’s neuroplasticity.

My biggest regrets in life are that I didn’t start things sooner. That I didn’t start saving for my future until I was 35. That I didn’t learn to swim until I was 37. That I didn’t pick up the guitar until I was 38.

To an outsider, this may seem inspiring. Proof that an old guy can still learn new tricks. And with that perspective in mind, I’m happy to share my stories.

For me, I’m forced to imagine what I could have learned if I’d had the courage to fail in my teens and 20s.

Let us fail hard and often, iterate on what we learn, and become the people we desire to be.

I Regret Not Failing Sooner

About 40 to 40
In the 40 days leading up to my 40th birthday, I’m sharing 40 lessons I’ve learned over 40 years. One each day. Some are stories. Some are truths. All of them are Letters to my Former Self—and maybe yours too. You can view all stories in this series by tapping here.

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