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“Resisting pain only increases its intensity.” — Chogyam Trungpa

I am 47 years old and I have made a lot of mistakes in my life — both professional and personal ones. I hope I make many more.

It’s true.

I have hired the wrong people on my management team. I have taken too long to fire people after I realized they were wrong for the company. I have lost deals. I have signed deals that nearly killed my company. I have promised things I shouldn’t have. I went left when my entire team said to go right. I have neglected my family in favor of work. I have screwed up my personal finances. I have misjudged entire markets. I have made poor investments with no discernible analysis — just going with my gut. And, I have hidden my emotions when I should’ve just let it all out.

These are just a few of the mistakes in my endless list. But, I am happy I made every single one.

Why?

Because every time I zigged when I should have zagged was a moment for growth. With every painful moment, I learned loads about myself. I learned to be a better me — a person with more humility, less bias, an open mind, and better at making decisions.

I now embrace the pain that comes with original mistakes because, after some reflection, I’ve learned that its where the learning happens.

How do I make sure I learn when I make a mistake?

Below are the steps I take to make learning from my mistakes a conscious habit.


“Love your mistakes. Learn from them. Realize […] that personal evolution and mistakes, and imperfection [are] a part of our lives and know how to deal with it well.” — Ray Dalio

1 — Make time.

I take time every month and every year to reflect on my mistakes and what I call “key learnings.” I am usually away from the office. You’ll find me sipping green tea at a coffee shop. I’ll spend the morning thinking about the major missteps that month. For the annual one, it’s usually on a beach somewhere in the Caribbean during the week between Christmas and New Years. It’s amazing what a few margaritas, a little sun, and an ocean breeze will do to quiet the mind and awaken the learning genes.

2 — Write it down.

The mistakes aren’t always readily apparent. But, when they do become evident, you know. I usually get a sharp pain on the left side of my neck. That’s when it’s time to get it out of your head and write it down. I like to use good old fashioned pencil and paper — then I store it in Evernote. When I am in the coffee shop, I reflect on the ones from the past month. Every January, I write down the top three mistakes that negatively affected my goals in the prior year. I will admit, this is not easy. As humans, we tend to seek out evidence that confirms we made the right decisions and to ignore data that proves we were wrong. Take it from me, continuing with such an approach is just an act of self-deception. Avoid it.

I try to find cause and effect relationships between my decisions and my wiring. | Photo by Markus Spiske on Unsplash

3 — Reflect.

Self-reflection is the most challenging part of the process. Examining oneself is probably the hardest thing for we homo sapiens to do. I started meditating about two years ago — using the Headspace app. (I also do other forms of guided meditation.) Through this practice, I have learned to step outside of myself and really examine my actions, thoughts, and feelings. I try to find cause and effect relationships between my decisions and my wiring. “Have I made this mistake before?” I ask myself. I look for places where my ego is the primary obstacle. I look for biases that have crept in. It is only through this introspection that I unlock a better understanding of myself.

4 — Share.

This year I put my full list of mistakes for 2018 in an email and sent them to my wife. She was blown away and it opened an entire dialogue we’ve never had before. I shared my learnings with my team at work and they did the same. The act of sharing is a powerful tool for locking in your evolution. The communication — at least for me — brings closure and growth. Most importantly, I offer people an apology where it is appropriate.

“We have to do with the past only as we can make it useful to the present and the future.” — Frederick Douglass

5 — Evolve.

In the reflection phase, I make a list of the things I need to do differently to prevent making the same mistake again. Then — to evolve — I put those changes into action. I also add it to my master list of “key learnings.” When it’s time to make a decision again, I review the list to make sure I don’t relapse.


Mistakes and the pain that comes with them are your friends. In them, you’ll find a healthy dose of vitamins and minerals to fuel your personal and professional growth. Embrace them — especially the original ones.

Some of my favorite books on learning, bias, and meditation can be found here.