Embracing Regrets and Failure Resumes

by | Productivity

Freedom Journal goal

Daniel Pink's book The Power of Regret: How Looking Backward Moves Us Forward talks about why saying no regrets doesn't make sense and that we should all have regrets. If we didn't, it would mean we didn't try anything new or push ourselves. It's what makes us human and helps us get better. Having regret can improve future decision-making, boosts performance, and provides more profound meaning.

And by the way, the tattoo removal business is a $100 million-a-year industry. Take that in for a second. Wonder how many of those are removals of a tattoo that says no regrets!

He says regret is a marker of a healthy, maturing mind. People who don't have regrets would be seriously ill. 

If we don't regret our poor decisions, we won't make better ones in the future. We could be delusional, pretend it didn't happen, and continue making a wrong choice.

Failure Resume

Pink also proposed keeping a Failure Resume. I loved this idea and wrote mine down in my journal for the year. It reminded me of how Jocko Willink will say “good” when something goes wrong because he can learn from it. If leaders, business owners, and…well, everyone would talk about what they've messed up at, we might not be as afraid to test our limits, and we could keep others from making the same kind of mistake.

A ton of research shows that disclosing our thoughts, feelings, and actions by talking or writing about them brings us physical, mental, and professional benefits.

There are four foundational regrets:

  1. Stability and security.
  2. Missed opportunities.
  3. Moral – belief in our own goodness.
  4. Connection – neglecting people who give our lives purpose.

I've written 1.5 pages of failures so far and will share a few with you here.

Ironman 004 Marcey
Ironman Wisconsin
  1. Launching the masterclass in March 2020 during COVID is self-explanatory. I thought about postponing it, but I don't believe it would have helped if I had, and we would have never guessed it would have lasted so long. I had worked for months leading up to this launch. While I don't feel like there is anything I could have done, I consider it a failure because of the small number of people who joined. It ended up being a tight-knit group, and we had core members who received the equivalent of private coaching for a minimal investment, but as far as launches go, epic failure.
  2. Not finishing my first Ironman. It was raining cats and more cats, and in the 50s. An epically miserable day where I got hypothermia so bad, I ended up paradoxical undressing and was pulled out. I was told I could go to the warming room or home, but I couldn't continue.
  3. Making an insulting statement to the physical education majors at my university when I was a junior and giving a presentation on my Exercise Science program. I still feel bad about it.
  4. Being a roommate. In my first year, I roomed with my best friend, which was a big mistake. I thought as an extrovert, I would love dorm life. I'm really an ambivert and need a LOT of privacy. Turns out I don't enjoy living with anyone, and the one roommate I had that I got along great with was because we had completely different schedules and were hardly home at the same time. My friendship with my high school pal was never the same.
  5. Testing out the Tip Jar with this podcast! Many podcasts take donations and gifts to fund them, and we thought we would try it out too, because people listening told us to. It didn't align with our brand and while people are willing to pay top dollar to invest in a workshop or coaching, investing in the podcast wasn't a priority. The people who suggested it didn't even tip us themselves, so we ended it.
  6. Training for ultra-endurance events when I was also traveling 48 weeks a year. I was gone all week for work and then from my husband on the weekends to train. No bike ride, run, or swim was worth the strain it put on my marriage. 
Freedom Journal goal
Todd Rader, me, and Lilly Ferrick discussing Lessons Earned in 2016.

Every month, quarter, and year I reflect back on Lessons Earned. I started doing this several years ago with my friend Lilly Ferrick and my brother, Todd Rader. We still do it. My Speakers With Impact mastermind does it every month, and we always learn from each other. In my Powered Path™ Playbook, launching in 2023, Lessons Earned is a prompt.

I challenge you to start your Failure Resume. If you can't think of many, I challenge you to do more hard stuff. Sara Blakely, founder of Spanx, had a dinner ritual growing up of her dad asking them to share their failures, and he would celebrate their efforts.

Write down your failures and celebrate the efforts that have made you who you are today.

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“Your Weekender Snapshot and Tim Ferriss’s Five Bullet Friday are my favorite emails I receive.”

jim west

Principal and Managing Director, GFF Architects


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