What motivates you to do the impressive things you’ve done in your life? Where does that inner drive come from?
I know where it comes from for me because I’ve been asked the question many times, whether it’s about running 100 miles, writing a book, etc.
Much of my motivation stems from a fear of regret.
It’s true. Anytime I’m on the precipice of taking an important, growth-minded but uncomfortable action, I ask myself the question:
Am I going to regret it if I don’t do this?
When I ask this question, I envision myself 1, 5, 10, 25 years in the future, and whether the answer is yes or the answer is no, it makes the decision easier.
For example, two weeks ago I ran the Lake Wobegon Trail Marathon with my brother. It was our 14th marathon together.

Finish line in St. Joseph, MN, 10 miles from where we grew up
Anyone that has heard me talk about this race knows it has a lot of sentimental value.
It starts in a small town called Holdingford, runs through Albany (our hometown) and finishes in St. Joseph about 10 miles away.
And when our parents were alive they both used to come out to cheer us on. I remember that like it was yesterday.
So when the opportunity came to be able to do the race this year, I jumped on it.
Logically, it didn't make a lot of sense. It was a week after my wedding, I hadn't done that much training and, quite honestly, I would have rather been in CO relaxing and spending time with my new bride 🙂
But when I learned my brother was randomly going to be in MN (and when I got the bride's blessing!), I knew I would regret it if I didn't do it. The decision was easy.
And I'm so glad we did. Life happens and I legitimately don't know when, or if, we'll ever do the race again.
Not sure how this message is landing with you but whether it's a micro daily decision to stretch yourself or a macro one-time decision like a marathon, questioning it through a regret filter might help make the answer for you.
Keep Outperforming,
