A favorite organization of mine, Reboot has a wonderful newsletter that you can subscribe to here:

https://www.reboot.io/

I’ve written at length about their offerings in old issues of Carrot Cake (check the archive). The link below inspired today’s piece.

https://www.reboot.io/from-both-sides/

People are terrified by the word regret. I can’t tell you how many times I’ve heard people say, “I don’t regret anything. All of it has made me who I am today.”

If this is you, I understand the point, but you don’t regret anything? Are there no choices that you could have made that would improve where you stand today? I reckon that people say this to avoid the darkness of self reflection.

I ruminate on regrets as a favorite pastime. A helpful framing (from Reboot link) is below.

If you look back over your past and see mistakes, what were those moments? What do you wish you would have done differently? How do you approach similar things now?

In my experience, these are questions that you need someone else to ask. Someone who can ask them gently without judgement. Ruminating on regret without doing the reflection that Reboot suggests leads to low levels of self worth and getting stuck in the kind of stinky, grayish, low tide mud that will steal your joy and your flip flops.

A story.

I graduated from Babson in 2006, worked 12 months at EMC, quit, and was on the cusp of signing a lease for a very shitty second floor walk up space in Braintree where I would start the next chapter of my career. I cashed out the EMC stock that I bought through the employee purchase program (maybe 3500 dollars worth? Did I correctly file my taxes that year? Who could say.) and used it to buy barbells and rubber flooring. My plan was to be the next Mike Boyle.

Right around this time, I got a phone call while sitting on the couch at my parents house, where I was still living. My friend Carl was playing pro hockey in Norway. His team was getting ready for a playoff run and had a rash of injuries on the blueline. Carl, being the crafty prick that he is, convinced the GM of that team to offer me a deal to fly over and finish the season on their club. They’d find me a place to live and pay me a handful of Kroner each week.

I was anxious to get started on my new business venture, but truthfully, I was terrified by the prospect of flying overseas to play hockey. The idea of walking in to a locker room full of strangers as one of two or three “imports” was daunting.

I justified passing on the opportunity by saying that I had already signed a lease and had clients who were relying on me. This was way overstated. I could have started a shitty gym two years or ten years later.

I continued down that path and owned an unsuccessful gym for seven years. We trained a lot of high school and collegiate athletes and adult fitness clients over those years. It was a fulfilling, exhausting experience that failed. Hundreds of people got great results, but I was bad at business.

I had many prompt paying, delightful clients, but I also trained a lot of people for free. When the gym ultimately closed down, I had more pro-bono clients than I did paying clients. I still cling to a sliver of resentment towards people who trained there for years without paying. Some of the kids who were late or never payers (or their parents) went on to have really solid careers in college and the pros. Some of them have been interviewed on high profile shows or in magazines. I always secretly hoped for a little hat tip. “They never paid, but at least they were grateful.” Never happened.

I gave a lot of myself during those years. Could I have been a better business owner? Definitely. I should have spoken up for myself, but I rarely do. I should have fired bad clients, but instead, I slowly pressure cook my insides in silence.

This is why I insist on paying full freight to service providers who operate small businesses and I think you are an asshole if you don’t.

At least once a week, I consider what experiences I missed out on by not going to Europe to play hockey. It’s never about the hockey. The scars of regret stem from choosing safety instead of uncertainty and exploration. I’ve only ever lived in Pembroke, Quincy, Wellesley, Braintree, and Weymouth. Pull up a map and draw a circle around those places. Zoom out. It’s a small life.

So did I learn from any of this? How do I approach similar things now?

Last December, my brother Geoff and his wife Jenna had an opportunity to relocate to London for a couple of years for work. Geoff told me about the opportunity on a morning that we met up for bad iced coffee at Panera bread on Berkeley Street. I shared my regrets and implored him to go.

“You can come home at any time if it doesn’t work.”

I know they made their own choice but I was happy with my two cents.

The pursuit of a meaningful life happens out on the skinny branches and I push myself to shimmy out there as often as I can.

What do you regret?