#46 - Why I paid an Accountability Coach for 2 years. And why I stopped.

All my adult life, I’ve been in search of the perfect “groundhog” day. A day so perfectly designed from sun-up to sun-down that, if executed every day for the rest of my life, would help me achieve all of my goals.

And when I moved to Boston 3 years ago, I had a lot of goals.

• Become a highly-respected name inside my company, Boston Dynamics.

• Build a million-dollar side-hustle outside work hours.

• Become a lethal pickup-basketball player.

• Get (and stay) in the best shape of my life.

• Write a newsletter with a massive following.

• Call all of my friends back in Canada regularly.

• Maintain and grow a network in Boston.

• the list goes on...

I crafted a long list of habits that I felt were the right set of inputs for all these goals. And I tried my hardest to stick to it.

But I just couldn’t keep juggling all those balls for more than a few days before one or two dropped. I made progress on all those goals, but could never declare victory on any one of them.

Of course, my self-flagellating mind chalked this up to a lack of effort on my part. I could do all these things, if only I had the grit to stick to the program.

So about a year after landing in Boston, I went on Fiverr and hired a great guy named Michael to be my ”accountability coach”.

Every morning, I’d text him Michael a plan for the day. And every evening, I’d text him a reflection on the day along with screenshots of my habit tracker.

In the year that followed, my effort and consistency improved, but my results were more or less the same. I never “broke through” on any of my goals, and I’d still drop a ball every few days.

Until 8 months ago, when I wrote my first line of code for Wednesday Waffles.

That’s when every ball dropped.

There’s discipline and then there’s devotion. Discipline is about forcing oneself to act, often through self-control and willpower. Devotion is a more natural, love-driven commitment that makes actions feel effortless.

I was disciplined with my habits. I was devoted to Wednesday Waffles.

Waffles was—is—an opportunity to make a meaningful difference in the world, and do it while working alongside some of my best friends.

Few things feel as important when compared to that. And, honestly, few things are.

Some things—like staying healthy and spending time with your loved ones—are important no matter what season of life you’re in. But some things—like working on your lefty layup at the YMCA—are not. You need the wisdom to know the difference.

But out of sheer habit, I kept working with my accountability for a few months after starting Waffles. I’d send the morning plans and evening screenshots, same as before. But my heart wasn’t in it.

I gave myself permission to let go when my father passed away. He lived “groundhog day”, working tirelessly towards every one of his professional goals every single day, until the day that he died. And it didn’t look fun.

I’m now choosing to see life as a cycle of seasons—each with its own weather, each asking something different of me.

This season is Waffles. My job is simple: show up, ship joy, repeat.

So I’ve thanked Michael for all his help these past couple of years and am now taking things one day at a time.

My new metric for a good day is one line long: Did I push Waffles forward? If the answer’s yes, that’s victory.

Some balls have dropped. Rubber ones—like learning how to dunk—bounce. The glass ones—my health, the people I love—will stay in hand.

Everything else can wait til next season.