Hi Reader,

I can't help but think about my youth and simplicity.
Back when I played sports; games always ended with a winner.
Most tests had a defined solution.
Things often reached tidy conclusions.

Matriculating through the educating system, you realize what a set up that had been.
We would need a host of skills, talents, and luck to navigate successfully.
We would need patience to participate in the indefinite.

The more responsibility we gain over revenue or headcount, the more we have to find some comfort in puzzles.
Hindsight makes easy work of past challenges.
Great leaders have a way of shapeshifting the complex into simple, high leverage decisions.

I was experiencing my own little disconnect.
I love puzzles; therefore, startups and I get along.
But, if you stare at the big puzzle too long, you lose sight of the little mini ones along the way.

"You're never going to feel finished. There is no finish line."

This was a reflection Erin Hill, former Executive Director of ActBlue, said in our recent episode.
It was arresting.
She's right.

Life is a giant tapestry of mini puzzles.
We're often working without an image on the front of the box.
Worse, it's impossible to know if you have the complete set of pieces inside.

"I always assumed I would feel finished at some point."

Exactly. The universal leadership struggle.
I imagine this mountaintop.
After I meet a milestone KPI or sell a company, I imagine I get to hoist my flag on the ridge.

At times, those moments never come.
Other times, a win is dwarfed by the ground shifting below.
Sometimes, ambition immediately carries you to the next puzzle.

This episode was a not-so-subtle reminder of impermanence, stamina, and reflection.
Celebrate wins.
Pace yourself.
Keep objective prompts at the ready.

Erin led ActBlue for 17 years, processing $11 billion in political contributions.
When she finally stepped down, it wasn't because she felt finished.
It was because she recognized the work needed a different kind of leader.

That takes a different kind of courage.

How would you pace yourself knowing the race is indefinite?
How would you adjust your strategy if you fully accepted you didn't have all the answers?
How could you be easier on yourself to create internal sustainability?

Everyone has internal guideposts.
Using them helps us complete more puzzles.
Ignoring them, welcomes burnout.

🎧 Listen now wherever you get podcasts:
​Apple Podcasts | Spotify | YouTube​

Warmly,
Justin

P.S. What's your approach when you realize there's no finish line? I'm curious how other leaders navigate the indefinite game. Hit reply—I read every response.