The Top 57 at 57: The Only Award I’m Probably Going to Win

Every year, on or around my birthday, I give myself an award.

Not the kind anyone else would recognize.
No stage.
No audience.
No polite applause.

Just a list.

It’s a shortlist of things I’ve learned.

Or more accurately, things I’ve finally stopped arguing with myself about.

Not the big, impressive lessons.
Not the ones that sound good when you say them out loud.

Just… what actually feels true. To me.

This year, I turned 57.

So this is my Top 57 at 57.

The only award I’m probably ever going to win.

What’s strange is that none of these feel new.

There were no breakthroughs.
No defining moments.
No sudden clarity that changed everything overnight.

It’s been quieter than that.

More like noticing what’s already been there.
Patterns I’ve seen for years, finally refusing to ignore them.
Perhaps things I’ve known for a long time, but only recently decided to trust myself with.

I’ve realized that most of what I call “thinking” is just circling in my head and in the “air”. Thinking about… thinking.

That clarity doesn’t arrive fully formed.
It shows up after I start.
After I commit.
After I remove the exits and escape routes.

And that most of the friction I feel… isn’t the work.

It’s the resistance to choosing.

I’ve spent years building systems, frameworks, ways of seeing things.

Partly because I enjoy it.

But mostly because I don’t tolerate chaos very well.

(Although, if I’m honest… some of that chaos is self-inflicted.)

Not external chaos - that’s everywhere, now.
Internal chaos.

The kind that comes from too many options.
Too many directions.
Too many things that could work.

If this “award” measures anything, it’s probably this:

What I’ve stopped pretending not to know.

I don’t need more ideas.

I need better filters.

I don’t need more time.

I need fewer directions.

And I don’t need to figure everything out.

I just need to stay on course long enough for things to start working.

There’s also a quieter realization underneath all of this:

Not everyone wants to see what I see.

And that’s fine.

Because the work isn’t to convince people.

It’s to make things clear enough that the right people recognize it immediately.

So this isn’t really a list of lessons.

It’s a set of selections.

A personal shortlist.

Things I’ve noticed.
Things I’ve tested.
Things I’ve gotten wrong enough times to finally stop arguing with myself.

Some are obvious.
Some are uncomfortable.
A few I’m probably still resisting.

But they’ve held up. At least for now, this year.

And for now, that’s enough to make the list.

If you’ve never done this before, I’d recommend it.

Once a year. Around your birthday - becuase it’s easy to remember.

Give yourself your own version of this award. Your own 57 of 57; and 58 of 58… this could go on for awhile, hopefully. If not, well, people could always go back and read yours to see what you were thinking back then.

Not for what sounds good.
Not for what you think you should have learned.

Not for a soundbite on instagram or tiktok.

Just for what actually feels true right now.

You might find something in there you’ve been ignoring.

Or avoiding.

Or already know… but haven’t fully accepted.

And that’s usually where things start to change.

Here’s mine…

✈️ The Top 57 at 57

(The Ones That Held Up)

1. I don’t get stuck - I lose interest in things that no longer feel true.
2. Most people don’t have a strategy. They have a to-do list with confidence.
3. You don’t need more ideas. You need fewer, executed properly.
4. Drift in life & business is silent. That’s why it’s dangerous.
5. I don’t need more time. I need fewer directions.
6. Busy is the most socially acceptable form of avoidance.
7. Systems beat motivation. Every time.
8. I think in systems because chaos is expensive.
9. Most breakthroughs are just finally doing the obvious thing.
10. Momentum often feels like confidence, but it’s just movement.

    ---

11. You can’t outsource thinking. You can only delay it.
12. I can see patterns faster than I can explain them.
13. If you don’t design your days, someone else will.
14. Every “yes” is a quiet trade-off you’ll feel later.
15. Complexity is often insecurity in disguise.
16. You don’t rise to your potential, you fall to your structure.
17. A bad system with discipline beats a great idea with none.
18. The first version is always uncomfortable. That’s the point.
19. Nobody is thinking about you as much as you think they are.
20. Most people are one honest conversation away from progress.

    ---

21. I don’t struggle with ideas, I struggle with choosing which ones deserve altitude.
22. Avoiding decisions is still a decision.
23. Agency is built, not found.
24. The real work starts after the excitement fades.
25. You don’t need permission, but you’ll keep looking for it anyway.
26. The map isn’t the territory, but it’s still better than wandering.
27. If it’s not written down, it doesn’t exist.
28. The more options you have, the harder it is to move.
29. Simplicity takes longer than complexity.
30. The best opportunities rarely feel comfortable.

    ---

31. I don’t want more opportunities, I want better filters.
32. You can’t optimize nor scale something you haven’t really defined.
33. Most people quit right before it starts working.
34. There is no right time, only earlier and later.
35. Energy matters more than time.
36. Attention is the real currency. Everything else is accounting.
37. If you don’t measure it, you’ll rationalize it.
38. People don’t buy solutions, they buy relief from confusion.
39. You don’t need a new tool. You need a decision.
40. Consistency looks boring from the outside and unstoppable from within.

    ---

41. I’ve outgrown things quietly, long before letting them go publicly.
42. If everything feels urgent, nothing is strategic.
43. The problem isn’t lack of knowledge, it’s lack of application.
44. Progress compounds quietly, then suddenly looks like luck.
45. The clearer you get, the fewer people will understand you.
46. You can’t build momentum while constantly restarting.
47. Perfection is just fear wearing a nicer outfit.
48. The best decisions often feel like a loss at first.
49. You can’t skip the uncomfortable parts. They are the path.
50. Most goals fail because they’re too vague to act on.

    ---

51. I don’t need to scale yet, I need to prove it works.
52. Feedback is data, not identity.
53. Most people don’t want depth, they want relief.
54. You don’t need more content, you need more signal.
55. Strategy is deciding what to do, what not to do, and actually meaning it.
56. You don’t think your way into clarity, you act your way into it.
57. I’m not building a business. I’m building a body of work.

    ---

Bonus (Because it never really stops

58. The more you explain, the less people listen.

59. A clear “no” is more valuable than a polite “maybe.”

60. Most plans fail in execution, not in design.

61. You don’t need more accountability; you need ownership, agency.

62. If it works, it’s obvious. If it doesn’t, it gets complicated.

63. Every system eventually reveals what you actually value.

64. You are always training people how to work with you.

65. In the end, it’s not about control. It’s about agency.

Happy Birthday! What would yours look like?

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