Issue 176, Part Time CEO Newsletter

Hey, it's Dhiren 👋,

Six grown men have played the same game of tag for almost thirty years. Real men, the real game, the one from the school playground. They plot for months and fly across the country to catch each other off guard. You might have seen the film. What gets me is the end of it, when the photographs come up. The friends themselves, decades on, still playing. They never stopped.

Most of us did. We stopped playing the day we decided to get serious. And serious comes with a rule. Know where you are going before you move.

I did the serious thing too. I wrote a four-year plan to scale Elevated Entrepreneur as one-to-one coaching. More clients. A team of coaches doing what I did. The same thing, made bigger.

Four years on, it is Council. A room full of founders, not a queue of one-to-ones. Something I could not have named the day I began.

The plan was not wrong. My certainty about where it would end was.

You don't get to know the ending

We start a business expecting to know two things. Where we are going, and the route that gets us there. The whole industry feeds it. Buy the course, follow the steps, arrive at the destination printed on the box.

Fifteen years across two businesses taught me this: the route out of the operator trap is knowable. I can draw it for you on a napkin. Where your business actually ends up is not. Same effort, same hours, two founders, two completely different endings. You do not get to know yours in advance.

The pain does not come from the unknown. It comes from pretending the unknown is known. You draw a straight line to a destination you invented. Then every turn that is not on your line feels like you failed. You did not fail. You found information you did not have when you drew the line.

This is why comparison wrecks you. You watch another founder move in a clean line and assume you are the broken one. You are not seeing their line. You are seeing the version they drew after they arrived.

So you play your way there

So what do you do when you cannot see the destination? You stop planning toward it. You start moving toward it. You explore. That word makes founders squirm, so here is the honest one. You play.

I watch my three-year-old pick up something new. No destination. No plan. No fear of looking stupid. She tries it, it goes wrong, she tries it another way. That's why children learn faster than every adult in the room because they are not protecting a map. We lose this under pressure and call the stiffness "being serious."

Playing in business has a shape too. The key is to make it a rhythm that you can lean into.
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One experiment, every twelve weeks. One bet, written down. Time-boxed. Committed for the full quarter, then judged. Twelve weeks is long enough to learn something real and short enough that a wrong bet cannot sink you.

And judged on the right thing. Not only whether it hit. What did it teach you, and was it a good bet to place. An experiment that fails and points to your next move did its job. An experiment you quit in week three taught you one thing only, that you flinch.

Council runs on exactly this. A fresh twelve-week experiment every quarter. And the part that still gets me: Council itself is the result of one. I did not plan a community. I ran something, watched what came back, and followed it. It did not arrive all at once. Gradually, then suddenly. The destination found me because I kept moving while I was unsure.

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Your Turn

So pick one. One experiment, twelve weeks. The bet, the day it ends, and what you want out of it even if it flops.

I am sitting in this question myself this quarter.

What am I refusing to start because I cannot see where it ends?

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📢 Dhiren’s Updates

Once a month I clear a morning, book a table, and fill it with founders.

We call it the Part-Time Breakfast. No agenda, no pitch, no name tags. Good coffee, and the kind of honest talk you do not get to have with your team or your clients.

This month it is Saturday 27 June, here in Dubai. I would love to have you at the table. Reply with the word "food" and I'll send the details.
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Cheers