My client thought he was sabotaging his life and business.

“I get what I want and then I don’t want it.”

He was a badass at creating big visions and plans: Taking companies public, big titles, cash, stock options.

So why was he struggling to find motivation these days?

“I don’t enjoy what I create, so why bother?”

In the past he had a hypothesis — an unconscious hypothesis. “If I get to that mountain top, if I win this thing then it’ll all pan out.”

Remember, this is unconscious.

But here’s the rub. He never thought it through. He only focused on that mountain summit, the bottom line — the measurable win.

And when he achieved that win, what did he feel? Good for a little while. Important and admired and validated for a little while.

But it didn’t last. It didn’t quite pan out like he had hoped.

I asked him, “What was it like after you had the big win?”

“Once I achieved those things I felt stifled. I wasn’t having fun. Things got too complex. I was running and maintaining things. I wasn’t being creative anymore.”

He told me about another win, “After we rang the bell things got reorganized. I lost touch with my team. I lost my tribe. I felt alone so I left.”

No wonder why he wasn’t motivated. In his world, creating a win left him feeling stifled, bored, and alone. Who wants to create more of that?

So I asked him, “What if you committed, not to a measurable vision per se, but to creating the experiences of greater freedom, fun, and creativity? What if you were committed to doing the work that aligns with who you are? What if you were committed to working with the people who get you and what you’re about? What if, no matter what it looks like, those were the outcomes?”

“Let’s do THAT!” he said. He felt a huge sense of relief that he wasn’t some guy hell bent on sabotaging himself. He had merely been testing lousy hypotheses.

“But here’s the thing,” I said.

“You’re not going be able to map this out. It’s not going to fit on a white board or a five year plan. This way of doing things is going to steer you straight into uncertainty.”

And he got it. This shift in perspective meant that the short term certainty he gained from having a great vision or plan would give way to a commitment to creating the experiences he truly wanted. The plans and goals and actions and experiments would be in service of these experiences — freedom, fun, creativity, connection with others — first and foremost.

He’d have to let go of his old way of doing things. “If I just get the win, then everything will pan out.”

But without the metrics and numbers, how would he know if he was off track? In the past it was about coming back to that objective, external vision and comparing that with reality. “What are the numbers saying?”

But now, his metrics would be subjective. He will be using his emotional guidance system. Is he feeling more or less free? Is he being creative more or less? Is he feeling more or less connected with the folks he loves to work with? Is he more or less fired up about the work he’s doing?

This approach scares most folks.

They like to have it planned out. They don’t like course correcting as they go. They don’t trust their internal world. “It’s too wishy washy. It’s too convenient to bail when the going gets tough.”

That’s very true for the amateur — but not the professional who is disciplined and willing to step into his fears.

And look around. Look at the “walking dead”. The reason why many, many “successful” folks are dissatisfied is because they only committed to the measurable wins, to the numbers, to the external outcomes.

To end up in this hell they had to abandon their emotional guidance system ages ago. Why? Because it became too damn painful otherwise.

In other words, they merely assumed that if they created that vision it would all pan out.

So here’s my question for you:

What are you hoping will “pan out” if you get this next “win”?


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