Obama's mentor told him the truth

"I argued that windows of opportunity for running for the presidency close quickly. And that he shouldn't assume, if he passes up this window, that there will be another."

I've met thousands of people who claim they want to be entrepreneurs. Very few ever do it.

Part of the dissonance is the reputational risk. Talking about your big idea is exciting, energizing, and cool; trying to turn a big idea into a sustainable business is hard, risky, and humbling.

The other big reason would-be entrepreneurs never start a company is faulty forecasting; they assume there will be a better opportunity, with less risk, in the future.

But what happens if this myth -- the inevitability of better chances -- is wrong?

What if, like Obama, we have one and only one chance to make the best move?

Many people I know think about their careers (and earning potential) as an incremental up-and-to-the-right process. But some careers -- business ownership, entertainment, writing, politics -- don't follow this logic.

Properly executed, the right move -- like running for and winning the presidency or starting something new -- can accelerate a career in ways that most people under-appreciate.

The best way to deal with this tension is clarifying one's intent. There are no right career paths. One approach is high-risk, high-reward; the others are lower-risk, lower-reward.

But I think the challenge – the reason older men buy yellow Mustangs – is when the expected better chances never come.