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, written by Jeremy. Read the commentary.

I battle an internal suspicion that I’m too naive for business. Maybe I think too big, measure obstacles as too small, and expect too much? But maybe we live too small, ask too few important questions, focus on the middle instead of the edges of possibility, and because we don’t expect achievement of any significant magnitude we never get to see it. Obviously, I usually settle on the second side, naivety be damned.

One particularly naive thing I expect is that if something is worthwhile, you should first do it for free. If it really sings, then sing. Do it on your own when no one is looking and no one is paying.

Of course it’s plain silly to do everything for kicks. So, the other naive expectation I harbor is that I should be paid exorbitantly well for things I’m willing to do for free. As a friend said, “I don’t expect much, just $350,000 per year to work three days a week at something I’d do for free. Oh, and a yacht. A big one – really, really big.”

The tension between these two expectations is my consolation that I’m not near as silly as I feel, sound, and look. The two, together, provide perfectly offsetting incentives. It’s a bit of what drives Hugh’s Sex/Cash theory.

If I’d do it for free, I am likely to be passionate and convinced it’s worthwhile. It will exceed my value systems and overwhelm the cost of doing all the work. It’s going to hold my attention through all the muck of making it go.

If I expect lots of cash, it better be worth it. It must exquisitely satisfy some acute need. It should be compelling, all on its own, because I’ll be so busy managing the bucks it’ll have to take care of itself.

Silly right? But look where the tension puts us – right in the middle. To me it looks a lot like the best of business and the best of life.

… naivety be damned.

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The thesis you present assumes (1)being passionate enuff to do something for free assumes you are good at it – the market is not usually so agreeable, unless you can skip from one sacked or dissatisfied customer to the next without contamination, (2), that investing up-front for free means a pipeline of well-heeled interest emerges to satisfy…well, those yacht-ical urge or other extravagances, and (3) that interpersonal skills are well suited to the nature of the investment.

Of course I’ve assumed one through three are given – you are marketable enough to deserve big bucks, you a capable of generating outcomes so grand that yacht-ical extravagence is a silly bit of dabbling, and you jive like song-birds.

The question isn’t whether the “you” is capable – they’re perfect. The question is whether they buy in so deeply that they do it for free.

… I said it was naive. But are you saying it is naive? Or are you pointing out corollaries to the theory?

“…focus on the middle instead of the edges of possibility”

Change usually occurs on the margins, but isn’t change driven from within?

Yes. That’s what I was trying to say – be so driven and so passionate to do things without pay or recognition.

I suggested it as a measure of one’s ability to create change.

Did you think I meant something different? Or were you just agreeing?