The Plan Paradox

I’m not great at planning things. I’m even worse at writing ‘em down. In the words of the Joker from the “Dark Knight,” “I’m like a dog chasing cars. I wouldn’t know what to do with one if I caught it.”

And for the most part, this has led me down some pretty interesting, if not completely misguided (pretty much stupid), paths. Even though I regret nothing — taking each misstep as a lesson learned rather than time wasted — I oftentimes ask myself if I had plotted a more complete course, would I have taken the same path?

The answer is invariably “no.” But lately, I’ve been asking, what I feel to be an even more important question. Would I have taken any action at all? And I find the answer is, in fact, also “no.”

Which brings me to the paradox between plans, particularly business plans, and actions. We all know the conventional wisdom is to write a business plan way before you ever start a business. This, they say, is because writing a business plan forces one to consider everything involved in getting said business off the ground, and everything one would need to run it.

Both the pros and the cons of business plans have been written and talked about extensively. And I’m certainly in no position to give advice about neither pros nor cons having never fully written one myself. Nor am I a business guru. My forays into business have all ended in abject failure. (And not even the “spectacular rise and fall into obscurity” kind. But the “never take off and fizzle into non-existence” kind.)

I just find it puzzling that business people and analysts alike have yet to reach consensus on such a fundamental issue in starting a business. I mean, even the college or no college debate is more understandable — to me at least. Those that are proponents of going to college are usually people who have been to college themselves (and therefore are probably trying to convince themselves, as much as others, of the benefits of that substantial investment), or are part of the institutions, in which case the asking your barber if you need a haircut metaphor applies aptly.

But with this issue, you’re just as likely find an entrepreneur who advises you to write a detailed plan as you are to find one that says just wing it, even though there is no “establishment” to upset either way. (Maybe the banks… But if you don’t have a plan they, annoyed, just tell you to go away.) On top of that, even those that do say you absolutely HAVE TO write a plan, usually add that as soon as you’re done writing it, chuck it out. Because everything you assumed — which is probably a lot — is more likely than not, wrong.

Like… WTF?

All this leaves me, at least, as a would-be (wannabe?) entrepreneur a little perplexed, to say the least. Do I write a plan or no? Do I throw caution, and projections, to the wind and wing it?

What I suspect, like with most things in the business of startups (annoyingly), it’s relative. If your potential business needs a mountain of startup capital (which are few and far between these days), then you’re probably gonna have to spend months hunched over keyboard, typing out spreadsheets. If it doesn’t need a load of cash to try it out, then it’s probably wise to try the Lean Startup method.

Although, this does not imply that you can get by with no planning at all (also quite annoyingly). As the cliche goes, you can’t get to where you’re going if you don’t know where that is… Or you can’t start your journey if you don’t know where it ends… I’m a little fuzzy on the exact cliche right now. But the point is you have to at least have a destination you’d like to reach even if you don’t know how exactly you’re gonna get there. And as the cliche about cliches goes; cliches are cliche for a reason.

(Did I say cliche too many times for one, mostly cliche, paragraph?)

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