The Entrepreneur’s And The Founder’s Conundrum

I speak with a good number of founders, entrepreneurs, and executives who are involved in the same kind of conundrum. How a countercultural philosopher like me came to speak with such individuals–well, that’s a story for another day. Today I’d like to tell you about that conundrum.

Let me begin with an analogy from Robert Wright’s book Why Buddhism is True. Suppose, Wright says, that someone prone to neuroticism is told that there is a snake in the bush so that every time this person comes close to that bush he is on his guard. Suppose, further, that, say, 99 times out of a 100 there is no snake in the bush–but one time there is. Wright’s lesson? Evolution has ‘designed’ human beings so that we’re ‘primed’ to be neurotic because evolution ‘wants’ us to pass our genes on to the next generation. The unfortunate consequence, however, is that we must sacrifice our happiness to ensure our survival. In other words, our lives are one big trade-off: our negative thoughts may save us from harm but not without causing us to sacrifice the prospect of genuine happiness.

I don’t know whether Wright is actually correct here about the conundrum faced by homo sapiens (I don’t know that he’s wrong either), but I do think that his anecdote sheds some light on a style of thinking that, because of my long acquaintance with certain conversation partners, I’ve come to be quite familiar with.

Their version runs: I should think about every possible scenario, most especially the worst case for fear that not doing so could lead me to be blindsided, to miss an opportunity, or to be forced to grapple with an existential threat to my business. Therefore, I must always be on my guard since, owing to accident or ill-preparedness, I may otherwise fail to foresee something especially significant.

The faux-meditation mantra or Zen Lite piece of advice–“Be in the present”–just won’t do. So far as I can tell, they’re right to believe that thorough deliberative thought is called for. And yet, I don’t believe that such thorough deliberative thought must entail the loss of happiness.

Ergo, what might be a way of having our caking and eating it too?

Some napkin suggestions:

  • First, we need to examine the ways that our identities are unnecessarily tied up with existential threats to some such entities (here, startups, companies, etc.). Can I be willing to let this thing die without thinking that it spells my symbolic death also?
  • Second, we need to be able to be more like mathematicians, as it were. Can we dispassionately, methodically, and inquisitively deliberate upon sundry scenarios, looking at things from different perspectives in the hope of being as thorough as possible? I underscore the dispassion here. The kind of mathematician I have in mind is animated by inquisitiveness, not by the fear of symbolic death. She genuinely wants to think something through to the very end.
  • Third, after we’ve thought something through to the end, can we lay it–and also, therefore, the mind–to rest? You might tell me that, ah ha, something new may always come up and that something new may change the considerations or the conclusion arrived at. Fair enough. Yet if we’ve really turned over almost every possible, hypothetical, and actual stone (so to speak), then this new piece of information could very well be folded into our prior considerations and our conclusions.
  • Sometimes, to be sure, something new and monumental does come up, yet, according to the understanding proffered here, we should reserve our uber-alertness or our alarm bells just for those cases where, yes, the case merits our vigilance.

How persuasive is what I’ve written above? I don’t know; try it out and see whether you can square dispassionate, methodical deliberations with peace of mind. It seems to me a matter of training–indeed, a training in concentration. So used is our mind to flying off of the handle that it may take some gentle suasion, and some time, to bring the mind back to dispassionate deliberation. I see no reason why meditation and philosophy can’t be twinned.