imagine the perfect night’s sleep.  For me, it involves sliding into cool bedsheets, closing my eyes, marveling briefly at how tranquil and undisturbed my thoughts are, and fading into a deep and restful slumber.  Maybe I wake up once, around 2am, marvel at the fact that I have 4 or 5 hours more hours of rest ahead of me, and fade gently back to oblivion.

In the roughly 7 years between the day I quit my secure (and pretty easy) job to start Right Media and the day I left Yahoo 7 years later I literally cannot remember a single night’s sleep like that.  There may have been a few, but they were infrequent enough that i truly can’t conjur a memory of one.  Not on vacations, holidays or even when dosed up with more NyQuil than doctors typically recommend.  

I don’t think I’m alone in this.  I don’t know any active entrepreneurs who sleep soundly at night.

one of my favorite entrepreneurs in the world was telling me the other day about a study he read that said that in certain people making money had the same stimulating effect as cocaine.  ”This is why I can’t sleep at night!” he exclaimed.  (and he didn’t mean cocaine).

This struck me as funny for a couple reasons.  First of all, I don’t think this particular founder/ceo is remotely interested in money.  he’s already got way more than he needs, and as far as I can tell he doesn’t entirely know what to do with the wealth he has already generated.  i don’t think he’s staying awake at night dreaming about a bigger house, the high stakes room at the Wynn resort, or his own personal jet.  

it kinda begs the question - what keeps people who have already had so much success awake at night?  they should be comfortable, happy and should sleep like babies, right?

when I think about what keeps me awake at night (thankfully, less frequently than in the past) I think it boils down to 2 things:  fear of failure and the double edged sword of success.  

fear of failure is fairly straightforward.  failure in business means embarrassment, probably public. it means dealing with conflict of all sorts.  failing, even gracefully causes problems with investors, partners, employees, spouses and so on.  so naturally, we stay awake worrying about failure, particularly when things are not going well with our venture. do we have the right product?  have we made the right bets?  will our cash hold out long enough to get to breakeven, or raise another round?  can we afford the new vp of sales we just hired.  are we personally up to the task of being founder, ceo or whatever our role is.  the list of ways to fail is endless, and its damn near impossible to keep from running over and over it in your head when you should be resting.  

success on the other hand - now that ought to give us some rest, no?  i think not.  in some ways its worse than fear of failure.  yes, fear of failure tends to retreat to the shadows of your mind a bit when things are going well, replaced by the prospect of bright, shining success!  which of course occupies your mind just as intensely as fear of failure.  you start thinking of all the ways you can accelerate the success you are starting to have.  you see the future laid out in front of you, a series of clearly defined steps.  how can you sleep when you know what needs to be done?  

success of course also creates new opportunities to fail.  once you start thinking about those - how your customers will respond the the downtime caused by your unprojected growth, the organizational and cultural growing pains you will deal with, keeping your burn rate under control in the face of escalating costs caused by usage, customers etc- the more success you have, the more you understand how much you have to lose and how much more public your failure will be.  which leads you right back to fear of failure.  kiss a good night sleep goodbye.

so, how does one sleep soundly as an entrepreneur.  i’m afraid i’ve got nothing for you. i have no idea, and I don’t know anyone who does it.  i don’t think it matters how successful you’ve been, how much security you have, or anything else. entrepreneurship is about seeing the world in a certain way and then making that vision a reality. for me, that is the essence of it, and that is completely decoupled from financial success, reputation and all the other trappings of being a successful entrepreneur. which means no matter how secure you are, and how satisfying your previous experiences have been, you will have the same anxieties and dreams and sleeplessness every single time.  

i wish i had a better answer - but i’m pretty sure most entrepreneurs just don’t sleep well at night.