"Do something hard and lonely to prepare yourself for the rigors ahead."
This nugget of wisdom is buried in an otherwise forgettable book of simple business advice entitled How To Become CEO. But this concept has stuck with me for years, and it is a simple way to gauge your interest in becoming an entrepreneur. Do you gravitate towards group sports/activities or solo ones? It says a lot about whether you'll enjoy the road ahead.
Long runs at the crack of dawn, practicing free throws in the gym, working late to put the finishing touches on a client presentation long after all the others have gone home -- any athlete or business leader will tell you that everyone remembers the moments of glory when the spotlight is on you, but these moments are only made possible by the countless hours spent preparing and training in which you toiled away in obscurity.
Being an entrepreneur is no different. In a similar vein to my previous post on grit & determination, there are going to be plenty of times when you have to walk a lonely road, whether it is with "friends" who seem to disappear when times are tight, with VCs who won't give you the time of day, or even with your fellow founders at times (assuming you haven't scared them off with your antics yet ...!).
Get used to it. Startups are rarely rosy and more likely to be messy affairs than not. Founders leave, customers leave, your employees leave -- just anticipate it, plan for it, assume it as your default and you'll wind up happier. The more you can condition yourself to be prepared for this reality, e.g., through hard & lonely sports or activities (rather than group outings), the more likely you will be able to pull your startup through the inevitable bad times -- when you are all alone, literally or figuratively -- and help lead the company to the spotlight of better times at some point in the future.
Good luck, and see you on the trails (just don't run with me, I'm trying to run alone ...!).
