Early retirement is a mirage when you’re physically and mentally capable of doing more. Humans are generally not built to derive sustainable happiness from sipping mojitos on a picturesque island somewhere in the pacific. Once you’ve tasted the sweetness of a dedicated purpose, it’s near impossible to be content just sitting on the sidelines.

I’ve talked to a handful of start-uppers who build the company of their passion and then cashed in for this dream. But the pattern was pretty much universally the same: Six months of doing nothing but indulging pleasure is as long as most highly capable individuals can take.

So after a much-needed vacation, the retirement is canceled and they’re back to start a new company. (Not always with as much passion as the first time around, but that’s another story).

Jordan couldn’t stay in retirement either
The inability to enjoy the passive enjoyment of retirement life is not confined to entrepreneurs either. Look at how many times the mega stars of sports have thought mojito island was what they wanted, only to find out that they couldn’t let go of the excitement and flow of doing what they did best. Michael Jordan, Lance Armstrong, Brett Favre, the list goes on and on.

Giving the overwhelming evidence that even when you get all the money in the world, you still want to pursue your talent and passion, landing the stereotypical web-startup lottery payday doesn’t seem that appealing. If you’re good enough to build a company that can be sold of umpteen millions, you’re probably also in the category of people who can’t “retire” and be truly happy.

If you get out, then what?
Now given that, what’s the rush to get out? The big question will come knocking on your door very soon: What are you going to do then? If you cash out at 35, then what exactly are you going to spend the rest of your life on?

The difference in lifestyle between extracting a few million dollars a year from an operating business vs selling it all for a one-time payday of, say, $40 million is not as significant as it may appear. Much less significant than the difference between waking up in the morning to a passionate purpose versus yet another day of aimless pleasure.

Now it’s true that some company founders don’t really like what they do. That there’s another greater calling that they’d like to pursue but can’t until they’re free from the man and can set their own tune. Maybe they want to play jazz music all day.

I don’t think that person exists as often as the idea of the artist-beneath-the-suit would romance us to believe. And I think that plenty of people underestimate the difference between a fun hobby and a full-time pursuit, but I digress.

In short, the bliss of selling and giving up your business is overrated. It’s a long life and it’s often best spent enduring the ups and downs of pursuing something of significance. Don’t be so eager to give it up.