A few weeks ago, I was at a startup investor event--my first time getting back out into the local scene in ages--when I was introduced to a founder I'll call Brian, by an investor friend of mine who had invested in the  seed round of Brian's company.

That investment was eight years ago. The company was doing well, better than well actually, and the investor was all smiles, but Brian was visibly  uncomfortable. See, the two of them had been having a discussion about the future, and Brian wasn't happy. 

The investor, an older guy who has seen it all before, was nodding in knowing empathy as Brian finished detailing his concerns. And since I had just strolled up, the investor decided I was the perfect person for Brian to talk to about powering through the inevitable entrepreneur burnout. 

In retrospect, I probably shouldn't have said what I said. But at least it was the truth.

The Reckoning 

For me, the reckoning moment happened two years ago, as I began my initial descent into Austin, where I'd be giving a talk at SXSW in less than 24 hours about the technology our startup had pioneered on its way to being acquired by a private equity firm.

The CEO of our startup, my partner over the seven-year journey, had left the company three months earlier. Now, the minor "differences in strategy" between us and the acquirers--the kind that accompany any acquisition--were about to erupt into a schism, leaving me alone against the billion-dollar PE firm.

It had stopped being fun a while ago, and now it was about the future and how much of a role I wanted to play in it. I had been perfectly content to continue fighting the good fight when my flight to Austin had taken off some four hours earlier. By the time we touched down, I knew I was done.

And I still had a talk to give.

Not Every Day Is Going to Be Your Favorite 

One of the sayings I was known for at that startup was something I said when we signed our first big sales deal--one that would expose our awesome technology to the public. The sale was supposed to close at the end of May, but like all deals, it got delayed, and it didn't close until mid-June, leaving us to scramble to meet an unmovable deadline of August 31. 

As we rallied the troops to push through what was going to be a brutal summer of 16-hour days and unrealistic expectations, I ended my talk with this hackneyed platitude:

"Look. Not every day is going to be your favorite this summer. When that happens, talk to us. Talk to me. I'm not going to tell you what you want to hear, but I may give you what you need to know."

I could have put it better, but again, at least I was telling the truth. And we delivered on time and crushed it. 

Here's the Secret No One Tells You

After every success, big or small, in business or otherwise, there's an immediate period of letdown equal in proportion to the magnitude of the work it took to get there. 

When success comes easy, when you trip over it, that letdown is a blip, if it happens at all. And that kind of "accidental success" will happen and should happen quite often on the road to achieving your startup's ultimate goals. You'll land that customer you didn't see coming, a random investor will appear out of nowhere to oversubscribe your round, that brilliant employee will decide that they'd rather work for you than take more money somewhere else.

But the big successes, the ones you have to work 16-hour-a-day summers to even stand a chance of seeing happen, when those hit and the celebration dies down, you're usually left with one single, ugly question:

Is this all there is? Is this what I've been killing myself for?

With age, experience, and wisdom, the impact of that emptiness can be explained away. I still feel it, but I'm too cynical--let's call it "wisdom"--to worry about that empty feeling as anything other than a natural phenomenon that I need to get over. Like when I have to get up at 5:00 a.m. and I dread the alarm going off. Still. At my age.

But when you're younger--and I'd peg Brian at about 35 years old, so let's call it "younger"--it's really tough to see past the emptiness. It happens to athletes all the time, people who generally achieve all their life goals in their mid-30s. I've talked to a bunch of them, and they tell me the silence that follows the cheers into retirement is deafening.

You Are Not Your Goals

You probably didn't expect this out of an advice column, but I'm going to tell you that you are not your goals, your achievements, and especially not your failures. They are part of what makes you who you are, but when you define yourself by them, you live and die by them. And when I say "die," what I mean is that when they happen, you feel a great swell of satisfaction, but also loss. 

"'When Alexander saw the breadth of his domain, he wept for there were no more worlds to conquer."

Don't let me fool you. That's Hans Gruber from the movie Die Hard.

Is this the right thing to tell an entrepreneur in the middle of their brutal journey?

Maybe. I know I got off that plane in Austin and gave one of my best talks ever. Then I met about 50 people who stood in line to ask questions afterwards. It was one of the best days of my life, actually.

Because I was free.

Not free of the startup, that would come later. Or even free of the schism, that got uglier once I got back to town. But I was free of the remorse of tying my self-worth to the valuation of my startup. I was now doing it for the reasons I started doing it in the first place--to make awesome technology and to launch that rocket as high as it would go.