One curious question people often ask about successful leaders is: "Do they ever feel fear?"

My answer is always yes, yes, and yes. I don't need 1,000 academic studies to back this up. In fact, some of the most successful people are some of the most worried and insecure. That's partly what drives them to do big things. You rarely see them display any insecurity because if there's one thing great leaders know, you almost never want to show people how scared you really are. Gillette made a killing out of this idea: "Never Let Them See You Sweat." Fires may be burning around you but you must command, decide and motivate. What great general would cower in the middle of a battle? Zero.

The downside is we often don't talk about what happens when the inevitable thing hits the fan. You lose a deal. A major investor pulls out. Your partner leaves and takes your staff with them to build a rival business. This stuff happens and it is the biggest punch in the face. In fact, being literally punched in the face sounds more pleasant. Even the most optimistic people want to go home and cry-like for a week. Some drink. Others eat and get fat. You find yourself moving over to "The Dark Side" where everything seems dank, barren and inhospitable.

Anyone who's ever been to The Dark Side and comes out will tell you three things. Remember them because they will give you perspective:

1. It is never as bad as you think it is. Rest assured, I know it can be bad. Not being able to make your payroll or building your company while a parent is terminally sick are all stories I've heard from entrepreneurs. Somehow, they manage to make it through in one piece without being homeless. As someone once said to me: "My worst days are better than the best days for many people around the world. I still have a car, a home, a family and friends." When you are out of The Dark Side and look back, you'll realize that things could have gotten waaay worse.

2. Some people will desert you. It happens to everyone and I frankly don't blame anyone for that behavior. People are motivated by different things and if a person doesn't see what you can do for them anymore, he or she is less inclined to continue a connection. Now, these are strictly work-related relationships I'm talking about. Your family and friends shouldn't desert you and if they do, never speak to them again, that's unacceptable. The best way to answer anybody's desertion is to channel that energy into succeeding. Then see how many people come knocking on your door again.

3. They were grateful for that time. People from The Dark Side may not have enjoyed the time there but they learned more about themselves than at any other point in life, except maybe the teen years. The Dark Side roughed you up. It made you uncomfortable. You had to be creative. And it made you appreciate what you had. Life never goes according to plan and while the outcome might be different from what you planned, it might actually be better. I don't know anything about the Big Guy in the Sky but I do know that some mistakes are luckier than others. You figure that out.

So how do you get out of The Dark Side? Ben Horowitz writes about it in his book, The Hard Thing About the Hard Things, except he calls it "The Struggle." (Note: Read the book, it's a fascinating account of someone who hit The Dark Side many times and is now one of the most respected venture capitalists.)

Whatever you call it-The Trough, The Endtimes, The I-Eat-Ice-Cream-All-Day-Times-Horowitz has one observation that is essential for any entrepreneur: you only need ONE option to get out of trouble. He recounts in the book how many times his company, Opsware, was on the brink of extinction, at one point trading at 35 cents a share. Nobody would talk to him except one person and that person saved his company. Again, you just need ONE option. For anyone who's in The Dark Side now, there is always a way out-start finding it now.

Published on: Sep 30, 2015
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