Last week, I got a call from a friend of mine who's an entrepreneur that was probably one of the hardest calls he's ever had to make. He was calling to tell me that he hadn't raised a dime for his fledgling company in six months, hadn't taken a salary in almost a year and was about to miss his mortgage payment on his house for the third month in a row (after three, the banks tend to begin the foreclosure process).

His call got me thinking about how many more entrepreneurs out there were in exactly the same boat he was in but just either (a) couldn't bring themselves to make the call or (b) were still in a stage of denial where they didn't know their ship was sinking.

Now if this were some first-time, twentysomething entrepreneur, you'd probably think that 90 percent of the reason he was in this mess was a combination of naivety, lack of experience and/or youthful brashness. What was so particularly disturbing to me was this friend of mine was a mature, experienced executive who'd "been there, done that" many times before. How could someone like that get into such a hole? As if he'd anticipated my question, he volunteered, "At every step, it seemed as if I were making the right decision."

If you've ever had an entrepreneurial failure, I'd bet you can relate to his comment. No one becomes an entrepreneur to fail. From the time we have our "great vision" until the time we finally decide to take the leap and try and make it happen, we do so with the absolute expectation that we'll succeed.

But as the saying goes, "If it were easy, everybody would be doing it," and for many entrepreneurs, that soon becomes a personal reality. With few exceptions, every entrepreneur must struggle through some very dark and difficult times before eventually, if their luck matches their determination, pulling out a winner.

Unfortunately, for every one who succeeds, there are far more who don't. For them, their hidden pain is both complex and deeply personal. But they share some common concerns:

The Doubt Demons
"Dare I tell anyone of my doubts? If I show my doubt, will all my supporters crumble with me?" You have no idea how much pressure this one thought alone can place on an entrepreneur. On the one hand, history may show that an absolute irrational belief by the visionary entrepreneur may be the only thing that leads some companies to success. On the other hand, it's also the main cause of many a company's failure. So how do you know if you're the cure or the disease?

Fear of Disappointing Investors
For most entrepreneurs, once you've experienced that magical moment of someone demonstrating their belief in you by writing a check, you'll practically die before letting them down. Some entrepreneurs complicate this feeling because they've gone back to their investors more than once to get some help to get though a crisis, and each time, the mental hole they dig that obligates them to succeed gets deeper. How do you know when the best thing you can do for your investors is to quit?

Never Quit Too Soon
"What if I quit the day before something big finally breaks for us?" History is full of stories about entrepreneurs who were going to quit the day after something big happened, and of course, that event changed the outcome. Naturally, this attitude is further complicated by the basic feeling that quitting is never an option anyway. So when is the right time to quit?

Killing a Dream is Hard
To an entrepreneur, quitting is the fundamental equivalent of committing suicide--when you kill your dream; you're killing a part of yourself. Therefore, it's extremely hard for an entrepreneur to make this decision on their own. Generally, they need help from advisors they actually talk to and who'll help them decide exactly when there's nothing more that can be done to keep the dream alive. Preferably, these advisors need to be people of influence, like board members, shareholders and/or fellow team members, so they'll have the option to use leverage (if necessary) to force you to see the light. Just when should you consult these people and take their advice, no matter what it is?

The Question of "What's Next?"
Sometimes it's easier to deal with the devil you know than with the devil you don't. The longer an entrepreneur has been involved with pursuing his or her dream, the harder it is to extricate themselves from the muck. It's a bit like a stunt pilot taking a plane into a power dive straight toward the ground. There's a point where, if you don't pull up, no amount of effort after that point will keep you from crashing. Entrepreneurs do worry about their situation. But at some point in their cycle, if they end up doing it too long without success, they tend to struggle with the following thought demons:

  • Where do I go from here?
  • Entrepreneurial tendencies are neither valued nor wanted in corporate America.
  • Who will want to hire a seasoned but older, failed entrepreneur?
  • Since I've drained every once of cash from my savings and borrowed from everyone I know, how would I survive during the time it would take to find another job?

If you're reading this article and you know an entrepreneur who hasn't yet grabbed their brass ring, you might just tell them that you feel their pain and encourage them to open up.

On the other hand, if you are an entrepreneur and any of this comes way too close to where you are or how you're feeling, call someone you respect and give them an earful about what you're feeling. At best, it may just give you the energy and/or perspective you need to turn things around. At worse, you may just feel better knowing you're not alone and that there's a way out.

Jim Casparie is the "Raising Money" coach at Entrepreneur.com and the founder and CEO ofThe Venture Alliance, a national firm based in Irvine, California, that's dedicated to getting companies funded.