When There Seems to Be No Way Out – Customer Discovery for Your Head

As an entrepreneur at times you forget that being in charge doesn’t mean you have to know everything. When it feels like you’re trapped facing an unsolvable dilemma, and wrestling with a seemingly intractable problem, remember that “getting out of your head” is the personal equivalent of the Lean Startup mantra “get out of the building.”

Learning this was a big step in making me a more effective entrepreneur.


As a young, driven entrepreneur I prided myself on my ability to plan my way out of most business problems. But at times in my career I’d run into a problem I couldn’t solve. Sometimes these problems would keep me up at night worrying, thoughts racing around my head like a tornado between my ears. I’d imagine only the worst possible outcomes, thinking there were only black and white solutions, or no solutions. I’d get trapped in this loop with my wife telling me to “go to sleep,” until I finally passed out anxious and exhausted. At times this went on for days.

If the problems were about corporate politics, I’d show up the next day defensive and ready for a fight. (Relationships with sales versus my marketing department was a typical food fight and problem). If it was a meeting my boss called, I was convinced I was going to be fired (even though I couldn’t think of any rational reasons why). Half the time I’d be amazed to discover the problem or obstacle I had been worrying about didn’t even exist. I had magnified a comment, document, or an interaction, and my imagining the worst possible outcome let it spiral out of control.

It took me a long time to see there was an easy way to break this obsessive cycle and end up with much better options. The key, I found, was getting out of my head and talking to other people.

You are not alone

When I was younger, I didn’t realize:

  1. Often, the problems I experienced at work were common problems. Others have these problems now or encountered them before
  2. If others had the problems, then there were solutions or at a minimum, good advice was available
  3. If I had shared that I was stuck, and needed help, lots was available
  4. Not only was this true for problems at work, but even more so at home

1. These were common problems; others had these same problems now or encountered them before

When I was in the middle of trying to solve a problem, it never occurred to me that these problems were not unique to me. I felt they were my exclusively mine and that meant that I alone needed to solve them.

Since I hadn’t run into this problem before I assumed no one else had. (In hindsight this was likely due to my age/lack of experience.) Later in my career, I began to see common problems recur. But at the time, I never considered that others had encountered these same problems.

2. If others had faced these problems, then there were solutions or at a minimum, good advice was available

Here’s the critical opportunity that I missed. There was a whole world of people who went through, or were going through, what I was struggling with. Some of them had figured out how to solve it, some made bad decisions and didn’t solve it, but all had experience in seeing a resolution one way or the other. Some could tell you stories of what they went through, others could tell you what worked or didn’t, and a few had real wisdom to share. And often I would discover what I thought was a critical problem really wasn’t. It wouldn’t end my career, or no one would really care.

3. If I had only shared that I was stuck, and needed help, lots was available

Seek out the advice of others? Ask others for help? The thought never crossed my mind. (See item 1.) And if it had, I would have rejected it. Why? Well a loss of control, admission of failure, loss of stature, embarrassment, etc. I thought I should have all the answers.

Getting out of my head and asking for others for help also required a network of mentors/coaches and advisors. Early in my career I didn’t have any/many. Later I realized how valuable they were. As I began connecting I learned to ask not just about how to solve my specific problem, but also, what did they do when they felt stuck? How did they learn to do this rather than stay in their heads?

When I was an entrepreneur a face-to-face meeting or a phone call was the only way to get advice. That was a barrier to many. Today, the Internet has eliminated most of those obstacles. You can go online and with a simple search find others who have had the same issues you’re wrestling with and read how they solved them.

4. Not only was this true for problems at work, but even more so at home

Like most people, at times I had problems outside of work with personal issues like dating, marriage, etc., that made me distracted and less effective at work. I finally realized that getting out of my head at home gave me space to be more effective at work. However, it’s often even harder to ask for help because of embarrassment, denial, etc. On the other hand, there are entire support communities for non-work issues (psychologists, group therapy, etc.) There are even manuals that describe common psychological problems and their treatment.

Lessons Learned

  • The “get out of your head” strategy is the personal equivalent of the “get out of the building” mantra of the Lean Startup
  • Don’t spend a lot of time obsessing. Reach out to mentors, coaches and advisors for personalized advice. Use the web to find generic advice
  • “Getting out of my head” to seek advice and the wisdom of experience was a big step in becoming a more effective entrepreneur

7 Responses

  1. Thank you Steve!!!! Great piece of advice!!

  2. I completely agree.

  3. So true for me. Thank you Steve. Love to read and learn from your experiences

  4. Gracias. Saludos desde México

  5. This is an invaluable piece of advice Steve. Thank you, as always!

  6. Nice. Beautifully described

  7. Thank you for putting those problems that entrepreneurs face in such a tangible and heart-felt way.

Leave a Reply to Frank Cancel reply

%d bloggers like this: