Confessions of an Entrepreneur

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This post has been brewing in me for a while, especially since I shared the Iceberg of Life.

This isn’t a rant. It’s not meant to engender sympathy for me. And it isn’t a confession of my own thoughts, doubts, worries, insecurities for therapeutic reasons.

It is meant to help other entrepreneurs know one thing: 

You’re not alone. 

Most everything on this list has been something I’ve struggled deeply with at one time or the other in my time as an entrepreneur, and/or heard numerous entrepreneurs talk about consistently.

I’m not saying any of these are valid or right. I’m just saying they are part of the experience.

Entrepreneurship is tough. It’s lonely. It’s a roller coaster. Sometimes it’s just awesome and other times you’re ready to puke and get off the ride. Overall, I can’t imagine a better gig for me.

So rest assured if you identify with any, or all of these, you’re not alone.

You’re just a human doing a very tough job. 

Confessions of an Entrepreneur

Old wooden confession booth

  1. “I got really, really lucky because I’m definitely not this good or talented.”
  2. “I’m carrying the weight of the world right now, and I’m crumbling under it.”
  3. “I’m anxious and worried all the time. I might have an ulcer.”
  4. “No one really knows or understands what I’m going through or dealing with.”
  5. “No one understands me.”
  6. “No one really cares about me.”
  7. “When people rely on me, I feel good. I want to feel relevant and valuable. But now, everyone actually is relying on me and I don’t have any time for myself and I’m drowning.”
  8. “I’m angry and frustrated all the time.”
  9. “I’m worn out, burned out, and just tired and weary.”
  10. “I feel alone, empty and lost.”
  11. “I’m not worthy of this.”
  12. “I’m unhappy and unhealthy. In fact, I’m quite miserable and most of it is self-inflicted.”
  13. “I loathe criticism. I could close a huge deal, have 3 others closing soon, get 500 accolades from my clients, but that one stupid person’s comments has consumed me all week and I can’t get past it.”
  14. “I’ve got problems and they are huge, and unique, and I’m the only one dealing with them, or who even knows about them.”
  15. “I’m not sleeping at night because I’m worrying too much.”
  16. “I’m the most insecure person in this room.”
  17. “If I fail, what will people think and say about me?”
  18. “What am I anymore if I’m not doing this?”
  19. “Juggling family and business responsibilities is so tough that I just want to crawl under my desk and hide.”
  20. “Sales are down today. Oh God, the world is ending!”
  21. “Will I have a heart attack at 50?”
  22. “This new competitor just entered my space and is younger, better, faster and cheaper. Is this the end?”
  23. “I’m a fraud. I suck. It’s hard to look at myself in the mirror.”
  24. “People think I’m successful. I have it all. But they have no idea of the true cost of it, and that I’m miserable.”
  25. “What surprise B.S. issue or problem or challenge will happen today to me?”
  26. “My back hurts so bad it’s tough to sit in a chair, but I have to work or I don’t get paid.”
  27. “I’m so stupid … I can’t believe I didn’t see that problem or issue until today. And now it might be too damaging to fix.”
  28. “The mistake that I or someone else just made could doom all of this.”
  29. “I need help, but I’m too prideful to ask for it.”
  30. “Everyone on my team should work just as hard and be as committed as me.”
  31. “I’m jealous of everyone else. It’s eating me up that so many other people are doing better than me, even though I’m busting my butt.”
  32. “My friends and family still thinks I should have done X, instead of this. I have no support.”
  33. “What if this doesn’t work?”
  34. “If everyone knew what really goes on inside my head, they wouldn’t want to know me.”
  35. “I don’t have any friends.”
  36. “Would these people be my friend if I wasn’t doing this?”
  37. “Is this as good as it gets?”
  38. “Sometimes I wish I just had a 9-5 job. And could clock in and clock out, and leave all of this at the office, for someone else to deal with.”
  39. “I’m so ready to quit.”
  40. “Someone I trusted deeply betrayed me. I’m pissed. And now I doubt everyone I know.”
  41. “I don’t know how I’m going to pay my mortgage this month, let alone salaries.”
  42. “Sometimes I really can’t stand people. Business would be awesome without the people.”
  43. “All I do is put out fires all day, every day. It seems like problem after problem after problem.”
  44. “I have absolutely no clue that the decision I just made is the right one.”
  45. “I’m down, life sucks, but I have to put on a happy smile for everyone else and act like nothing’s really wrong.”

OK, these are the Confessions of an Entrepreneur, so far anyway, as I’m sure there are more.

Again my goal isn’t to rant or get sympathy or to hurt anyone’s feeling, I simply hope it resonates with those entrepreneurs who might read this and be right in the middle of a tough time.

For you, I hope you can say because of this: I’m not alone. 

And if you’re one of those people in a low time, check out this post I wrote detailing 5 Ways I Deal with Lows in Business here. I hope it helps you wade through to the other side.


If these confessions resonate with you … it might be time to join an entrepreneurial peer group.

I’ve been a part of four entrepreneur groups over the last 6 years and they have had a profound impact on my life.

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