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Startups Anonymous: The Secrets of a Startup Founder



[This is a weekly series that brings you raw, first-hand experiences from founders and investors in the trenches. Their story submissions are anonymous, allowing them to share openly without fear of retribution. Every Wednesday, we’ll run one new story chosen by Dana Severson, who operates StartupsAnonymous, a place for startups to share, ask questions, and  answer them in story-length posts, all anonymously. You can share your own story here.]

We entrepreneurs keep a lot of things bottled up inside. We tend to want people to think that we’re on top of our business and everything is going exactly as planned.

The truth is, we often have very rational concerns about what we’re doing and how we’re doing it. Unfortunately, we tend to keep our fears hidden because we’re worried about how they may be perceived.

Having moderated the stories and questions on StartupsAnonymous.com for nearly a year now, I can tell you that no entrepreneur is alone. Whether you talk about it openly or not, most entrepreneurs have a very healthy fear of failure and discontent.

To illustrate my point, the following are the fears that follow me around every day that I’ve never told anyone …

  • I’m not getting any younger. Will I look back 10 years from now, and regret what I’m doing today?
  • Have I missed my window on success?
  • Will I ever get to see my vision followed through completely?
  • Am I good enough at what I do? Everyone seems smarter than me.
  • Will my product work like I hope it will?
  • Will I be broke forever?
  • Will I ever be able to raise money again?
  • Will I always be jealous of other people’s ideas, businesses, and successes?
  • Will I have to work for someone else?
  • Can people tell that I’m full of sh*t at times?
  • If investors are investing in me, when they say “no”, does that mean I’m not good enough?
  • Are others working harder than me?
  • Am I even doing the right things?
  • Does any of this even matter?
  • Will I ever satisfy my hunger, or is it just an endless road?
  • Do I have what it takes, whatever that is?
  • Will I ever lose the chance to be an entrepreneur?

Can you relate? What are your secret fears?

– Dana Severson @danerobert

[illustration by Brad Jonas]