Entrepreneurs and Insecurity: A Perfect Match?

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For the past few months, Karen and I have been eagerly interviewing entrepreneurs from across the country for our upcoming book. We’ve noticed several recurring themes when it comes to personality traits and life outlooks among those we’ve interviewed. One common trait is their optimistic outlook on life. Another, which came as a complete shock to us, was that many of the most successful entrepreneurs with whom we spoke described themselves as insecure.


Throughout our interviews, we’ve asked, “What is the most difficult thing about being an entrepreneur?” Repeatedly, we’ve been told self-doubt, and the feeling that he or she didn’t belong in the elite category of “successful entrepreneur.”

Peter Shankman, author, entrepreneur, speaker, and a worldwide connector best known for founding Help A Reporter Out (HARO), said this regarding his biggest obstacle: “Self-doubt. If you don’t believe in yourself, no one else will. When you are good at what you do, it is easy to convince others, but it’s really hard to convince yourself.”

New York real estate mogul and star of NBC’s Shark Tank, Barbara Corcoran, said the hardest part of achieving her success was learning to ignore self-talk. She added, “It’s hard when you’re afraid…feeling like you’re not entitled to your success. And having the feeling like, ‘I shouldn’t be here. They hate me. I don’t belong, etc.’”

The other consistent theme we’ve discovered is how insecurity is used as a source of strength for entrepreneurs, rather than a source of weakness. Some entrepreneurs commented that they use the self-doubt as leverage to push themselves forward to prove to themselves that they can accomplish a task. Many also commented that they have learned “positive self-talk.” In other words, when they feel themselves doubting their abilities or feeling insecure about a situation, they give themselves an inner pep talk to boost their confidence.

Karen and I are looking forward to sharing with you the many wonderful stories that we are collecting. We hope they will inspire you to either pursue becoming an entrepreneur, or to continue forging ahead with a business that you are working on now.

If you’d like to share your entrepreneur stories with us, please post for us here, or email me at susan@susansoutherland.com. We would also love to hear about how you conquer your insecurities.

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Showing 4 comments
  • Jean Norton

    Thank you so much for writing this – excellent confirmation for me.

    Somehow always finding myself in a male dominated industry, the hidden “self-doubt” is often there. Even when people speak directly to me with amazement on what I’ve accomplished, I minimize it as no big deal.


    Jean Norton
    Real Estate Investor

    • Susan Southerland

      We are taught to be humble. Sometimes that can be counter productive to our success. Take those compliments to heart!

  • neva

    Oh my goodness this is so true. I just doubted myself this weekend. The way I dealt with it was I sat down and wrote down all the amazing things I’ve conquered within the last year of my life. After I flushed out the list I felt much better and laughed that I ever doubted myself. I actually started to think ” who is that amazing woman I just wrote about, oh yeah that’s me” 🙂

    • Susan Southerland

      What a great way to deal with that insecurity! It’s so important that we give ourselves credit for our talents and our hard work. Putting it in writing helps to make sure that we don’t dismiss it.

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