Breakout and Define Your Success On Your Terms!

Join the Sisterhood

Create Your Pathway to a Passionate Personal and Professional Life

What I Learned From Interviewing 163 Entrepreneurs About Failure

Dorie Clark

Dorie Clark

What I Learned From Interviewing 163 Entrepreneurs About Failure
Share on Pinterest

This post is co-authored by Dorie Clark and Matthew Turner.

We always hear about the success stories. Mark Zuckerberg launching in his dorm room. The WhatsApp guys selling for $19 billion. Uber disrupting the taxi industry, and pretty soon everything else. But along the way, even the most successful entrepreneurs have made their share of mistakes. That’s the part Matthew Turner was interested in, and he’s spent the past 2 ½ years interviewing 163 successful entrepreneurs, a number that continues to rise. (I met Matt when he reached out to interview me about the ways I’d screwed up.) He’s now in the launch process for his forthcoming book, The Successful Mistake, which is available for pre-order.

I asked him to share some of the lessons he’s learned through hundreds of hours of interviews. Here are his thoughts.

Enter Matt.

The Definition of Success.

I’ve noticed lots of patterns along my Successful Mistake journey, but one of the most important is that successful people understand what success means to them, whereas the rest of society strives for a version of success defined by someone else (which usually involves making a million dollars, buying a big house, etc.).

The forgotten question throughout this journey is, why? Why do you want any of these? But speaking to the likes of Steve OlsherLinsi BrownsonCorbett Barr, and Dan Miller among many others, I found a common sentiment surrounding success: that it’s about who you want to be and what kind of legacy you want to leave. It’s not about what someone else wants for you. I wrote about it in this Medium Article. I now realise one of the key differentiators of truly successful people is that they understand what success means to them. For me, it’s no longer about the quest for money; it’s about legacy. I want nice stuff, but only if it brings real meaning into my life. I wish to grow as a business and person so I can touch more people with my stories and art, not for the mere self-satisfaction of ‘making it.’ I need money, but only enough to lead my lifestyle and help those I wish to help.

It’s OK to Feel Scared.

If I’m honest, I feel rather hopeless and scared 80% of the time. As such, I compare myself to the likes of Mitch JoelChris Brogan and Pam Slim, forever placing them on some unattainable pedestal. But I realized that every person I interviewed – no matter how big and impressive their portfolio is – felt scared, and still feels scared, by new launches and projects and ideas. They’re confident and believe in their abilities, just like I do, but demons plague their mind just like they do mine.

What I learned from folk like Debbie MillmanNatalie Sisson, and John Lee Dumas, who all shared stories of fear and vulnerability, is that I’m braver than I give myself credit for. Sometimes I felt intimidated by the people I interviewed. But day-by-day, I realised I’m no different than those I read and follow and look up to. They may be further down the road than me, and have a different personality, but we’re built of the same guts and glory.

It’s Important to Ask for Help.

The moment I decided to interview 150+ entrepreneurs for The Successful Mistake is when I relied on asking for help – a lot. Asking for help unnerves me. But when you ask for help, most people do (including the entrepreneurs who shared their time and advice with me). Not everyone can. Not everyone will. But many will surprise you. Asking for help continues to trouble me, but I’ve learned to push it aside and ask anyway.

Matthew “Turndog” Turner is an Author, Brand Storyteller & Speaker who spends each day Discovering, Creating & Sharing Inspiring Stories. He’s currently writing The Successful Mistake, a book about overcoming your #GreatMistake and transforming it into your best idea yet.

Dorie Clark is a marketing strategist and professional speaker who teaches at Duke University’s Fuqua School of Business. She is the author of Reinventing You and the forthcoming Stand Out. Subscribe to Dorie’s e-newsletter.

Originally published here on

  1. Stacey Sullivan 3 years ago

    Wow, I really needed that. I have just closed a portion of my business. Even though I made the choice to do it, because I had lost my passion for it. I find myself caring to much what others think and what they want for me.

    I am finally beginning to see that I can build a whole new life for myself. That my mistake can be a learning tool but I still get fearful about making another mistake, it is crippling me. I am afraid to take the next step, so seeing that others have had to deal with being afraid and have used that as a positive helps me put it all in perspective.

    • Michelle Glover 3 years ago

      Hi Stacey! I am Michelle, the founder of BWE. Thank you for sharing!

      I have been through those times when things are so difficult. You are right; you can build a life for yourself that nurtures you in real and meaningful ways. For each one of us, it takes courage to get up, brush ourselves off, learn our lessons and take even a small step forward in that new and heartfelt direction. Even if we make mistakes, which we will, that is something we can be very proud of. I am proud of you for sharing your story as a way of helping us all move forward;))

  2. Dorie Clark 3 years ago

    Stacey, I’ll second Michelle’s response. Thanks so much for sharing your story. As someone who started my career with “three strikes,” so to speak (not getting into the PhD program I wanted, getting laid off from my first job as a newspaper reporter, and then working for two losing political campaigns), I was eventually able to find my way into a good place professionally (as I discuss in my first book, Reinventing You). But it does take time, and mistakes, and learning from them. Good luck!