Fail As Often As Possible

“My father used to encourage us to fail when we were younger. We would sit at the dinner table and he would ask us what we had failed at that week, and if we didn’t have anything, he would be disappointed. It was one of the biggest gifts in my life…”

– Sara Blakely, founder of Spanx


I recently read this quote in makeup artist Bobbi Brown’s new book, Pretty Powerfuland thought this idea must be responsible for Blakely’s success as an entrepreneur. Blakely goes on to share that to her, failing meant she was “constantly pushing [her]self out of the box and trying new things.” To Blakely, the real failure (as the rest of us would define it) would be if she didn’t try something because she was too afraid. This is a great perspective every small business owner should try to embrace.

Another interesting take on failure comes from author, entrepreneur and Stanford professor Tina Seelig, who has her students create a failure resume. The idea is to make the students acknowledge what they’ve learned from the mistakes they’ve made in their lives. Seelig points out that people move forward in their lives because they’ve got experience. And experience comes from what you learn. So, she says, try lots of things, keep what works, learn from what doesn’t and use that experience to your advantage.

Still afraid of failure? Make a game out of it.

Rejection Therapy has one rule: you must be rejected by another person, at least once, every day. The idea is to push past your fears of rejection and take a chance on what might come of taking a risk. In other words, the game teaches you to embrace failure (playing cards available here). Wonder if Blakely’s father had anything to do with the making of this game?

How often are you failing? Are you pushing your brand to the limit and testing new ideas consistently? What’s on your company’s failure resume?

Please leave comments below and share your tactics for overcoming the fear of failure.



  1. I don’t think I ever really understood the value of this until the last year. Being a perfectionist I never allowed myself to fail, without a lot of internal berating. It’s not that I never failed, it’s just that I couldn’t see it as a positive thing. Yes, I would learn from failing, but I could never do it in a way that was kind to myself.

    My Year of TED project, and all of the amazing things I have learned from the TED talks, have allowed me to find a new appreciation in failure. I still have a long way to go before I would be comfortable failing every day, but I’m a lot further along than I was even 6 months ago.

    Great article, thank you for the reminder.

  2. OMG!  I love the idea of rejection therapy.  Boy, does that shift perception, an important goal of mine on my way to conscious living!  Years ago (not saying how many) Jack Canfield presented us with an activity.  In “cocktail party” mode, circulating around the room, half of the people were directed to ask a question and the other half to say NO 9 times and YES on the 10th query.  So as you asked your question, you got many rejections but randomly a YES!!  This served me well as I looked for a job that seemed like a needle in a haystack but eventually panned out.

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