Sara Blakely: Learning to Fail

At the dinner table, most kids are usually asked some variation of this question: “So what did you learn today?” Or maybe, the vague question: “How was school today?”

But in a recent interview, Sara Blakely talks about how she and her brother were asked a very different and unique question by their father. That question was: “How did you fail today?”

Failure as a Great Teacher

This unique question wasn’t meant to be off putting, cruel or to surface negative emotions. Rather, it was meant to help the Blakely children foster a healthy relationship with failure. To see trying, and not succeeding (at least at first), not as en embarrassment, but rather as an essential ingredient of success.

That the journey itself, including all of the small speed bumps and outright face-plants, are an integral part of arriving at success.

This is a special, and unusual approach, and an excellent reminder that children, and all of us, can often best view failure as among our greatest teachers.

Blakely talks about how she carried this lesson into her business and professional life. She talks about how it comes down to “training herself not to worry what other people think” (a lesson we could all learn from!). She tells great stories about how even up to the current day, she’ll do things to intentionally feel “embarrassed.” The purpose of all of this is to intentionally maintain a relationship to fear, failure, and embarrassment that doesn’t hold her back, but rather empowers her.

One example Blakely gives is that she might just start singing in a quiet elevator full of strangers. While this might seem like odd behavior, Blakely explains that she views situations like this, that most would view as embarrassing, as instead golden chances to connect with others. That being vulnerable with others opens the door to greater connections.

Reframing failure

Blakely discusses how in her household, the term “failure” had a different context and connotation. Because of the questions her father would ask, and the overall spirit in which trying new things was embraced, Blakely learn to fail well. Accordingly, Blakely has a much different relationship to failure than most people. In her household, the true failure was “not trying.”

As if this wasn’t a powerful enough reframing of risk taking and failure, the questions Blakely’s father asked had an essential second benefit. Together, they could discuss and appreciate the wisdom, learnings, self awareness, and positive developments that came along with the failure of the day. And therefore be set to try new things the next day.

More on Blakely

As a little background, Blakely explains that her father was a trial attorney, and her mother was an artist and stay at home Mom. Perhaps Blakely’s father learned to “ask better questions, and get better answers” in his line of work as a lawyer. Whatever its origin, the question “How did you fail today” is a fascinating and powerful question to pose to one’s children. It views taking chances, and failing, as fantastic learning and growth opportunities. It places failure in a much different context than is likely experienced in most households.

In the interview, Blakely also discusses how she initially wanted to be a lawyer. However, she explains that she didn’t do well enough on the LSAT to get into law school. So she instead spent seven years as a door-to-door salesperson.

Fortunately for her, Blakely’s journey (speed bumps, failures, and all) eventually led her to become an incredibly successful businesswoman. Today she’s best known as the billionaire founder of Spanx, and as a philanthropist who uses her wealth and influence to provide more opportunities for women around the world.

Household Tone

In one take, this story about the Blakely household is a variation on the theme of “that which doesn’t kill us only makes us stronger.”

But this also touches on something else. Something deeper. And that is the “tone” or “atmosphere” we establish in our households. Not just around risk taking and failure. But around growth and development. About education and truth seeking. About self awareness and independence of mind. And many other essential aspects of growing up.

We won’t always get it right. But we can become better.

Further Reading

For more thoughts on cultivating courage and the reframing of fear, please check out Tim Ferriss’s article on “Fear Setting.”

For more about cultivating a household tone of curiosity, learning, and tolerance of mishaps and failures, please read our article on “Richard Feynman and Breaking Things.”

If you have thoughts on this, or other topics you’d like to hear about, please feel free to email me at

Sources: TR podcast episode, CNBC article


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