“What did you fail at today?” 

That was the everyday dinner table question her father used to ask her growing up. 

Every real answer was met with high-fives. Not trying was met with disappointment. Each incident or blunder was celebrated, making Sara Blakely think of failure like a normal part of a lesson: “If you can laugh about it, you can learn from it”.

To say that I love Sara, would be an understatement. In my head we’re besties. I’m manifesting that just like she manifested Oprah for her business. I’ve watched her interviews, talks with Tony Robbins, seen her on shows, stalked her Instagram and took her MasterClass (highly recommend). 

Fast forward recap of her amazing journey from putting her own butt on the line to becoming a billionaire badass

Sara grew up wanting to become a lawyer, like her dad, but bombed the LSATs (which was clearly a destiny thing). The next logical move? Deciding to play Goofy at Disney World, but ended up as a Chipmunk instead (obviously, a height issue).

Her “Training day” moment lasted 7 years: She sold fax machines, door-to-door. She had a genius idea but knew nothing of the biz and how she’s going to get it done. 

She did it anyway, on her own terms, redefining the industry and creating an apparel empire. She put her own butt on display, literally, and became a badass. The youngest self-made billionaire. 

On her first sales trip to the UK, while she was live on the BBC when: 

“The interviewer asked, “So Sara, tell us what Spanx can do for the women in the U.K.” And I smiled really big and said, “Well, it’s all about the fanny. It smoothes your fanny, it lifts it, and it firms your fanny.” I knew instantly I had done something seriously wrong because the interviewer had lost all the colour in his face. He stopped me and said, “I think you mean bum.” I said, “Yes, right, bum.”

When I got off the air, I found out that fanny means vagina in England…”

She hangs out with the likes of Warren Buffett. She was on the cover of Forbes, Inc., appeared on 60 Minutes, Shark Tank and The View. She wore a dress backward on “Good Morning America.

One of her most recent embarrassing moments happened on plane, as she so delightfully explains in a public post:

Let me explain… I’m headed to Seattle, I’m craving chicken wings. I’m in back to back meetings and don’t have time to eat my homemade wings. I board the plane and think… “am I really going to be that person who gets out a full chicken wing spread on a plane?” Yup. I’m hungry.  I put my headphones on and try not to look at the man next to me… sauce everywhere, fries, celery sticks, blue cheese dipping sauce… oh and I’m wearing a “work in progress sweatshirt” @spanx @bowanddrape – you get the picture. Anyway… I say out loud to myself “At least I will never see this man again.” Fast forward… I’m at a cocktail party at @thisisbillgates @melindafrenchgates home and a man comes up to me and says, “you look really familiar. I sat next to you on the plane… aren’t you the girl with the chicken wings?” Swipe to see a picture of Rich who happens to run one of the largest companies in Florida TechData. Of course he does! A company based in my hometown Clearwater, Fl no less. I’m at this event surrounded by impressive men and then he says, “It wasn’t so much the chicken wings that got me, it was the family size bag of Cheez-it’s you ate.” What’s the most embarrassing thing you’ve brought on a plane to eat? #DontBringWingsOnAPlane #MondayMotivation” 

Sara’s take on mortifying moments: embarrassment can work to your advantage

Of course, it takes practice to master it, and comes with commitment, meaning you have to be willing to embarrass yourself on purpose on a regular basis. 

“I’ll sing in an elevator for no reason, with other people in there, and my heart will be pounding and everyone is like uncomfortable and it is awkward and embarrassing,” she says. “Or I will ask a question that I know really sounds quite stupid, but I am curious about it and put myself out there.” 

As far as I can tell, both Sara and I agree on this: perfection is the nemesis of progress. 

In her quest to make women comfortable in their own skin and garments, she managed to wipe out visible panty lines – bye, bye VPL – but kept her own vulnerabilities for everyone to see. 

Her business M.O. is humor. Empathy. Talking to customers like friends. Solving problems. And last, but not least, not being afraid to fail. Or to care the most. 

“Encourage failure. When you’re disruptive, there are bound to be missteps. Celebrate mistakes and lessons learned. That’s what reshapes your culture. It’s also important to share your personal mishaps—being vulnerable as a leader opens up the team.”

While her brand is made for comfort, her life philosophy is not as convenient, because she admits that she deliberately put herself out there: 

“If too much time goes that I haven’t embarrassed myself, I can sense it in myself and I’m like ‘I’ve got to do something embarrassing,’ because it loses its power over me,” she said on the “The James Altucher Show” podcast.”

Re-shaping rejection

All those years of door-to-door sales trained her not to take the word “no” so seriously. The cold-calling experience was humbling. She used to get escorted out of buildings by security, have her business cards ripped off in her face a couple times a week. So rejection became just a game of numbers for Sara, instead of a permanent stop. 

“When I started my company, I’d reach out to hosiery mills—which were all run by men—asking them to manufacture Spanx. I called them all on the phone at first, and they all pretty much gave me the runaround. So I took a week off of work and drove around to all these manufacturing plants that were all mostly concentrated in North Carolina. I had my lucky red backpack from college with me, and I would walk in, and they would always ask me the same three questions. They would always say, “And you are?” And I would say, “Sara Blakely.” And they’d say, “And you’re with?” And I’d say, “Sara Blakely.” And then they’d say, “You’re financially backed by?” And I’d say, “Sara Blakely.”

She heard a lot of “We’re not interested.” lines, but somewhere along the way, she developed a very definitive, confident language. “If you’re only given 30 seconds or a minute to try to make your pitch, you need to also figure out how you can make it about who you’re presenting your idea to, and what’s in it for them. So I did that all along the way of my journey.”

Another thing she did to embrace embarrassment: stand-up comedy. 

Before Spanx, while still in her 20s, he went on stage at the Punchline, in Atlanta, and gave it her best shot. There’s nothing more nerve-wracking than being in front of everybody. She admits that was one of the most embarrassing things ever, but since getting over the fear of embarrassing yourself and using humor in business are of paramount importance for her, she actually shared her first time on stage with her Instagram audience, to let everybody know that you shouldn’t take yourself too seriously. 

Plus, she planned a little surprise for her team, announcing that: “Every employee @Spanx is going to get on stage at a comedy club I rented out for the day. As part of our “Be Bold” Boot Camp at Spanx, every employee has been working wIth a comedy coach @jeffjusticecomedy”. I bet bits about the CEO were highly welcomed!