Wondering why you’re not there yet? In 2021, Sara Blakely became the youngest self-made female billionaire. But here’s why her story could have very easily never happened.

We have all had that imposter syndrome of “well, what if I did this or what if I did that?” Or “oh, well, somebody else is already doing this. I couldn’t possibly do that.”

You’re probably struggling with those questions, or you have struggled with those questions at some point in your life. Or maybe somebody has sent this to you and they’re just saying that it’s gonna be okay—here’s what to do.

Why Sara Blakely’s Story Matters

Sara Blakely is the founder of Spanx and she became the youngest self-made female billionaire in history in 2021.

What Are Spanx?

Spanx are basically just a control top hosiery. So essentially from the bottom of your bust all the way down to basically your ankles—there are different lengths as well. From boobies down to ankles, it is a control top hosiery.

So essentially it just sucks everything in and makes everything smooth. Whether it’s that weird donut that you can get from your bra down to your underwear when you’re wearing a tight skirt, or it can be your thighs. Maybe they’re not as smooth as you would like, or maybe your butt’s not super smooth.

It literally makes you like a sausage casing and makes everything so smooth.

This Existed Before Spanx

This idea existed before Spanx, right? In varying degrees. So there was like a girdle that you could wear. I mean, corsets had been around—there are a lot of historical precedents to this. But this was like a modern way of being able to wear essentially a corset.

The Moment of Innovation

In 1998, Sara Blakely already had the control top hosiery, but they had feet on them. So she couldn’t wear the shoes she wanted to wear because you would see that she has these weird smooshy looking feet.

What she ended up doing is she cut the ankles and the feet off of the hosiery that she had. So she was able to wear the pants she wanted and look the way that she wanted and feel the way she wanted to feel.

But here’s the thing—that one idea made her a billionaire. But that one idea today, say she could have easily come up with that idea in 2025 and been like “this works well, let me make a TikTok and tell people to do this.” And that could have been the end of the story.

The First Potential Quit Point

In the 1990s, before YouTube and TikTok, you still could blog and do all these things where you could tell your friends and spread the news about whatever. She could have easily just been like “oh yeah, people can just do this.”

So that was the first time she could have just quit and said “there’s nothing here. This is just an idea and something that’s helpful to me.”

But she realized this should exist because there were a few refinements that could have been made—like elastic around the ankles, things to hold it in place so it doesn’t just roll up your leg as you’re walking around.

Years of Development

She spent years trying to figure out what type of elastic to use and how to actually hold the ankles in place to have everything smooth and work the way she wanted to.

Once she started to find things that worked, she went to manufacturers and she was turned down every single time when she was trying to get anyone to try to make a prototype for her.

And without actually having a prototype, how can she sell to anyone? So she was sort of dead in the water.

The Oprah Moment

I think it was about two years after she had the idea and had been working on it—she just worked in sales, she still had her day job this whole time, she’s trying to do this—there were many, many roadblocks in the way where she could have easily quit and been like “oh, it’s not worth it. Just tell people to use scissors.”

It was about two years in when she had Oprah on. Oprah’s on her show saying exactly what Sara Blakely figured out. Wouldn’t that just be gutting?

On Oprah’s show, Sara Blakely’s watching and on the show she’s just like “look, I’m able to wear these shoes because look, I cut the bottoms off of the hosiery.”

That easily could have been a moment where Sara Blakely was like “okay, now it’s really out there. Everyone knows—this is the biggest show in the world and everyone has heard this. Now why would I keep going?”

But she used that as inspiration to be like “no, I have an idea here clearly. Now someone else who I respect came to the same conclusion. It tells me there’s something I need to actually make happen.”

The Final Push

So that was the point she sort of pushed the pedal to the metal again and kept going. And her story goes on from there. It’s several more years until everything clicks and it’s sold at Neiman Marcus and all these other stores.

And then by 2021, so like 20 years later, is when she becomes a billionaire.

But the whole company could have never happened if she just sort of kept thinking small and let all of the obstacles stay in her way rather than sort of the stoic perspective of “the obstacle is the way” and knowing “no, I need to keep pushing through this because there’s something better on the other side.”

The Gut-Wrenching Reality

It’s difficult to not get discouraged by, especially seeing Oprah in the nineties—that was huge. I mean, I never watched Oprah, but I know that she was a very big personality, presence. The show was huge, which also was here in Chicago.

Having literally one of the biggest daytime TV talk show host celebrities of the time period be like “oh, just do this”—that would be so gutting to see.

That’s something too in the social media space, which is where one of our businesses, MAVEN, is based. We film social media content with realtors and small businesses around the country.

If you ever see something that is like “oh, well I thought of that, but I didn’t have time, or I didn’t get to do that, or whatever”—that’s like the worst feeling. Because it’s like “well, shit, I should have doubled down on that because look at this person—they’re doing so much better with it because they stuck with it or they tried it or they took the shot.”

It’s gutting. And you just can’t let that hold you back.

Just because you haven’t yet pushed through doesn’t mean you’re an imposter. You just haven’t gotten to the point where you’re a full pasta.

What We’ve Been Up To

This week we recorded with one of our Top Bananas, which is very fun. Top Bananas are the realtors and small businesses we film hyperlocal social media content for and with.

So we filmed here in Chicago. But we tried something new. We tried a new type of filming, which is very interesting. And it’s something that’s being very prevalent in the real estate space right now. They’re called scoops and it’s sort of a news anchor type delivery.

Constant Evolution

What we are always doing is trying to iterate and sort of improve our business consistently because nothing is just stagnant and the same. Things are always changing and things are always evolving, so you need to actually do the changing and evolving.

Otherwise, if we were doing the same thing we were doing two years ago, it could work, but that’s not how the landscape is. Just continuously building and trying to make new and better things.

It’s almost a running joke every time you email a Top Banana before we’re filming—you’re like “so everything’s new again.” I just leave that part at the top of the email because I copy and paste from the last email. There are certain things that I just don’t change and I just change out the date, but obviously I change out all the copy and all the ideas.

But it’s always just like “hey, as usual, everything’s changed again.” And that’s the thing that I have at the top of every email, which I find funny. They may or may not even care or notice, but everyone says that they love how we’re always evolving.

People that have stayed with us for a very long time, almost since the beginning, they’ve seen this complete evolution of different things. But that’s a necessity.

Strategy Versus Tactics

It’s what works now and the evergreen approaches always work, but then there’s always—we talked about tactics versus strategy. The strategy always works. Our strategy has never changed, but the tactics we’re using for that strategy are constantly evolving.

Other Projects

And I’m making some music, which is always fun. They’re very—they just make me so happy and make me laugh. They’re so weird, but they’re silly. I feel like the description would always just be “songs that make me laugh.” That’d be the way to describe everything I make.

We are also still working on Hiveway and our products and trying to bring our Top Banana experience to sort of the product space to let people create their own content without having to figure out what to create.

Hiveway itself has even evolved tremendously since the beginning of what it was gonna be because with technology and everything, it’s like “okay, well this is what we were thinking.” And then now it’s just pivoted to such a different product and I know it’s gonna keep growing into something else.

It’s still the same where it’s content prompts and you know exactly what to make, but the depth of it is so much richer. Just different types of content.

How to Push Through Obstacles

So how can someone apply this thinking? Pushing through obstacles, thinking bigger and sort of really deciding—is this a moment to accept that “okay, maybe I am feeling imposter syndrome, maybe I am out of my depth,” or “no, this is something I need to push through”?

The Passion Test

I know it sounds really trite and like what everybody says, but if you have the passion or the belief behind it, you’re not gonna stop. And I think that’s what Sara Blakely had.

To almost obsess over making hosiery for women to feel confident and good in whatever they wear—that’s like a severe passion. Thinking about the outcome of “wow, I could make at least 10 women feel better in their evening gowns when they go out for a night with their husband or partner”—whatever it is.

So first, figure out if you do have that passion and that “yeah, I want to do this.” Because you have to at least love a little bit of what you’re doing, otherwise you are going to hate it. And that is what burnout is—when you just don’t like what you’re doing. Point blank.

The Burnout Theory

I know this is kind of controversial, but I don’t believe that burnout exists. I believe that you hate what you’re doing. That’s it. You don’t get burnt out on something that you love. It’s purely just “I hate doing this and I’m just pushing through.”

And maybe that’s a time when you should reflect and be like “maybe I don’t wanna be a baker. Maybe I don’t wanna be a pirate. Maybe I don’t wanna do this.”

I think it’s also if something is too easy or too hard. Because if it’s way too easy and you have to keep doing it, it’s just like monotony and it’s like “oh, I hate this.” Or if it’s way too hard, you can never get the sort of positive outcome feedback because you’ve dialed the knob way too far.

So you’re sort of in no man’s land on either side of too easy, too hard. There’s a non-burnout sweet spot somewhere in the middle.

Don’t Get Discouraged

Just trying to not get discouraged is also very important. So not only do you have the passion, but then you need to actually have the practical ability to balls-to-the-wall get it done. Because that’s also very important. Act on what it is that you want to do.

Try not to get discouraged. It’s very, very difficult, especially nowadays with globalization. Everybody can connect and talk and have ideas together, and maybe you’ll meet somebody who has the same exact idea as you do of having a topless donut shop, and you’re like “well, I wanted to do that.”

But somebody could have your same exact idea. But what you need to remember is even if somebody has the same exact idea as you, you are what’s gonna make it different. How you go about solving that problem, making the product—all these things, that is what’s gonna make it a different product altogether.

Your Unique Context

In our episode last week where we were talking about fluency, which is familiarity versus disfluency, which is the unfamiliar—we love the fluency, we love the familiar, because it feels familiar to us.

We also talked about how looking at just a random piece of art doesn’t really give you much, but as soon as you have context for it, that changes how you look at it completely.

So the same is for your ideas of what you wanna be. For example, because we work with a lot of realtors, using realtors as an example—there may be certain markets that you want to tap into. But you don’t feel like you can because either somebody or a whole team is already there, and that’s quote-unquote “their territory.”

I’ve heard this verbatim from numerous realtors, and my immediate thought is “so what?” You go in there, you be unique and you take over. What’s the problem?

Don’t Be Afraid to Compete

There’s sort of a block there that I personally don’t understand where I’d be like “I’m gonna burn it down to the ground”—not the houses, because you need to sell those—but just don’t be afraid to go in there.

Don’t feel discouraged if it’s like “well, Bobby and Susie have been there for 700 years and they’re like a generational real estate family.” Okay, cool. Maybe Todd and Bob who live down the street are new to the area. They don’t know who Susie and Kelly are. And they’re just like “oh, I’ll work with you because you’re cool and you ride a motorcycle. I wanna work with you.”

Everyone Is Different

Because everyone’s different. When we first started, we filmed with some people who were in the exact same neighborhood in Chicago. Like literally down the street. Complete polar opposite people. They were such different people.

We’ve been asked since, “are you ever afraid of filming with the same people in the same market?” And it’s like we don’t typically film with people in the same market out of respect to our other Top Bananas because it’s not something that they always would want.

But there’s no actual practical reason why we don’t, because we worked with people that we like, people we relate to, people who we are fluent in.

If you’re a religious mother of three who has this whole laundry list of things, there’s certain people who are like “that’s my person.” But then the established people in the market might be 73 years old and they’ve sold houses since they were 16. That’s a different type of person who would go for them.

Copy and Make It Your Own

Don’t be afraid to be you and to also go for it. And the same thing with social media content too.

If you see that something’s working—which again, as we always say, followers and views do not equate to business or any monetary anything—but if you see somebody doing something on social media and you just personally want to do it because you’re like “I think that would be fun or whatever,” do it.

Don’t be afraid that somebody else is doing it, even if they’re in your market. Just do it. Copy it. “Steal Like an Artist”—best book. Just steal it. Make it your own. Put a little flavor on it. Put a little cayenne, a little bit of cumin—that is your own zest. And make it yours.

Everything Is a Remix

That book is by Austin Kleon, “Steal Like an Artist.” The whole premise of the book is that art is stolen 100% of the time because everything we make is influenced by everything we’ve consumed.

So if we wanna make a movie and we’re like “this would be so much fun,” you’re gonna make a movie similar to the movies you like because that’s what influenced you. That doesn’t mean you stole in a bad way, but you have taken those ideas and thoughts and molded them into something new.

“Steal Like an Artist” because that’s all of anything ever made is just a remixing of the past and our experience with it.

This was Useful Not Famous. If you found this insightful or you have a friend who is struggling with imposter syndrome or just that “well, yeah, but they’re doing it,” definitely send this to them. Or even if they just want a nice little giggle.

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