Insecurity, Ambition & the Outlier Effect

Note: The following contributions are personal impulses from Max Eckel. They represent individual reflections and are intended to stimulate discussion and further thought.

I couldn’t have told you a single Taylor Swift song yesterday. Not one. Then we were in a small bookshop, and my kids picked a book from the Little People, Big Dreams series: TaylorSwift.

I remember standing there thinking: Okay. But is she actually a good role model? After the kids were asleep, we watched Miss Americana. I expected pop. Maybe some tour footage. A bit of PR. But I actually was genuinely impressed. There are multiple scenes of her in the studio, crafting lyrics on the spot. You see, this is obsessive work. Real talent. Not accidental success. She’s clearly an outlier.

“Everybody in music has their own sort of niche specialty thing that they do that sets them apart from everybody else. And my storytelling is what it is for me. And I know that without me writing my own songs, I wouldn’t be here.” She’s done pretty much everything there is to do in the music industry. The tours. The awards. The cultural impact. If “leave a dent in the universe” applies to anyone in pop right now, it probably applies to her.

But I was especially triggered by this quote: “We’re people who got into this line of work because we wanted people to like us. Because we were intrinsically insecure. Because we liked the way it felt when people clapped. Because it made us forget how much we feel like we’re not good enough.” By that, she says the obvious but uncomfortable thing: If your self-worth depends on people clapping, they can break you by simply stopping.

Now here’s where this connects to my world. My controversial take: I don’t think she would be where she is without that insecurity. That drive to prove something. To be exceptional. To be undeniable. That’s fuel. In the venture world, we romanticize this all the time. The founder who wants to build the category-defining company. The one who can’t sleep because the product isn’t perfect yet. The one who wants to build something so big it changes an industry.

If we’re honest, a lot of that is insecure overachievement. And I don’t even mean that negatively. I actually embrace it. I love working with people who want to build something truly big. Europe needs more of them. But that kind of self-awareness that Taylor is displaying in the documentary is rare. Especially at that level.

And yes, I’m happy my kids picked that book. I’m also happy my kids grow up seeing strong, ambitious women who own their story and that you can be world-class and still honest about your vulnerabilities.

If you care about outliers, about ambition, about strong women, showbiz, or about the strange psychology behind exceptional performance, I can genuinely recommend Miss Americana. We spend a lot of time teaching kids to be confident. Maybe we should also teach them what to do with insecurity.

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