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Are insecurities driving your ambition?
Entrepreneur Steven Bartlett on the difference between "real" and "fake" ambition
“The real skill of quitting isn't necessarily knowing—because you can't know. But it's knowing that you can't tolerate the current situation. It's knowing that uncertainty is a better hand to have than misery.”
Self-made millionaire and British entrepreneur Steven Bartlett began building businesses at 18, rising from a university dropout to success by 23. He's a regular on Dragons' Den, the British equivalent of Shark Tank, and now runs the business podcast The Diary of a CEO. In his interview with author and podcast host Simon Sinek, Steven talks about the importance of focus in business, the difference between “real” and “fake” ambition, and how to motivate teams.
You can catch the complete episode (1 hour) on Spotify.
Focus may seem boring—but it’s critical. Growing up, Steven saw his mother start 25 businesses within the span of a decade. They weren’t successful, except for maybe one—a restaurant. Yet despite its success, Steven’s mom often got distracted by other business opportunities. “I watched the restaurant crumble as she tried to give 50% to things when both of her competitors and those industries were giving 110% to each,” Steven recalls.
Steven describes another example where the lack of focus undermined long-term success. After finding immense popularity, one of the UK’s biggest YouTubers started a variety of new channels for content about fighting, gaming, football, gambling, and so on. He also switched platforms and moved onto Twitch. Over time, “he lost sight of his authenticity and would take opportunities based on their lucrativeness” rather than their resonance with his audience. The result: His team left and the YouTuber texted Steven asking for a loan.
Fake ambition is driven by insecurities. Asked about his motivation for starting his earliest businesses, Steven explains that it was multifaceted. He wanted to become rich, but this desire came from his biggest insecurities growing up in poverty and feeling different. This wasn’t obvious to him at the time, though. Steven realized this later on through personal introspection, observing, “The things that invalidate you when you're a kid often become missing things you seek validation from as an adult. For me, I was invalidated by a lack of money, by no romantic interests, and by my family being quite bizarre.”
Steven goes on to describe this kind of ambition as “fake.” It’s fueled by the desire for rewards and validation. Real ambition, on the other hand, is driven by intrinsic passion. Steven describes DJing and his podcast as being fueled by real ambition. “They’re the things that you would choose to do if in a world where you didn’t have to worry about money,” he explains.
How do you know you should quit something? When despite all of the effort put into it, it’d still leave you unhappy. “You fight for something when you believe that the fight is worthy of the eventual cause,” Steven says. He calls himself a “remarkably good quitter” since he quits without worrying too much about his path forward or the path behind him. This is reminiscent of Annie Duke’s work in decision science—if not quitting means continuing down a path of definite unhappiness, it doesn’t make sense to stay.
People are motivated by progress. Steven once interviewed the famous cycling coach David Brailsford on his podcast. David, who led the British Olympic cycling team to incredible success, attributes his teams’ big gains in performance to the psychological sense of progress.
For Steven, creating a sense of progress and forward motion in his team is crucial. This means giving them autonomy and a healthy amount of challenges, and also reminding them that where they’re headed is worthwhile.
In my opinion, the most profound takeaway from this conversation is Steven’s explanation of fake versus real ambition. Here’s a quote that stuck out to me:
“What I came to learn over the years was that my ambitions were fake. They weren't ambition, they were insecurity—and there's a big distinction. Most of our lives are dragged by insecurity and shame. They're not driven by ambition, and it's a tragic truth that most of us are going to have. … It's something that I think a lot about: How do we get people to realize that these limiting beliefs and ideas that are driving their lives are illusions?”
According to Steven, some hugely successful people like Gary Vaynerchuck deliberately avoid therapy “because of what it might change in them, [or] what it might remove.” Like the drive to succeed.
This is utterly fascinating—and a great prompt for some self-reflection.
When you consider your own goals and ambitions, can you find any trace of deep-seated insecurities in them?
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