The Real Danger for Men Who Chase Big Dreams

There’s a right and a wrong way for a man to chase a dream. It’s linked to people’s willingness to give you a chance—which fades over time. You’d be surprised at how many men just don’t get it—and with major consequences. 

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RECENTLY I advised a young man who was preparing his first CV. He was concerned that nobody would be interested in his debating club and chess captain gold stars or in his athletic achievements. Not at all, I said. It’s all they have to go on. At least it shows your range of capabilities and that you’re interested in doing stuff. It’s a conversation opener for your interview, to find out how you think—whether you do even think, whether you can even hold a conversation.

When you’re starting out, it’s as simple as that. People have an eye out for anything you might do or say that will show a spark of something: initiative, intelligence, creativity, responsibility, accountability, discipline. They’ll want to know if you’ll show up on time, take feedback, learn from your mistakes, just as much as they’ll want to know if you can do the job and do it well.

But there’s a limit to that idea. People’s willingness to give you a chance fades over time. By your mid-thirties and especially into your forties, people are much more interested in your track record. What have you achieved with all those chances you were given? What hardships have you overcome? What character have you demonstrated? Have you stuck it out when the going got tough, or did you just bounce from one easy-seeming option to the next?

Now this may sound obvious, but you’d be surprised how many men just don’t get it—and with major consequences. I’ll deal with older guys in a minute but first let’s stay with the young guys who are starting out. There’s a short video doing the rounds on social media. It shows a young male graduate being asked to stand in a square in exchange for money and how his life shrinks once he accepts the offer. It’s meant to show how getting a job restricts you. It’s meant to encourage you to break free and live your dream.

Now I’m all for that. After all, it’s how I lived my life. At the same time, precisely because it’s how I lived my life, I know that there’s a right and a wrong way to go about it. And by the way, if I could have my life over again, knowing what I know now, having gone through what I’ve been through, I would do both: I would take that job and still pursue my dreams.

There are layers to this, so stay with me. I’m going to show you when and how the big pursuit of dreams can be a problem.

Try all you like, but keep your feet on the ground

What usually comes up in the minds of some young men when they hear this is that they, unlike everybody else, are a secret genius who will one day emerge as the next Steve Jobs or Elon Musk. Guys, I hope that’s you, but believe me, if it’s you, then it’s not going to be the 999 guys around you. And if it’s one of them, it’s not going to be you. If I was you, I’d bet on it being one of them and act accordingly. That doesn’t mean don’t try, it means keep your feet on the ground while you try.

Make sure you build a real, honest and true track record. If you can’t do something, or fail while trying, own it.

And as I mentioned in my previous episode, those Steves and Elons are already on the path. They are not trying to get on the path, they’re just on it. If you’re one of them, you’ll know, because you’ll know this: you’ll know it’s not an easy path, but it is an inevitable one. It’s not a path you’re trying to get onto. If you think about it at all, it will be to ask whether it’s a path you can escape from. Those are the people who have biographies written about them. Then we read them and think if we just do this or that, we can reach the same heights. That, my friends, is a misguided notion.

And if you get it wrong, there can be major consequences.

You see, if you don’t make it, then when you get into your forties, then life—in the form of other people—is a lot less interested in your ideas and their potential and much more interested in your track record.

Men without a track record turn to failing forward

Here’s what happens to men who don’t have a track record.

They become, at best, hopeless dreamers. Or, worse, swindlers. And, worst of all, downright fraudsters and hucksters.

Let me explain why.

Let’s say you start out making big promises so that you can get someone to buy into your idea and raise a round of funding. Not let’s say that idea doesn’t work out, and you’re convinced that you’re the next Elon, what do you do? You go again. And you should, after all nine out of ten business fail, right? Use other people’s money! Isn’t that what they teach in entrepreneur school? I know, I’ve been there, I’ve done that.

Only problem is, I was one of those you never hear about: the ones who don’t make a billion-dollar exit. They don’t often tell their stories, why? Because they’re ashamed, and so they slink off into the shadows.

But let’s say you’ve been watching the videos of one of those six-figure exiters and you’re convinced that you’re next, and if you just stay on track, you’ll get there.

Now let’s say you fail again, and again. Or maybe, even worse, you have an early success and you become cocky and arrogant and you go and raise a huge round for your next venture. Then let’s say that one fails, but, undeterred, you go again, you find a new idea and a new funding target, and you raise yet another round.

This is called failing forward.

There are men failing forward around you, every day

You probably know one or two men like this.

There’s the one who dresses half his age and always has a new young woman on his arm. He’s always got a new scheme going, and he makes excuses for the fact that he still lives in—well, come to think of it, nobody actually knows where he lives, nobody has ever actually visited that place.

Or there’s the guy who plays the same game but lives at the other extreme. He dresses in top-end fashion and lives a grand, flashy lifestyle—with a glam wife or, as with the previous guy, always a new glam girlfriend. This guy appears to have all the shiny objects to suggest he’s making it. But you also struggle to put your finger on what he does, and if anybody had to dig, they’d discover that he’s been spectacularly successful at one thing: failing forward.

Failing forward means he’s done many things, few of which have worked out. But what he’s done following each failure is he’s found the next person he can talk a big game to—each time a bigger game—and by doing that, he’s landed himself an even bigger job, or even more funding for his next venture. In other words, he’s failed to build a track record and he’s managed to hide that, and to sell himself instead on his potential.

Some men’s stories get so big that eventually there’s nowhere left to hide

Let me tell you where these guys end up. Their stories get so big that eventually there’s nowhere left for them to hide. Their false promises and empty track record gets exposed and they end up in jail—or dead. Seriously. Here are some names you can google: Bernie Madoff, who ran one of the biggest ever Ponzi schemes. Brett Kebble, a South African mining magnate whose empire turned out to be a house of cards and who hired somebody to kill him so he could escape the shame and leave his family a life insurance payout. He failed forward right into his grave.

Fictional versions of this kind of guy include Jay Gatsby, the protagonist in The Great Gatsby, Frank Underwood in House of Cards and Thomas Crown in The Thomas Crown Affair.

Younger versions in real life—who are still alive, but have all been sentenced to jail time, are the likes of Jordan Belfort, also known as the Wolf of Wall Street; Simon Leviev, the Tinder Swindler; Billy McFarland, the Fyre Festival guy; and crypto bro Sam Bankman-Fried, who’s still in prison. Maybe they’re lucky they got caught young. They have time to redeem themselves.

Pay your rent and let the big deals come to you

So, now you know why I’m warning you against becoming one of those guys. And the way to make sure you don’t end up like that is to do two things: one, as I’ve said before, always pay your rent through honest graft and not through borrowed money; and two, make sure you build a real, honest and true track record. If you can’t do something, own it and own up to it. Don’t pretend. Stop what you’re doing and start again—at the bottom if you have to. You’ll soon recover, and you won’t have anything to be ashamed of.

I know what I’m talking about because I’ve worked with many of those guys. They come to me having had glory in their younger years, but now they’re floundering. The first thing I tell them this is to take on this motto: Big deals are vanity, cash flow is sanity. In other words, take care of the small numbers. Pay your rent. Then the big deals, if they’re going to come, will come. Honestly, I’ve seen this work.

This is what I mean when I say, if you’re going to follow your dream, also keep your feet on the ground. Build a solid track record, don’t just build castles in the sky.

And here you can see why I say that for men to grow up, they need to grow down. Look at those words: track record, feet on the ground. It’s about walking the plane of the earth, taking two steps forward, getting knocked back three, then going again, but always on the ground.

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