The Corruption of Ambition
“The life which men praise and regard as successful is but one kind.” — Thoreau
My work coaching dads has helped me break new ground in understanding that our relationship with work is the central tension between the dads we are and the ones we want to be. It’s a topic I’ll be exploring in depth in the book, and this week’s essay is a sneak peek of a chapter that is waaaaay too long on how to break free from being defined by our careers.
The essay will explore why we’re wired this way, then a few dads will share their stories of trying to swim against the stream. I’m also inviting a small number of you to join REBOOT: a group coaching program to help radically rethink your relationships to work, home, and everything in between.
The life which men praise and regard as successful is but one kind. Why should we exaggerate any one kind at the expense of the others?
— Henry David Thoreau
Ambition and success. Fine bed fellows you’ve got there.
If success is planting your flag at the top of the mountain, ambition drives you to the summit. Success is the end result—the job title, the salary package, the perfect body, whatever sits at the end of that perilous path—whilst ambition is the fuel that gets you out of bed every morning, rising, grinding, crushing your to-do list (and competition) on your way there.
When success and ambition align, they act as powerful forces to push you towards a better future. But not always. Their relationship can launch you into a downward spiral, as you furiously try to pull the plane up, the ground approaching fast. My path felt pre-ordained, or at least well-trodden, for most of my twenties, and the lion’s share of my thirties too. Things changed when I had kids, but not as I expected. It wasn’t a stark, everything-changes-in-a-heatbeat shift: more a slow burn that eventually envelops all it touches.
It’s not unusual for new parents to ponder fundamental questions about the direction they’re heading. What does success even mean now? Society tells us that to be successful is to be wealthy. To be ambitious is to be hungry for the accumulation of wealth. If you were part of an alien race, observing from afar, and asked to rank Earth’s inhabitants in order of “perceived success”, you’d end up with something not a galaxy far, far away from Forbes Billionaire List. This annual collection of the world’s 100 wealthiest people started in 1987, the same year Michael Douglas’ Wall Street-trading Gordon Gecko would tell a young Charlie Sheen: “Greed, for lack of a better word, is good.”
This is the corrupt perversion of ambition: the pursuit of wealth at all costs. We don’t have to look hard to see how such a fundamental belief shapes our understanding of fatherhood. Walter White was stuck in a job he hated, working for students that didn’t respect him, harbouring resentment after selling his part of a company for thousands of dollars that would have eventually been worth billions. Spite can be a powerful motivator, and his journey to becoming Heisenberg was an attempt to reclaim his dignity, power, and the wealth he felt he’d been denied. What is Breaking Bad but a 62-episode saga of revenge porn, born out of a misplaced sense of ambition? Break all the rules, destroy your enemies and go out in a blaze of glory, whilst promising everyone who will listen that you’re doing it for your family—before finally admitting it was all for your ego.
For time immemorial, we’ve been spoon-fed tales of ambition through the shows and movies we watch. In 1992, Glengarry Glen Ross explored how deeply interwined success and survival were, with Alec Baldwin threatening poorly performing salesmen with the sack. Ed Harris wonders who this new slick dealmaker commanding the room might be, asking a simple question—“What’s your name?”—leading Baldwin to tear into him with an ostentatious tirade on how things he owns are all the proof of success he needs:
“Fuck you! That's my name! You know why, mister? You drove a Hyundai to get here. I drove an $80,000 red BMW that's parked right outside. THAT'S my name! And your name is you're wanting. You can't play in the man's game … this watch costs more than your car. I made $970,000 in sales commissions last year. How much you make? You see, pal, that's who I am, and you're nothing. You're a nice guy? I don't give a shit. Good father? Fuck you! Go home and play with your kids.”
Mad Men hinges entirely on the illusion of identity, and what it means to cosplay success: at work and home; to your wife, your children, and your boss alike. Don Draper’s existence depends on maintaining a mirage of victory in the office, his ambition fuelled by the need to escape the demons in his past—voices questioning who he really is under that suit and title. Who is Don without work? He knows the answer deep down, and spends seven seasons of spectacular television running from it. And at home? His fatherhood is performative—gifts, vacations, the same charm he can turn on in the office—but devoid of real emotional depth. The cycle of intergenerational trauma continues, deepened through dishonesty and destructive coping mechanisms.
And when whatever yardstick you use to measure success is achieved, then what? What role does ambition play now? If you find your dream job, hit that desired salary cap, or make it to the level of seniority you long felt you’ve been unfairly denied, then what? Without a new destination, the train rolls to a stop. So you jump back on the hedonic treadmill, point your finger towards the horizon, and create a new definition of success that is just like the old one—”everything will be better once we get there”—a road that extends into infinity, or until you die—whichever happens first.
If that’s all we’ve been fed, it’s no wonder we become disillusioned by the idea of what success can be. Of the world’s top 20 billionaires, only two are women, and there are 18 Forbes Billionaire Dads—every single man on the list—with an average of 3.8 kids each. (Musk’s 10 kids pushing the average up for everyone else.) When I think about these dads, and the life they live, it sure doesn’t feel like success to me. But when the world only tells us one story, how can we imagine another?
“I suppose it is tempting, if the only tool you have is a hammer, to treat everything as if it were a nail."
— The Psychology of Science, Abraham Maslow
How are other dads thinking about success?
I’ve been going through the vast archive of TNF comments as I weave the book together. I’ve always said this conversation is less about me and more about every dad intentionally trying to raise kids differently, conscious of the role they want to play, rather than buckling under the weighted expectations of society and generations passed. Here’s what a few dads said back in 2021 when I asked them what success meant after becoming a parent:
Whenever I look outside of my own life, I'll find myself feeling fairly unsuccessful without even thinking about why I'm feeling like that. I'm talking about reading about and subconsciously comparing myself to people online, in the news and on Linkedin. But it's a cliche, as soon as I look at what I have around me at home, wife, son and time together, I do feel more successful. And, since having a kid, looking at what I have at home has become more and more easy for me.
Every time I play with my son, it immediately makes me feel like I've done something good with my life. The older he gets, the happier I am moving time from my career to investing with him. Investing sounds cold, but it's an unconscious thing and that's what it is, it's investing time to have a great relationship with him. If that means I'm not going to climb the ladder to the top of a big company then I'm fine with that—actually, relieved is the word. I'm new to this whole Dad thing but it really is a game changer and I do feel more 'successful' just being a good dad.
— Mark
I left my birth city, NYC, 19 years ago with one mission: make it. Ask me what that meant at the time, and I could not tell you. Beyond some vague idea, images of success I’d seen in magazines and TV, and dollar amount (maybe a cool million?) I now realize that I had no clue what ‘making it’ actually meant for me.
Now I’ve come to understand that what I intended to achieve leaving New York all those years ago was perhaps some form of reasonable freedom and peace of mind. Safety, not having to worry about where my next meal or dollar would come from. I’ve also come to learn that ‘making it’ is different for everyone. Primarily being dictated by where you come from, what your upbringing was like, and what your story is.
I’m going to try and instil similar values into my daughter. Help her to choose her life goals consciously. It doesn’t really matter what they are, as long as she chooses and makes an intentional effort to achieve then I know she’ll be okay.
— Kervs
Success to me is finding the things worth doing and then moving your life in that direction to enable you to do them. I tend to conceive of success as having two chapters. The first chapter is about succeeding on some societal metric, before eventually graduating to a second phase in which you define your own metrics. This second phase is about a personal and internal feeling over an extended period, and it is very much about channeling aliveness and the work that matters to you.
— Paul Millerd
It seems to me like we get sold a version of success when we're young that we (most of us, anyway) come to realize isn't really compatible with living a healthy, well-rounded life, with family, friends and room in our days to pursue hobbies that aren't work-related.
What I think of success is having physical health + exactly what I've described above—at a certain point, unless you have super-expensive tastes, what is success for, anyway? I heard Dana Carvey say once in an interview that "fame is good for one thing: meeting women. But when you're a happily married man, why do you even need it?" I think a similar thing could be said about career success—once you reach a certain point, you can easily make a fault of a virtue.
— Terrell Johnson
Introducing REBOOT: The anti-business school for dads
Over the last few years, I’ve coached dozens of dads and have seen patterns emerge. The creeping realisation they’re following a path they inherited rather than one they wanted. A desire to rethink their relationship with work into something more healthy and under their control. Increasing clarity they’re working what David Graeber memorably called “Bullshit Jobs,” and torn between providing for what poet David Whyte called “The Three Marriages” in our lives: to our partner, to our work, and to ourselves.
These conversations have shown me something profound: there's immense power in creating space for fathers to talk through these things together. To question. To doubt. To imagine new futures. To be vulnerable and open. To be free from the pressure to perform to society’s norms around ambition and success. And, most importantly, to do it together.
That's why I’m excited to unwrap something I’ve been working on for a while—something that's grown organically from hundreds of hours of conversations with dads just like you. Starting in March, I'm bringing together a small group of us for a six-month group coaching program called REBOOT. It's everything I wish I'd had when I left my traditional career path behind: monthly group sessions where we hold each other accountable, one-on-one coaching to work through personal challenges, a tight-knit community of fathers who get it. This isn't traditional executive coaching—though we'll undoubtedly talk about goals, values and transitions. It's not therapy either—though healing always happens when dads can open with each other. It's something different—a radical reimagining of the relationships in our lives: with work, technology, family, friends, and ourselves.
You can think of REBOOT as business school in reverse. Traditional business schools teach us how to scale, optimise, and maximise: more money, increased growth, improved efficiency. They don't teach us to question the machine—only how to keep it running and to sacrifice everything at the altar of shareholder value. REBOOT is for unlearning the toxic patterns, beliefs and behaviours that got us here, and build new monuments in their place. This isn’t about stepping back—it’s about stepping up and designing a life that feels intentional, sustainable, and deeply fulfilling.
Because what unites us aren’t jobs titles or LinkedIn histories—it's that nagging feeling that something's gotta give. That the way we're working isn't working. That somewhere between Slack notifications and the school run, between quarterly reviews and the hundredth reading of The Gruffalo, we lost something essential about who we are and what matters most. “20 years from now, the only people who will remember you worked late are your kids.” Maybe today is the day to do something about it.
REBOOT is for dads who are …
… done being told the hamster wheel is a career ladder
… tired of working to others’ definitions of success
… ready to stop delaying that leap towards what’s next
… finished with performative success and primed for real change
This isn't about efficient task optimisation and better work-life balance. Over six months, a carefully selected group of dads will work together to write a different story. To find solid ground in the storm. To move beyond surface-level change into genuine transformation. The group will be intimate—just 6-8 dads per cohort—because this work requires trust, vulnerability and the kind of conversations you can only have in small circles. The gap between the man you are and the one you want to be can be vast—it isn't something you should have to cross alone.
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Really, really loved this, Kevin -- and thanks for the shout-out! I keep thinking about this all the time; I'd even forgotten I left that comment way back when! So if misery loves company, just know it's something I still meditate on and struggle with...
Rad. Big ups to launching reboot and your first cohort of rebooters.