Rethinking Ambition is the silent hurdle facing high-performing men who’ve spent decades chasing external milestones. Host Daniel Weinberg sits down with ambition strategist Hugo Brooks to dissect what happens when you build a massive career only to realize you’ve been running on an endless treadmill. You’ll learn why hitting a multi-million-dollar exit rarely delivers the peace men expect. Hugo shares how a single question from his wife forced him to confront the hollow nature of performative success and rebuild his entire life around conscious values. They unpack how early family dynamics and silent comparison drive men into workaholism without a clear stop button. This candid conversation offers the practical blueprint you need to step out of the exhaustion trap and finally define what’s truly enough.
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What Are You Trying to Prove? With Hugo Brooks
In this episode, we talk to Hugo Brooks, where we discuss what you are trying to prove.
Hugo, it is so good to have you on the show.
Great to be here. Thank you so much for having me on.
I am looking forward to this discussion. I’m going to dive straight in. Your life’s quite interesting. We talked about it a little bit before. I can resonate. There are some of these turning points in our lives. You spent more than 35 years building, growing, and selling businesses. You’d buy some of the world’s largest brands. You were in the big game. Your wife asked you a simple question that sucked everything in your tracks, which was, “Are you sure you want to do this again?”
It’s this thing where you keep rolling over, and you’re like, “Next one.” I want to ask you. Before we get to understanding the impact of that, how would you have described success up until that point where you’ve been a rolling entrepreneur, doing businesses, and working with some of these big brands? You were quite successful, but how did you define success pre-that turning point?
It’s a great question. Many of us have such rigid ideas about what success is. In the last ten of those years that you’ve talked about, it was to sell my company for XX million. That was it.
This is what most men fall into the trap of. They’ve got either a number in mind, or they’re simply assessing their value, their performance, or their success based on how much they’re going to make, the number. I would lay on top of that that they’d also be looking around at other people they know and make those references as well to see where they are in the game.
Breaking The Illusion Of The Finish Line
Certainly, a lot of comparison goes on for a lot of people. It certainly did for me. Also, when I say sell my company for XX million, that is a shortcut for an imaginary moment in my life where I no longer have to be doing this daily striving. I no longer have to be struggling for anything. Everything magically turns into a Disneyland-type arrangement whereby I’m lying on the beach. I never have to worry about where the next dollar is coming from. Everything is sorted in my life. I feel complete and fulfilled. From that moment on, I’m living in a dream world that requires no more of this hard work and striving that I’ve been doing.
Let’s call it absolute freedom.
That’s why I say XX million rather than the number because the number changes.
It’s different for everyone.
It changes over time. My number gradually began to fall as I approached what was nearer the end of my career. I thought, “I’m probably not going to hit the XXX million.” It dropped down to the XX million and then probably the X million before I finally asked the question properly. When you’re young, the sky is the limit. What being so ambitious requires is quite a lot of fantasy. It requires imagining what this wonderful thing could be, which is not a bad thing. It’s a very necessary thing. As you get older, reality begins to interfere with fantasy. The declining line begins to be met by a rising line of reality and experience. You tend to change what the XX is in the million, perhaps.
When do you think that happens in the arc of a man’s life?
It varies a lot from individual to individual. There are two key moments. The people that I work with tend to be in 1 of 3 moments, but these are the 2 key ones that we’re talking about. There’s a midlife crisis point. Nothing better than to call it that cliché.
That’s around the 45 to 55. That’s the range.
That happens. That is normally triggered by some sudden sense of your mortality. One of my experiences in talking to people is that when you’re younger, we will have this imaginary horizon line that’s somewhere up ahead of us. We’re heading towards that point. When you’re younger, you keep heading towards that point, and that point keeps moving further away. It goes on forever. It’s an infinite horizon. Something happens in your midlife, like you get ill or someone you know gets ill.
It’s either divorce or a big financial impairment. Let’s call it a monumental event that shakes up the current status quo, per se.
Confronting The Shifting Midlife Horizon
What happens is that horizon line that’s been moving away from you stops moving away from you, and you start moving towards it. The question in your mind changes from what shall I do, to what shall I do with what’s left? That change causes all sorts of panic. We all go out and buy the Harley-Davidson and all the other things that we’re all famous for because of that panic around, “Suddenly, this isn’t endless. Turns out, it isn’t endless.” That’s one of the key points. The other key point is even later in life when you’re beginning to go, “This isn’t going to go on forever. I may be in my 50s or 60s. There’s a social idea about retirement. Maybe that’s coming. So what am I going to be after I’ve stopped doing this?”
I call that Act III. Act I is what you described in the beginning. Act II is that midlife crisis moment where you become the real you and you blossom. Act III is we’re walking down the mountain here.
That’s it. That is another interesting point. We’ll probably go on to talk more about this, but this idea that there’s a particular age or a particular number that you hit, or whatever it is, at which point your ambition will be turned off like a switch.
That’s what happens.
What a wonderful idea that is. There’s no evidence that that happens. What we set up for ourselves is, “What’s going to happen is when I get to that number, I’ll be happy to lie on the beach all the time or when I get to that age, I’ll be happy to go and play with my train set,” or whatever it is. That is a bizarre idea. Why would age or a number of dollars decide what goes on with your internal ambition? They’re not connected. That’s certainly what happens.
You said to your wife, “I want to start again. I want to do the next thing.” What exactly excited you to do that after such a long journey already? Were you trying to create something to keep you busy? Were you trying to feed the ego because you still wanted to be a boss again or be like, “I’m an entrepreneur.” Tell me what you were excited about superficially, but I want to know inside what you were solving for genuinely.
I think it’s a question and an experience that a lot of people go through. For me, what happened was I had been on this roller coaster of continual reinvention for the 30-plus years. The nature of my business was that it’d be successful, and then it’d be terrible. When it’s going up, you think it’s going to go on forever. When it’s going down, you think your job is to fix it. There’s no way you’re getting off the roller coaster. You are stuck there.
The wife asked the question, and then I said, “I’m not going to do it. You’re right.” It was slightly through gritted teeth, but I was like, “You are always right. This is another example of you being right, which is that if I do ask myself this question, I don’t want to do it.” I stopped. Since I was more of the down part of the roller coaster than the up part of the roller coaster, it’s a lot easier to stop doing that when you go.
Chasing an arbitrary buyout number won't magically solve your life. Real peace starts when you stop running from yourself. Share on XYou feel like you’re giving up a lot of opportunities there. The opportunity costs are diminishing.
It’s almost impossible to stop when you’re going up. You always tell yourself, “I’ll stop when I get to the top.” I did stop. I had a business, and I released myself from that business. Then, I sat there and went, “Who am I? What am I for? What’s going on?”
I think it is extremely typical for men. What men tend to do is they tend to assign the value of themselves and the way they see themselves based on their performance. Performance, meaning where are they title-wise, where are they company-wise, financial, and all the work associated. What ends up happening is that value becomes very highly correlated or associated with that.
People work in companies for a long time. The first job I ended up working in, I’m still involved with it. I was working operationally in that business for twenty years. It almost becomes a part of you. When you leave, a lot of people get trapped into, “I’m now not where I was.” You almost feel exposed, like, “Am I the king who wore no clothes? You’ve taken that away from me. What’s left?” A lot of men go through that.
Also, simply, “What am I for?” You have this huge question of, “What am I for?” For me, what that question led to and what’s been interesting about my journey since is that it led me then to ask the question after, “If I’m feeling like this, why have I been doing this for the last 30-plus years? Now that I stop, what was that all about?” I realized that there is this drive in us that I call ambition. I became fascinated with ambition. The question led me to what I did next, interestingly enough.
I then started writing and researching about that. I went out and spoke to lots of very ambitious people. It was 40 or 50 people, mainly business founders, but not only. There were people who were ambitious in other areas. We tend to think ambition is always about money, but it isn’t. It can be about many different things. I went and spoke to them all and realized that ambition is this independent force that we have inside of us. It’s this drive inside of us. It is nothing more complicated than the desire for tomorrow to be better than yesterday.
Tomorrow needs to be better than yesterday. I need to feel like I’m leveling up a little bit every day.
Separating Pure Drive From Predetermined Destinations
It’s a raw and neutral force that human beings have within them. What we then do is attach it to a particular direction. We then say, “The way that I’m excited about making tomorrow better than yesterday is that I’m going to find a cure for this illness, or I’m going to make a company that makes this much money, or I’m going to do whatever it is.” Ambition in itself is not your objectives, your direction, or your goal. It is this force within you that is very restless. It does not like to sit there doing nothing. Your ambition does not welcome the beach. It is not looking forward to that. That’s a different part of you that’s looking forward to the beach.
You’ve interviewed 40 or 50 highly ambitious people. People in society have various degrees or levels of ambition. Where does ambition come from? Is it inherited from our family? Are we taught about it in school? Do some communities drive more ambition than others? What would you say is the source?
What’s interesting about it is that I think it exists in all creatures in some form. Without getting too heavy, it’s an evolutionary necessity. That’s why species develop and progress. It’s because they all have something of this desire to make it to progress.
Are you saying that happens in the animal kingdom as well?
I believe it happens in the animal kingdom. I believe it happens everywhere, but there’s a difference with the human species. Maybe this is why we are so successful, although that might be a controversial term. It’s because we don’t have a stop button. A lion goes out and kills an antelope because it wants to get food for the pride. It has this desire to make sure that everybody is fed.
That’s more driven by survival. Will lions go kill five extra antelopes to have excess?
They won’t go and build a warehouse to store frozen antelope in and then try and sell antelope to other prides at twice the price. The difference with the human race is that we don’t have much of a stop button. We all start with this very open-ended drive. When we begin to talk about, “He’s got more ambition than he has” or those sorts of things, that is often very circumstantial.
I’ve got five kids. I’m quite confident that there will be five levels of ambition here. They’ll all be unique in their own way. I’m trying to understand. At the core of it, what can I put down to where one has more ambition than the other? What would you say are the variables or the driving factors that lead to that?
You begin to get into things like culture, parental behavior, encouragement, and facilitation. These are individuals who are encouraged and rewarded for their ambition from an early age. By ambition, remember, I might be talking about very simple things. I’m not talking about whether he has set up his own company by the time he’s twelve. I’m talking about as you do try and improve things in your life, in yourself, and the rest of it, are those strongly rewarded? Are those children put in an environment where A) It’s rewarded and B) It’s facilitated? Are they encouraged and helped to try and grow?
It’s so important at this point in the conversation to unhook the difference between making tomorrow better than yesterday, the progression or growth in simple terms, from specific types of destination. What I mean is some people are brought up in a world in which the only form of success is you’ve got to go and become a doctor. That is it. I have a client who comes from this background. Unless you are becoming a known name in the medical profession, then you failed.
You lose self-esteem. Once you fail to meet expectations, it crushes you.
Your only value is that pathway. I was brought up in an environment where the only value was in academic success. My parents had no interest in money. In fact, they thought money was rather grubby. My response to that was a rejection of that. I was like, “I’m not going to do that. That’s a load of old nonsense. I’m going to prove you wrong and make my own path.” All I’m doing is shifting what was their ambition to my own particular type of ambition. It’s still exactly the same force driving those but in completely different directions. That’s what ambition does.
Again, I’ve got five kids. I’m going to create an unlimited scope. I’m not going to say it’s either a doctor. It is, “It could be any you want.” They’re going to get a very similar encouragement-reward framework. They’re all going to receive pretty similar offerings, let’s say, but at the end of the day, when we fast forward twenty years’ time, we’re going to have five different levels of ambition. What I’m trying to understand is what the variable factors are that create that difference in ambition levels. The following question would be, what can a parent do in a very healthy manner to generate a healthy ambition or enable a healthy ambition?
For the first part of that question, there are all sorts of other personality traits that influence your ability and desire to fulfill this ambition. For example, if you happen to be a very introverted person, how you deal with this inner drive may take you in a completely different direction from somebody who’s a very extroverted version.
It’s not just parenting. There is a whole social context which very much influences people’s ambition. We can see very obvious differences between the different generations that we label. You can see different responses in terms of ambition because of something to do with how their parents treated them, but also something to do with the social context.
Can you give us the state of affairs about the generations and their ambition levels?
It’s a broad stroke. I keep coming back to this. There’s a real danger about talking about ambition as if it were something you can meter, or as if there’s a scale, like, “He’s up there on ambition and then down there on ambition.” It’s not always that obvious.
Ambition isn't your goal or your company. It's just an internal engine waiting for you to pick a direction that actually matters. Share on XIt’s not a number. It’s improving yourself on a day-to-day, and that can be in any shape or form.
I’ve spoken to people that have gone, by some measures, from 1 to 5 in their 20-year life, and I’ve spoken to the people that have gone from 1 to 50 in a 20-year life. The struggle of the 1 to 5 person may well have been greater than the struggle of the 1 to 50 person because of the innumerable circumstances, personality traits, and all sorts of things. It’s dangerous to meter it. The other reason why it’s dangerous to meter it is that we tend to put our own values on it.
I’ve got two children. I’ve got a son and a daughter. I could look at my daughter and say she’s pretty ambitious. She wants to earn money. She generally works within the confines of my old-fashioned belief around what success was. My son is a highly creative person, and he has no interest in those things at all. His ambitions are entirely around creating beautiful things and getting a message across in an artistic way.
He might be more ambitious if you could meter it, but it doesn’t fit my particular value set or experience. We need to be so careful about this idea that ambition is something that you can measure. Coming back to your second half of the question, this is the thing the parent needs to do. I have got this so wrong, so I’m not an expert.
Don’t we all?
I’m not giving advice from a position of expertise. I’m giving advice from a position of failure. The thing that the parent can best do is try and be sensitive to where and how they want to grow and encourage and support that. What’s interesting about that is that the world is changing radically. If we’ve got a 5-year-old or a 10-year-old, when they become an adult, they are going to be entering a world in which the construction of society is probably completely different.
Not probably. It will be.
The idea that therefore they need to follow some path that I so wisely know is going to be the right path for them is naive at best.
You raise a very good point. This is one of those first times in history where that is the case. Before, the progression was extrapolation. Now, it’s like a hockey stick to something completely different.
That’s right. The speed of change is so fast that you cannot predict what is 5 years down the road, whereas my father could have predicted what was 50 years down the road. Therefore, there were things like career ladders in his generation. He started in a job, and his peers stayed in that firm or stayed in that career for years. Nowadays, a 30-year-old has probably tried 4 or 5 different careers by the time they’ve got there. Finding career ladders that look like career ladders is becoming almost impossible because they don’t exist in the way they did.
How can I as a parent say to my child, “You need to be following this path?” I can’t. What I need to do is say, “You have this desire to grow. I can see it. You are drawn in this particular direction. How can I help you, reward you, and encourage you to grow?” What happens to people who aren’t encouraged, rewarded, and facilitated in their growth is often a mental health issue. It’s often a social health issue. We can see in society what happens if you don’t provide for people to be able to try and make tomorrow better than yesterday.
If you deprive people of hope of leveling up or moving one little step forward, or getting something that is progressive, then the feelings come out sideways in all sorts of dangerous ways. People become very susceptible to different and unhelpful forms of “hope.” That’s why it’s such an important subject that we never talk about. If I were running the country, my number two would be the Minister of Ambition. It is so significant in how we operate.
Your country needs a bit of levelling up there as well.
That is the truth. Finding any of that would be helpful.
The Minister of Ambition would be very helpful.
It would be extremely helpful. It’s that level of a significantly important thing. That’s why I’ve become so obsessed with it.
Can I ask you? From a personal perspective, was there someone whose approval mattered disproportionately to you than others? We often fall into the trap of also wanting to not prove to ourselves. We’re not doing it for us. We’re often either doing it to prove to a parent or partner. Was there anyone, if you had to be honest with yourself? You mentioned your parents. You went down a path that was very much against where your parents wanted you to go. Was that part of the drive? You were like, “I’m going to show them, and then at the end of the day, they’re going to tell me, ‘You’re right, son. You did good, son.’”
It’s a question I often ask people I work with. It’s very revealing. My personal experience was that I felt like the alien in the nest. I was convinced when I was younger that I must have been adopted because this did not appear to be my family as far as I could tell. Whatever they were doing, that wasn’t what I was doing.
Did you have siblings as well?
I had siblings, and they were all part of this very cohesive unit. It was hell for me, but it was probably hell for them, too. This thing arrived in the nest, and it was like, “I don’t want to do that.” It didn’t make sense to me. Quite a lot of people do experience that. A lot of what influenced me was about being different from the environment that I was in.
You’re the rebel.
It’s not that I loved being a rebel.
You went against the grain because that was not your grain.
I was like, “I don’t know who these people are or what they’re doing, but it turns out, I’m here. I got to stick with it for the moment,” which didn’t make their lives very happy, or mine. That’s one level of answer to your question.
Were you trying to prove to them?
That’s where it gets deeper, isn’t it? On the surface, what I was trying to do was the opposite of whatever they wanted me to do. That’s what I was doing. I remember when I was seventeen, I got a job working as a kitchen porter, which was washing the dishes. It’s a posh name for a dishwasher. I was living in the accommodation provided by the hotel that was riddled with cockroaches, and the toilets didn’t work. The fire escape signs led you to a locked door in the basement. It was a fantastic, extraordinary accommodation.
Navigating The Phantom Need For Parental Validation
My parents didn’t live in London, so I was up to the big city doing this. I remember phoning home and explaining the situation I was in. I can’t remember whether I heard my father say in the background or my mother told me that my father had said, “He won’t last long there.” You can bet I stuck that out. You can be 100% certain I was there for the duration. It was hell, but I was there for the duration. It was only later when I thought about that, and I thought in some way, what that means is that I want my father’s approval.
Even though my behavior was rejection, what I was looking for was parental approval. In my case and in a lot of people’s cases, it’s like going back to an empty well. It’s never going to happen. I haven’t chosen the right path for that to happen. When I became fantastically successful, and I had all the toys, the show-off, and the evidence of my success, and the people were like, “He’s living in New York and London. He’s doing this and doing that,” and all the rest of it, my parents still didn’t give a toss.
You were chasing something that was never going to arrive.
Their reaction was still, “Really?”
When did you let go of that? That’s the exercise that one needs to do and realize, “That’s not my stuff. That’s their stuff, not mine.”
That’s the step. Believing that you can truly let go of it is a bit of a myth. The process is that you become aware of what it is. You become aware of the fact that this was given to you rather than something that necessarily is yours. You begin to be able to separate the given thing from your thing, and then you begin to learn to develop your own sense of what’s important. There’s always something with that. To think it’s gone completely is slightly denial. It partly shaped you. It partly made you who you were.
It definitely shaped you.
It did happen. It will still come back. I like to think that I’ve done the work. Therefore, I look back at that, and there’s some clear blue water between that and who I am. I know that some of that washes into my life sometimes. I know there’s still a part of me, even though I’m quite ancient and very much my own person, that would quite like for my father to approve of me. It’s that I know what that is. I can see that in me, and I can work around that.
Also, my father was a highly admirable person who a lot of people loved very much. I know that there are parts of his personality and character that I try to emulate. That’s a good thing. I don’t think it’s about casting it aside completely. It’s about becoming aware of it, fully understanding it, and developing your own. It is then choosing what of it you want and what you don’t and choosing when you want to let it influence you and when you don’t. We all get caught sometimes going, “I was being that old person for a minute. Excuse me. I’ll get back to being who I am now.”
Another trap men, in particular, fall into is comparison. How does comparison change our sense of what is enough? Why do we fall into that trap?
If I stay with my original idea that you’ve got this ambition, which is this neutral driving force where all it wants to do is drive you forwards, if it drives you to run, then you will run. Each day, you will try and run a little bit faster because that’s what ambition does. Gradually, you’ll get faster and faster. If what the world does is then present you with somebody who’s going to run alongside you, then your ambition gets a benchmark. It goes, “I don’t need to run faster than I did yesterday. I need to run faster than that guy running next to me.”
Why?
Dismantling The Comparison Trap Fueling Endless Hustle
I think it’s an evolutionary trick. I think it’s what has proved to work to drive this progress.
They’re different components of the system pushing each other to keep doing it.
You can see how evolution creates. If two people running means that they both end up running faster, then evolution is going to like that. There are going to be more people that do that. It’s Darwinian theory in practice around ambition. This comparison thing is like turbocharge for your ambition. Your ambition loves it because it gets a benchmark. It gets something to then go, “Now, I can achieve this versus that.” It’s like turbocharged energy. That happens on a societal level.
Without wishing to get overly political, we’re in an environment where we can see what very extreme comparative ambition delivers. It is capitalism off the scale of wanting to be bigger, better, and more successful than you are, and where that ultimately takes you. What’s fascinating about that is that if you then stop and work with people and go, “Let’s imagine your ambition is completely independent. Let’s look at what’s important to you in the values of your life and what would be a life well-lived for you,” if you take those two things, your ambition is forced in one hand and the values for a life well-lived in the other hand.
You put the two together. What is the life that you would create for yourself? That might come up with a very different answer to the question of where you’re going because where you’re going has been created by a set of social norms and conventions and fueled by comparison all the way through. Ambition does a great job of you not asking questions, keeping going, and forever trying harder. Look at the moment that you, as an ambitious person, pass through and achieve a goal. You have this moment of euphoria, this pat on the back of, “I’ve done it. I’ve been successful.” That passes in minutes, days, or hours.
That’s interesting. When you talked about selling a company and were like, “I sold the company for X.” What’s the feeling? Explain the feeling and how long it lasts. A lot of people focus on that being an ultimate goal.
I’ll tell you a story that’s happened to me. I’m a member of quite a few founder entrepreneurial network groups. I was in one of these social networking things. It’s quite a close-knit group. We were getting together for a drink one evening. One of the guys had sold his company for £20 million the day before. Clear. No earn-out. No ties. It was that money in his back pocket. He completed the deal the day before.
Everyone was patting him on the back and saying, “That’s fantastic. Well done.” Somebody said, “How does it feel?” He said this curious thing that I’ve thought about ever since, which is, “Do you know what? That wasn’t it.” What he meant by that was that whatever it was he’d been driving towards or striving for 15 or 20 years with this company, that moment of selling the company wasn’t it. It doesn’t do it.
It didn’t satisfy. It wasn’t the end of a process. It was a moment in time. Not that he was ungrateful for or not happy about the money in his pocket, but what he meant was, “Having now got there, I now don’t feel the satisfaction, fulfilment, and sense of completion that I have believed for the last fifteen years I would as a result of passing through that moment.”
That’s fascinating. I believe that 95% to 99% of people will have that same experience.
Comparing yourself to the guy in the next lane turbocharges your hustle, but it blinds you to what's actually worth running toward. Share on XYou can tell I’m big into analogies. The way that I visualize this in my mind is that the goals that we set, particularly those big goals, are like doors. For some reason, in my mind, they’re like doors in a cowboy movie in the saloon. They’re those double doors that swing. In my mind, that’s a goal, and you’re in the corridor heading towards that goal. The double doors are up ahead of you, and you are in this corridor heading towards those double doors.
The reality is that when you go through those double doors, the experience of going through them takes seconds or minutes. You’ve spent fifteen years in the corridor for those few minutes of passing through those doors, and immediately, you’re on the other side. You might spend a few weeks lying on the beach. You might do this.
You might buy the new house, the cars, or whatever it is, but immediately, you’re then going to sit around, look around, and go, “Where are the next set of doors? Somebody give me a new set of doors quickly. I do not like this.” Your ambition does not want to sit there doing nothing. It wants to get busy and get you on another corridor. We all recognize that.
Living In The Corridor Instead Of The Doorway
When you look at a life and look back at what has made up a life, and this is relevant to my experience in the 35 years and so on, if I added all of the moments of blowing through those goals and passing through those doors, they might come to a week’s worth of time. If I add up all the time that I spent in the corridor, that’s my life.
That’s the journey.
Since we become overly fixated on the doors, we don’t always think about whether those doors are right for us. They tend to be highly influenced, very simplistic, like my XX million. It’s such a simplistic idea. It’s not about life. We become fixated on that and completely miss out on our lives. That’s the danger. Add a little bit of competition and comparison in there for turbocharging, and you’re off to the races.
Your premise is that ambition can become compulsion quietly. This is a big trap a lot of men fall into. When they move from doing meaningful work into a pattern where they’re going into workaholism, it becomes right into the compulsion in a sense. It’s endless, “I have to work.” You see that it becomes so unbalanced. I, fortunately through my own journey, got to a place where I can take the foot a little bit off the pedal and my cup is very full. I don’t want more. It’s quite a balanced situation.
I’m able to have conversations like this with you. I’m not in that mode. I have friends who are still in that mode because they’re still trying to get to that place for the XX dollars or a place where they feel like, “I’ve hit where I need to hit.” There are some in that group that have taken the compulsion territory. The balance is not there. How do we manage that?
The first thing is that it’s a very real thing you’re talking about. It’s a real danger that a lot of people experience. Some people come out the other side of it, and some people don’t come out the other side of it so well. I talked about ambition as being a force without a stop button. At the end of the day, this feature of no stop button is what addiction is. Addiction is fundamentally a lack of a stop button.
The fact that ambition can become addiction, compulsion, or whatever it is, is not surprising. It’s like any addiction, it becomes entirely self-serving. It becomes its own world. You close off other possibilities around you. Your work becomes the only thing. Achieving those goals becomes the only thing. If you think of it like somebody who’s got a substance addiction, it exhibits some very similar features of making your world smaller and narrow. The only thing that you’re interested in every day is heading further towards that goal and getting that fix.
Many of the features of it look a lot like we can see in what we would normally call addiction. It’s something to be wary of. Unlike normal addiction, you could go up to an addict in the street and say, “Why don’t you think about stopping doing that?” The addictive part of that person will tell you where to go because the addiction feels threatened by that idea that you might want to stop and think about it.
It’s exactly the same with your ambition when it gets into that kind of condition. It does not want to stop and think about where you’re going and why you’re going there. I work with people one-to-one on this subject. I help people get control of their ambition. Before I do that, I have to interview potential clients. Probably 70% to 80% of the men I talk to are not ready to ask the questions.
When you’re saying ask the questions, do you mean challenge themselves on why they are doing this?
They are saying, “Thank you very much. I’ll keep going. Don’t ask me to look out of the window. I am going.” That’s much higher in men than it is in women. That, for me, is interesting. I’ll leave the addiction comparison here. Until you’re ready to look at it, there’s nothing I or anyone else can do other than maybe what we’re doing, which is having it talked about in an open forum and making people aware that they’re not unique in this experience. It’s a human experience, and there’s an alternative. Until you’re ready to stop and go, “I want to question where I am going and why I’m going there,” there’s very little that can be done.
When you are willing to do that, then bizarrely, it’s a fantastic moment of empowerment. As soon as you begin to see this power or this force that you’ve got as independent and not attached to a particular goal or outcome, then you have a choice about what you want to do with it. You can put that energy into meaningful things, which it might not be going into at the moment. You can put that energy into stuff that will make the corridor a meaningful experience for you rather than it being a means to an end that’s rather paper-thin.
If you were to reflect on yourself and extrapolate what is quite related to what we talked about, what do you think your own ambition costs you with regards to relationships, presence, and identity? What we’re talking about is addicted ambition and not wanting to reflect, try to understand, and gain control, as you put it. With your own learnings, what you see with your clients, etc., at what cost? When you’re doing that, you’re gaining in some respects, but there are costs that are associated. You understand from your relationships, whether it’s a partner, kids, parents, or your friendships, the idea of being present and your identity.
I’ll give you one example, and then I’ll talk about it may be slightly more generally. I mentioned earlier that it was a stage in my life when I was being very successful. I had all the toys. I was living the life and all of that. Unfortunately, that happened to me quite young. I often say probably one of the worst things that ever happened to me was to be so successful so young.
I’d like to claim it was all down to my own genius, but it was much more circumstantial and being at the right place at the right time. I was living this life where I had an office in London, and an office in New York. I was flying backwards and forwards between the two. I had the house, the cars, everything. I had two homes. One day, almost overnight, the whole thing went wrong.
Explain.
The nature of my business then and for many years afterwards was that I was reliant on clients like Coca-Cola, Unilever, Mars, Nestlé, and people like that spending large amounts of money with me, my firms, and my companies. When the economy gets bad in the particular industry that I’m in, it’s the first tap that gets turned off. My space is a creative marketing space, brand development, and innovation space, which is a canary for the economy. I didn’t know that when I was 28. I had gotten onto this thing, and it was going like a steam engine. I was king of the road. Do you know what I mean?
You’re killing the game.
I was very pleased with myself.
In that industry in particular, from my experience over the years, I’ve met a lot of English people. Whatever it is in London, England wider, quite dominantly plays globally within that madman game of brand development, ad execs, etc. I’ve honestly spoken to so many people of English origin.
There was a whole thing that went on with Thatcher’s Children, of which I was one. It fed straight into the ad agencies. I was living this crazy, fantastic life at far too young an age, but then it all went horribly wrong. It all stopped virtually overnight. Clients stopped spending money. Warren Buffett has a phrase which is, “You don’t know who’s not wearing shorts until the tide goes out.” That was me. I certainly had no shorts on whatsoever and the tide went out fast.
I had the experience of bailiffs coming up my gravel drive to my mansion to repossess my television. I lost the whole thing. We lost our home. There are some obvious points, like making sure that you have properly capitalized business, but ignoring all of those sorts of things, the point about that story was that what was going on in my life at that moment was that I was starting a young family. I was at that age. I was married. We had one child and then had another one. I was in that young parent stage. What I was doing in my life was I thought I was a fighter pilot. I thought I was Top Gun. I was out there.
If your twelve-month goals don't align with what you want read at your eulogy, it's time to course-correct your ambition. Share on XYou believed your own stuff.
There’s so much evidence that it was great. I was surrounded by evidence of it. Clearly, I was brilliant, and I needed to do more of this. It’s a great example of not stopping and asking the question. My ambition was running the show, not asking the question about, “What is suitable for where I am in my life? What should I be doing at this stage of my life?”
I should have been building security more than anything else. I should be laying foundations and doing all the things that are good to do when you’re starting a young family, such as spending more time at home, supporting your wife, and those sorts of things. My ambition had completely taken over and was running the show.
I wanted to ask you. How do you know you’re climbing the wrong mountain when you’re good at climbing it? Not only that, everyone’s applauding you. They’re like, “You’re doing so well. It’s so impressive what you built.” If you were to reflect with your younger self, what do you think you could have done for that younger self to get you to see that when you’re in that mode of, “I’m a legend. Everyone’s telling me I’m a legend. Why are you telling me otherwise?”
It’s a great question because the answer is it is, under normal circumstances, very difficult to stop when you’re in that place. If you’re particularly in a business or anything that’s going well, you believe it goes on forever. You can never imagine a point that it isn’t going to be doing that. It’s hard to. The simple answer to your question is, you’re probably not going to. It’s hard to.
The slightly more hopeful answer to that question is the more we talk about it, and people hear stories like mine and stories like yours, and you do more episodes like this, the more people are going to realize that maybe they should be asking that question. There was certainly nothing going on in the world that would have made me want to stop and ask that question at all. It was completely rewarded all of the time. There were three different age groups that I work with, which are the midlife crisis and the end-of-career people. The other group that I work with is the new generation of Gen Z and Millennials.
Are you a life coach?
Yes. I’m helping with this thing around ambition. One of the things that’s interesting about them is that they arrive with a lot of these questions.
That’s interesting. You didn’t tell them to do that.
I did not have those questions. It wasn’t an environment in which questions were asked about those things. That has changed such that younger people now do arrive with questions.
That’s driven by the fact that they are skeptical that taking the same path that we took will not end well for them. They’re flipping it, going, “I’m not going to be able to do what you did. You got lucky. If I were where you were 35 years ago, I’d also be in a good position to have these lovely chats and be relaxed about life. I don’t think that’s going to be possible for our generation.” They’re asking those questions upfront as they’ve climbed up the mountain. That has the opposite effect of putting a dampener on ambition because their outlook is slightly more negative and cynical. They don’t believe it. They’re like, “No matter what ambition I have, the odds are against me.”
This is where it gets interesting. It goes back to the nature of ambition. You’ve nailed it. That’s exactly what’s going on. They do not have the belief that it’s achievable or that they can ever get there. Also, they’re presented with success as being such an extreme thing. For a lot of those people in a social media environment, if you haven’t got four Lamborghinis by the time you’re 21, you’re a waste of space.
The idea of success has become very extreme and therefore even harder to achieve, or even less likely, quite apart from the realities of it being hard to achieve. In one sense, they’re coming from a negative place. As I did when I stopped after those 35 years, the question I went to is, “How do I therefore create a meaningful life?” They are coming with that question.
Having been frustrated from, “Maybe I’m not going to be able to get my first house when I’m in my twenties or I’m not going to be able to do this or I’m not going to be able to do that because it’s such a remote possibility,” because ambition doesn’t get turned off, ambition turns back to a healthier direction. It is, “How am I going to make tomorrow better than yesterday? If it isn’t about the house, the salary, or whatever it is, what is it going to be about?”
Young people, when I work with them, are much more open to the idea of designing a life that works where things like goals and corridors are much better balanced. It’s much more values-based than I was. I find that a great source of hope. That encourages me to do what I do. For a lot of older people, getting off the travelator and questioning where you’re going is so hard, particularly if it’s going in the right direction or feels like a rewarding direction.
If you were to give some parting words to my audience, which are predominantly men in an older bracket, like a 40-plus bracket? At that point in their life where they should be questioning, “What am I chasing here?” Which is a real check-in, what advice would you give them to help them understand whether they’re climbing the right mountain, whether they have a healthy balance, or they’re not sacrificing things like relationships and presence, or they’re not missing out on sunsets? How would you get someone to start to do a little exercise with themselves to check in whether they are as aligned as they think they are?
Aligning Daily Ambition With A Living Eulogy
I’ll give you a simple little exercise, which I use a lot. It seems to be powerful. You get a piece of paper. On one side of the piece of paper, you write down the first twelve-month goal that comes to mind, whatever that is. It is whatever you’re heading towards, the thing that you’re focused on most days. You’re like, “That’s where I’m heading for. I’d like to get there in about twelve months.” Write whatever that is on the piece of paper, and then turn the piece of paper over.
I want you to imagine that you are dead and your best friend is standing beside your coffin, reading your eulogy. What is it that you want your best friend to say at your eulogy about you and your life? You’ve got a unique opportunity here, which is to write your own eulogy that somebody else is going to deliver for you. You’re in full control. Write down what it is you would want that person to have said, and all of the people standing around in the church or wherever will be nodding and going, “That was him.” Write that down on the piece of paper.
What you need to do is look at what you wrote on the first side of the piece of paper, the twelve-month goal, and say, “If I add multiples of those sorts of goals together over a life, will they create the life that’s being described on the eulogy side of the paper?” If there isn’t a good fit there, then it’s worth beginning to ask some questions about what you’re doing and where you’re going.
Is that bringing mentality forward?
It does, but by writing that eulogy thing, what you’ve written is probably some of your core important values. You’ve written down the things that are probably meaningful and important to you. That is the best way that you can start this process. If you combine that with the idea that your ambition is an independent force that you can push in any direction.
You can say, “I’ve got this amazing ambition. I’m going to drive it in the direction of those values.” If that turns out to be exactly the direction that you’re already going in, then all that will happen is that you will have new motivation, vigor, and excitement about what you’re doing. If you need to course correct or radically change, then you’re in a great place to start to do that.
Well done. That’s excellent. I appreciate the time. It was fascinating.
I loved it myself. It was great.
I had a whole lot of other questions that I could have asked you.
We’ll do that next time.
We were rambling on. A lot of the things you’re talking about are so typical and so current with what’s happening. I see it with the people I know. There’s that dissonance between what they’re trying to achieve. They’re effectively creating this whole imbalance in their life by doing something they think is getting them somewhere that they don’t appreciate. They’re focusing on the destination rather than being on the journey and enjoying the journey. It is to be consciously aware of that and make sure that they’re on the right path as opposed to the path that’s going to lead them to not a good end state. This was fascinating.
Thank you so much for giving me your time.
Before we go, I ask all my guests five rapid questions at the end of every show. I’m going to shoot. Who would you like to say sorry to, given the chance?
My previous two wives.
You’ve also got two ex-wives. Me too. What are you proud of being or doing in your life?
The thing I’m most proud of is, at a very old age, I’ve reinvented my life. I feel like I’m living a whole second new life. I feel like I’ve been born again, doing something that I was meant to do.
When did you receive kindness while needing it most, but expecting at least?
There was a stage of my life where everything was very dark for me. I was a lost soul. I didn’t see where any kindness could ever come from. I won’t go into detail, but it appeared from an unexpected place and changed my life. The day before that happened, I couldn’t have gone looking for it. I didn’t know where it was, but it appeared.
I love those stories. What did your mother or father teach you that you frequently remind yourself of?
My father taught me that kindness is everything.
Finally, what is your superpower?
My superpower is that I can handle both myself and with the people that I work with a combination of emotional surgery and practical ways of moving forward at the same time.
Thank you.
Thank you very much.
I look forward to chatting again.
I’ll look forward to it myself.
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About Hugo Brooks
Hugo Brooks is an Ambition Strategist, speaker and author who helps founders, business leaders and ambitious creatives rethink one of the most powerful forces shaping their lives: ambition.
After more than 35 years building, growing and selling brand, innovation and communications businesses, Hugo reached a turning point. Having advised global organisations including Coca-Cola, Unilever, Nestlé and Virgin while navigating the highs and lows of entrepreneurship himself, a single question from his wife changed everything: “Are you sure you want to do this again?” That moment led him to step off the entrepreneurial treadmill and dedicate his second career to helping others build success that is consciously chosen rather than unconsciously inherited.
