Ask Faleskini - The Midlife Crisis Clarity Compass
This is the Ask Faleskini - The Midlife Crisis Clarity Compass podcast. All the Life Lessons You Need to Thrive in Midlife. This is your Guided Path from Chaos to Clarity, Confidence, and Purpose.
Peter Faleskini and his guests discuss everything midlifers are worried about or interested in.
Peter Faleskini and chosen guests will help you distinguish what is sustainable in life, relationships, health, and the economy from what is not. Not everything that shines is gold, and not all mud is dirty.
Ask Faleskini - The Midlife Crisis Clarity Compass
Can Rethinking Your Ambition Save You From a Midlife Crisis and Severe Burnout? Hugo Brooks
Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.
Most high-achievers spend decades driving down a "success highway," constantly comparing their progress to others without ever asking where the road actually leads. When the momentum slows or the goal is finally reached, many are left facing an unexpected existential wall: a midlife crisis accompanied by deep, chronic burnout.
In this episode of Ask Faleskini, Peter sits down with serial entrepreneur, author, speaker, and executive coach Hugo Brooks to unpack the hidden dynamics of human drive.
Hugo shares his personal turning point—closing a business after 30 years when his wife asked a simple question: "Are you sure you want to do this?" Together, they explore why society's toxic obsession with goal-worship fuels burnout, and how redefining your relationship with ambition can unlock lasting clarity and purpose.
Key Takeaways in This Episode:
- The Serial Entrepreneur Trap: Why riding the business roller-coaster without questioning your motives eventually leads to burnout and identity loss.
- What Ambition Really Means: Moving away from status, wealth, and ego, and returning to the fundamental human drive to make tomorrow better than yesterday.
- Goals as Directions, Not Gods: Why worshipping 1-second finish lines ruins the 99% of life spent on the journey—and how to shift your perspective.
- The Eulogy Test: A powerful exercise to cut through societal expectations and align your daily drive with your actual personal values.
Are You Ready for the Questions?:
Why 40% of people aren't ready to dig into their true motivations, and how to tell if you are ready to pivot.
About Hugo Brooks:
Hugo Brooks is a London-based serial entrepreneur in marketing and design turned author, speaker, and coach. He runs workshops and coaches driven leaders on how to understand, direct, and master their ambition across every stage of life.
Website: https://hugobrooks.com/
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Welcome to the Ask for the Skinny podcast with a guest. I'm proud to present Hugo Brooks. Hugo, welcome to the show. Please tell us more about yourself. What is your story?
SPEAKER_00Thank you so much. Thank you for having me. And uh real pleasure to be here. So my my story, obviously, I could go on for hours about my story, but I'll try and keep it short. Um, but my my story is that I uh I've been running businesses most of my professional life. I guess I'm what's called a serial entrepreneur. Um and um the the business area that I've been in has always been in marketing and design and communication creativity, that kind of space, which is a very roller coaster type of an industry. When it's good, it's good. When it's bad, it stops very suddenly. And I got very used to that pattern of ups and downs and living on the roller coaster. And uh about three and a bit years ago, um, the roller coaster had just kind of passed over the peak and was just beginning to head back down again, which is very familiar to me. Uh, and I was making my plans as to how to reinvent my company for the tenth time, um, how to adjust to current market conditions and you know, all the things you need to do to get ready when things are going into decline. And I was explaining this uh this these plans to my wife, who'd heard them many times before. Um, and she turned to me and she said, Are you sure you want to do this? And I realized in that moment that I had never really asked myself that question. Was I sure I want I I just did it automatically. When it's going up, you think it's gonna go on forever, so you're not gonna stop doing it. And when it's going down, you have to fix it, you have to make it right. Uh, so you're not gonna stop it doing it then. It just becomes a permanent trap. So I I I I stopped I actually genuinely stopped and asked myself this question, and the answer was I didn't want to do it. I just it just became what I did. Um and so I stopped doing it uh and I and I closed down my company, or or rather, I I sort of passed on my company to some junior people in the team, um, and I I stopped out, stopped out of the business altogether, and I then sat there and went, Oh, now I don't know who I am or what I'm for or why I'm here. And and that was sort of the first question. And then the second question was, Well, why have I been doing this for the last 30 years without ever asking myself the question? And that started my interest in something that I'm going to call ambition. Um, now, ambition means different things to different people. I'm very aware of that. So it's just it's just a word to describe um this drive that we have inside ourselves. And I think the drive is nothing more than the desire to make tomorrow better than yesterday. So some people think ambition means, you know, being Elon Musk. Um, uh, and some people think that's great, and some people think that's terrible. Um, but really it's not that. It's it's just this human desire to make what happens tomorrow be more meaningful and better than it would than what happened yesterday. And uh, and so that has become my obsession, is has become ambition. What is it? Um, how does it work? And as you go through different life stages, what is the role of ambition? And how do we how can we use it much more deliberately and consciously rather than being driven by it in the way that I just described my life?
SPEAKER_01Amazing. I would like to um discuss a bit about societal expectations. Are we all victims of societal expectations to the extent uh that we don't know what is our ambition at all?
SPEAKER_00Great question, and and absolutely the answer. The answer is quite simple, yes. Um uh and then and then not just societal expectations, they're they often start in our in our families. Um so our families are influenced by their families, and you know, it goes back through through history, um, and uh it creates a great creates a great influence. And then obviously there is this enormous social pressure and set of conventions about what success is. Uh, I often say it's a little bit like we all drive onto this highway. Um uh, you know, when we when we start in our adult lives, we drive onto this highway, and there's loads of other cars driving on the highway. We look at each other's cars and go, my car's better than your car, or I'd like your car, or I'm gonna go faster than you, or I'm gonna go slower than you. We're all doing this thing of comparing and and looking at looking at the whole thing. The only thing we're not asking ourselves is where we're all going. And uh that's the question that doesn't come up. And uh and I think there's a there's a there's a real opportunity, and actually with the changing world, a real necessity to open up the question about what you would like success to mean for you as a person. Um and you know, it it may be that success for you is, you know, it are the social conventional forms of success, but it may be that there are completely different things that would make you feel successful as a person. And uh part of getting hold of your ambition and understanding it is about asking those crucial questions, um, which are really what are the what are what's the life I want to create type questions. That's that's that's really the crucial the crucial thing. And there is no stage in life where it's too early or too late to ask that question. Um, you you know, whether whether you've got, you know, whether you've got 90 years still to run or 10 years left to run, you know, there isn't there is no stage at which it's too late to stop and go, what do I want to create?
SPEAKER_01I have a question that I ask so many of my guests. I believe it's it it it fits right uh in his conversation. Um you've done it all, so the books, you're a speaker and also a coach. Um what is the best way to um to ask yourself uh this question? Are uh books or is reading a book sufficient to spark this aha moment? Do we need to go to a conference or a holiday event or even a weekend workshop? Or uh should we hire a coach and get down and start uh listening and start exploring with the coach? Um and of course get some accountability with the coach as well because with the boot, we don't have any accountability. We just say, yeah, I always wanted uh, I always knew what I want at the end. And then and then we we we are stuck in, or at least I was stuck in uh this confirmation bias that we create for ourselves because we are under so much societal and family pressure and all these stuff.
SPEAKER_00Yeah. So I I think I think it's really interesting that that question because I think I don't think there's one right answer. Um uh I think you know reading books is is great. There, you know, there are some great books, and and the point about reading books for me has always been that it stimulates the brain and it makes it makes me think. Um uh so so I think that's really useful. And listening to podcasts similarly, you know, opens up your mind, helps you see other people's stories, opens up the world, so it really widens your thinking. And the the benefit of working one-to-one with somebody is is that it is, as you say, a much more accountable relationship. But I I'm I'm not a big fan of coaching in the sort of traditional, you know, like a sports coach type coach, where we're gonna set a goal, we're gonna train you to get there, um, and you're gonna be accountable to me as to how fast you ran last week. Um, that's that's not really what I think most people need these days. That that that's that's kind of very performance related. Whereas I think the discussion we're having is a bigger discussion than performance. So I think it's if you're going to work with a coach, it's definitely about finding the right person that understands what and can help you get to what are the right questions. So all three of those things reading books, listening to listening to things, and working with somebody are all about getting to the right questions. Now, there's always a caveat with that, which is that you have to be somebody who is ready, willing, and open to asking questions. So it's quite interesting. I I interview quite a lot of people to potentially become clients of mine, um, in as as as me as a as a one-to-one coach. And I would say that 40% of them probably aren't actually ready. They aren't what whatever I'm going to do or say, however many books they've read or podcasts they've listened to, they're not actually ready to get down and dig in and answer those questions for whatever reason. Um and it's not necessarily life stage related, it's probably more personality related. Um, so one of the things that's interesting is that you know, working, I work with quite a lot of young people who are sort of found a startup in a startup environment, and young people tend to arrive with questions in the way that my generation didn't when they were at that age. So I think you know, the younger people are becoming more questioning, more conscious, more self-aware in the first place. Um, but but I think it is this willingness and and learning and belief that if I ask the right questions, I can get to somewhere new and interesting. Um, and if you are that person, then I think you you know you're already halfway on the path to that. Then you've just got to find the right guidance and advice that really works for you. Um and you know, that can be about the personality of the coach, it can be about the the type of book. You know, there are certain types of books that I just don't like to read. They're probably very good, they've probably got a lot of good advice, but there are certain types of writing that just don't, you know, I don't I don't engage with. I don't engage with being preached at and being told this is the right answer and the only answer. That tends to turn me off. But for some people, I think that's exactly what they're looking for. So I think you've got to go and explore a lot. But you, if you're listening to this, you're probably a questioner, or you're probably at a stage in your life where you are questioning, and that is the greatest opportunity ever. It might feel like confusion, it might feel like I'm I'm last, I don't know where I'm going, I don't know what to do next. But all that means is that you have a wonderful opportunity to really take a bit of an overview, get a better perspective, and ask yourself the right questions.
SPEAKER_01Amazing. Um can we uh just uh get a bit back to to the ambition? Uh our society is obsessed with what they call ambition. But is that really uh the ambition that you're talking about, or is that uh just uh a buzzword used in motivational speeches?
SPEAKER_00So uh as I said, the the the problem with the word ambition is that it it can mean very different things to different people. Um and I think we we are certainly in an ambition-obsessed uh or or rather a goal and achievement and performance-oriented obsession. That's that's that's what we've got. Um and that's a real social problem, to be honest, um, because one of the things that's happening today is that the traditional paths of success or of being successful, of progressing in your career or your life or whatever it is, are getting narrower and narrower. So they're available to less and less people. There are going to be less and less jobs, you know, in the future. So the at this, but at the same time, we're telling people that unless, you know, particularly young people through social media, unless you've got three Lamborghinis by the time you're 25, then you're it's not worth getting out of bed in the morning. And and and and so we've got this two things going on where we're we're ramping up what success looks like all the time. It's got to be more it's gotta be more, it's got to be more in order for you to count yourself as a success. But we're removing the ladders and the pathways for people to progress. So when I talk about ambition, I'm literally talking, I'm not talking about where it gets you. I'm talking about the drive that you have to get somewhere. And that's that's that's what it is. It's it's a human thing, um, it's uniquely human, it which is this desire, this endless desire, as I say, to make tomorrow better than yesterday. And that can take many, many different forms. So when I started this quest into the world of ambition, I spoke to 30 or 40, probably more like 40 plus people who considered themselves to be very driven. And a good proportion of those weren't driven by money or material things at all. They were driven by, you know, they were a scientist who was driven by the need to find a molecule that would do solve a particular problem. It wasn't money, it wasn't about selling something, it wasn't about being rich. Uh, it wasn't about being the having the career title, it was about solving that problem. Um, and what I learned was is that we all have this drive inside us, but what we don't often do is apply it in a really conscious way. And once you separate the two and you go, okay, I've got this drive, that's not the same thing as I want to become a this or I want to earn that. I've I have this drive. Wherever you put me, whatever you do with me, I have been, I've been born with this drive to improve things. Uh, and that then becomes something that you can really direct in a conscious way and give make yourself a much more fulfilling life. Um, I know so many people who have lived a life. I'll give you a great example. So I was in a in a sort of networking meeting a few months ago with a group of business founders, uh, one of those things where we kind of, you know, all get together and complain about how hard life is, um and uh and all of those sorts of things. And uh one of the people there had sold his business the day before for a lot of money, and he'd sold it absolutely clean. So he'd literally just put the money in his back pocket and walked away. Um, and uh he had this extraordinarily large amount of money that he didn't have the day before. And everyone was congratulating him and telling him, Well done, and you know, all the rest of it, a little bit of jealousy probably in the room. And somebody said to him, So, how does it feel? And he said, Well, to be honest, that wasn't it. And what what he meant was that he'd spent 10 years, 20 years striving towards this moment, this goal that he had set himself. And now that he was on the other side of the goal, whatever that drive and need that he had that had got him there hadn't gone away. He'd just passed through the goal. So it didn't satisfy him, it didn't complete his his experience. He was just the same person on the other side of the goal as he was when he was striving to get to the goal. That drive, that need to make tomorrow better than yesterday, was still exactly the same. Of course, he went and enjoyed a few weeks on the beach and you know, and had a great time, and he wasn't complaining about having the money either. But in terms of the drive that that that that remained, and I think one of the things that society does is it imagines that you will reach a point in your life where you will no longer be ambitious, you will achieve a goal or you will get to an age, or you'll get to a point where you just drop the drop the curtain and go, okay, I'm done now. I don't, I don't, I don't need to drive anymore. And that is just not human nature. Um, you know, that that whatever you achieve in your life, whatever age you are, your ambition is still there. And if you don't recognize it and feed it with something, give it something to hook onto and to drive for, then you know, you you you just sort of shrivel up and die. And and uh that's you know that that's not not a healthy way to be.
SPEAKER_01I have a question here, and I I I believe I believe you're the best uh person to answer. So our society looks at everything from like we have these special KPIs. If you have X amount of millions by uh uh the age you are uh 50, then it's okay. If not, then you're a loser. It's similar with the health. If you have uh these literal levels and these markers and that markers, uh then you're healthy, if not, then you're um you you're ill or uh you have to do something. Um but as as you described, if I understood correctly, it's uh more about the journey than the destination. And everything in our society is so goal-oriented that our goal is not to be on the right journey, but it's to be on the right or in the right place at the right time. And that is the problem because nobody takes care about the process anymore, nobody takes care about the journey, and everyone just thinks, okay, this is the destination we want to be. So it's the same with the health. It's not we have to do something uh about our health every day. We have to strive to have enough movement or exercise, we have to have healthy food, and the same is with ambition. We have to be ambition to do something, as you said, better than we did uh yesterday. Uh and uh we just don't know where we are going, and we are completely uh lost, although the the uh quantifiable goals should make things simpler, they just uh complicate everything because it it might be about the destination and not about the goal. Uh, what's your take on that?
SPEAKER_00I I I mean I I think you I can't I I really agree totally. I I think we you know as a society we have become absolutely fixated with goals. Um, and uh it's not that there isn't some value in a goal, but when you create a goal and then worship it like it's a god, um, and you apply your entire will and effort and everything to trying to get to that goal, what happens is exactly what you've just described, which is that you miss the journey. So if you think about the man that I described who'd sold his business, he I think of goals as being like walking through a pair of doors. The actual moment you you you've you've decided that some point in your future you want to walk through that pair of doors. That is your objective, and you're going to do whatever it takes to walk through that pair of doors, whatever that goal is that you set yourself. But the actual moment of walking through that pair of doors takes a matter of seconds. You literally Walk through it, and then you've walked through it. That experience is then over. Goal has been achieved, the finish line has been crossed, the KPI has been achieved, the sales figures, you know, whatever, whatever it is, whatever the markers are, as you say, that that takes a matter of seconds. But the process of getting there may have taken months or years or decades of effort to get there. So when you get towards the later in life and you stop and you look back, the vast, vast majority of your time, 95, 99% of your time has been spent in the journey, and 1% of your time has been spent in crossing the finish line. And therefore, where does the meaning and value and usefulness of life come from? It doesn't come from achieving the goal, it comes from the journey to get there. And if we rethink about goals and think about them differently, and this is this is one of the ways in which I work with clients, is stop thinking of them as being this iconic thing that you must achieve at all costs, and start thinking of them as actually being directional. That's what the useful thing of a goal is. The useful thing of a goal is when you walk out of your front door in the morning, are you going to turn left or are you going to go right or are you going to go straight ahead? That's what a goal is for, is to tell you which way to go. But the important thing is actually what you experience once you start walking. And that this change from thinking of a goal as a God to thinking of a goal as directionally helpful, and actually then focusing on the pathway, on the steps that you're going to be taking and what you're doing on each of those steps every day is what's going to change your life when you look back later on, from having been a sort of meaningless slog to get to a goal to actually having been a really valuable experience. And it's it's that shift that I think we need to make socially and individually. And that's what I help people do one-to-one, is I really help people get back to kind of really thinking about firstly, firstly, recognize. I think the first step is recognize that you've got this energy, this power, which I'll call ambition. If you've got it, let's just put it to one side for a moment. Then I think the next step is then to think about what's really important to you as a person. Uh, one of the techniques I use is I it's not unique to me by any means, but is to ask people to imagine that they've died and uh that their best friend is standing by the graveside reading their eulogy. Um, and what what do they what do you want that person to be saying about you? It's probably not what you know what is what what the what the person's BMI was or what the exit value of their business was or last quarter sales figures or their job title, it's going to be some things that are much more important. And those things that you would want them to be saying about you are probably your values. So if I've now got this sense of what my values are, and I've got this knowledge that I have this power and energy, how do I put those two things together to create the life I want? How do I use my energy to deliver against the values that are really important to me as a person? That will help you get a sense of a goal that's a real direction, as opposed to a blind god that you're worshiping. Um, and it will also help you dramatically on the path and the next steps you take to experience and learn from what you're doing every day rather than living permanently in some imagined fantasy future.
SPEAKER_01Amazing.
SPEAKER_00Uh it's very easy. Uh uh if you go to hugobrooks.com, you'll find me. That's H-U-G-O-B-R-Dou-K-S.com. Um, and there you can find the stuff that I've written. Uh, you can find uh stuff about me speaking, and I run workshops and do group activities and and do keynote speeches. Um, and you will also find how to talk to me about working one-to-one with me.
SPEAKER_01Thank you very much for all these insights. You're amazing. I really like listening to how you uh portray or describe ambition. Thank you. I have learned so much during this interview, and thank you again for being my guest tonight.
SPEAKER_00Thank you very much.