I Don't Remember the Last Time I Had Fun

INTRODUCTION

Greg Scheinman:
Fun to me means joy, happiness, smiling, and laughing. I think it's very mature. It's really short-sighted and, quite frankly, immature not to have those things in your life. 

One of the best things we can do, and one of the first things we need to do, is to put ourselves first because self-care is not selfish. Self-care is one of the most selfless things you can do. 

I'm embarrassed for some of these guys. At what point do you stop buying bigger pants? You’ve got to be willing to put yourself out there and try different things to learn what might inspire you, what might energise you, and what might be fun for you. 

Mediocrity happens by default; maximisation happens by design.

Paul Sutton

Greg Scheinman is the author of the book Midlife Male and publishes a weekly podcast of the same name, in which he talks to high-achieving men about how they find fulfilment in their lives. 

When I started to be brutally honest with myself about what was going on in my own life, one of the biggest things that hit me was that not only did I not have much fun anymore, but I didn't even know how to have fun. I didn't even know what fun was. And as it turns out, I was far from alone among midlife men. 

The truth is uncomfortable, and if we're all so miserable, how do we get happiness back?

<THEME MUSIC>

PS: I'm Paul Sutton, and this is Middle Man, the show for midlife men and the people who love them.

EPISODE

PS: Welcome to Middle Man, Greg. You were actually one of the first people I came across several months back when I started realising that maybe I had an issue with midlife that I wasn't aware of. There were things I wasn't happy with in my life, but I didn't know why. I didn't know what was going on, and I came across you. 

I read your book, I've been reading your newsletters, and I've listened to your podcasts, and I've got to say, you've really helped me out. How did you get into this space? Am I correct in saying you're 51 now, but you've only been really looking at midlife for, what, five years or so? How did you get into that in the first place?

GS: First of all, thank you for having me. I appreciate the support. That's what this is all about. I mean, when I talk about maximising middle age, it's about making a difference. It's about being of service. It's about having fun, which we're going to talk about a bit more. It's about reframing and redesigning what this phase of our lives really looks like. So, you know, people ask me now, "What inspires you? What fuels you? What’s really kept you from crisis? What helped you through crisis and out of it?" It’s conversations like this. It’s hearing from men like yourself saying, "Hey, this is helping me out." 

We’re not alone in this. We’re sharing different stories and experiences and situations and circumstances and going, "Hey, here’s an opportunity to see things differently, to live differently." So, that's what really gets me out of bed in the morning. People ask, "What do you do for fun?" I say, "This is what I do for fun. This is exciting." 

But to answer your question, I really started taking a good hard look at this at 47. Okay, so you’re right, I’m 51 now. I’ll be 52 in December, and 47 was the age my dad died, right? So I was 17 and my dad was 47. It was my 10-year anniversary with the firm I was with. I was a partner in a large risk management insurance firm. I had equity, a big book of business, and an office on the 25th floor overlooking downtown Houston. I was in the car park of the office, on my 47th birthday, 10-year anniversary, and I just could not get myself out of the car and into the building. It was one of those moments where I thought, "Is this it?" Like, is this the conformity, the complacency, the redundancy of what my life has become and what it’s going to continue to be? 

And from the outside looking in, Paul, everything looked great. Fancy car, reserved parking spot that all the partners get, a beautiful house with a beautiful mortgage, by the way, you know, beautiful cars with beautiful car payments, a beautiful wife, okay, with expensive taste, beautiful kids, two boys, now 20 and 17, with private school tuition—two tuitions, all of this stuff—and something was missing. 

That’s when I really started to take a look at it, thinking, "What if I didn’t go inside?" or "What if I really needed to operate differently?" What were the choices and options that I had? Because right then, if I stopped, this was as far as my dad made it, so I could either squander the opportunities ahead, or I could pour some rocket fuel on this, do things differently, and make this next phase of my life, what I call "bonus time," the best phase of my life.

PS: So where did you turn? Because, like I said, I came across you and a couple of others. Where did you turn at that time when you were sat in that car, thinking, "I just can't do this anymore"?

GS: I’m going to circle back and ask who the others are because that’s exactly how I did it. Okay, I didn’t know where to turn. I knew the "why." I knew why I wanted to be a better husband, why I wanted to stop drinking, why I wanted to get myself back into the shape I used to be in, why I wanted to be more present as a husband and a father, why I wanted to still make all the money, okay, why I may not want to do exactly what I’m doing right now, but I didn’t know "how," and I didn’t know who to turn to, because I wasn’t going to go and say this to my business partners. I wasn’t going to tell them how unhappy I was, how I was trying to navigate my way out of there, or how I couldn’t afford to quit and just follow my passion and throw all of this away. I wasn’t going to bring it home to my wife and vent to her the stereotypical midlife crisis. 

I wasn’t looking for a Porsche. I wasn’t looking for an affair. I wasn’t going to tell my kids. And I really didn’t even want to be the guy who goes to his friends and complains all the time. You know, the guy, "Oh, here comes Greg, always complaining." 

So where I turned was, "If I don’t know the answers to the questions, I’d better start finding the right guys and asking them the right questions." Maybe that could help me figure it out. And I also have a big narcissistic ego, and I don’t like to admit that I don’t know what I don’t know. I’ve struggled and have always pushed the boulder uphill by myself. It’s been that self-reliant thing since my dad died. Like, "Hey, there’s no business to go into. There’s no father figure around. There’s no real mentor, so I’d better go and do this myself." 

So I’ve always operated that way, much to my detriment. Over time, it’s been successful in some ways but detrimental in others. So I had this idea that, okay, I’m going to start a podcast, because this way I can bring a microphone, and there’s a barrier. I can invite anybody I want on to ask the questions I have, and now I have an obligation to ask those questions, to get vulnerable, to ask them how they do it, to extract information from them, and effectively try to see how I could apply that to make my life better, to answer some of these questions I had. And that’s really how I did it. I said, "Okay, I can’t afford to quit my job right now. I don’t have another multi-million-dollar idea." 

So I said, "What can I do?" That’s around the time I launched my podcast, and I said, rather than quit my job—which, by the way, whatever problems you have in your life, I can assure you that quitting your job isn’t going to solve them right away—because if you think you’re unhappy when the money’s coming in and the benefits are there and all the other stuff, just wait until they turn that tap off, and you still don’t have the answers. You’ll be even more unhappy, stressed, and anxiety-ridden. So I decided to take a step back. "What if I just reframe it?" I’m going to use my job and leverage my position in my career to get paid really well to host this podcast, which means I make no money on the podcast, but I’m just keeping quiet, not telling anybody anything. I’m just going to do it, and that’s really what I did, Paul. 

I started the podcast. I invited people on who I thought were smart, who I thought were interesting, who I thought could be helpful. I was in risk management at the time, so I looked at this as risk mitigation. The difference was, I was the risk. I’m the product. How can I make myself better? How can I mitigate the risk of a midlife crisis in the next phase of my life? And those conversations led me to my own interpretations, my own behavioural changes, testing and retesting different things, which led me to start writing the newsletter, which was literally a tree falling in the woods in the backyard. Every Sunday, I’d go out and write about what I was thinking and what I was learning. 

Gradually, over time, the newsletter gained an audience. The podcast started to gain an audience. I also "outed" myself, if you will, about all the changes I was making and the things I was doing by making the mistake of putting everybody on my initial newsletter list—clients, friends, everyone. And when people started getting this newsletter, it was like, "What is he doing?"

PS: Did it bother you? I mean, I guess not, because you did it. But the response you got from, like you said, clients or prospective clients, did you suddenly think, "Oh shit, I probably shouldn’t have said all that"?

GS: So it was both. It was a tough period. One, it bothered me greatly to have people question what I was doing and make certain statements because I’m pretty sensitive. I’m pretty sensitive and pretty insecure. And I think if you look at a lot of people who work out a lot and care a lot about other things in this bravado, really, we’re doing it to cover up all the galactic insecurities and confidence issues and traumas that we have—at least I do. So, yeah, it bothered me greatly. I lost a lot of friends over it. I lost a lot of clients over it. I lost a lot of sleep over it, and, quite frankly, for a period of time, I lost a lot of money.

PS: Did you regret it for a while?

GS: No, because one thing I learned was that chasing authenticity where authenticity does not exist is exhausting. And I was exhausted for years because that’s exactly what I was doing. Where I found myself was at this intersection, or this kind of valley of despair, where now that I was acting authentically, what was it doing? It was starting to attract and repel exactly the kinds of people and opportunities that it should. 

So everyone who was running, everyone who was getting angry, everyone who had something to say—that was the stuff I didn’t need. What ended up happening over time was that you’ve got to ride through this if you’re really committed and say, "I’m going to come out better on the other side." So I had to fake my courage, conviction, and confidence, but I was going to come out better on the other side by doing things this way, by continuing to talk about it. 

And if you tell people that you don’t want to go golfing, you don’t want to be drinking, and you don’t want to be friends with the other dads at the school with whom you have nothing in common, guess what’s going to start happening to you? You’re not going to get invited to play golf, okay? The dads at the school aren’t going to talk to you as the stuff gets passed around. These are the things that are going to happen, and you’ve got to go and replace that with what does work for you. And I actually found that to be quite simple. Now, it’s hard. I always say simple is hard. Everything I talk about is really simple, but simple is really hard, which is why most people don’t do it.

PS: I agree. The concept of a lot of what you say is very simple. Doing the work behind it is difficult because you have to face up to a lot of things, I would say, that are uncomfortable, that you maybe don’t like about yourself, or you feel very vulnerable, even if that’s with yourself. And so, yeah, the work behind it can be difficult, absolutely.

GS: But, you know, I started to think differently in this regard. And what I mean by things starting to get better and attracting and repelling exactly what you deserve, and how it became easier to live authentically, is like another one of those things you say, like starting a sentence with, "I’ll be honest with you." If you’re really honest, you don’t have to start a sentence with "I’ll be honest with you"; you just are. 

It’s the same thing with authenticity. Like, I shouldn’t have to use this word all the time if you’re just operating authentically. I like working out. I wanted to get back in shape. I started going to gyms and group exercise classes and putting myself in different environments. And guess what? I made friends. Why? Because that’s what those people liked, and that’s where they were, instead of being at bars late at night or doing other things. I was in gyms in the morning, and those people were very welcoming. I didn’t have to fake anything, and I wasn’t worried about failing anymore. It was incredibly supportive. 

So certain things started to change, and it was the same in business. I didn’t leave the job. This was like a three-year process until we ended up selling our firm and all of that happened. I just turned over my book of business. These were clients I was dealing with—clients that I didn’t have much in common with personally. I wasn’t heavily vested in the industries or businesses they were in. I was chasing the salary, the title, the commissions, all that stuff, which, don’t get me wrong, is not a bad thing. But I had trouble separating those two lifestyle-wise, personally and professionally, and I started to shift that and think, "Well, what if I just chased what I liked?" I like to eat great food. I like to drink. At this point, it was protein shakes, you know, supplements and powders and everything. And I like to work out. So I started going after clients in industries I really liked, where my passion was. 

And in that regard, I found it actually much easier to land business, ironically enough, because I could call that fitness equipment manufacturer and say, "Hey, I own £10,000 worth of your stuff, and I use it every day, and I’m doing it, and by the way, this is what I do, and I have some questions for you about this." And when you’re a customer, when you’re a client of theirs, when you’re a supporter of theirs, when you’re an unpaid ambassador, when you fit the exact demographic of what these businesses and brands are looking for in their customers, they have to talk to you, and not only do they want to talk to you. 

So every restaurant I would go into and spend my money in, you know how easy it was to ask for the owner while you’re sitting in his place, spending money and eating his food? They’d come over, sit down, talk to me. "Hey, who insures your restaurants? How fast are you growing? What are you doing about this? I love this place. Can I get an opportunity?" "Oh, yeah, by the way, I haven’t seen my agent in two years. He doesn’t eat here. He doesn’t use my stuff, does he?" "You mean I can work with someone who actually combines personal passion with professional expertise, someone who actually gives a crap?" That’s when the light bulb went off. That’s when this stuff all started clicking.

PS: Listening to you, I recognise a lot of what you’re saying. Maybe if I go back a few months, that’s kind of where I was. One of the first things I did, actually, was to implement some small changes in habit. But one of the first things I did was time blocking, because one of the things that had been getting to me was the feeling that I had lost control. I had so many obligations in my life that I had no time—no time for myself. 

So I went through and blocked out my week as to when I had to do things. You know, I’ve got to take the kids to school, I’ve got to do this, I’ve got to do that, I’ve got to work. But identifying time where I could make time for myself. Now, one of the problems, or the biggest problem I’ve had with it, is related to time and making time for myself. Why do you think it is, from all the people you’ve spoken to, that we stop making time for ourselves and stop having fun? How do we even get to this stage?

GS: I think we become very reactive. I think as men, we also take on a lot of responsibility—we are here to serve. We are here to be, again, husbands, fathers, providers—we’re here to serve. And that can be incredibly draining. It’s fulfilling in a lot of ways. I think it starts out very noble. It starts out exciting; it starts out very noble. This is what I get to do, okay, not even I have to—this is what I get to do. Look at what I… And then it gets into what you were just describing. "Oh, I have to take the kids to school," or "I have to do…" No, I get to take the kids to school. 

It’s a shift over time that happens from what used to fill our tank to what starts to drain it, and we start seeing it differently. What I’m saying is we’ve got to bring that back in there. And by being so reactive over time, and by giving so much of ourselves to others, we start draining our own tanks, which leaves us feeling very unfulfilled. It’s not reciprocated. I’m not getting paid enough money in my job for this. Okay, when I come home, nobody’s super excited to see me. Okay, I’m not getting all these things. And we’re like, "Wait a minute. This is not being reciprocated. What we’re putting out is not coming back to us." 

Whether that’s true or not, it’s a feeling that I think a lot of men start to get. And then the question arises, "What am I doing all this for? How long can I keep doing this like this? Where’s the line on staying at this job or getting promoted or making more money, or where is even my relationship now? I’ve been married 10, 15, 20 years, and now we’re getting into all these other things of attraction. Do we have anything to talk about other than the kids?" We’re just two ships passing in the wind and all of this life is just happening. None of that I’m describing sounds like a whole lot of fun, Paul.

PS: No, no.

GS: And that’s what happens. And I think it’s our responsibility again to take it back. You were alluding to things about self-care and time blocking. I think one of the best things we can do, and one of the first things we need to do, is to put ourselves first because self-care is not selfish. Self-care is one of the most selfless things you can do. Self-care is what allows you to show up better as a husband, father, provider, and man. It allows you to stand up a little bit taller, puff your chest out, change that energy, be in a little bit better shape, be a little bit happier, eat a little bit better. You know, it’s the oxygen mask on the plane analogy. When they drop down, they say, "Put your mask on first before you help anyone else." 

You’ve got to take care of yourself before you’re even capable of taking care of anyone else. And when you start doing that, things become very different in the perspective in which you operate. So I just think a lot of the time, it’s not so much what we’re doing that makes the biggest difference; it’s what we stop doing.

PS: Yeah, I tend to agree. I came to a point of thinking it’s not fair on my wife, my kids—I mean, I work for myself, so there are no colleagues—but certainly my wife and my kids. It’s not fair on them if I am not looking after myself and being my best self. That’s just not fair on them. More than anything, it’s not fair on me either.

GS: I completely agree. I think the situation, as far as that stuff goes, is as you described. I think it’s our responsibility to take care of ourselves so that we can best take care of the people that depend on us, and by the way, the people that we want to take care of. This is about being self-reliant. This is about being capable. That’s really, really important. 

And as men, I think that gives us a sense of pride. I think that gives us a sense of accomplishment, achievement. And I like being looked upon as a strong guy. I like being looked at as a healthy guy. I like being the dad who’s the outlier at 51. I want my boys to see that. I didn’t have that. I want my wife to see that. 

Sorry, this may go right down the middle, and it may bug some people too, but it’s like, I’m embarrassed for some of these guys. At what point do you just stop buying bigger trousers and say, "No"? The way forward, like, the answer is not to just buy bigger trousers. The answer is to actually lose some weight. There’s not a great accomplishment in saying I’m six waist sizes bigger than I was when I graduated from university or when I first started. I don’t think there’s a whole lot of glamour in, "I’m going to die at my desk instead of seeing my kids more often." 

You know, regret is a big thing. And I think one of the things that gets guys thinking a lot of the ways you’re talking about is that they’re starting to sense regret. They’re starting to feel like some of the decisions they’ve made, the actions they’ve taken, the choices they’ve made, are not necessarily the best ones. And if they continue with this, they’re going to end up with a lot of regret, and regret is really scary to think about. That I did all this, all this, and I’m going to end up regretful. 

So it’s like, "Well, what can I buy to get me out of regret?" You know, like, "What can I buy? What can I do to get…?" And that’s also where some poor decisions, some impulse decisions, come up, versus, "Let me take a step back, think about what I really want, write down what I really want, and then really map out a way to make that happen." Because I’m a believer that it’s not only possible but highly probable for you to have everything you want if you’re willing to put in the work. And I’m not talking about the nonsense stuff. I’m not saying like, "Oh, we all have to fly private, and we have to have big yachts, and we have to do this." 

Now, again, I’m not against any of that. I don’t think these things are mutually exclusive, but let’s be realistic about what a really good day looks like. And then how many of those can we string together?

PS: Yeah, when I was doing some of this work that you’re talking about, one of the biggest problems I had was with the "fun" element because I was asking myself these sorts of questions and thinking about, "What do I want to do in my life? What do I have that’s missing from my life? What don’t I have?" And I was reading through your book, and I came to the fun part, and it really jarred with me in a way that was, I don’t know, a bit depressing. Maybe that’s a bit strong. But to think, you know, I sat down and started to write, "What do I find fun?" and I had this big blank page in front of me, which was quite shocking to me. And it took me a little while even to write a basic list of five or six things that I might find fun. Why do I have a problem with fun?

GS: Well, first, that’s not uncommon, and you’re certainly not alone, and it’s certainly not too bad. I would offer one thing first: replace the word "problem" with "challenge," meaning it’s not a problem, it’s a challenge. I just don’t know what is fun, necessarily, anymore. So now I have a challenge. I also have an opportunity to rediscover what I find fun. A blank slate, if you will. Here’s what I maybe used to find fun. Here’s what I thought was fun. Here’s what I was doing for fun, realising I’m not having any fun doing it. So here’s where I’ve arrived right now. 

A blank page is an opportunity, and when people ask me where to start, or they come to a situation like, "You’re at this intersection where, man, I have a problem," I say, "You know what? You don’t have a problem. You have a challenge and you have an opportunity. And by the way, you know what’s fun? Overcoming challenges and seizing opportunities." And now we’re smiling, and now we’re laughing and going, "Okay, great. Now what’s my biggest challenge in life? Having fun? What a great opportunity and what a great challenge." 

So what am I going to do? I’m now going to start putting things on my calendar that I think are fun, but I don’t even know if they’re fun. But I’ve got to find out. Because how am I going to find out if I don’t experiment with new things, embrace curiosity, and get back to figuring out what fun even looks like for me? Now, if I go out with my friends and I play poker until four o’clock in the morning, and I have seven drinks and I wake up the next morning hungover as hell and I can’t do anything, I may check the box and say, "I don’t think that’s so much fun. That’s not the kind of fun I want to have." 

Or you may go, "Yeah, it’s worth it to do that once a month with my friends, but I’m going to make sure I don’t schedule anything the next day." Or, "I don’t know, is hiking fun, or is aerobics fun? Is yoga fun?" I used to play in a band when I was in university. I played guitar, and in university, I played in a band. And then, of course, what happens is you don’t play for 10 or 15 years—jobs, kids. My guitar started to go under the bed. Then I get married, and my wife is like, "Why are all these guitars under the bed? Why don’t we set them up?" And I go, "Oh, well, I’m going to put them up on the wall." "Don’t put those things on the wall. They’re ugly." Like, "No, they’re not ugly. They’re art. That’s thousands of dollars’ worth of playable art." 

You know, and all these things go, and then in my 40s, I started to play in a band again, and it was a lot of fun, and it was no longer pressure. It was like, let’s put a couple of really good guys together, and now we have the money. Let’s rent the bar, invite our friends, play the songs we want to play, and once a quarter we would play a gig, and it would be great. But you start to rediscover what fun looks like for you.

PS: And was that a conscious decision on your part? Did you go, "Okay, look, I don’t…" Did you hit a stage like I did of going, "I don’t know what fun is, so I’m just going to try stuff"?

GS: Absolutely, 100%. And I do it in all areas of my life. That’s the whole "aggregate, curate, and eliminate." In order to curate and eliminate, you’ve got to aggregate first. You’ve got to try different things. And again, I was the guy who didn’t know how. The phase of life where the fun I was having for a long time all revolved around inherited relationships, meaning it was the little league parents or the school parents or the work clients and everything. So they were golf outings. They were retreats that I didn’t necessarily want to go to. There was a lot of drinking, there were late-night dinners, and other things going on. All these things that were going on, and they were "adult fun"—dress up and go to this benefit for a cause you don’t care about, you know? 

And it was all sorts of ego involved in the whole thing, doing what you were supposed to do. "This is what we’re doing on the weekends, Friday and Saturday night, we’re going out with these couples or to this thing." It was supposed to be fun, and it might be for some people, but it wasn’t. What do I find fun? Now, look, I find this fun. I find having good conversations fun. I find exercising fun. I like to try. I’m doing these pool workouts now, you know. First, I thought I was going to drown. 

Now I really think they’re a lot of fun. I put something on my calendar every quarter that’s a big challenge. I was never a big hiker before. Now I’ve climbed the equivalent of Mount Everest twice, and we’re taking 17 guys back in September to do it again. You’ve got to be willing to put yourself out there and try different things to learn what might inspire you, what might energise you, and what might be fun for you. Some people have book clubs, chess clubs, whatever. 

That’s my point: anything and everything you want is available to you. You just have to be willing to put yourself out there. And here’s the other thing: if it’s not fun for you, you can extract yourself right back out. I have gone to high-performance lifestyle training events where I’ve been put through Navy SEAL activations for the weekend. I’ve gone to places like Soul Degree and Modern Elder Academy, where you’re sitting in the round in circles, passing talking sticks and getting all vulnerable. You’ve got high highs, low lows, all of these things exist. 

But the point is, you get to decide. That’s why it’s your personal operating system. That’s why it’s your midlife action plan. You get to choose what’s on it. What I help you do is provide the framework, the tools, the strategies and insights you need, and that preparation, accountability, discipline, and consistency to keep you moving towards what it is you want. But part of the joy in this, Paul, is figuring out what you want and trying these things. And it’s not about needing all this money to do it or anything. People are always going to look to find excuses or reasons that they can’t. 

Almost any hobby, almost anything you want to explore, is available to you on this wonderful thing called Google, a podcast platform, you know, or many of these other places. You can start looking and downloading and trying and living and learning and dipping your toe into different things before you decide to make even bigger commitments to stuff.

PS: You talked about inspiring yourself and energising yourself and having joy, basically. Is that what you would describe as fun? Because the word—and maybe it’s just a word thing, maybe it’s just me—the word "fun" almost means childlike joy to me, but that seems like a stretch.

GS: I debated a lot about whether "fun" was going to make it into the F’s, you know, because it sounds juvenile. And the reality is it’s not. I think what’s juvenile is thinking that we have to stop having fun as we get older. Now, I really don’t care what adjective you call it. I really don’t care about any of these things. I really don’t care if my F’s are your F’s. Choose whatever you want. People write to me, "Well, shouldn’t you include faith?" or "Shouldn’t you include this?" and "Why is fashion in there?" What are you talking about? I really don’t care. 

The point is, my F’s don’t have to be your F’s, but what we should be striving for is, what does a holistic metric for success look like for our life? What does total life wellness look like? As the goal, to me, that’s mature, that’s not juvenile. Fun to me means joy, happiness, smiling, and laughing. That’s very mature. I think it’s really short-sighted and, quite frankly, immature not to have those things in your life or to think that you can’t as an adult. 

I still look around at a lot of my contemporaries, some younger, some older, people around my area, and I think, "Man, that guy acts so old." Why are we doing that? And that doesn’t mean you can’t be serious in business and in life, and about real obligations and responsibilities, but it doesn’t mean we can’t have fun. And I say, "If I’m not having fun, then I’m done." Like, what’s the point of all this? Am I going to have a real conversation after this one, like business? Am I going to be transferring real money? Am I going to be doing real stuff? Absolutely. And is all of that fun? No. 

But after that, there’s a block of time on my calendar where I’m going to go exercise, and I’m going to go box, and I’m going to do some things that are fun, to restore and reset and come back. I just think it’s an integral part of maximising middle age.

PS: So if there are people listening to this—men listening to this—thinking, "Do you know what? I don’t know what fun is, or I need to define what fun is to me," and they go out and do the work, and they try some stuff. What if they have more fun in their life, more joy? What do you think that brings to them in middle age?

GS: I think it brings contentment. I think it brings happiness. I don’t know a lot of unhappy people who are having a whole lot of fun. I mean, if you think about it, if you are having responsible fun—here’s the difference: responsible fun, not irresponsible fun. The kind of fun where you blow it out, you have all this fun, and you come home and think, "Oh, I can’t handle the bills." You know, "I can’t afford the kind of fun I had," or "The squeeze isn’t worth the juice; the risk wasn’t worth the reward." "I’m hungover, I’m this." Irresponsible fun, where you think, "If I keep doing more and more of this, I’m going to end up in a worse and worse place"—that kind of vicious cycle. 

But if you’re having responsible fun, meaning, I’m spending quality time with my kids, we’re going on good experiences, we’ve managed our responsibilities, our obligations, and we’re allocating a proportionate amount of time for fun, fulfilment, enjoyment, experiences, curiosity, and health—man, that’s what it’s all about. There were years that I went on holiday and came home needing a holiday from my holiday. There were years when you’d start flying back and you’d start adding up the numbers in your head and going, "Oh crap," and you get back to regret. You can’t have one without the other. 

It’s all about alignment and harmony, you know, in there too. So when you build that map, when you have that harmony, when you have that alignment, you also now have opportunities—things become more fun. It wasn’t much fun to look at messy books, you know? It’s a lot more fun to look at a cleaned-up set of financials. It’s a lot more fun to operate off your budget or define what real wealth or prosperity or certain things look like to you. That’s a real reset button. And I get asked this all the time because I think it does attach itself to fun, but it’s like, "What does wealth look like to you?"

PS: Yeah, what does it look like?

GS: I just want to have enough to do what I want, with who I want, when I want, for as long as I want. And if we can tick those boxes, now we can start optimising and start having fun. But if you don’t know where to start, to answer your question, and I can’t tell anybody what their version of fun exactly is—if you don’t know where to start—I would simply offer that today is the day you start and try one thing. Try going for a walk. Try, I mean, you may want to get a dog, I don’t know. 

Like, think about what you take a look at your life. Think about what’s missing. Take that blank sheet of paper out, and each day, write one thing on it and try that. Now, some of these things that you try are not going to be like, "I did this once, and it’s the most joyful thing I’ve ever done in my life." It doesn’t work like that either. This whole test and retest is to give yourself some time to build some momentum in these processes. Sometimes it’s to be able to say, "Look, day one of working out, when you haven’t worked out for six months or six years, you’re not going to feel so great the next day."

PS: No, absolutely.

GS: But when you start developing momentum, when you keep going, when you keep showing up, and you start generating momentum, all of a sudden, you start having more fun, start meeting more people. You’re going to start getting in better shape. You’re going to walk by that mirror, and instead of avoiding it, you might think, "Oh, looking a little better, feeling a little bit better there." This is when this stuff starts to really perpetuate into growth, and that’s going to lead you into other areas of curiosity because you’re not going to be as scared anymore of trying that new thing, of doing that new thing, because now you’ve done it.

PS: Well, I have to say you’ve inspired me to go out and buy the Pearl Jam ticket I’ve been debating over for the last couple of weeks.

GS: Yeah, the new album is great.

PS: It is, isn’t it? 

GS: Yeah, I think we’re supposed to see them in, I think, October.

PS: Okay, yeah, we’ve got one coming up in London in about a month’s time. So I’m going to grab that ticket quickly.

GS: Go grab that ticket for sure, you know. But that’s the thing, like, and we can end on this: go seek out experiences and opportunities that may even be, you know, I plan a lot of this stuff out now, like a year in advance. I really like doing that and putting things on my calendar and then getting the ticket, you know? Like, I’ve got back here, like, this is September 5th of this year—I bought this event ticket a year ago, put it on the calendar. 

And now you’ve also got to work towards it: I’ve got to make enough money for this. I’ve got to free the space on my calendar. I’ve got to organise where my clients are around this. You’ve got to do it. Now you’ve got something to look forward to. I’ve got to train for it. You know, you have those goals, those commitments that you make, and then you honour those commitments. 

You talk about what’s fun. It’s fun to honour your commitments. It’s fun to set standards and then actually adhere to them. And in order to do that, you often have to think ahead. The closing statement I’ll give you is that mediocrity happens by default; maximisation happens by design. So when you design your life and you plan these things out, that’s the day you immediately start to transform.

OUTRO

PS: I hope you found today’s show, well, fun. You can connect with Greg at midlifemale.com. 

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Next week, we’ve got something different with a personal story of someone who’s going through a complete career pivot in midlife.

Dirk Singer:

I think that one of the biggest challenges people at our life stage face is, you know, overcoming that almost… I’ll call it prejudice, like, you know, that once you pass a certain age, you can no longer get to grips with things that are new or do something different.

PS: See you then.