Midlife Stories - Dirk Singer Transcript

INTRODUCTION

Paul Sutton: Hi, ahead of this week's show, I'd like to ask a favour of you.

Now, there's a reason why every podcast asks you to rate and review their shows, and that's because it really helps with podcast discovery on Apple and Spotify. But while I'd love for you to do that, I have a different kind of ask.

If you've been finding Middle Man interesting and valuable, what I'd really like is for you to tell people about it - discuss the themes we raise and ask them to listen. I started this show because I genuinely want to help people, and I know from the messages I've been receiving that what we're doing here is really impacting men who are going through a tough time without really knowing why. So yes, you getting more people to listen helps me out a ton, and I really appreciate that. But more than that, you never know what the impact of that discussion might be on the people around you.

Thank you. Here's today's show.

Dirk Singer: Being 50 now is a lot different from how it was in our parents' and grandparents' time, and we have to think very differently about age and what you can do at certain ages. The idea of doing nothing when you're 65 or 70 - why? That seems very dull to me.

The other day, I was at a conference about sustainable aviation fuel, and it was like I'd been transported to another planet. I thought to myself, the me of 20 years ago would never have believed that I'd be sitting in this conference with people I would never have met in a million years. It's a bizarre experience.

I've realised that I'm in the autumn of my career, and I want to finish it off on a high, doing something I believe in - and, to be honest, something that is financially lucrative too.

PS: Over the last few years, Dirk Singer has undergone a substantial midlife career pivot, and on today's show, he's telling us his story. 

This episode is the first in what will become a regular series of shows featuring the personal stories of midlife men who have been or are going through some kind of midlife transition. 

Dirk talks about the challenges of raising his disabled son, finding your passion in midlife, and the prospect of retirement on the horizon.

<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, Dirk. I think we've probably got a lot in common, not just because of our age and stage in life, but first, we've worked in the same industry for 15 to 20 years or so.

And second, I think it's fair to say that we've both outgrown that industry. I'm putting it politely there, and I know you, as a result, have transitioned into something else, which I'm keen to talk to you about. But before we get into that, what have been your experiences of midlife on a broader scale?

DS: You see, I've transitioned into doing something completely different from when we first met, working in a similar field. One of the things I'm always aware of is the expectation that as you get into your early 50s, which I gather we both are, there's this idea that you can't teach an old dog new tricks—that you become set in your ways and can't transition to something else. But of course, that's very false. If you think about it, both of us worked in the digital marketing, social media, and PR industry, broadly speaking. We had to learn new things all the time—new industries, new companies—and pick it up quickly. 

So it's absolutely not true that you can't learn new things or pivot into different areas. I think one of the biggest challenges that people at our life stage face is overcoming that prejudice that once you pass 40 or 45, you can no longer get to grips with newer things or do something different. But I believe you very much can because all our careers and experiences have taught us to do just that.

PS: Yeah, I totally agree. It's interesting when you say you can't learn; of course, you can. I think my perception, and maybe I'm speaking from personal experience, is that I've lost the desire to learn some of that stuff rather than the ability. Twenty years ago, in our industry, I was all over every new app that came out, every new development, every new digital marketing strategy. Now, I’ve lost the desire to keep up to date as much as I did, especially with things like AI, for example. I just don't have the same passion for that industry anymore. Maybe that's what happens?

DS: I think passion is the right word. I’ve thought about this in terms of my earlier career. The work I did was interesting and fun; I met great people, like yourself. But did I really believe in it? Did I really believe in the people I was working for? One of my clients was an internet software virus company—did I really care if more copies of that virus software were installed on people's machines? Or back when I was promoting squash, did I honestly care if more squash was sold in supermarkets? Now, I can say I didn’t. 

Back then, I was into it and keen to make an impression. Now, you become more discerning, and if something doesn't speak to you, you concentrate on what matters. But isn't that a good thing? Because time is the most precious thing we have—it's a resource that, once gone, is gone. If you lose money, you can get it back, but not time. So, as you get older, you spend your time on what matters to you. I'm fortunate that I'm now doing something I actually believe in and, for the first time, something that in my small way, I feel is making a difference.

PS: Yeah, that's really powerful. You mentioned selling squash—one of the campaigns I always think back to was selling crisps. At the time, I loved working on it. It was brilliant, fun, and creative. But does it actually matter? No, not at all. That's why, although I'm still doing digital marketing at a more strategic level, I’m more discerning. Right now, I’m working with a client focused on cancer diagnosis. Now, that means something. Crisps? Not so much.

DS: I often liken our industry to being a footballer. Working in a PR and social media agency is a young person’s game, much like a footballer's peak years are in their late 20s. After that, players might progress to management, coaching, or punditry, which is similar to what you do. Or they might do something else entirely. 

A friend in the industry once told me, "The last thing I want to be is a 50-year-old account director." It’s just not credible at 50 to be picking up the phone to a journalist asking if they received your press release or organizing some Instagram influencer activity. That’s how I see our industry. Rightly or wrongly, there’s this perception that it's for people in their 20s and 30s. After that, even if you stay in the industry, you need to progress to something else.

PS: I totally agree. I think my perception, and it’s probably true for most industries, is that you’ll reach a stage where you top out in your 40s, which causes a lot of problems because men then look around and think, "Okay, I’ve gotten here—now what?" And like you said, you’ve lost the passion for selling squash or crisps, so you’re looking for meaning. And you’ve reached a stage in your career where it just feels a bit blah, for lack of a better word.

DS: Exactly. My history was very agency-based. I’m right in saying you founded a couple of PR and then social agencies, right? How did you find the experience of founding those companies, working your way through that, and where did you end up 20 years down the line when you looked around and thought, "Okay, I founded some agencies—now what?"

DS: Looking back at the companies I worked with, one is still in existence because I co-founded it. The agencies I founded, I think, were critical successes but commercial failures. I was good at creating environments where we won a lot of awards. In my time, I’ve won or been a finalist for 25 different industry awards, but I never figured out how to turn that into commercial success. I’m not a good salesperson. I liken it to an art-house film that critics love, but it doesn’t make box office success. 

The last agency I had, Rabbit, didn’t work out well. When someone I knew in the industry, quite a big name in digital PR, set up a new agency called Honey, I became one of the founders. That agency has been going for about eight or nine years now. I gave up Rabbit at that time, but I’m still an associate partner and a non-executive director, so I still have a hand in the game.

There were also life changes. I have kids, and one of my children is disabled. My son is like the child portrayed in the film about Ed Davey’s son. He’s 13, but his mental age is like that of a one- or two-year-old. So, my life is exactly the same as it was when he was a baby. He goes to a special school now, but I’m very reliant on carers. I have a carer coming in this afternoon. Summers are hard because I need more flexibility. I can’t have a job where I go into an office at X hour and leave at Y hour. At one point in my career, I was looking after 40 people, and I can’t do that anymore. I need something where I can adjust my hours as needed and where I have a certain amount of work to do, but whether I do it at 2 pm or 2 am is up to me.

One of my interest points was the aviation industry. When I was with Rabbit, we worked with several aviation clients. We did digital strategy work for London Gatwick Airport, Manchester Airports Group, and British Midland International (BMI). Through that, I got to know a consultancy called Simple Flying, which is like the McKinsey of aviation. I started doing contract work for them—consultancy work for clients, editing a magazine, writing articles, and so on. The work was totally flexible, which suited me well. 

Around 2019, I became more aware of the flight shame phenomenon that started with Greta Thunberg in Sweden. It spread across northwestern Europe, where flying was becoming socially unacceptable due to carbon emissions. I saw that as the biggest issue the industry had to face because if you cut the social licence for air travel, you cut at the very essence of what these businesses do.

I produced something called the Flight Shame Report, my first foray into the sustainability space. Then, of course, COVID happened, and everything was turned upside down. I don’t know what you did during that time, but we actually started a testing business. I have no scientific background whatsoever, but during that time, I produced a daily newsletter about travel restrictions worldwide, different vaccines, and different border controls. I could tell you all about PCR versus antigen tests, different vaccines, and test manufacturers. 

We created an online platform, a kind of white-label platform we sold to airlines for testing services. For example, we worked with the Mexican low-cost airline Volaris, creating a site and platform to connect passengers flying from Mexico to the U.S. with testing labs. That kept me going during that period.

PS: Was that kind of a COVID project, like, "Right, I’ve got to do something"?

DS: Yes, because, working in marketing and air travel, I lost three-quarters of my income during that time. People weren’t doing marketing, and travel was shut down. So, we pivoted to a testing business, which wasn’t what we expected. Then, when borders opened up again, we went back to sustainability. I’ve been doing that for the past three years. My title is Head of Sustainability for the business. 

I speak at conferences, produce reports on everything from hydrogen to electric aviation, and we’re launching an accelerator to work with startups in the climate tech space. This is something I believe in because I believe climate change is the issue of our time. I also believe that mobility is a force for good, and I’m trying to reconcile those two things.

PS: When you started doing that work five years ago, give or take, was it something you were immediately drawn to—something you had a spark for? We talked about passion. Did you suddenly think, "I really believe in this stuff, and I want to do more in this space"? Or did you move into it more gradually?

DS: It was a bit of both. Just a bit of personal history—I’m not originally from the UK. I’m half American, half German. My parents met in Germany, I came here, went to school here, and ended up staying. So, essentially, I’m a product of air travel. My eldest son, who is neurotypical, is 16, and I want him to have the same benefits I’ve had, but without polluting the planet. I’m also very aware that global warming is the issue of our time. As I heard someone say at a conference, people talk about COVID, but there is no vaccine for climate change. And the direction of travel, unfortunately, is only one way, and it’s causing a lot of the problems we have in the world at the moment. 

Take migration, for example. Migration is a hot-button issue in the Global North, in the US, and here in Europe. People talk about the small boats or people coming in from Mexico. I often say, "What do people think is going to happen if we pass two and a half or three degrees of warming? Large areas of the world will become inhospitable, and it’s going to make what’s happening now seem like nothing." 

So, if people are concerned about migration now, these issues will become much worse on a warming planet. It touches on so many current issues that we face, and that’s why I believe in what I’m doing now. I have no formal training in this—I’m not a scientist or an engineer. I studied history at university. Sometimes I feel like I’ve been transported to another planet. The other day, I was at a conference about sustainable aviation fuel—alternative fuels made from non-fossil fuel feedstocks—and I thought, "The me of 20 years ago would never believe I’d be sitting here talking about alcohol-to-jet fuel, hydrogen, electric fuel cells, or non-CO2 emissions." Sometimes it’s a bizarre experience, but it’s where I’ve ended up.

PS: Yeah, it’s one hell of a pivot. I completely agree with you. I’m quite envious that you’ve pivoted to what seems like wildly different things. You mentioned the "ticking clock," in quotes, being one of the reasons for this pivot. I wonder whether that ticking clock is not just about your career—thinking, "Well, I’m 45, 50; I’ve got 15 to 20 years left to work," but also the ticking clock of the climate and those two coming together. You’re thinking, "Right, I’ve only got a certain amount of time left on this planet, actively and professionally doing stuff. I need to make that count." Is that the case?

DS: I think so. You’re absolutely right. I have no plans to retire anytime soon. I intend to work for as long as I possibly can, partly because caring for my son is going to be expensive, so I need to keep an income coming in. But I also see myself in the autumn of my career, and I want to finish it off on a high and do something I believe in—and, to be honest, something financially lucrative too. 

The climate tech space is a huge, growing area, and it’s reasonably recession-proof because of regulatory pressures, public pressures, and because climate change is becoming ever more real, putting pressure on companies, especially those dependent on fossil fuels, to decarbonize and do something about it.

PS: It’s interesting that you mentioned having no qualifications in this area—you’re basically self-taught. Is that a personality trait for you? Were you self-taught in digital marketing as well? I know I was. You went out there because you had a passion for it, taught yourself, tried things, failed, and tried again. You also went from not having a qualification to writing a book on climate tech. Is that right?

DS: Yes, that’s right. I’ve written a book about aviation’s challenges in reaching net zero, profiling companies in the space—both established ones like Embraer, the Brazilian aircraft manufacturer, involved in creating a new type of hydrogen-electric aircraft and electric air taxis, and startups focused on everything from hydrogen-electric engines to fuel made from carbon dioxide and renewable electricity. 

The fact that I could put together 65 to 70,000 words about a topic I knew nothing about 10 years ago shows you can teach yourself. Writing that book was one of the hardest things I’ve ever done. In my previous career, I must have turned around thousands of pieces of copy. So, when I was tasked with writing this book, I just assumed I could do it. But when I submitted the first chapter to our editor in the US, I was crushed. He didn’t even bother highlighting or tracking changes—he just highlighted entire paragraphs, saying there were so many changes needed. I was horrified. 

But after feeling sorry for myself for a few days, I decided to get a grip. I went back to the editor, Ryan, and said, "Rather than you doing this, tell me what I’m doing wrong, and I’ll produce as many drafts as necessary until I get it right." For the first two chapters, it went back and forth two or three times. But by the last chapter, there were only two changes. It proves you can skill up and learn something. Not only did I learn about the topic—some fairly technical things about climate change and sustainability—but I also now have the skills to write a book, which is very different from writing a white paper, press release, or promotional copy for a client.

PS: Very much so. Has this whole pivot scared you at any point? You mentioned financial commitments, needing to look after your son, which isn’t going to stop anytime soon. Did you ever hesitate, thinking, "Should I really be doing this from a financial perspective?"

DS: No, just the opposite. I think if I had been working in an agency, I might have had skills and knowledge that were still useful, but there would always be that nagging thought, "Do they think this guy’s getting on a bit? If we need to cut people, maybe I’ll be the first to go." Let me turn the question to you—do you think that’s one of the reasons why you’re self-employed rather than working for an agency with a bunch of people?

PS: Financially, yes. I’m far better off now self-employed than I was in agencies. But at the time, that wasn’t my main consideration. I got to a stage in my career—this was 10 years ago—where I’d either go work for a big agency in London in a strategic role (and I don’t live in London; I live in the Cotswolds), which would mean working long hours and commuting, or I’d set up on my own. 

What drove my decision was designing my life so I wouldn’t have a long commute, could spend more time with my kids and family, and could earn more independently anyway. That’s what drove my decision—not purely finance. But now, I’m not content with what I’m doing professionally. I’ve felt this way for a couple of years. I’ve lost the passion for certain aspects of it. But now it’s different because if I wanted to pursue something new, like climate or sustainability, it would scare me. I have more financial commitments now than I did 10 years ago, so it’s different. People’s lives flex in that way.

DS: Right, and I agree that there’s sometimes only a certain window in which you can pivot into a certain area. I did an interview recently with a trade magazine, and I told them that I’m the last generation—and probably the only generation—of sustainability heads that are self-taught. I’ve come through something else, learned everything myself, and know enough about the topic to write a book about it. 

But sustainability through the ranks now is learned through an MA in sustainability or something similar. By 2030 or 2035, I probably wouldn’t be able to do this because that window would be closed.

PS: That process of being self-taught and learning is something you really enjoy. Was that part of the driver for this pivot? Rediscovering a passion for something and then going out, learning, and writing a book, which you said you never would have thought of doing before?

DS: Yes, it drives me forward. I learn something new every day. Just before we started recording, I was writing a huge white paper to launch our accelerator, discussing the benefits of hybrid-electric aircraft—a bit like a Prius in the sky. I learn something new every day. I also like being exposed to smart people and interesting startups in this space. These startups are created by people who want to do something good for the world, and that makes me more optimistic. Being exposed to a sector where people are trying to do good drives me forward on a day-to-day basis.

PS: You used the word "optimistic," and I think optimism should be a prime driver for how men deal with midlife. To have discovered something you’re optimistic about is incredible because that will keep you going through tough times, in all areas of your life.

DS: I know it’s a cliché, but I don’t even see it as work. In my free time, I listen to podcasts about climate tech, educate myself while walking around the park or the wharf near where I live. So, my free time and work time blend into one. I’m quite lucky to be in that situation.

PS: It sounds like you’ve discovered a purpose because when you have that purpose, things don’t feel like work. You’re genuinely interested in it. For example, doing this podcast—I’ll sit in the evening, scoping out guests, topics, or editing, and my wife looks at me like, "Why are you working in the evening?" 

But it doesn’t feel like work because I’m genuinely interested in doing it. If you’ve got a job, you work nine to five and go home. But when you’ve done this pivot, was there a point where it became an intentional career move? Or was it more of a gradual process?

DS: COVID was a useful thinking time for all of us, but it was clear to me that I’m no longer working in digital PR. I’m doing this now. That was probably the time—around 2021—when I stopped thinking of myself as working in the PR industry and deliberately shifted to sustainability.

PS: You mentioned retirement earlier, saying you probably won’t retire at 65. But do you look ahead to retirement at all, or is it something so far away that it’s not worth thinking about?

DS: I see it as something in the distance, though I’m aware it’s not that far away. And this ties into one of the themes of your podcast—being 50 now is very different from how it was in our parents’ and grandparents’ time. We have to think differently about age and what we can do at certain ages. When I’m 65 or 70, obviously, I won’t be as fit, but my mental faculties will still be there. 

Why can’t I keep doing this, especially since I believe in it and don’t see it as work? So, from a financial and personal point of view, I want to carry on. The idea of doing nothing when you’re 65 or 70 seems very dull to me. In our parents’ or grandparents’ time, it was expected—at 60 or 65, you retire, do your round-the-world cruise, play golf, or do your gardening. That just seems crashingly dull to me, and I don’t think I’d get much fulfillment from that life.

PS: No, you’re right. It has changed a lot in a generation. I remember when my dad was approaching 60, and he took early retirement. But I got the sense that he was always working toward retirement. They moved down to Devon, got this beautiful house with a lovely garden, and that was the life. But I’m the same as you—I can’t get my head around that as a way of life, doing nothing.

DS: My dad was the same. He retired relatively early. My parents live in Germany, have a nice house and lifestyle, walk the dog, and my dad plays golf. Good for him, but I would find that just—oh. Having nothing to occupy your day other than meeting friends, walking a dog, or playing golf doesn’t seem like something I want to aspire to.

PS: No, absolutely. I think I agree with you. There’s a statistic, and I can’t remember it off the top of my head, but you’re more likely to die shortly after you retire, and it’s linked to exactly what you’re talking about—losing that purpose and drive. It’s almost like you retire on Friday, and by the next Friday, you’re dead because you’ve got no reason to live anymore. I know I’m being extreme, but there is a statistic like that.

DS: Do you think it’s also because your mind becomes less active?

PS: Yes, I think you’re right. It’s not just about not having a job—it’s about not using your brain enough.

DS: You drift, and I think it’s easier to—without generalizing—go downhill when you’re not focused on something and when there’s nothing occupying your time on a day-to-day basis. You just drift.

PS: Exactly. It makes me think—my dad died last year, but I look at them now, and he retired when he was 60 or 59, and they lived in Devon for nearly 20 years. Yes, they went on nice holidays and had this beautiful garden, but they spent a ton of time in the garden. We used to tease him because before he retired, he worked as a scientist—he was a physicist. When they moved down there, he set up spreadsheets of weather trends in the local area and stuff. We used to tease him about it, but recently, I realised why he was doing it. It wasn’t that he was particularly interested in weather trends—it was that it kept his mind active, to do this stuff. I never realised that at the time.

If someone listening is around our age and feeling a bit fed up with their professional life, and they’re listening to this and thinking, "This guy’s had a total career pivot in just a few years—how do I do that?" What would your advice be to them on how to approach it?

DS: First of all, you have to believe in yourself and that you can do it. You have to remind yourself that decades of experience have prepared you for this. All of us at this stage in our careers have managed people, been exposed to different sectors and industries, seen good times and bad, and all that experience prepares you to do something different. And as you get older, you can work through things quicker and pick things up faster. So, look at what you’ve done and see it as transferable. 

The skills you’ve developed can be a bridge to something new that you want to do. But I understand it’s hard—you might have financial constraints or difficulty finding the right industry where people welcome your previous experience. So yes, there are hurdles, but I’d say look at your past experience as a bridge to what you can do next

OUTRO

PS: I hope you found today's show interesting. You can find Dirk on LinkedIn.

If his story resonated with you, please tell someone who you think might benefit from this. 

You can also sign up for the Middle Man newsletter, which features articles and resources based on the theme of the week's show at middlemanpodcast.com.

Next week, we're taking a more in-depth look at career edits with someone who helps midlife men identify their values and purpose.

Laura Allen: Men go through their 20s and 30s with a lot of ambition, drive, and mindsets curated by their surroundings, family, and communities. Eventually, they hit burnout, and once you reach that point, it forces you to sit down, readjust, and ask, "What am I doing this for? What is my purpose? Why am I here?" 

PS: See you then.