What did you always want to be when you grew up? MR PORTER meets six second careerists who found a way to be that man.

How many children, when asked what they want to be when they grow up, would say digital marketing manager, facilities coordinator or client services liaison officer? And how many adults can claim to now have the job that they once aspired towards as a child? The truth is that many of us – perhaps even most of us – are stuck on a career path that we didn’t consciously choose, the trajectory of which was largely determined by a handful of decisions made at a point in our lives when we were perhaps not best qualified to make them.

Little wonder that we find ourselves so prone to career anxiety. What if I made the wrong decision? Have I missed my calling? Will I ever fulfil my potential, or am I destined to wither on the vine? In direct conflict with these anxieties is another kind of fear altogether: the fear of failure. We might regret the decisions that we made in the past, but the idea of starting all over again can seem just too daunting to even consider. It’s hardly surprising that for many men the dream of escaping the rat race remains just that: a dream.

But there are still plenty of men chasing it. For our Second Career Issue, we spoke to a few of them in the hope of finding out what it is that drives us to seek out change in our professional lives.

“You do sometimes wake up in the foetal position, cradling your knees”

Mr Chris Weston, 30, was born and grew up in the East Midlands, England. His career began at Red Bull, where he worked during his time at Manchester Business School. That was followed upon graduation by short stints with a number of marketing and advertising companies. He had always harboured ambitions to run his own business, and in June last year his hand was forced when he was made redundant. He is now in the early stages of setting up a country-inspired clothing company, Wexton, with an initial range of contemporary waxed-cotton jackets.

So, have you always dreamed of running your own business?

Yeah, from a very young age. My father went straight into the family business – insurance – and that’s all he’s done for his entire career, as was the norm for his generation. I’ve had the benefit of that, of course, and I appreciate it, but I’ve never had any interest in pursuing it myself. I’ve always felt a subconscious urge to do my own thing, but it’s taken me a long time to a) figure out what that is, and b) have the confidence to actually go out and do it.

Was being made redundant a catalyst?

In a way, yes. Being thrust into a situation where it’s no longer a choice but a necessity can force you to do things you wouldn’t otherwise have done. But if you’re thinking about changing career, then I’d strongly recommend that you don’t just leave your job. Try to hold on to it for as long as you can – even if that means negotiating to go down to three or four days a week. Having an income will mentally reassure you that you’re still working.

Had you remained in your job, would you have had the confidence to make that step?

I think so – but I could already feel myself getting drawn into that trap of easy employment. You get locked into something that you think you’re good at, and you’re getting paid a decent salary. Everything’s stable. You’re receiving a monthly pay cheque. To throw that all up in the air can seem like utter madness.

Do you thrive on the pressure of being your own boss?

Failure is one of my greatest fears, and there’s a fine line between finding it motivating and debilitating. You do sometimes wake up in the foetal position, cradling your knees, wondering what the hell you’re doing. But you’ve got to draw on that fear and say: I’m going to make this work, because I’m not prepared to let it fail.

“A lot of us carry fantasies of a parallel life. It’s a bit like that movie from the 1990s with Gwyneth Paltrow”

Mr David Waters is a therapeutic counsellor who also serves on the faculty of Mr Alain de Botton’s School of Life, where he teaches classes on communication and relationships. In his previous life he was a journalist, chiefly as style editor for British Men’s Health, a position that he held from 1997 to 2007. He still writes, occasionally.

What prompted your interest in therapy?

During my time at Men’s Health, I went through a very painful break-up. A friend of a friend very kindly arranged for me to go and see a therapist, who I saw for maybe three or four months. I felt so much better for doing it. A couple of years later, I was mulling it over and I thought, “Oh, I wonder what happened there? I’d like to know more about that.”

When did you realise that it could be a potential career?

It was all very gradual. I signed up to an “introduction to counselling” course, having no ambition whatsoever for it to become my life. But from the moment I started the training, I found it utterly intriguing, and I stuck with it. Two or three years in, I was beginning to gain professional qualifications, and it suddenly became a real option.

Why did you decide to change career?

Fashion was beginning to become… well, there were lots of things that I really liked about it. I liked the travel, I liked the relationships and the creativity. But I’d been doing it for a long time, and it had got to a point where it was becoming rather routine. Which is not a criticism of the magazine or the industry in any way: that’s going to happen in any career at some point.

Do you wish that you’d realised your potential as a counsellor sooner?

No, I don’t think I’d have been able to appreciate it. Becoming a counsellor would be an odd thing for a very young person to do… you need to have had some life experience. It’s no coincidence that I came to it from a bit of a crisis of my own.

What would you say to someone who is feeling unfulfilled in their career?

I’d say think about it, because the grass isn’t always greener. A lot of us carry fantasies of a parallel life. It’s a bit like that movie from the 1990s with Gwyneth Paltrow [Sliding Doors]. You get to a point in your life where you start to look back and think, “I am the result of certain decisions that I made in the past.” In someone’s parallel life, they’ve got a beautiful house in the country and a beautiful partner, and it all could have been theirs, if only they’d made different decisions. I think it’s very unhelpful to think like that, because it stops you from appreciating what you do have.

“There was something inside of me that needed to get out”

Mr Guy Buchan, 40, was born in Melbourne, Australia, and grew up in Perth. He earned his Bachelor of Arts in Design from Curtin University, majoring in multimedia, and shortly thereafter moved to London, where he began a career as a UX (user experience) designer. In 2003, he set up his own agency, Integrate London, which has worked closely with clients such as UBS. A keen sculptor whose work has been exhibited in the West Australian Art Gallery, Mr Buchan has always felt a strong desire to express his creativity. In 2013 he set up his own luxury eyewear brand, Bold.

First things first: how does a man with a talent for sculpture end up designing financial products for banks?

Well, I graduated in 1996. It was the start of the internet, really, and I saw an opportunity to ride the wave of something that was going to change the world. I chose to go down the finance path because the industry has some very complex issues to solve.

Does your day-to-day job leave you creatively fulfilled?

There’s something very satisfying about solving complex problems through design. It requires both the creative and analytical sides of your brain. In 2003, though, when I started the agency, my work shifted from design to people management. I had a bit of an internal crisis: the creative part of me was thinking: Is this what I thought I would be doing? It felt like there was something inside of me that needed to get out. I needed to express it, and I felt that time was running out.

How did you address this?

I originally looked into making T-shirts. I went to [trade show] Première Vision in Paris to investigate different materials and panelling, did a pattern-cutting course and visited a knitwear factory in Wales. I believe that if you’re going to communicate your ideas, you need to be able to speak the language first.

What was your goal when you set up your eyewear brand?

My original goal was to create something that was all of the things I wanted to do. It had to be a vehicle for self-expression; a business, in that it needed to be sustainable; and an opportunity to experiment. I didn’t want to compromise with Bold.

Did you have any doubts?

I started in the downturn and people said, “Why are you doing this?” It’s a crowded marketplace, and there’s a lot going on. But it felt right. I had to listen to my intuition. I felt like I needed to do it. It’s hard to explain.

“I’m working with my best mate”

Messrs Hayden Wood, 32, and Amit Gudka, 31, met five years ago at a music festival in Croatia. At the time, Mr Wood was working at Bain & Company and consulting for clients in the energy retail market, while Mr Gudka was working for Barclays Capital in wholesale gas and electricity trading. They left their respective jobs in the summer of 2014 and late last year they founded Bulb, an energy supplier that offers 100 per cent green energy at competitive prices.

You both came from corporate environments, where hard work is the norm. Do you now work more or less than you did before?

Mr Gudka: I definitely work a lot harder now. It’s a completely different mindset. When you leave work, you’re not really leaving work. You’re always on. On the other hand, though, it’s so much more satisfying.

Mr Wood: Work used to feel very much like… work. The separation between work, which took place in the office, and life, which took place outside of it, was very clearly defined. Now, the lines are much more blurred. I’m having fun, I feel so much more relaxed and I’m working with my best mate.

Do you miss any of the creature comforts of working at a large organisation?

Mr Wood: I enjoyed working at Bain. You don’t realise how much you’re looked after, how many things are taken care of for you. And then there’s the monthly pay cheque, of course. When we set up Bulb we made a commitment to ourselves that we wouldn’t receive a salary until we had customers. That first month was a relief.

Mr Gudka: But the trade-off of greater freedom, and that feeling that you’re on a common mission, is more than enough to compensate for it.

What made you think it was the right time for you to jump career?

Mr Gudka: It’s an exciting time in the industry, with the market for renewable energy ready to take off, and we both had the required experience to just go for it. It just made sense. Eight years, which is how long I’d been at Barclays, is a good amount of experience in a particular field.

Mr Wood: If you leave it too long, it’s easy to get tied down with other responsibilities. It’s finding that point in your career where you have a balance between experience and relative freedom.

“My only regret is that we didn’t do it sooner”

Mr Nemanja Borjanovic, 35, was born in Serbia but has spent most of his life in London. He spent his twenties working in the City as an investment banker, during which time he also set up a wine importing business. It was after a trip to San Sebastián in northern Spain with his girlfriend, Ms Melody Adams, that he was inspired to leave his job and start up a restaurant. The couple’s first restaurant, Donostia – named after the Basque word for San Sebastián – has since been joined by a second restaurant, Lurra, and a successful meat importing business, Txuleta.

Did you enjoy working in finance?

No. Not at all. I felt like a glorified data-entry guy. I was paid a lot of money for it, so of course it made sense to stay for a while. But it’s not all about money, and sooner or later you’ve got to do something that you enjoy.

Which brings us to food. Is that something that you’ve always enjoyed?

Well, I like to go out and eat! Probably more than your average Joe. But I wouldn’t say that I’ve been passionate about it for my entire life. Melody and I brought it out in each other, I think. When we went to San Sebastián we realised that if we were going to do something privately, it was going to have to be in food.

The restaurant world is a tricky place to succeed. Did people think you were crazy?

Can you imagine what my mother said? A proud Serbian mother, her investment banker son in London leaving everything to open a Basque restaurant? And on Seymour Place..? [Laughs] You’ve got to remember that there were a lot of failed restaurants on that street back then. Though we did get a good deal on rent…

Do you think that it was the right time for you to move career?

My only regret is that we didn’t do it sooner. What we did four years ago, I wish we’d done a decade ago. I look back at my time in finance and it feels like I was never really a part of it – it’s almost as if it was someone else living that life.

Do you miss anything about it?

Lunch. There’s a really good curry mutton guy in Spitalfields Market. That’s the only thing that I miss.