Well, the first thing you do is stop telling yourself it’s out of the question to change your mind, or that you’re stuck. “Switching careers can be such a big impossible-sounding thing to wrap your head around,” says Portland, Oregon-based journalist (and former lawyer) Mr Jay Willis. “You often don’t know where to start.” Mr Will Sutton, a landscaper in London who initially worked in advertising, concurs, noting that the mental hurdle of changing gears can be debilitating. “I had some fear. I remember thinking: ‘All of my friends are in jobs that they love and are really passionate about, why am I not like that?’”

“Do yourself a favour,” says Willis. “Let that part go and focus on the task at hand because that’s challenging enough.”

Both men emphasise the importance of starting small. For Willis, who knew he wanted to write instead of practising law, that meant blogging on his own time for a year. A standout day was when a legal blog linked to one of his Wordpress pieces, but otherwise, “there was no meaningful pay off,” he says. The accumulation of work, however, meant that he felt bold enough to apply for a job at a magazine. He didn’t get the job, but secured freelance work and made some connections, all of which eventually led to a nights-and-weekends blogging job, and then a staff-writer position, which completed Willis’ transition from lawyer to journalist. All it took was a couple of years, and a lot of determination.

“You’re probably not going to get your dream job in a different field in the next day or the next month, or even in the next year,” he says. “But if you start small and you agree to yourself that you’re going to build on that over time, that’s how you get to the decision of really being able to make that change.”

Sutton eased into the change by simply admitting to himself and others that a change was necessary. “When I started sharing [my desire to change careers] with more people, they were like, ‘Oh, that’s really interesting and cool,’” he says. “The more I spoke about it, the better I felt.”

Up until then, much of Sutton’s career had felt almost accidental. He had fallen into advertising after university, starting with an internship that turned into a job that led to an almost decade-long career. At first, he loved it – he could wear his own clothes to work, the social aspect was enjoyable. But at a certain point, he realised that he didn’t want what his boss had and he didn’t see a way forward for himself.

Sutton wanted to be outside; he wanted to work with his hands. So he did a little online digging and found a landscaping course that he could take two days a week while continuing to work at his ad firm the other three. After the course ended, he returned to advertising until finally pulling the trigger on the switch. “It was my wife who pushed me, she was sick of me complaining about work.” He’s been landscaping for four years now and loving every moment.

Something to consider is how hiring managers and recruiters will react to a sudden switch on a CV. Ms Nicole Balsam, director and head of brand and digital at the NYC-based executive search firm Eastward Partners, says not to worry about it. “When I see a candidate who has made a switch mid-career, it doesn’t raise any red flags for me at all,” she says. “Skills acquired in seemingly unrelated industries are often extremely transferable to other kinds of roles.”

But, she does echo what Willis and Sutton discovered for themselves: you may have to go back in order to move forward. “Understand that if you are moving into an entirely new industry or career you will likely need to be comfortable taking a few steps back (in terms of title and/or compensation).”

These are, of course, real considerations – both Sutton and Willis were 29 years old when they started to explore a career change in earnest, both engaged or in serious relationships, both living in large expensive cities. Taking a leap away from your career can be financially daunting and a time-consuming numbers game.

“It’s just full of possibilities for failure and rejection,” says Willis. “That might be the biggest mental hurdle of all. Probably 95 per cent of the earnest emails, calls, pitches, job applications, DMs that I sent out went unanswered. But you’ve got to keep doing it, because it only takes one yes to get you started.”

Neither men have any regrets about their paths. Money spent on graduate school, time spent building a career they hated, sure it’s easy to look at that as a waste. But for both of these men (and for my husband) their “wrong” careers served as important steps toward the right ones.

“I don’t regret it at all,” says Sutton. “I genuinely really enjoyed my life in advertising to start with and I’m really enjoying what I’m doing for work now, it’s really working out. It was all for the best.”

Balsam (who, incidentally, made a career change herself from acting to recruitment) sums it up nicely: “It’s definitely scary to make a leap to something completely new, but life is too short to not follow your heart.”