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The Smartest Way to Make a Major Career Change

Miserable with your career? Time to make a plan.

Connor Robinson for Fatherly

Wanting to leave your job has been a long, national pastime. But the last 17 months of working from home, however inefficiently, and not having to wear shoes or sit in traffic has intensified the question, “Is this what I still want to do?”

For some, the answer is, “No way.” 

They’ve had it with bosses, meetings, the subject matter, and a bunch of other things. They’re, in a word, done. 

But the thought isn’t about merely leaving a company. People do that constantly. This is the bigger-picture step of making a career change. So the question becomes: How do you change careers, especially when you might be a bit older and have a couple of kids? 

You might have always had a tamped-down desire to be a therapist, teacher, or baker. But now the feeling is bubbling up, and it feels right. But then you start thinking of everything involved: Going back to school, starting at the bottom, earning less money, all against the backdrop of having young kids. It’s easy to look at all the steps involved and think no way in hell

These are real concerns. But what also stops you is that passed-down message that it’s called work for a reason. It’s not supposed to be fun and you’re not supposed to like it. 

“You’re not even allowed to say you don’t like it,” says Allison Task, career and life coach in Montclair, New Jersey, and author of Personal (R)evolution. 

The reality is that while the grind is unavoidable, there can be a payoff to work that you don’t have to wait endlessly for. “You can derive fulfillment from your job,” she says. “If it’s, That’s my job and it’ll end in 30 years, that’s not enough.”

You can find a better fit, and the thing about change is it can take many forms. It could be a total reboot or coaching your kid’s team, and the net result is the same. You get re-energized, more in control, and “that sense of meaning in work that drives most people to change their careers,” says Mark Newall, owner of Flat Rock Careers in Marblehead, Massachusetts. 

While the change itself doesn’t always have to be huge, it does require work. You need to reflect, answer some questions and then take some action because this isn’t a keep-it-in-your head process. 

If you want to make a successful career change, here’s how to figure out your plan.

How to Change Careers: Don’t Do Anything Rash At First

Chances are, you’ve stayed in a field for 10-15 years for a reason. Not being able to fully leverage those skills and contacts is a risky move, so before you do anything, it’s good to examine your whole life; the job is only one part of it. Task will have clients look at areas like health, spirituality, love, fun, and rate the importance and level of satisfaction of each from 1-10. 

You might think your job is the issue, but you could discover that things aren’t good with your spouse, you’re feeling bad as a parent, or, in what’s a common one, you’re disconnected from friends. “You’re simply lonely,” she says. 

There’s a good reason for this. Men often socialize shoulder-to-shoulder, like while watching a game, but the pandemic knocked that out. The remedy? Volunteer with your kid’s team or do school pick up and drop off. It’s not necessarily the cure-all, but the intake might scale down the work. It’s not unlike a house project, Task says, where a clear eye discovers, “It’s not the roof. It’s the window.”

If the job is truly the issue, it’s good to figure out what you really want for your next one. Newall suggests thinking about the top five talents that have gotten you this far, then come up with two more. Of those, whittle it back down to five to get “which muscles you want to flex,” he says. These are the things you’re good at and still want to be doing. (Sorry, project management and numbers crunching.) When you start reading job descriptions, you have a clearer focus and an ability to recognize new, possible fits.

Job searching in general is a good exercise. Task recommends to do it at least once a year, and when a recruiter calls, answer it. You get out and interviewing reminds you of your strengths. It keeps you current and up on the competition. 

“It’s occupational tourism,” Task says. And it gives you perspective. The more places you see, the better or worse your current gig looks, and leaving, or maybe staying, isn’t as hard.

The challenge in this, Newall says, is that some people have never searched. Jobs have simply come to them. So if you’re contemplating a change, reach out to connections, and tell them what you’re thinking and that “I have these five skills and I want to do X” Since it’s a different field, your circle might not be able to help directly, but they can lead you to someone who could. You’re now on the radar, well before a position gets posted. “It’s the hidden job market,” he says. 

‘Perhaps You Need a Pivot?’ And Other Big Questions

The dramatic career change might also just be a pivot, because you may realize that the work remains satisfying. It’s just all the other stuff: the meetings, politics, not being able to be home when you’re home, which you hate and leaves you feeling stalled, Task says. 

The answer could be to ask for a transfer, new projects, or even become a freelancer for the company. Yes, this hinges on your relationships and how much you’re valued, but it comes down to having a conversation with your manager about finding something different, be it less bureaucracy or more growth. Whatever your end goal, fundamentally, you’re taking control of your career, defining what it can look like, and that might be the power you need.

All the above work might lead to making the full-on change and then it’s about planning with your spouse, looking at finances, deciding what you can do without and possibly starting to save in the face of an eventual earnings hit. 

That prospect can certainly feel overwhelming, but it can also be done in steps. You can stay in the field but in a different role, like going from big-firm attorney to in-house counsel, or merely shift from high-tech to biotech. Give yourself a time limit on that short-term job, say three years. Broken down into smaller chunks, the big move becomes less daunting, because change is no longer a mystery. 

“You get partially out of your comfort zone,” Newall says, “and that makes it easier to get fully out of your comfort zone.”