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The Ultimate Checklist for Anyone Considering a Career Switch

What to consider before making the transition, during your job hunt, and after landing a new role

Deanna Pai
Mar 12 · 8 min read
Credit: Anna_Isaeva/Getty Images

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Most of us have, at one point or another, fantasized about starting over in a whole new career. Maybe you wonder each time you open a spreadsheet if your attention to detail might serve you better in something like event planning. Maybe you spend meetings daydreaming about abandoning office life and opening a bakery. Maybe you’ve always secretly believed you’d make a great doctor.

It’s easy, especially if you’ve ever experienced more than a fleeting frustration with your job, to understand the appeal of starting from scratch in a new industry. What all those fantasies typically fail to acknowledge, though, is that actually following through with a career change is both a challenge (you’ll likely be working your way up from the bottom again) and a gamble (you may not even like it).

This doesn’t mean a career switch is always a bad idea — just that it requires plenty of preparation and diligence. The first step is to decide whether a career change is what you really want and to make sure you’re interested in it for the right reasons. From there, a number of things can help ensure a smooth transition to and guarantee satisfaction in your new career, from whittling down your debt to giving your résumé an overhaul. Here’s everything to you’ll need to know to make your career transition a step-by-step success.

Stage 1: Preparing to make the change

First, sleep on it

This isn’t a decision to make at the spur of the moment. “The most common mistake is to react to an unsatisfactory situation with an impulse instead of a plan,” says Larry Smith, an economics professor at the University of Waterloo. “Sometimes the impulse is away from an existing career or employer; sometimes the impulse is toward a new career.”

Either way, it’s a decision that can often be driven by emotion. But without research and careful forethought to anchor this transition, you run the risk of landing yourself in a similarly dissatisfying new career. “While you are looking for a career you will enjoy better than the one you have, you find that enjoyment with a methodical search,” Smith says. “You do not ‘feel’ for it.”

Assess your current job situation

This step isn’t so much to gripe about your job, but to glean insight about what makes you tick. Often, “what people love about the job isn’t the job itself,” says Kerry Hannon, author of What’s Next? Follow Your Passion and Find Your Dream Job and several other books on making career transitions. “It’s the opportunity to travel, the opportunity to continue to learn, or the mission of the organization.”

Hannon recommends journaling about your job to get a better sense of what you do and don’t like about it. At the same time, try to reengage in your work, since people often get frustrated and seek change when they’re simply bored. If you find a renewed interest in your current work, you might not need to make a change after all. If, however, you can’t bring yourself to feel connected to it anymore, then use your reflections to start researching potential alternatives.

Make sure you’re changing for the right reasons

A dream salary doesn’t always translate to job satisfaction, especially if it has you consistently pulling late nights or getting spreadsheet-induced headaches. So, you should next question exactly what lies behind your desire for a career change. If your sole reason is to make more money, achieve status or prestige, or obtain more security, Smith cautions that making the switch may not actually bring more career happiness.

To set yourself up for the greatest chance of success in finding the right fit, he suggests asking yourself: “What exact characteristics should my new career destination include?” Because, he notes, “the fuzzier the destination, the more likely you will be dissatisfied when you arrive.” In other words, leave your current career behind only when there’s a specific, more appealing alternative — not just for the sake of leaving.

Set yourself up financially

“Debt is really a dream-killer,” says Hannon, who notes that the biggest obstacle in a career transition is typically money. You may take a pay cut when starting in a new field, need to invest in your education first, or go without paying yourself if you’re starting a business.

Hannon suggests planning ahead to build up a financial cushion before making the leap: “Where might you be able to trim back and get lean? Can you downsize where you live?” she says. “The further in advance you can get started, the better.”

Do your due diligence

Once you’ve set your sights on your new field, it’s time to do your homework. Research the requirements for entry, like whether you need to enroll in a course or technical program, and also talk to those in the field. “See if you can job-shadow,” Hannon suggests. The more you learn about the new industry — and the more people within it that you meet — the better off you’ll be for the next step: Getting a job.

“Think of it as redeploying your skills. You’re redirecting them, not starting from scratch.”

Stage 2: Landing a new job

Reframe the transition in your head and on paper

People tend to think of their career as a core part of their identity, and a change in that can be overwhelming, even if you want and plan for it.

Instead of thinking of the change as a complete break with your old career, “think of it as redeploying your skills,” Hannon says. “You’re redirecting them into a new arena or a new field — you aren’t starting from scratch.” Not only will that make the thought of starting fresh less daunting, but it’ll also help you sell your skills.

“Think hard about your day-to-day work,” Hannon says. “Almost everything we do in our work lives can be done in a different field.” Certain skills and experience, like project management and strong writing abilities, can translate across sectors.

Be open to every opportunity

If you’re starting on the lowest rung of the ladder, you’ll likely have to chase entry-level positions or contract or temporary jobs. “Anything you can do to get in the door is great, and if you’re not happy, you can keep doing side gigs too,” Hannon says. “It’s the nature of the job market. Don’t say no to temp. Don’t say no to contract.” It’s an easy way to form connections without the stress of networking, and if a permanent job does open up, you have an in with the company. In the meantime, you’re learning the ropes.

Tailor every résumé you send

Sending a unique résumé for every position may sound like a lot of work — and, okay, it is — but it also increases your chances of getting an interview, and not just because it shows you’re interested. If you’re applying online, many companies use applicant-tracking systems to filter résumés for certain keywords, says Donna Poudrier, a career coach and recruiter. And if yours doesn’t have the desired keywords, it won’t be passed along to a human.

The best way to get around this is to analyze the job description and incorporate similar wording in your résumé. “That speaks to the need to customize every résumé for every position you’re going for,” Poudrier says.

Start networking

Yes, networking can feel painfully awkward — but it can also be very effective. “Talk to people who have the job you want,” Hannon says. “Start with informational chats and build a relationship, and eventually they may recommend you to somebody else.” There’s nothing wrong with a cold email if you don’t know anyone in your desired field.

You can also sign up for industry conferences or join a group on LinkedIn. “Use your network in all different ways — alumni networks, LinkedIn networks — because you never know where the next job is going to come from,” Poudrier explains. “A way to find like-minded people is to join different LinkedIn groups. You can contact them just by becoming a member of the group.”

At the very least, send out feelers to family and friends. And talk about your career transition to anyone who will listen — the more people who know what you’re looking for, the more potential there is for a connection.

Perfect your pitch

The toughest question in an interview might also be the most common: Can you tell me about yourself? “You need to be prepared” to sell your past experience as it relates to the job at hand, Poudrier says. “Say, ‘This is my background. I can utilize these skills in this situation and help your company by doing such-and-such.’”

Creating a cohesive, concise story that sells your key attributes and how you can adapt them is the first step. The second is remembering it well. Practice until it sounds natural so you can share your pitch confidently whenever the moment calls for it, whether you’re at an informal coffee or with a recruiter at a job fair.

Stage 3: Succeeding in your new career

Set new goals

No one else can set your personal timeline for career growth. After all, you know when you want to retire, whether there are any personal milestones coming up, and what you want to accomplish over the long term. Once you start your career over again, you’ll probably need to revisit whatever goals you’d previously laid out for yourself.

“Keep reading, learning, and taking classes. What can you do to add value to yourself?”

“I like the idea of keeping a journal and keeping yourself accountable so you don’t get stuck in a rut,” Hannon says. “Look at what you’ve accomplished this week and what you want to accomplish next week.” Keeping an eye on your achievements and growth week to week can give you a sense of your broader, more long-term goals. If, say, you realize you’ve been crunched to meet deadlines, getting better at time management can become something to focus on.

Map out your career trajectory

As soon as you land in your new industry, you should be trying to understand how you can progress to the next point. “Your focus should be on ‘How I can grow here?’” Poudrier says. “If it’s not the salary you were thinking of and it’s not one you negotiate, ask, ‘What are the opportunities to advance?’ It’s okay to ask that.”

Then, if you want to advance, you have to back it up with action: Offer to help out with tasks that don’t fall under your job description, see everything as a learning opportunity, and be a good, enthusiastic colleague to work with. In addition to working hard at the role itself, you’ll want to continue your industry research. “Keep reading, learning, and taking classes,” Hannon suggests. “What can you do to add value to yourself? What can you be doing to add an extra skill set or to make yourself more valuable?” Others will take notice, which can raise your status as an employee and your desirability as a hire.

Keep making connections

Even after you have the job, networking never stops. “When you go back to those people you talked to about getting into a new field, ask them who else you can talk to,” suggests Hannon, who credits past colleagues and peers with recommending her for some of her jobs. “You want to learn how they got there.” And there’s no better way to set yourself up for your next gig than with the right recommendation.

Deanna Pai

Written by

Writer, editor, and West Coast-hater in New York.

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