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Advice / Career Paths / Career Change

5 Ways to Test-Drive a New Career

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Stuck in a cube, dreaming of freelance writing from a distant exotic island? Coming up with yet another PowerPoint deck, while desperately wishing you could devote your life to something that means more to you than someone else’s deliverables for someone else’s clients?

I’ve been there, too. And I can tell you that it probably means you should consider pursuing another career path.

That said, it’s hard to know whether the new job you have your eye on will be a better fit for you than the one you’re in. The “grass is always greener,” after all, and it’s easy to romanticize new avenues, thinking that moments of hair-tearing, heart-pounding frustration are exclusive to your current position.

Not so, my friends. Transitioning fields is a commitment, so you want to make sure to test-drive one (or many) of them before you speed off the lot into the sunset. Here are a few simple ways.

1. Read and Write

This first tip is the easiest one of all. Remember that, no matter what you’re trying to do in your career, someone else has done it before you. And thanks to the internet, you are guaranteed to find several very solid descriptions of the career you’d like to pursue.

Get started on your own little research project, and collect resources as if you were going to write a thesis on your new job of choice. Outline the possible career options, the best and worst aspects of the job, possible companies you could work for, the types of work these companies do, and the personality types these fields attract. You will be an expert in no time, and you’ll be able to more accurately gauge whether you’d like to make a transition.

2. Commit to the Hard-Core Informational Interview

Scrap everything you’ve heard about informational interviews.

Once you’ve done your research, find a friend or a connection who will be painfully honest with you and fill you in on all the facets of the field: the good, the bad, and the really ugly. If this person is a disgruntled inhabitant of the career space you’re trying to get into, even better.

Then, sit down and collect all of the gritty details about this career path, and don’t hold back. Ask questions like, “What was your worst day in this industry?” “What tends to make people burn out in this field?” or “Name three surprising things—and not the good kind—about this career path.”

Sounds harsh, but this is a great way to dismantle your illusions and realize what you’re really getting into. You can realistically measure the challenges that will come your way with a career switch and decide whether you’re up for all facets of the field.

3. Walk Through the Valley of the Shadow of Careers

I know—shadowing someone sounds so very high school. But then again, how many times do you wish you had shadowed someone for a day before accepting a job offer? I wish I had—for every single job I’ve ever taken.

So take a cheeky sick day, and follow around a gracious individual who is willing to show you the ins and outs of the profession. There’s nothing quite like first-hand experience to get a feel for whether you’re really excited about a certain role. Remember to ask very politely, and offer to help out for the day in exchange for this person’s time (read: actually do some work, don’t just observe).

4. Freelance

Freelancing is a great thing, and it serves dual purposes: You gain experience in a certain field, and you get introduced to an industry without having to permanently commit.

So, see how you might be able to lend your skills to some outside projects on your nights, weekends, or time off. It’s great if you can get paid, but don’t worry if you have to volunteer at first (or even be labeled an intern). Labels don’t matter—developing skills and contacts does matter. Whether it’s writing, programming, content strategy, or project management (to name a few), the more work you have under your belt, the easier it will be to take on new clients for a fee or find a paying role in that field.

5. Get Creative About Your Income

At some point, you may want to leave your full-time job to truly dedicate yourself to honing a new career path and a different set of skills. And in this case, it can be helpful to find alternative ways to make money. Whether you Airbnb your apartment, take two part-time jobs instead of one full-time job, or moonlight as an eBay rockstar, ticket reseller, or Etsy vendor, remember that income is possible from a variety of sources. Don’t be afraid to do some experiments while you explore new professional outlets.

It’s great to dream about a new career path, and I promise that it’s not impossible to turn your dreams into your new reality. Arming yourself with as much information as you can before you take a step is the best way to go about it. So, go get test driving!