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Advice / Job Search / Resumes

How to Explain Your Winding Career Path to a Hiring Manager

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Eva-Katalin/Getty Images.

I recently counseled a yoga teacher turned real estate advisor turned HR person—who’d just come to the conclusion that, without question, she didn’t want to be an HR person anymore.

Don’t anybody freak.

This type of epiphany is completely common and totally OK. There’s absolutely no law that says you have to stick to the same gig forever. In fact, sometimes our best career moves come only after these big "aha" moments that make a new path, a fork in the road, or even a U-turn absolutely imperative.

The challenge, however, for this woman and for any other professional who has a winding career path, lies in making your value proposition (or, as I call it, your “so what?”) clear to hiring managers and interviewers. Further, you’ve got to figure out how to present this divergent background in a way that affirms to decision makers that you are not, in fact, going to leave them in a bind by changing your mind again.

So, how, exactly, do you do this? Here’s the advice I offered to the yoga teacher turned real estate advisor turned HR person.

1. Have a Target Audience, and Speak Directly to It

This is super important for any job seeker. It’s especially critical for those whose career histories involve several jobs or industry sectors. You’re not going to be able to just list out your job history (which spans sales, marketing, and business development) and expect a financial services hiring manager to instantly deduce what you have to offer. Instead, you will need to angle all of your messaging in a way that makes it obvious what you’re trying to achieve, and why you’re heading in that direction. To do this:

2. Find the Common Threads

Look for a theme that runs through several of the jobs you’ve held, and present your choices in a way that shows common threads running through each of your career decisions. For instance, in the case of my client, much of what she has done has involved advising, guiding, and helping people. This works out nicely, considering she wants to become a college advisor. And so, on her resume, we showcased several career instances in which she successfully helped, guided, and coached others.

3. Showcase Performance

People hire performers, so no matter how jumpy, windy, or unusual your career path, present yourself as a high performer. You can easily do this on a resume or in an interview by using phrases like, “Invited to…” or “Recognized for…” or “Promoted to…”  or  “Known for…” And, certainly, showcase your key wins and accomplishments at every position, especially the ones that you think will be enticing to your future employers.

4. Remember Your Best Defense is a Good Offense

A good rule of thumb is that, if you’re worried how a certain position or experience is going to be perceived on your resume, there’s a good chance that someone is going to make the exact conclusion you don’t want them to make. That said, you should plan to go on the offense and manage the message.

For instance, say the moves you’ve made along the way make you look, at least on paper, like a bit of a job hopper. It’s best to add a quick statement in each section of your resume that briefly explains the jump. I often use phrases like, “Following a family relocation to Dallas…” (makes the job switch obvious) or “After a significant corporate restructure…” (makes it clear that your job was axed). If you’re simply pursing a new career path, you can state that in your cover letter, briefly describing your reasons for the change.

5. Don’t Over-Explain

I can spot someone who’s nervous about how her career path reads a mile away. Often, that’s because she’s talking quickly and nervously and way over explaining whatever it is she thinks reads like a liability. Do not do this. Think through how you’re going to present your choices and career path to a potential employer, present them briefly and confidently, and then refocus the discussion on your commitment to this role and what you can walk through that company’s doors and deliver.

On that note, there’s one final point, which is the same point I made to my client:

Go easy on yourself.

There are very few people out there who have a pristine, straight-line-toward-the-sky career chronology. You are competing with people who, in all likelihood, have at least one or two twists and turns on their own resumes. And they’re probably feeling a little vulnerable, much like you.

So rather than panicking or avoiding opportunities that seem amazing, use your energy to strategize and position yourself as your future employer’s solution.