Skip to main content

How to get started:

Feel like you’re at a crossroads? Ellevate 101 introduces you to the community that can give you a career kickstart.

We’ll walk you through some light intros and give you space to connect about shared career experiences. You’ll also learn how to use your Ellevate program to continuously make moves towards success at work.

Our next live welcome session is .

Register here for your chance to get started

4 women lined up supporting each other

Struggling With a Career Change? Try Looking at it Like Dating

Struggling With a Career Change? Try Looking at it Like Dating

I have a friend who started law school in her late thirties. There were plenty of reasons for her not to change careers at that point in her life. She had a good job with a major, blue-chip consulting firm. She was making a decent salary and had a lot of flexibility, often working from home. She was also pregnant with her third child. And yet, she'd always wanted to be a lawyer.

One day, I asked her how things were going. "It's fantastic," she replied. "It's like finally dating the guy I had my eye on my entire life."

Wow, I thought at the time. She's really made the right choice for herself.

Fast-forward fifteen years. I, too, am in the midst of a career change. It's not my first time changing careers, but my friend's comments about law school all those years ago seem all the more prescient this time around.

Here are five reasons changing careers can feel like dating.

[Related: Ten Fears Keeping You From Achieving The Career Of Your Dreams]

1) It takes a while to sift through the options.

I stopped dating before online dating became a "thing." But even before it was as simple as swiping left, dating had always been infused with the idea that you should just keep putting yourself out there and wait for your pitch. It can take a while.

In a similar vein, career changes don't happen overnight. Shawn Askinosie, author of Meaningful Work: A Quest to Do Great Work, Find Your Calling, and Feed Your Soul, notes that it took him five years to bring about his transition from criminal defense lawyer to chocolatier. So don't rush it.

Once you’ve narrowed down your possible career options, make sure you "try on" different options - possibly through job shadowing - to make sure they work for you. As with dating, you may need to go out with a few duds before you find Mr. or Ms. Right.

2) Beware of big egos. Including your own.

One of my worst-ever dates occurred when I was 23 years old. I'd just moved to Washington, DC, and was looking for a policy job. My father, trying to be helpful, asked a friend of his with powerful connections to set up a few informational interviews for me around town. One guy I met with couldn't really help me find a job, but he did invite me out to dinner.

We spent two hours doing nothing but talking about him: How he'd been voted one of the "50 Most Influential People Under 50" in D.C. How often he worked out at the gym. I gobbled down my pad thai and ran for cover at the earliest opportunity. But I learned something on that date that has stood good stead through several career shifts: Don't ever let someone's ego - including your own - drive you in life.

If you're going after something because of the title, the brand name, or the corner office, you're probably not going to be too happy. It's okay to make a few mistakes. Useful, even. That's how you learn (for example, I never again went on a date with someone I'd interviewed with). But if you're making a career change, try to listen to yourself and get rid of the "should"s. The "should"s are often pointing you toward legitimacy, not authenticity.

3) Trust your gut.

"Stick a fork in me. I'm done."

A friend of mine uttered these words at his wedding, in a speech explaining how he'd met his bride. He'd played the field as a young man, and well into his late thirties. But when he met his (now) wife - whom he'd actually known most of his life - he realized that he'd found the right person to marry and settle down with.

I've never really believed in the notion of "the one," whether in jobs or relationships. But I do believe that in both spheres, your gut will often tell you when you're onto a winner. In my case, I'm currently launching my own communication consultancy. When I left my job a year ago, I had no inkling that I'd soon be running my own business. That wasn't my ambition at all. But as I thought carefully about my skills and interests, I realized that this particular career move made perfect sense.

"You didn't find your job, it found you," as a friend of mine put it. She was exactly right.

[Related: Your Values Can Help You Find the Job of Your Dreams]

4) Something old.

Okay, so I've skipped ahead from dating to marriage. Shame on me. But I'm really drawn to that erstwhile wedding rhyme, "Something old, something new; something borrowed, something blue."

Face it: When dating, we all have particular types we gravitate toward. It might be athletes. Or redheads. Or artists. And even if it's only a glimmer of that quality, we tend to look for it when we're on the market for a partner. In a similar vein, most people tend to bring something of their old work selves with them when they change careers.

It might be a skill set, like editing or line managing. It might be a body of knowledge, such as accounting or environmental science. This is a good thing. It's hard to get a new job doing something wildly different than what you did before. Most career gurus advise against radical shifts, at least at first. So having a "type" - a part of you that you like and want to re-fashion - is advantageous.

5) Something new.

Even if you have a dominant dating type, it's often refreshing to switch things up and go out with someone completely different. So, too, with career changes. Be considerate in your choice, but once you know what you want, be bold. If there's something calling your name about working outdoors - even if you've spent twenty years at a desk - go for it!

I can't tell you how many friends I have - including myself - who've wanted to try something really different career-wise, but ended up going for the safer option. And ended up disappointed. That doesn't mean it's always the right time to take risks. But having that spark, that newness, is what will keep you motivated to "keep on, keeping on" in your new professional journey.

[Related: How to Find Your Calling When You Don’t Know What You Want]


Delia Lloyd is an American writer and communication consultant based in London. Her writing has appeared in The New York Times, The Financial Times, The Washington Post, and on the BBC World Service. She blogs about the journey of adulthood at RealDelia. Follow her on Twitter @RealDelia.

Have more questions? Follow up with the expert herself.