Tag Archives: how career change is like dating

Tips for Adulthood: How Career Change Is Like Dating

LoveI have a friend who started law school in her late 30s. There were plenty of reasons for her not to change careers at this 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.

“How’s it going?” I asked her casually one day.

“It’s fantastic,” she told me. “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 or so and 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:

a. It takes a while to sift through the options. I stopped dating before online dating became a “thang.” But even before it was all as simple as “Swipe Left, dating has always been infused with the idea that  just keep putting yourself out there and – to deploy a baseball metaphor- “wait for your pitch.” It can take a while. In a similar vein, career change doesn’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./Ms. Right.

b. Beware of big egos. Including your own. One of the worst dates I ever went on occurred when I was about 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 me in 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 or the brand name or the corner office, you’re probably not going to be too happy. It’s OK to make a few mistakes. Useful, even. That’s how you learn. (I never went out on a date with someone I’d interviewed with again.) But particularly if you’re making a career change, try to listen to yourself and get rid of the “shoulds.” The shoulds are often pointing you towards legitimacy, not authenticity.

c. 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 met his bride. Per (a) above, he’d played the field as a young man. Indeed, well into his late 30’s. 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 this 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 on to a winner. In my own case, I’m currently launching my own communication consultancy. When I left my job a year ago, I had no inkling that I’d be running my own business within a year. Indeed, that wasn’t my ambition at all. But as I thought carefully over the past year 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.

d. Something old. OK, 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 towards. It might be athetes. 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: Editing. Line managing. Or it might be a body of knowledge: Accounting. Environmental science. And that’s a good thing. It’s really hard to get a new job doing something wildly different than what you did before. Most career gurus advise against a radical shift, at least at first. So having a “type” – a part of you that you like and want to re-fashion – is advantageous.

e. Something new. Back to our wedding rhyme. (Well, you knew that was coming, didn’t you?) Even if you have a dominant dating type, it’s often refreshing to switch things up and go out with someone completely different. Trade in the cardigan-wearing preppy cheerleader with hoop earrings for the mysterious girl in the corner smoking clove cigarettes and smelling of Patchouli oil. So, too, with career change. Be considered in your choice, but once you know what you want, be bold. If there’s something calling your name about working in the 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” with your new professional journey.

Image: Love Couple Happy by Skimpton007 via Pixabay

Note: This article was originally posted on The Ellevate Medium page

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