Illustration: Oscar Ramos Orozco

Turn Your Wandering Career Path Into a Secret Weapon

For those of us who’ve experienced the adventurous-yet-agonizing wanderlust of a post-college career journey – six months here, nine months there, never settling for long – there is nothing more fearsome than being interviewed and hearing the hiring manager ask this question:

So… You have quite the background! Youve done so many things. Tell me about that… 

Translation:

Yikes, youre all over the place. These are cool experiences but… too many things. This is not giving me confidence in your stability.

You understand their concern – you’ve bounced around before, and you’re likely to keep doing so. So why should they hire you?

In the year after I graduated from college, I worked for eleven different companies – some simultaneously, some on projects, some full time. I did everything from ecotourism and outdoor education to business plan writing and information design consulting, including some pretty unglamorous things in between (installing energy-efficient home insulation and building rain barrels). During that saga, I got asked the “What’s the deal with your bouncing around?” question a lot. So much so that I decided to make my answer to that question my primary strength – my secret weapon.

Don’t be fooled, it may feel like there’s no winning response, but that isn’t the case. Don’t miss the opportunity to turn this knuckleball into a homerun.

Follow these steps, and you’ll make them glad they asked:

1. Don’t shy away from your past. Embrace it.

You walked your path for a reason. Even if you were anxious and lost or undirected for much of it, you don’t need to talk about it that way. Think back on it as a grand adventure, full of twists and turns and intrigue – the stuff of legends! Talk about it with pride, with confidence, with a slight smile. 

“Yeah, those were the good old days! Some of my fondest memories, for sure.”

2. Find the common threads, and use them to tell a good story.

No matter how random or varied your experiences, there is always a common thread. An interest you have, or an experience you were seeking, or a skill you were trying to develop. So think hard, and find that thread. Use it to tell a story that says something about you as a person – something more compelling than just having “put your time in” at one job for several years.

“Absolutely. Well, I think the best way to describe that time was that I was searching for the best way to develop my creative side in a way that made sense, in a way that actually benefited people and I could feel the impact. It definitely took some time to find that.”

3. Sell your versatility.

That background is your proof that you can handle uncertainty and come out better for it. They don’t have to take it on a leap of faith that you can dive into new things and get your bearings quickly – the proof is right there. In a world where every company and organization is moving quickly in a changing landscape, and every hiring manager needs you to onboard quickly and as painlessly as possible, these are great traits to have. Use that as a source of confidence for yourself.

“I’m sure I can come up to speed on this quickly. The situation seems similar to when I did XYZ – and that project went well in terms of bla bla bla. I’m also reminded of my time at ABC where the main challenge we faced was [insert here] – just like this role/project.”

4. Explain why they are the exception to the rule.

Especially if you’re using the narrative that you were searching for something, that’s a perfect lead-in to telling them why they are the company who can tame your wild heart once and for all. Do your homework, and be able to describe to them in detail why you think they’ve got what you’ve been searching for. The more specific, sensible, and heartfelt you can be, the better.

“I’m glad you asked. I think why I’m so excited about [their company here] is because I can tell that you guys have the mix of X and Y that I’ve been looking for, and in a setting where I don’t have to settle with regards to Z. To me, that’s the holy grail. It’s literally my dream job.”

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If you play these cards, you should be in good shape. And relax, everyone’s career path is winding and jumbled these days – so it’s much less of a liability than you think. Just make sure you know how to defend it correctly.

How about you?

Do you have a wandering career path? How have you handled it?

More insights on: Self-Marketing

Nathaniel Koloc

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Nathaniel is the co-founder of ReWork where his team is determined to change the world by helping people find work that they love.
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