How to Find a Job When You Have an Unusual Background

When you are a square peg looking for a square hole, life is good. But when you don't fit neatly into a job search box, you might need to change the questions you ask. Get-It-Done Guy explains how.

Stever Robbins
5-minute read
Episode #350

Job hunting is a horrible, soul-sucking experience for everyone. But if you have even a slightly nontraditional career path, it's even worse. It's as bad as getting an Oreo Ice Cream cake for your birthday and having to offer everyone else a piece before you get your half.

The problem, of course, is industrialization. I just love living in an industrialized society! We're so efficient at everything, and it's all because of mass production. Henry Ford invented the assembly line and boom! Our products had consistently high quality because we made each one the same way. Then a marketing genius discovered that you get higher profits through "planned obsolescence," and now we make everything at consistently low quality, because we make each one the same way.

The only fly in the ointment is people. And people aren't even flies. Not only that, but those pesky people don't all behave the same. They blather on about "individual differences" and wanting to "bring their whole selves" to work.


Would you look at the statue of Michelangelo's David and think, "I wish Michelangelo had brought the whole block of marble to the showroom?" Nonsense. You want the version where they've chipped every single teeny, tiny bit of individuality, leaving only the exact product you want.

I recently toyed with re-entering the workforce, myself. I've alternated between entrepreneur, self-employed executive coach, senior management curriculum designer, consultant, and speaker for many, many years. We call that "focus." But despite looking like a manly-man version of Michelangelo's David, I didn't know where to start. I consulted Debra Feldman, the JobWhiz Executive Talent Agency about my quandary:

How do you approach a job search as a jack-of-many-trades in a world that's looking for single-focused specialists?;

Stop Being You

My concern was wanting to be me. "I'm an executive coach, entrepreneur, speaker, curriculum designer." Oddly, Monster.com turned up zero job listings looking for executive-coach-entrepreneur-speaker-curriculum-designers.

If you can't find answers, try changing your questions.

Many of us define ourselves: "I'm a web designer," "I'm the smart one," "I'm a good communicator," "I'm a merchandising procurement specialist." These are all stated as "I am ... something." That's an identity statement, a statement of self-image, of whom you believe yourself to be. As we covered in the episode about telling people they're wrong, we take our self-images very seriously. We cling to our self-image, even when it doesn't serve us.

Once we have a strong self-image, we interpret our skills, abilities, and work history through that lens. "I'm the smart one, so I need a job that requires smarts." That sounds great, but it filters out the many, many jobs that are fun, pay well, but only require average intelligence, if even that. When you're changing careers or have a checkered past—er, I mean, a broad variety of experience—then clinging too tightly to a particular identity won't serve you.

Debra suggests instead to think of yourself in terms of capabilities and characteristics. Not, "I'm the smart one," but "I can be a genius at doing X, Y, or Z." In my case, not, "I'm a smart executive coach," but "I can effectively bring out the best in a person or team, both professionally and personally." Phrased that way, it suddenly becomes obvious that possible careers include managing people, doing high-touch sales, or becoming the Kardashian's business manager. (Kris Jenner, if you're listening, give me a call.)

When talking to people at cocktail parties or networking events, a capabilities-based conversation can go much more interesting places than an identity-based conversation.


About the Author

Stever Robbins

Stever Robbins was the host of the podcast Get-it-Done Guy from 2007 to 2019. He is a graduate of W. Edward Deming’s Total Quality Management training program and a Certified Master Trainer Elite of NLP. He holds an MBA from the Harvard Business School and a BS in Computer Sciences from MIT.