Nail your next career move by asking yourself this one question

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Adam Levine is an American singer, songwriter, and the frontman of the pop rock band, Maroon 5. He’s received three Grammy Awards, two Billboard Music Awards, two American Music Awards, an MTV Video Music Award and a World Music Award. He has his own menswear collection, record label, fragrance line and, oh ya, my wife has a total crush on him! “Sure…but can he nail next quarter’s sales forecast with 5% variance?!?” I often remind the mother of my three beautiful children. Yet, despite how close entrepreneurial sales leader and award-winning rock star are on the coolness spectrum, my attempts to equate us often fall flat.

That’s ok though. There’s a high probability that Adam Levine isn’t a credible threat to my marriage. He’s a cheat list guy. You know. Someone who, if your partner had a chance to spend one night with, you’d be cool with…at least in principle. The funny thing is, I’ve found the cheat list metaphor to be one of the most helpful when it comes to career planning.

The challenge when it comes to architecting your ideal career is two-fold:

  1. Great careers aren’t designed, they unfold: my long-time friend, colleague, and doppelgänger Daniel Debow said it best in a recent post about, what he calls, the career stumble. Keeping your eyes open, working hard, and leaping to opportunities that excite you is a truer North star than a preordained master plan that leaves no room for improvisation.
  1. What we think we want isn’t what we actually want: as I mentioned in a recent post on my favorite sales reads, one of the key lessons of the book Essentialism: The Disciplined Pursuit of Less, is that our vision for the future is often shaped by the forces around us rather than our true desires. I see this all the time in talented Sales professionals earlier on in their career. The desire to get promoted, make more money, and seller to larger, more complex customer is fuelled by seeing their colleagues seemingly strive for the same goal. Secretly, however, many yearn for a different path.

To cut through the noise I propose asking yourself this simple yet powerful focusing question centered around the cheat list principle:

“What job could you be offered today such that you would immediately and without hesitation, quit your current job to pursue?”

In other words, what job would be on your cheat list?

Many of us typically contemplate our next move with due care and consideration. We weigh pros and cons and solicit the input of our friends and trusted advisors. However, in a sea of perspectives, data points, and opinions, the simplicity of the career cheat question can very quickly help you zero in on the few key elements that matter most.

As you ask yourself that question, here are a few things to keep in mind:

  1. It doesn’t have to be a job that exists today: growing up, my father would always tell me that the job I’d likely do in the future, hadn’t been created yet. He was right. Social media, cryptocurrencies, SaaS software, and even blogging are all fields of opportunity created by relatively recent innovations.  Don’t get too hung up on specific job titles you’ve seen in the market or in your own company. Like the ideal partner, sometimes times the perfect job is the one you create in your head first. If you had to architect the ideal job for you, what would it look like?
  1. Think characteristics, not role: roles and titles can be misleading. In fact, the nature of the same job at two different companies can vary greatly depending on factors such as working environment, culture, or degree of autonomy. Because the characteristics of the job are often more important than the job itself, start there. Do you want to work for a big company or a small one? Do you want the flexibility to work from home or remotely? Would you prefer to have the company provide you with a tried and tested playbook to execute in your role or are you more interested in creating that playbook?  Are you looking for a role that’s high risk-high reward or something less intense? Don’t get fixated on a specific role. The characteristics are just as important.
  1. Keep moving incrementally closer to your goal: Love to speak in public, lead a team, or travel the world? Hate having to complete weekly summary reports, craft performance reviews, or be away from your family every week? Don’t worry about nailing the perfect role with your next move (although that would be awesome!). Instead, focus on incorporating more of your ideal job characteristics into each successive role. More of the things you want. Less of what you don’t.

Planning your next career move can be tough and it’s easy to get caught up in your head contemplating different options and opinions. When it doubt, picturing the role you’d give it all up for without hesitation (at least for one night) can put you on a quicker path to personal and professional fulfillment. Now if you’ll excuse me, my wife is watching season 10 of the voice and I have a fake power outage to orchestrate.

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