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7 Questions to Ask Yourself When You’re Facing a Tough Career Decision

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Crystal ball

Your 20s are an important time. We’re told the personal and professional choices you make during this decade set the foundation of your adult life.

No pressure, right?

A good problem you’re likely to face is which job to take: The one that promises security or the one that promises experience? The higher-paid one or the one with fast growth opportunity?

Or, your significant other wants to move across the country to pursue her dreams — do you quit your new job, pack up and follow her? Or do you follow your dreams, even when they’re hazy and sometimes change by the time you wake up?

These choices can’t be made with a simple pros and cons list. You can find yourself longing for a crystal ball that can make the decision for you.

A personal story about taking a big career risk

Staring down my late 20s, I had already faced a fair share of these complicated decisions. One of the most recent came three years after college graduation. I was 25, leading an internal sales consultancy at a publicly traded company. I was fairly happy, well-paid and had opportunities rare for someone my age. Even though I wasn’t looking for a new job, I received an offer to work for a small healthcare startup.

After endless conversations with peers and mentors, dozens of pro/con lists and multiple sleepless nights, I made the first instinct-driven decision of my career.

I’m still unable to provide a definitive reason why, but I vividly remember launching from bed at 1:47 a.m. knowing I had to take the new job offer. Despite the advice of friends and family, I accepted the position.

A year later, I still work for that startup. And I love it. We provide healthcare organizations with a predictive modeling platform by analyzing their data to help clinicians make the best decisions for their patients. Fundamentally, these models help assess and weigh risks.

Wouldn’t a predictive model like this be useful for those big decisions in our early careers?

Based on my daily work using data to determine risk, I’ve developed a list of seven questions that can provide you with the data you need to consider when faced with life-changing decisions:

1. Does it motivate you to learn something new?

We’ve long been instructed to specialize — college majors, career trajectories, company ladders, etc. But specializing early at the expense of cultivating experience and contextual knowledge can limit your potential and stunt your self-discovery.

A familiar, comfortable job in a young career can be insidious. If an option you’re weighing will challenge you to stretch your concept of career, your long-term professional benefit will likely outweigh the short-term risk.

2. Does it push you to learn something about yourself?

Relative to risk, there’s usually no better time for self-discovery through work than your 20s. When considering a new opportunity, give more weight to the exploration and development possibilities of the role, rather than the job title or immediate responsibilities. Your early career experiences should give you room to grow and try something new.

My intended path was within the entertainment industry. I may never have discovered my passion for healthcare, technology and analysis without an openness to explore it.

Remain open to opportunities outside your original vision of career. You may have a hidden talent or interest that’s waiting to be discovered.

3. Does it scare you, just a little?

We grow most from those moments and experiences that force us to stretch beyond our limits. (Click here to tweet this thought.) Be unapologetically ambitious, even when logic and security suggest an alternate route.

4. Does it scare your friends and family, just a little more?

Naturally, those who love you most want to protect you. Because of that instinct, they may steer you towards a safe choice to limit your risk of loss or failure. Although their intentions are pure, their influence can be stifling.

If your near-and-dear are directing you away from an opportunity, consider the loving biases that they carry. Many times, the best decisions for our personal and professional growth are difficult for others to understand.

5. Does it change the way you evaluate success?

If you only measure your success by 401k balances, promotions and bonuses, you’ve mistakenly focused your attention on byproducts instead of the personal and professional experience along the way.

Give yourself opportunities to find what’s meaningful to you, and give yourself room to grow your ideas of success.

6. Will it surround you with passionate people?

Passion is contagious and powerful. Surround yourself with energy and innovation, and you’ll adopt the same vigor.

That fervent energy transforms our world every day. If you’re deliberating what’s best for you, consider the people who will teach you when you get there.

7. Does it excite you to talk about it?

Notice if you can’t stop rambling to your friends and family about the opportunity in question. It means something! Enthusiasm and buy-in is critical in an opportunity’s potential success.

Tally the number of times the opportunity organically comes to mind. Pay attention to what you’re thinking. Is it the experience? Earnings potential? Outcomes? There’s no wrong answer, but understanding your own drivers and interests will give you insight into what’s most important about your potential next step.

With every decision, embrace the privilege that you can chart your own path. But also allow that path early in your career to help shape you, too.

Cash Forshee is a healthcare technology professional who serves as the Senior Vice President of Medalogix, a Nashville, Tenn., based startup that equips post acute health operators with custom predictive modeling platforms to enable optimal patient care decisions. A Belmont University graduate, Cash is a Better Health 4Kids board member and a 2014 “Nashville Emerging Leader.”

Brazen powers real-time, online events for leading organizations around the world. Our lifestyle and career blog, Brazen Life, offers fun and edgy ideas for ambitious professionals navigating the changing world of work.

  • myfeethurt

    I like #5. Does he tell execs that when they have their hand out looking for their annual bonuses? “Here you go, look at all the great experience you’ve received.”

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  • http://www.liveitforward.com/ Kent Julian

    Love all of these questions. Outstanding. Will be using these with my career coaching clients.

    #6 is HUGE! I think most people miss this in their filter. If everything else is great but your working with draining people, it’s going to end up being a bad fit.