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Feeling Stuck In Your Career? Ask Yourself These 4 Questions To Discover Where To Move Next


Our careers are very rarely linear.

With corporate jobs, laid out neatly in org charts that show layers of management and increasingly ‘senior’ titles, it may seem as though your path forward should be a straight line up the ladder. But after spending 20+ years working for companies big and small, as well as helping hundreds of team members over the years advance their own careers, I have learned the next-best step forward isn’t always straight ahead. Sometimes, what seems like a step backward, or a move sideways, is actually an exciting opportunity to leapfrog where you were before.

In fact, I have seen people become more successful when they stop focusing on linearity and start pursuing opportunities they’re passionate about and are right in front of them. That’s when you end up operating at your best, doing your best work, and having the best results.

How do you pinpoint what those opportunities are?

Or more importantly, how do overcome the feeling of being stuck in the first place?

Here are 4 questions that have always helped me decide where to move next in my own career:

1. “Is it starting over, or is it starting something new?”

One of the biggest challenges for people to overcome when making a transition in their career is beating the feeling of “starting over.”

This one is surprisingly simple. Think of your journey as carrying “momentum” in the form of skills, both hard and soft. Yes, you may be changing direction but you’re not starting from zero. You’re doing it with skills that will carry you into your new role. For example, I’m now on Career 4.0—I started as a coder, moved into sales, followed by business development, and am now marketing. With each change I had to learn an entirely new skill set, but it was built on the skills I already had. Coding taught me creative problem solving, sales taught me the art of persuasion, business development gave me a long-term growth mindset—all of which have made me a successful marketer.  

On the surface, these jobs did not follow a linear path forward. And yet, I found ways to use the things I had learned from the previous role to give me a unique perspective on the opportunity to come.

2. “What do I enjoy? And what don’t I enjoy?”

In any career, you build skills as you move from job to job. The further you progress in your field, the easier it becomes to fall into the trap of “I’m good at this, so I’ll keep doing it to earn my next opportunity, even if I don’t love it.”

This is actually your moment to seize control of your career and make a decision around which skills you enjoy and want to keep in your toolkit, and which skills you don’t enjoy and want to start moving away from. For example, I know many people who have been promoted into management because they were great individual contributors. They have continued as people managers because they feel that this is the only path to income growth, despite the fact that they don’t really enjoy management. They obviously didn’t know that before they became a manager, and now feel trapped between the perception that career growth has to be linear and their less-than-ideal experience as a manager.

If you let go of the idea that your career needs to be a linear climb up the org chart and start thinking about optimizing it around the skills you love using, you’ll be surprised at how fast growth will happen.  

3. “Can I be passionate about this opportunity?”

A lot of my career has felt like it’s the result of being at the right place at the right time, but when I look back, it actually wasn’t. I took every good opportunity that was presented to me and made it great. 

“Follow your passion” is popular career advice, but I think that’s only the first step. The second step is to find ways to let your passion shine through in whatever it is you’re doing right now—so that you can continue “following your passion” all throughout your career. And the reason I say that is because what you are passionate about will change over time. 

Instead of thinking about “doing what you love” as a destination, I encourage you to think of it as a way of approaching everything you do. That way, you’ll stop searching for the perfect opportunity and see opportunities in every situation.

4. “Am I running away from something or am I running toward something?”

This is the most important question you can ask yourself, and the one I always encourage people to ask when they come to me with mentorship questions about their careers.

We’ve all found ourselves in a situation that feels unbearable. A micromanager for a boss, work that’s dull and unfulfilling, or any of a million other reasons to not want to go to work in the morning. So, when a new opportunity comes along you might be tempted to say, “anything’s better than this!” But that’s when you have to be honest about the answer to this critical question.  

Are you running away from a problem? Or are you truly moving yourself in the direction of something you want?

Optimizing for the lesser of two evils is rarely the best path forward. In fact, it’s often the recipe for finding yourself right back in the same situation once the honeymoon period ends.

Other questions I believe are helpful to ask:

  • “What new skills would I like to learn, and what opportunities would allow me to learn those skills?”
  • “Where will I be able to use my passion?”
  • “Am I making this decision out of a desire to just make more money? Or is there something more here to fulfill me?”
  • “Is there a way for me to test whether or not I would enjoy this new career path I am exploring before committing myself to it?”

In conclusion, I hope you realize that you’re not alone. We all go through periods of uncertainty in our careers. One minute, we think we have it all figured out, and the next, we are moving in a completely different direction—sometimes by choice, other times by circumstance. What’s most important is that you remember you are never really “starting from scratch.”

The most valuable skills are universal.

I am a marketing executive with a technical background and broad experience in corporate marketing, product marketing, business development and pre-sales. I currently lead Brand, Media and Advertising for SAP.

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