5 Questions to Ask Yourself to Get Out of a Career Rut

Photo: Tachina Lee/Unsplash

I know what it’s like to be in career quicksand. I’ve pursued opportunities because they seemed shiny and new — or because they’d save me from having to subsist on a diet of ramen and oatmeal. But there came a point when I finally asked myself: Was I doing what I was meant to do? I’d spent many years in digital marketing, but I wasn’t sure I could see myself at 70, sporting my finest muumuu, cranking out yet another social media strategy for yet another company I wasn’t passionate about.

When it comes to reinventing our careers, rarely do we look at the whole of our lives to draw lines and make connections. We might look at the last three jobs on our résumé and figure, “Well, I guess this company/role/project is the next linear step.” Or we’ll make moves out of desperation — maybe we’re hoping to escape a nightmare boss, burnout, or unemployment. But by stepping back to consider all the decisions we’ve made and paths we’ve taken, we can see how we ended up where we are today — and where we should go next.

I am not a woman of faith, but the Franciscan friar Richard Rohr’s words have resonated for me in my own periods of career uncertainty: “[W]hat I always tell the folks is there’s no nonstop flight from order to reorder. You’ve got to go through the disorder.” For many people, this moment we’re in — the “great reset,” as one might call it — is a strangely great time to uncover your own pivot.

I believe in methodology and the power of process, so I applied the brand-building techniques I’ve used over two decades to create a map that can help reveal the work you’re meant to do. If you’re feeling lost, burned out, or stuck in a rut, ask yourself these five questions to open up new mental pathways and get your creative juices flowing.

1. How do you want to spend your time?

The author Zadie Smith once said, “Time is how you spend your love,” and I believe this to be true. Time is the single resource we can’t get back, so how, where, and with whom we spend it is integral to how we thrive in work and life.

Ask yourself how you’re spending your days: For a week, write in your journal what you do every day, when you do it, the time it takes you to do it, and how you feel while you’re doing it, for both work and life. What are your time sucks? Why are they occurring? What do you want to be doing more of but can’t seem to fit in your schedule?

Now reimagine the week and write out how you would spend your time in an ideal world. Get specific. Describe what you’d be wearing, who you’d be interacting with, and which physical spaces you’d be occupying (including post-Covid).

2. What do you want to be known for?

If you could be known for doing one thing, what would it be? For now, forget the practical. Focus on what lights you up. When I did this exercise, I decided I wanted to be known for telling stories.

Determine why you answered what you did. Before you say “Because I want to make money,” know that everyone wants to make money. Instead, ask yourself why you want money. What benefits and outcomes would money afford you? Do you want freedom in how you spend your days? The comfort of living without panicking over your bank account? Do you want to make an impact? (If you want to spend more time with this line of questioning, check out Simon Sinek’s excellent book Start With Why.)

3. What are your three C’s?

One approach I’ve used to build brands — and that can be repurposed to help anyone figure out their pivot — is called 3-C Self Discovery: Analyze your company (you), your customer (your boss or client), and your competition (your peers). This is more than pulling out your résumé and scanning the last few jobs you’ve held — rather, this is an examination of your career, the skills and expertise that brought you where you are now, and any unexplored terrain worth navigating.

I’m old school and did this exercise by hand, but you can mind-map or use spreadsheets to get the job done. The idea is to see everything in one place so you can form connections and spark ideas.

  • Company: List every job you’ve ever had. Yes, every job. For each role, ask yourself: What bolted you out of bed? What made you scream into pillows? What did you learn, and what did you leave wanting to learn? What were your biggest achievements and missed opportunities? How did each role make you feel when you left?
  • Customer: For each of those jobs, define the characteristics of the people that lit you up. Who were they? What did they do? What about them was memorable and inspired you to be better at what you do? Sketch out a profile embodying all the traits and characteristics you admire.
  • Competition: For each of those jobs, what was the one thing (major or minor) that differentiated you from other people who did what you did? Was it your process, how you connected with people, or a certain knowledge or edge they didn’t have? What are some of the adjectives used to describe you in performance reviews and during client work?

4. What patterns do you see?

Once you’ve stepped back and assessed your responses so far, you’ll see words and emotions that repeat. Circle and pull out the common elements. The objective here is to mine for gold amidst the rubble.

Often, your next step will reveal itself here. Is there a role you haven’t pursued? A set of skills you already have that can be applied to a missed opportunity? The objective is to pursue your curiosity, not your passion.

5. What’s your new ideal job description?

Create your own job description based on what you love, what you loathe, what you know, what sparks your curiosity, and the kind of people with whom you want to surround yourself. What ideas does this spark about talents left unexplored, or new ways of working you want to pursue?

Don’t worry if this role doesn’t exist in the way you’ve defined it — we live in an era where you can define and create a job where none exists. If you can’t find it, can you build it?

Before I did this exercise, I was a novelist who worked in marketing to pay the bills. My artist self was distinct from my business self, but these steps made me realize both can play in the sandbox. Now I’m confident that I’m doing what I’m meant to be doing: I’m a data-driven marketer who knows how to tell compelling stories for values-driven businesses that aim to be better corporate citizens and human beings.

Our journeys never follow a straight line. There’s no map to chart our progress, no compass to determine our direction. So, what if we created a map? Imagine that this is a journey from yourself back to yourself that you’re willing to take.

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