This week I want to share four common traps that mid-careerists fall into when exploring what to do next. Knowing how to spot and reframe them will give you a formula for overcoming inertia and moving out of the career funk quickly and decisively.
I’ve fallen into these traps more than once in my career, but after nine pivots, I learned how to get around them.
Getting hung up on a title and pay grade
The “Either/Or” mindset
Searching online for the perfect job.
Overthinking before doing.
Let’s dive in!
Trap #1: Getting hung up on a title and pay grade.
“I want to do something entirely new (but it has to be a director or above, and at least $xxx.).”
We are wired to think that upward is the only acceptable (and respectable) way forward.
If you grew up in the ’70s, 80’s, and early 90s, your parent’s success formula shaped your beliefs and career expectations:
Good college → Good Job → [loyalty + hard work = promotion] * 5 to 7 cycles.
But a lot has changed in the last two decades. Today’s career paths follow a squiggly line. Framing your expectations around a linear progression will blind you from more creative options to find fulfillment.
What do you want more of in your life? What do you want to experience and learn in your next job? What is it about those things that matter to you?
These questions shift the focus from the job and its perks to the outcomes you are after: e.g., “spend more time mentoring people… have more autonomy … deeper connections with field operations… work with scientists….”
One of my clients, a B2B marketing executive, came to me feeling burned out by work. After two weeks of intense self-reflection exercises, she realized that making a difference in her community was one of her highest values. The daily grind at work consumed most of her mental energy and blocked her view of what truly mattered.
She carved out time to volunteer outside of work. This renewed her sense of purpose. She no longer depended on her job as a primary source of fulfillment. Liberating!
Setting your expectations around salary, title, etc., will keep your wheels spinning. On the other hand, shifting the focus to experiential outcomes can open your mind to exciting possibilities you haven’t considered.
Trap #2: Thinking “Either/Or.”
“Should I stay, or should I go?”
Dilemmas keep you stuck in a circular pattern. They are often an illusion.
A dilemma is when you can’t find a tie-breaker between two competing choices. For example, if you choose entrepreneurship, you give up stability, and if you decide on employment, you give up possibility.
With some creativity, you can stop telling yourself that you have an existential crisis.
Expand your options: think “Either/And”
Back to the entrepreneur vs. employee decision, why not get the best of both worlds? You could launch a side hustle. You could become an independent consultant to your employer. You could operate on a retainer basis. And why not combine all of the above?
A dilemma is a problem in need of imagination. Don’t limit yourself to two options.
Trap #3: Searching online for the perfect job.
“I’ll know what I want when I see it”
Online job boards are a powerful tool — only if you know what you are looking for.
It’s easy to assume that having access to millions of jobs you can filter by title, salary, geography, and industry will improve your odds of finding your best fit. This may be true if you are considering roles that are well-understood and narrowly defined (CPA, Attorney, UX Researcher, Project Manager, etc.). But when you’re trying to explore new uses for your skills, you’ll be like looking for a needle in a haystack.
Reframe: Connect with interesting people to widen your perspective.
Find someone working on something that intrigues you (e.g., a technology, role, industry, or market).
Ask what drove them to pursue their field, what a day/week in their life looks like, what kinds of projects they work on, and what the best and worst parts of the job are. Do you feel a buzz of excitement? That’s your first clue.
If your direction is unclear, you’ll get 10x more out of a one-hour conversation than a day sifting through hundreds of jobs online.
Trap #4: Overthinking before doing.
"Let me do some more research... "
At work, nothing ever gets approved without a bulletproof plan.
We are trained to research, weigh options, consider risks, calculate benefits, and predict scenarios. Once cleared, we launch and hope it all goes according to plan.
This mindset is why many intelligent, skilled professionals with advanced degrees agonize over their options. Finding a career direction is part logic, part intuition. Just like dating, you choose because it just feels right.
Reframe: Take a small step. See what happens. Then decide.
Start with a hunch and dip your toes: enroll in a course, interview someone, try it out, or prototype it. Then pay attention to signals: do you feel a buzz? Did it yield a small win? Did it open a new door? Follow the breadcrumbs.
This is the difference between startups and corporations. Startups start with a hypothesis, build a minimum viable product, test it in the market and tweak it until it’s a viable business. Only then do they get funding. This method is called LEAN.
Corporations do precisely the opposite. They throw money at a problem and hire consultants to give them a bulletproof plan. Then, they launch a polished product and hire more consultants to figure out why it went wrong.
Take your best hunch and make one small move to test it: an email, a phone call, a post, anything. You'll be surprised by what happens next.
Common traps to Avoid.
Getting hung up on a title and pay grade. Reframe to: What do you want more of in your life? What do you want to experience and learn in your next job?
The “Either/Or” mindset. Reframe: Think “Either/And” to expand your options
Searching online for the perfect job. Reframe: Connect with interesting people to widen your perspective.
Overthinking before doing. Reframe: Take a small step. See what happens. Then decide.
Thanks for reading.
See you next Saturday!