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This is how your professional trajectory shaped your mid-career crisis.

“I was once afraid of people saying, ‘Who does she think she is?' Now I have the courage to stand and say, This is who I am.” — Oprah Winfrey

The first half of our careers is about mastery. The second is about impact and legacy. And what separates both sides is a turbulent sea.

It’s called Mid-career Crisis.

A mid-career crisis can feel like a daunting existential problem. But this state of confusion signals that we reached the point where our career direction is no longer aligned with the person we’ve become.

Today, I want to talk about how the last 20 years shaped the mid-career crisis you’re experiencing and what you can do to get to the other side.


Before we begin, I have two favors to ask.

  1. Help me grow our community. If you’ve been enjoying The Mid-Career Pivoter, please forward this post to other seasoned professionals in your network who can benefit from these perspectives.

  2. Help me help you! Please drop me a bit of feedback and recommendations to improve this newsletter. What’s resonating (or not).? What questions and topics you’d like me to address or expand upon in future editions?

Thank you!


And now, the meat!

What does your career trajectory add up to?

During the pandemic, I put my career on hold for almost two years to become a full-time dad. I was almost 48.

Once my girls returned to school, I started looking for jobs, but nothing seemed like a good fit.

The problem was that most of my experience was with brick-and-mortar strategies (food, hospitality, professional services, etc.). Despite my high-profile achievements, I always lost the last round to someone with deeper experience in digital.

I began questioning my career decisions. Maybe I should have stuck to one industry, or perhaps I should have ventured into the tech sector in my 30s. Maybe at my age, I should have specialized in something.

One day, I was chatting with two friends: one, a clinical researcher, and the other, a CPA. Both shared how much they longed to pursue different career paths. But after 20+ years, they were completely locked into their domain expertise.

I never paid much attention to this before, but something clicked:

Specialists lack options. Generalists lack definition.

Why is this important?

Because the shape of your career trajectory defines the kind of mid-career crisis you’re likely experiencing today.

Are you a book or a magazine?

BOOK--> a central defined story, clearly organized by chapters.

  • Trajectory = mainly linear or undulating (upwards slope).

  • Lens = depth of domain, technical problems, industry, or functional expertise.

  • Ambition = to be recognized as an authority in a domain, industry, or role.

Mid-career conundrum:

  1. Feel like you hit the ceiling.

  2. Feel bored, uninspired, and disenchanted.

  3. Feel trapped and type-casted in the same role or industry.

Existential dilemma:

"I’m ready for something different, but I’m only qualified for this."

👉 If this is you, here’s my diagnosis:

Unless you’re in a dying profession, chances are that you still love what you do. There’s a reason why you stayed in this field for so long, pursuing mastery.

Your career funk has more to do with monotony and something intolerable about your current work environment, such as a toxic culture, high pressure, or a bad boss. Essentially, the scope and stresses of your current role are disconnecting you from something you care deeply about.

🤓 And here’s the prescription:

Often, a bit of reframing, creativity, and renegotiation is all you need to regain your mojo.

  1. Clarify your values and core professional aspirations.

  2. Identify the disconnect and reset your boundaries (e.g., have a heart-to-heart with your boss — bring up solutions, not problems).

  3. Consider creative strategies to satisfy these values and aspirations.

    1. At work — participate in a new project, ask for a transfer, collaborate with a different team.

    2. Outside— take a course, volunteer, start a side hustle, cultivate a hobby.

MAGAZINE --> a point of view constructed from different angles, using vignettes and short articles.

  • Trajectory = zig-zag, lateral, squiggly line.

  • Lens = generalist, multi-disciplinary, ambiguous problems, big picture thinking, connecting dots and people.

  • Ambition = versatile and adaptable across fields, industries, or roles.

Mid-career conundrum:

  1. Feel like a round peg in a square hole: lost, restless, and uncertain.

  2. Overwhelmed: looking for a needle in a haystack for something that fits.

  3. Everything seems too narrow and specialized: your strengths and combined skills belong to multiple domains but can’t fit neatly into a traditional role.

Existential dilemma:

"Am I condemned to specialize and prove myself all over again?”

👉 If this is you, here’s my diagnosis:

There is always a need for people who can see the big picture, connect the dots, break silos and translate across specialists. You’re part of a hard-to-define, ever-evolving "connective tissue" of organizations.

You can’t find a standard title or job description for what you do. It’s because your role is context-dependent — often created to address a gap that recently became obvious to the organization. These roles are hard to find in the open market because they are opportunistic. You need to network your way into them.

🤓 And here’s the prescription:

You need to think like an explorer — not a job-seeker.

  1. Minimize time spent sifting through job postings.

  2. Tap into the invisible job market by seeking connections with interesting people doing exciting things.

  3. Learn about their pain points and unmet aspirations.

  4. Build a point of view around what great looks like drawing from your breadth of experiences.

  5. Craft your own job description and sell it back.

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