Career Crossroads Are Inevitable — How You Navigate Them Changes Everything

There’s a moment in many successful professionals’ lives that feels deeply unsettling — and completely unexpected.

You followed all the steps that parents, teachers and professors encouraged you to do.

You chose a solid field.
You trained hard, performed well.

You delayed gratification in order to get a good job and show up with full effort.
You earned recognition.
You moved up.

And yet, around 7-10 years into your career, you find yourself thinking:

I’m not sure I’m in the right place. Why am I this tired? Why am I this dissatisfied? Why does this feel so far from what I signed up for?

If this is you, it’s ok! You’re going to think I’m weird for saying this, but… You are exactly where you are meant to be. This stage of life is a feature, not a bug.

You are standing at a completely normal — and rarely discussed — career crossroads.

It’s common to arrive at this point. But most people just put their heads down, barrel through, and continue living a life of underappreciated overwhelm and burnout.  

But there’s a different choice. The road less travelled: Navigating this rite of passage in a conscious, strategic, and powerful way.

The Pattern I See Again and Again in Coaching

In my coaching work, I regularly meet high-performing professionals who are surprised to find themselves burned out and disillusioned — even though they are technically on the path they intended.

Many tell me some version of this:

“I worked hard to get here. This was the plan. So why does it feel so wrong?”

The first 7–10 years of their career were energizing. They were individual contributors doing meaningful, hands-on work. They had strong colleagues, collaborative teams, and a clear sense of contribution. They were learning, building, producing, solving.

They felt useful and fulfilled.

Then — because they were excellent — they were promoted.

And that’s where the friction begins.

The Promotion That Changes Everything

The move into emerging leadership or middle management is one of the most underestimated psychological shifts in a career.

On paper, it’s a reward.
In reality, it’s a role transformation.

And often, it feels like it is bringing you farther away from who you thought you really were.

Suddenly, the work changes:

• Less hands-on contribution
• More coordination and oversight
• More meetings than making
• More decks than doing
• More performance processes than product impact
• Calibration seasons and performance reviews – need I say more?

Many newly promoted managers feel pulled in two opposing directions.

Pull #1 — Toward The Team
You feel responsible for the well-being and performance of your team members. Your team is awesome, after all, and usually understaffed and under resourced. Isn’t it the dream of every IC to say, When I’M a manager one day, I’ll make sure we hire more, remove more roadblocks! But when in the manager’s seat, you realize that it’s a lot more complicated.  You want to support your team, unblock them, advocate for them. But you no longer get to “be in the weeds” doing the technical or creative work you once loved. And your higher leadership seems to have other priorities.

Pull #2 — Toward Senior Leadership
You are now expected to speak a new language — strategy decks, vision statements, calibration meetings, KPIs, goal frameworks, performance cycles. Much of it can feel abstract, political, or disconnected from the real work that once motivated you.

The result?

Long weeks. Constant availability. Fragmented attention. Endless meetings, where you’re expected to do the “real” work on your kitchen table at 11pm.
And a creeping sense of disconnection from meaning.

“I’m Working More — and Getting Recognized Less”

Another painful theme shows up frequently at this stage.

High performers often expect that working harder will naturally lead to greater recognition and advancement. That’s the strategy that worked as an IC. But middle management introduces a new reality: visibility and impact are no longer driven by output alone.

Many professionals start noticing things that trouble them:

• Colleagues they perceive as less skilled advancing faster
• Others delegating more and self-promoting more… and getting rewarded
• Political awareness outperforming raw competence
• Strategic visibility beating technical excellence

And what the heck does “Be Strategic” even mean!? I’m a subject matter expert – I don’t know how to “be strategic”!

This can feel disorienting and unfair.

You think:
If I’m doing more than ever, why am I being seen less?

Without guidance, this realization can lead to resentment, self-doubt, and disengagement.

The Career Myth We Were Taught

Most of us were given a simple career narrative:

Train → Get hired → Perform → Get promoted → Lead → Retire fulfilled

Simple, right?

But real careers don’t follow this linear path. And certainly not anymore. The workforce has changed, and corporations have changed. There’s no slack in the system, and everything is running on extremely thin margins. There are “workforce reductions” rather than more hands on deck.

So at this time when you feel a professional crisis of identity, it’s a time when identity, motivation, strengths, and value are calling to be re-examined.

I’m a physician. I examine babies at key times during their first few years of life, to ensure that they are growing and developing on track. Accordingly, this professional fork in the road is a developmental milestone. A time to check in with where you’re going.

This is not failure.

This is maturation.

But because no one names it (who would put “I’m in my Professional Crisis Era” on their LinkedIn??), people assume something has gone wrong — instead of recognizing that something important is trying to evolve.

The Hidden Fork in the Road

At this crossroads, several real questions emerge:

• Do I actually want to be a manager or leader?
• If I continue to lead, how do I Work Smart Not Hard? What does that even mean?
• Do I want to return to deep individual contribution?
• Do I want a different environment or industry?
• Do I need to change how I work rather than what I do?
• Do I want impact, autonomy, income, flexibility — or something else?
• What kind of success actually fits me now?

This fork in the road is normal.

What’s not normal is navigating it consciously.

Most people drift through it reactively:

• staying too long
• burning out
• numbing out
• job-hopping without clarity
• chasing titles without alignment
• or quietly disengaging

There is another way.

The Extraordinary Path: Conscious Navigation

A small percentage of professionals treat this career crossroads as a strategic turning point instead of a personal crisis.

They slow down enough to reflect.
They get objective support.
They examine their strengths and drivers.
They learn the hidden rules of advancement.
They make deliberate choices.

This is where coaching becomes a force multiplier.

Not because coaching gives you answers — but because it helps you ask better questions, see blind spots, and make aligned decisions from a position of agency rather than exhaustion.

What Powerful Navigation Can Look Like

When professionals work through this stage with coaching support, the outcomes often surprise them.

Some discover they don’t actually want the management track — and they design a high-impact expert or specialist path instead.

Some choose to shift industries or roles entirely — with clarity and confidence rather than panic.

Some create a financial roadmap and business plan and realize they have enough to step out to consult, freelance or start their own business.

Some stay in leadership — but learn how to:

• work smart instead of endlessly hard
• focus on high-visibility impact activities
• communicate value upward
• delegate effectively
• protect energy and boundaries

Some rebuild confidence that was quietly eroded by years of overextension and under-recognition.

Nearly all regain a sense of direction and ownership.

If You Feel Stuck, Let’s Get You Back on Your Right Track

If you are feeling:

• burned out and exhausted
• underappreciated
• misaligned
• demotivated, procrastinating and scrolling
• unsure of your next move

Relax. I know, it seems impossible right now but… take a big breath deep into your belly, drop your shoulders, let out a big sigh and… Ahhhh.

Just know this: You are right on schedule for a meaningful career inflection point.

The key difference is, While most people hit this wall unconsciously, YOU can meet it deliberately.

Photo by Oliver Roos on Unsplash