The Power of an Intentional Career Pivot
- Jaime Diglio
- Jan 6
- 4 min read
At 28 years old, I walked away from a Marketing Manager role at Gartner to become a junior Business Development Representative.
On paper, it looked like a step backward—two levels down and a complete reset. My friends, peers, boss, and mentors all warned me about the risks of “starting over” at my age.
But internally, the decision felt clear.
I couldn’t fully articulate why at the time, but I knew it was the right next move. What I didn’t realize then was that this decision would become the foundation of everything I teach today about self-leadership, confidence, and the New ROI: Return on Interactions™.
This wasn’t the reckless move everyone expected.
It was an intentional career pivot for professional growth.
Why an Intentional Career Pivot Feels So Uncomfortable
Most professionals are taught that success should look linear.
More tenure leads to more responsibility. More responsibility leads to bigger titles. Bigger titles signal progress.
That narrative keeps ambitious professionals locked onto predetermined paths.
An intentional career pivot for professional growth disrupts identity, ego, and certainty all at once. You’re no longer protected by a title. You have to learn how to lead yourself without external validation.
Professionals I’ve coached who are considering a career change often sound like this:
“This won’t look good on my resume.” “People will think I’m failing.” “What if I regret this?”
This is what the WAR Room sounds like.
Self-doubt, uncertainty, and head trash take over your ability to think clearly, rationally, and creatively.
The Career Myth That Keeps High Performers Stuck
Ambitious, high-achieving professionals struggle most with career pivots—not because they lack ambition, but because they become addicted to progress that looks good to others.
This attachment to optics is how professionals end up successful on the outside and unfulfilled on the inside. I’ve lived that reality.
The fastest way forward isn’t always up.
Sometimes it’s inward.
Sometimes it’s becoming a beginner again.
Sometimes it’s choosing growth that doesn’t immediately make sense to others.
This is the shift from the WAR Room to the WIN Room.
The Psychological Cost of Playing it Safe
According to Gartner, over 70 percent of professionals feel disengaged at work, often due to lack of clarity and purpose.
Disengagement at this level is not a motivation problem.
It’s a self-leadership problem.
When people don’t feel ownership over their direction, disengagement becomes inevitable.
The fear of failure is temporary, but the regret of missed opportunities compounds.
Most professionals do not regret the pivots they’ve made; they regret the versions of themselves they never explored while playing it safe, even when they were disengaged.
How to Know If You Are Avoiding the Right Pivot
Conduct this quick self-leadership check and answer honestly:
Are you choosing security over alignment?
Are you more concerned with optics than impact?
Are you climbing a ladder you did not choose?
If you said yes, you are likely Working Against Results.
You are likely in the WAR Room.
Why This Matters More Than Ever
Career transitions are no longer optional. They are becoming a core leadership skill.
In the age of AI and automation, technical skills expire faster than ever. Titles change. Roles shift. Entire functions evolve.
The professionals who succeed are not the ones clinging to linear career paths. They are the ones who know how to intentionally reposition themselves as the game changes.
That is why career pivots today are less about what you know and more about how you communicate who you are.
Harvard Business Review consistently shows that leaders who communicate with clarity, confidence, and intention build more trust and engagement during periods of change. That matters most when you are stepping into a new role, resetting your career direction, or betting on yourself in unfamiliar territory.
This is where Return on Interactions™ becomes the real ROI of a career transition.
Every conversation you have during a pivot either reinforces confidence or feeds doubt.
Every interaction with a hiring manager, leader, client, or team either builds trust in your direction or creates friction.
When you lead a career pivot from the WIN Room, your presence carries the transition. When you lead from the WAR Room, your doubt speaks before you do.
That difference determines whether a career move accelerates your growth or keeps you stuck.
What Actually Makes a Career Pivot Work
An intentional career pivot for professional growth is not about leaving your job. It is about leaving autopilot, disengagement, and complacency.
It is about choosing clarity over comfort.
Presence over performance theater.
Self-leadership over external validation.
When you stand in who you are instead of who you think you should be, everything changes. Your confidence sharpens. Your communication lands. Your leadership becomes felt, not forced.
This is how you stop Working Against Results and start leading every interaction with intention.
The move you are avoiding because it does not look like progress to others is often the exact move that leads you into your WIN Room.
If you’re ready to make an intentional pivot with clarity and confidence, The WIN League is where high-achieving professionals learn how to lead themselves first so every interaction drives results.
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