Carolyn Regan Coaching
the Vital Shift
You've built success. Now shift to work and life aligned.
I partner with high-achieving leaders to
redesign how they work and live.
So completely aligned with their values that they wake up excited.
We move from measuring external success to authentic ambition.
From thinking about change to actually living it.
Not just a mindset change. A work + life redesign.
The leaders I work with...
Have built impressive careers and external success.
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You've done the hard work:
climbed the ladder, mastered the game, proved yourself by every external measure.
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Now comes the real work: designing your work and life around what's actually possible instead of the beliefs you inherited.
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Here's what we know:
When you choose to challenge what you think is possible,
when you choose to think differently about what success actually means for you,
you transform in ways you can't yet imagine.
Your decisions shift. Your leadership shifts. How you show up in the world shifts.
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You wake up excited. You make decisions from alignment instead of obligation. Your calendar reflects your values, not inherited expectations.
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You lead without performing. You have agency instead of autopilot. And you lead with strength—in a way people will remember.
It all starts with choosing.
Services
Depending on where you are and what's calling you,
I work in three primary ways:
One-on-One Coaching
Focused coaching for high-achieving people ready to move from autopilot to aliveness. Whether you're refining what's working, stepping into bigger leadership, or redesigning your life entirely—you'll bring clarity, intention, and alignment to your next chapter.
This is where the transformation happens.
Leadership Advisory & Fractional Support
Strategic partnership for leaders navigating growth or change. Working as your trusted partner within your organization, I strengthen your leadership presence, your team dynamics, and your people strategy through advisory coaching or fractional Chief People Officer support.
Gathering Facilitation
Intentional gatherings that create space for growth, connection, and forward movement. Whether it's a leadership retreat, a team offsite, or a strategic gathering for your organization—I help leaders and teams come together with purpose, deepen trust, and turn insight into meaningful action.
About Carolyn
For over 20 years, I led people and culture inside organizations—as a Chief People Officer, organizational development consultant, and executive.
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I was in the rooms where decisions got made. I felt the pressure from boards, bosses, and stakeholders. I built the systems that high-achievers climb within.
And at some point, everything felt misaligned. I was succeeding by every external measure while drifting from what made me feel alive.
That insight led me to step away and redesign how I wanted to work and live. I relocated, reclaimed my aliveness, and began coaching other accomplished professionals through the same transition.
Today, I partner with high-achieving leaders who are ready to choose differently. Because I've been inside, I understand what's real and what's inherited expectation.
Together, we design your next chapter: whether that's refining what's working, stepping into bigger leadership, or completely reimagining what comes next.
You're choosing from clarity, not from obligation.
Ready to choose how you work and live?
Ready to choose how you work and live? Let's explore what's possible.
I work with people like you to elevate how they show up with greater clarity, presence, and aliveness across their work and lives.
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If you are interested in exploring what this could look like, let's talk!