Hi, I’m May - Midlife Transition and Leadership Coach
You've built something real. A business, a team, a career, a life that — from the outside — reads as success.
And somewhere in the middle of building it, you stopped recognizing yourself.
This isn't a crisis. It's a chrysalis. A sacred, disorienting, necessary undoing — where everything you've built so far gathers itself to become whatever's next.
I help Gen X women leaders, corporate executives, and established founders pivot into their next high-impact act with clarity, strategic precision, and their healthspan intact — through a signature framework I call Chrysalis Coaching.
My methodology - Chrysalis Coaching for high achievers who are quietly coming apart at the seams of their own success.
You didn't expect this. You did everything "right" — built the business, earned the title, hit the numbers — and somewhere along the way, a low hum of restlessness moved in and never left.
Maybe it shows up as:
A business or corporate role built 10–20 years ago that no longer matches your current energy, values, or capacity.
The shift from raw hustle to strategic wisdom — feeling the pull to leverage your deep pattern recognition, mentoring capacity, and crystalline intelligence instead of relying on brute-force energy.
The weight of the "Sandwich Season" — managing perimenopause/health shifts, launching young adult children, and supporting aging parents while leading a company or team.
The desire for a strategic pivot — whether transitioning from corporate leadership to a portfolio/consulting practice or restructuring an existing business to give you complete time freedom.
Decision fatigue and physical burnout in a career or company you used to navigate effortlessly.
This is chrysalis work. Not breakdown — metamorphosis. The very real, very physical process of dissolving what no longer fits so that something truer can take shape. It happens to caterpillars. It happens to leaders. It's not comfortable, and it's not optional if you want what comes next to be real.
I work at the intersection — the place where your inner reckoning and your outer decisions (the business, the team, the next chapter) have to move together, or neither one holds.
Who This Is For
Gen X women leaders, executives, and business owners who are navigating a profound midlife transition.
You are likely experiencing one of two pivotal moments:
The Established Business Owner: You built a successful company 10 to 20 years ago. It served you then, but today, your energy, health, family dynamics, and personal values have shifted. You need to reinvent, scale back, or realign your business without burning it down.
The Corporate Veteran: You’ve spent decades leading in the corporate arena. Now, you’re ready to step into solo entrepreneurship or a meaningful second act built entirely on your own terms.
Whether you are juggling aging parents, raising young adults, or navigating your own physical shifts, this work is designed to help you align your outer enterprise with your inner truth.
How I Guide You Through It: The Four Phases of Chrysalis Coaching
My methodology follows the same anatomy nature uses — but with a guide beside you, and a map in hand.
1. Arrival(the ending) You arrive as the caterpillar whose world has stopped — a career that ended, an identity that no longer fits, a success that stopped sustaining you. In this phase, we honor the ending instead of rushing past it. We name what's over, what's lost, and what you're carrying with you. You can't begin a transition you haven't acknowledged.
2. Dissolve(entering the messy middle) This is the hardest and most important phase — the one most people try to skip. Here we let go of the old scripts, roles, and definitions of success that no longer serve you. It feels like falling apart, because in a sense it is. My job is to help you understand that the dissolving is not failure. It's the necessary undoing that makes reformation possible.
3. Reform(moving through the messy middle) Inside the chrysalis, the caterpillar's raw material reorganizes into something entirely new. In this phase, we do the same with yours: your values, your strengths, your hard-won experience. We experiment, test new possibilities, and begin shaping a definition of success that's actually yours — built on your terms, not the ones you were handed.
4. Emerge(the new beginning) The butterfly doesn't return to being a caterpillar with wings — it's a new creature altogether. In this phase, you step into your next chapter with clarity, confidence, and a life designed around what genuinely matters to you. Not recovered. Transformed.
What You'll Walk Away With
A Sustainable Business & Life Architecture: Restructure your work, schedule, and boundaries around your actual current capacity, health, and family priorities — not the hustle rules you followed 15 years ago.
A Strategic Blueprint for Your Next Act: Clear, step-by-step direction whether you're exiting a corporate career to go solo, or transitioning your existing business into its next chapter.
Strategic Energy & Leadership Mastery: The internal steadiness to navigate complex family dynamics (the sandwich generation) and high-stakes business choices without sacrificing your well-being.
A Trusted Human Thinking Partner in the Arena: High-touch, empathetic, and deeply strategic human guidance through identity transformation where AI tools and cookie-cutter frameworks fall short.
Why This Matters for You
If you're reading this in the middle of your own lifequake — the career that ended, the identity that no longer fits, the success that stopped sustaining you — I want you to know two things.
First: the dissolving you're feeling is not the end. It's the chrysalis. It has an anatomy, a rhythm, and a way through.
Second: you don't have to navigate it alone. I've walked this path — not just in theory, but in my own life. And I'd be honored to walk it with you.
What It Looks Like on the Other Side
"When I hit a wall as CEO, I thought I had a strategy problem. May helped me realize it was an identity problem. Moving through the Chrysalis framework gave me the courage and clarity to step down gracefully and launch my next venture without feeling like I was failing."
— Sean B, Former Founder & CEO, F&B Industry"I did everything 'right' on paper, but success felt hollow. Working with May gave me permission to stop white-knuckling my career. Within six months, I redefined my leadership role, restored my energy, and built a life that feels authentic."
— Doug M, Managing Director, Financial Service"I built a thriving studio and brand, but after 15 years, I felt like a manager of my own art rather than the creator. May helped me step through the discomfort of restructuring my practice. Now, I run a studio that feeds my creative spirit and aligns with who I am today."
— Maya R, Founder & Custom Furniture Designer