Dear Friends -
Many of you know how much I love tennis. Last summer I baked in the upper deck at the US Open, and just a few weeks ago I wandered the red-clay paths of Roland Garros grinning like a kid in a candy shop. When a Grand Slam match is on, everything else waits.
So when Novak Djokovic, owner of 24 majors and more top-ten wins than anyone, walked onto Centre Court for last Friday’s Wimbledon semifinal, I brewed the good coffee and settled in. Ninety-one minutes later it was over. Jannik Sinner beat him in straight sets, 6-3, 6-3, 6-4.
The commentators jumped to the big question: Is it time for Novak to retire? One tough afternoon and suddenly the talk is all about endings.
Djokovic wasn’t buying it. In the press room he smiled and said, “I’m not planning to finish my Wimbledon career today.”
That’s our cue. Retirement, whether from Centre Court or the corner office, doesn’t start with outside chatter. It starts inside. When the work stops lighting you up, that’s the signal. The answer isn’t to quit—it’s to pivot.
From Scoreboard to Springboard
Retirement once called to mind gold watches and a slow coast to the finish. In 2025 it can look more like Novak stretching on the baseline, ready for a fresh set. It is a chance to redirect your most limited resource, time, toward new courts of learning, service, and joy.
This issue shows you how to spot that moment and shape it on your own terms, without waiting for an injury timeout or anyone else’s verdict. Think expansion, exploration, and impact, not decline.
1. Signals it might be “right now”
Signal | What it really means |
|---|---|
Persistent Curiosity — you keep bookmarking courses, volunteer missions, or creative retreats | Your learning drive is louder than your ladder-climbing drive. |
Values Mismatch — you finish meetings thinking, “We could be doing so much more good” | Your purpose outgrew your position description. |
Energy Reallocation — the projects that once fueled you now drain you, while mentoring or community work feels effortless | Your internal battery is pointing to a new outlet. |
Calendar Envy — you glance at friends’ passion projects (or grandkids) and feel a warm tug rather than FOMO | Your priorities are shifting from possessions to experiences and impact. |
If two or more resonate, you’re likely on the cusp of a purposeful pivot.
2. Mini-Case: Lawrence’s Leap
Lawrence spent 25 years in corporate finance. His “signal” was a relentless urge to teach financial literacy at underserved high schools. He negotiated a three-month sabbatical to pilot a curriculum, loved it, and never looked back. Today, he consults two days a week and spends three in classrooms—earning less money but reporting record-high life satisfaction.
Takeaway: Prototype before you plunge. Small experiments expose the joy factor and the realities of a new rhythm.
3. Thought-Starter Prompts
Choose the format that fits you—handwritten journal, voice notes, or a walk-and-talk with a friend.
Future Memory:
“It’s three years after my pivot and I’m waking up on a Tuesday. I feel…”
Impact Inventory:
“If I had 20 hours a week to give back, where would the greatest ripple reach?”
Joy Audit (Last 30 Days):
List moments that sparked energy vs. moments that sapped it. What patterns emerge?
4. AI Exercises
Design My Purpose Prototype
Prompt: “I’m exploring a post-career chapter blending (list your passions). Suggest three low-risk pilot projects I can test in the next 90 days, outlining time commitment, cost, and expected joy factor.”Skills Transfer Scan
Prompt: “Here are my top career skills: (list). For each, brainstorm two surprising arenas—non-profits, startups, arts, education—where these skills could create outsized value.”Ideal Week Builder
Prompt: “Help me sketch a weekly schedule that balances purpose work, wellness, relationships, and learning in a ‘third-act’ lifestyle. Include morning and evening rituals. Please ask clarifying questions.”
5. Quick-Start Experiments
90-Minute Micro-Sabbatical: Block one morning to explore an interest—museum curation tour, coding workshop, wilderness hike. Notice your energy afterward versus a normal workday.
Shadow & Share: Ask someone already living a version of your desired pivot if you can shadow them for half a day, then treat them to coffee to debrief what surprised you.
Give-Back Gigs: Sign up for a single-day volunteer project in a field that intrigues you (habitat build, local accelerator, community garden). Evaluate the fit.
New Podcast 🎙️ Alert ‼️
Speaking of masterful pivots, I recently sat down with Kristen Cavallo—yes, the former Global CEO of both Mullen Lowe Global and The Martin Agency. Today, she’s channeling that powerhouse strategy brain into the nonprofit world as Executive Director of The Branch Museum of Design.
In this episode of Act Three, Kristen shares:
✅ Why she chose a museum over another C-suite gig
✅ How brand thinking translates to mission-driven work
✅ The exact process she used to sort out her third act
This a Masterclass in pivoting to a meaningful next chapter!
6. Let’s Keep Growing Together
Hit Reply: What’s one signal telling you it might be time? I read every note.
Share the Spark: Forward this to a friend pondering their own pivot.
Until next week, keep seeing retirement not as a curtain-close, but as opening night for Act Three. 🎭
Cara Gray
Third Act Consultant, CPRC, CEPA™️
P.S. If you want to start planning your third act, set up a time on my calendar for a chat: Schedule a Chat with Cara