About Cara Gray
I’ve held many roles in my life—professional oboist, C-suite executive assistant, social media agency owner, and now consultant—but each pivot was a conscious decision to reinvent myself, not some unplanned detour. I’ve always believed that as we age, we become even better—wiser, more confident, and freer to explore what truly matters.
Guided by my top CliftonStrengths theme, “Futuristic,” I’m energized by the possibilities the future holds, and I love helping others catch that same spark for their own next chapter. Today, my consultancy is me intentionally designing my own third act, blending my passion for travel with my longtime home in downtown Chicago, all while pursuing my curiosity for lifelong learning and desire to help others. My journey is proof that it’s never too late to redefine your life on your own terms and create your best chapter yet.
I am a Certified Professional Retirement Coach (CPRC), a Certified Exit Planning Advisor (CEPA) and a USC graduate.
+30
Years Experience
+25
Countries Visited
+50
Presentations Given
+100
Concerts Performed
My mission
My journey as a Third Act Consultant began with a deeply personal experience. In the 1980s, my father—owner of two shoe stores in small-town Iowa—faced an abrupt, unplanned retirement when a big box store decimated local businesses. While he managed the financial aspect, the loss of his identity, purpose, and community connection took a severe toll on his well-being. Witnessing his struggle left an indelible mark on me, illuminating the critical need for intentional planning beyond finances.
This realization became the cornerstone of my mission: to ensure that accomplished individuals like you approach life’s next chapter with the same strategic mindset that fueled your professional success. As a Third Act Consultant, I dedicate my career to helping executives, professionals, and business owners avoid the pitfalls my father encountered. My bespoke ‘Third Act Blueprint’ isn’t about securing your financial future—it’s about crafting a purposeful, engaging, and fulfilling next act that honors your lifetime of achievements while opening doors to new possibilities.
Third Act Blueprint Methodology
My methodology, “Third Act Blueprint,” is a hands-on, in-depth process that helps you shape a personalized plan for your next chapter.
Uncover new sources of purpose and meaning
Identify and cultivate passions and interests
Optimize physical and mental well-being
Enhance relationships and social connections
Design a lifestyle that continues to challenge and inspire
What people are saying
“One of the best things I've done since retiring just over a year ago was hire a third act consultant. I'm not big on life or business coaches, and I never would have thought to hire someone to help me with retirement, but then Cara Gray popped up in my inbox and lo and behold...
At 64, I feel like life is just getting started. 🌅
No lie. I now have a curated "third act blueprint," which lists a gazillion ideas and links for my social life, health and wellness, food, travel, purposeful work/volunteering, and I forget what else. Now if I'm ever wondering what to do with myself, because I'm no longer WORKING working, I go to my blueprint and I'm off and running again. If you're facing retirement and worried about what you'll do with all that "free time," I highly recommend investing in Cara's third act consulting. If not a consultant, start listening to podcasts on retirement. There's no shortage of them and you'll quickly learn how amazing your "third act" can be. 💃 🕺”
Jackie Mathys
Former Founder/Owner Mathys+Potestio
“I’m so glad that I got the chance to work with Cara. I was feeling lost, retirement was something I planned for financially but not what I’d do with my time.
Not only did Cara make it clear that I wasn’t the only person feeling this way, but she gave me direction. Talking through things with someone else helped me understand what it was I was missing and what I needed to fill my time with so I could get that sense of accomplishment I was missing.
Cara provided me with an incredibly detailed Blueprint with steps and action plans to hold myself accountable but it was also flexible enough to anticipate future desires when I wanted to take another path. Would recommend working with Cara to anyone considering, entering or already in retirement.”
Dan P.
Former CEO
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