Retirement gives you freedom. More time. Fewer obligations. A hard-earned reward for decades of work.
But in two conversations on The Retirement Wisdom Podcast, Deborah Santana and Monique Rhodes suggested something more provocative: retirement is an identity reckoning. And for many successful professionals, that’s disorienting, and can even be paralyzing.
Both women have backgrounds in the music industry and have navigated their own transitions. They have dealt with adversity and losses that ultimately fueled their reinvention. What struck me most was the different nuances in their approaches. They offer us two complementary but different ways for navigating later life.
Deborah Santana’s story is about a building a courageous encore life. Reflecting on leaving a 34-year marriage to musician Carlos Santana, she described the painful process of realizing that “a part of me was dying” because she had become overly focused on someone else’s life and success. When she finally stepped away from the marriage, and her career as COO of the music business, she said she had to let go not only of relationships and routines, but of her identity.
That insight will resonate with anyone who’s planning for, or in retirement. It’s easy to co-mingle our identity with usefulness, achievement and external validation. Then retirement arrives and the scaffolding fades away. The title disappears. The constant meetings, emails and texts stop. The day-to-day pace of urgency is gone. What remains feels undefined.
Deborah Santana teaches us that phase is not something to fear. She sees it as creative space. A space to embrace. “It’s a wonderful opportunity,” she reflected, “to create exactly who I was and determine what things I love, and I value and who I want to be going forward.”
Her approach to transition is mindful and energetic. She journals. Creates vision boards. Pursues a Masters. Mentors others. Builds nonprofits. Serves on museum boards. Explores creativity through writing and flower arranging. Her framework for later life centers around what she calls the “Four Cs”: Care, Creativity, Community and Contemplation.
Rhodes begins somewhere quieter. She argues that many people become trapped in retirement transitions because they resist uncertainty. We crave clarity. We miss momentum. We demand answers. We want to “figure retirement out” the same way we solved business problems.
But Monique Rhodes believes that instinct often makes things worse. “What those thoughts do,” she says, “is they actually only tighten that knot.” Instead of immediately diving headfirst into reinventing ourselves, she encourages stepping back. Learn to sit still inside the ambiguity. Stop treating discomfort as failure. Stop trying to optimize everything in your life 24/7.
That difference between the two approaches is fascinating.
Deborah Santana says: create.
Monique Rhodes says: step back.
Santana emphasizes contribution.
Rhodes emphasizes presence.
Together, they call out what’s really needed in transitions: both motion and stillness.
A flurry of activity without reflection can really be a form of avoidance. A way to duck the reflection that confronts what you need to resolve to chart a new course. Many retirees overbook themselves with travel, volunteering, golf or consulting work because silence is a very different feeling and unsettling. But also, too much introspection without active experimentation can lead you down the path of drifting toward isolation.
Both women shared skepticism of commonly accepted myths about happiness and success. Rhodes argues that one of the biggest misconceptions people bring to retirement is believing happiness comes from external achievement. After decades in achievement-driven environments, many assume fulfillment will follow once they finally have “enough.” But retirement flips the script. It’s not about the external markers. “Happiness is an internal job,” Rhodes said bluntly.
Santana arrives at a similar conclusion. She talks about the value of knowing who you really are beneath the performances, obligations and expectations. Her path includes meditation, simplicity, curiosity and service. Later life is less about acquisition and more about alignment.
Practical lessons emerge from these conversations:
- First, build reflective practices before you retire. Both emphasized meditation, silence, journaling and contemplation, noting that retirement magnifies whatever relationship you already have with yourself. If you cannot tolerate stillness while working, the absence of structure later may feel surprisingly difficult.
- Second, actively experiment. I believe that curiosity is one of the most underrated retirement skills. Rhodes encourages retirees to revisit childhood interests. Santana is a great role model for lifelong learning
- Third, reevaluate relationships. Santana’s observation that some people belong in our lives only for a “season” may resonate painfully but truthfully. Transitions can clarify which relationships nourish your personal growth and which stifle it.
Finally, stop expecting retirement to feel great right away. Uncertainty, loss and boredom don’t mean that something is wrong. They may just be signs that the time has come to do the work of finding out who you truly are.
Listen to my podcast conversation with Deborah Santana
Listen to my podcast conversation with Monique Rhodes
Explore The Retirement Wisdom Podcast – it’s a free Retirement School
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Joe Casey is an executive coach who also helps people design new lives after the world of full-time work. Connect on LinkedIn
