Like many successful people, Jack found himself in a new strange world. Retirement. He had planned for it for years, but now on a Thursday afternoon alone at home he felt unmoored. It dawned on him that, with the help of his financial advisor, he had figured out how to prepare to fund his retirement, but he had no idea how to live this new life well.
Retirement planning is primarily seen as a money problem. What’s my number? When do I claim Social Security? What’s my withdrawal rate? Make no mistake, those questions are critical. But they’re not the whole story. There’s a bigger question. And many people don’t give it the time of day. Until, like Jack, it hits them.
Do I want to really thrive in my retirement, or am I willing to just drift along?
It’s an important choice. And keep in mind that drifting is the default setting.
Two of my podcast conversations put this question high on my radar.
The financial services industry understandably keeps our eye on the retirement math problem. Hit that number and everything else will take care of itself. Except, in real life, it doesn’t. There’s a deeper question: what will make my time meaningful?
Sociologist Corey Keyes has spent his career examining the difference between flourishing and languishing, that feeling of being stuck and rather empty. It’s distinct from depression, but it’s a different kind of problem.
What separates the two? Keyes points to what he calls the Five Vitamins, drawn from a longitudinal study of what flourishers actually do.
- They help someone or something.
- They prioritize warm, trusting relationships where they feel they matter.
- They learn for the joy of it.
- They engage in something challenging and interesting. And they play. They’re about active participation, not just passive consumption.
Notice what’s not on the list. Money. Keyes says:
“Those five things, you do not need to go buy.”
He also cautions against chasing happiness as the main goal. He calls that the Cheeto Diet. It feels good but gives you no nutrition.
If Keyes tells us what thriving looks like, The New York Times bestselling author Daniel Coyle’s work tells us how to create it. After five years studying flourishing communities for his new book Flourish: The Art of Building Meaning, Joy, and Fulfillment, a key point stands out:
“Your life isn’t a game. It’s also a garden. It’s not just a game to win, it’s a garden to grow.”
Many of us thrived in careers playing a game we learned to win. We got the grades. We delivered the results. Earned the promotions. And that’s why retirement is a shock for many. It feels like a totally new game. But it turns out, retirement is something different. It’s something you cultivate. It gives you time to tend to the parts of your garden that have been neglected in your working years.
More time means more opportunities to explore. Coyle recommends being more open to walking through what he calls Yellow Doors, from Lisa Miler’s work at Columbia. The Green Doors are a clear yes. The Red Doors get a no way response. But the Yellow Doors are the maybes. Those invitations that the work version of you would have politely declined, because there really wasn’t time for maybes.
But they’re where the unexpected surprises often live. New experiences, hobbies, interests, friendships, and even second acts, can be sparked by an open-minded yes to something uncertain. All it takes is a willingness to try something new, now that you’ll have the time.
So, it’s question worth pondering: are you preparing to thrive, or preparing to drift? Coyle offers two starter questions to get you going:
Who do I feel most alive with?
What am I helping to grow?
Answer those honestly, and you’ve taken your first steps forward. Like Jack, we’re all a work in progress. But he’s on his way to exploring what works for him. Now. In this new strange world. Retirement.
You have an opportunity to create the life in retirement you’ve earned. Be intentional. Create one where you can thrive.
Listen to my retirement podcast conversation with Daniel Coyle on his new book Flourish
Listen to my retirement podcast conversation with Corey Keyes on his book Languishing
Explore The Retirement Wisdom Podcast – it’s a free Retirement School
Joe Casey is an executive coach who also helps people design new lives after the world of full-time work. Connect on LinkedIn

