A financial advisor’s guide to designing a life worth retiring into
By Tom Post, CFP®, Diversified Portfolios, Inc.
Key Takeaways:
· Why do some people struggle in the first year of retirement? Careers act as psychological scaffolding for self-worth. When that structure disappears, many retirees discover endless leisure isn’t what they actually want.
· How do you build a social life in retirement? It’s difficult to build community from scratch on day one of retirement; you have to plant those seeds now while you’re still working.
For forty years, my wife and I had a perfectly balanced routine. We shared breakfast, we shared dinner, and the hours in between belonged to our work. But a few weeks ago, she retired from school teaching, and we suddenly found ourselves standing in the same kitchen at noon on a Tuesday, blinking at each other. She looked at me, completely serious, and said, “Tom, you can’t retire yet. I need the space to figure this out.”
An old line my parents used to say flashed through my mind: “I married you for life, not for lunch.”
I’d heard it countless times, but experiencing it firsthand makes you realize something profound about the geography of a long life together. It also makes you realize how much of retirement has nothing to do with money at all.
The Illusion of Endless Leisure
I once had a client who was convinced his ultimate post-career dream was to play golf, all day, every day. He retired, grabbed his clubs, hit the greens…and made it exactly sixty days before hitting a wall of unhappiness.
For decades, our careers act as a psychological scaffolding for our self-worth. When that scaffolding is suddenly ripped away, we often discover that we didn’t really want endless, empty leisure.
The answer for this particular client wasn’t to quit golfing altogether and head back to his nine-to-five. Instead, he took a low-hour job at the golf course as a starter (the person who organizes groups and send them out to play). Did he need the money? Not at all. But by stepping into that role, he found a daily structure, a constant stream of human interaction, and renewed sense of purpose.
The financial part of retirement is essentially a math problem. The human part of retirement is a social, physical, and cognitive transition, and it’s infinitely more delicate. As a financial advisor friend of mine wisely put it, “You don’t retire from something; you have to retire to something.”
Related: “Why Does Spending Feel Harder Than It Should for New Retirees?”
The Art of Planted Seeds: Starting Your Transition Now
I watched my own father handle this transition to retirement beautifully. He spent his entire life building deep roots within his community on a barrier island along the New Jersey coast.
When his career finally ended, he continued to pour his energy into volunteering for local sailing regattas. Even in the dead of winter when the boats were all dry-docked and the water was freezing, he would sit happily at the table, meticulously planning the logistics for the next summer’s season. It kept his mind completely sharp, kept him moving, and allowed him to naturally connect with younger friends who shared his passion.
The lesson he taught me is simple: You cannot build a community from scratch on day one of your retirement.
You wouldn’t start saving for retirement after you retire. Similarly, you have to plant the seeds of physical, cognitive, and social health while you’re younger. That’s why we’re not just asking about your bank account balances in our regular check-ins. We also want to know what give your days meaning, what communities and clubs you belong to, and what hobbies you enjoy most.
Related: “What Would Your 81-Year-Old Self Tell You Today?”
Your Field Guide for the Next Chapter: Tom’s Tips for a Happy Retirement
1. Invest Your Time and Resources into Mentorship
True fulfillment often comes from finding a local project where your life experience can directly impact the next generation. This is where retirement becomes not an ending, but an extension of a life dedicated to something larger than yourself. Even though I’m not retired yet (and don’t intend to for quite some time), I’ve found two distinct nonprofits that sit at the heart of my daily purpose:
- Racquet Up Detroit is part of the national Squash Educational Alliance, where we use squash and tutoring to help less-advantaged youth navigate the path through high school to a viable career and potentially college. Many of these kids come from families where college wasn’t even on the horizon. When they walk into our program, they get tutoring, mentorship, and the tools to see a different future. What I get back is immeasurable: genuine relationships with young people who remind me why education and opportunity matter so deeply.
- The other is Little Traverse Sailors up in Northern Michigan, where we’ve built a robust scholarship program so local kids can learn to sail right alongside summer residents.
Find an organization where your unique story can bridge a gap for someone else.
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2. Find Something That Moves You (Literally)
It’s not an accident that my volunteer projects also keep me physically active.
Finding an activity that forces you to move consistently is vital, especially if you dream of a retirement full of travel. Traveling is wonderful, but it’s also physically demanding, so you need a routine that keeps you in shape for it. Join a walking group, a running club, or dive back into a sport you loved when you were younger. The trick is finding an outlet that is regular and structured.
3. Reclaim an Artistic or Intellectual Curiosity
Retirement gives you permission to go backward and reclaim the parts of your younger self that got squeezed out by a frantic, forty-year career.
Look at our retired partner, Bob Toal, who picked up the guitar alongside cycling and mountain climbing. My wife spends her hours creating incredible flower arrangements, cooking gourmet meals, and reading.
Of course, that doesn’t mean you have to wait until retirement! In my own life, I realized how much I missed being an avid reader when I was young. I spend thirty minutes of my morning with a novel, and my mental well-being is vastly improved.
4. Tackle Real Problems in Your Community
Staying cognitively sharp requires mental stimulation, and for many individuals, nothing keeps the mind alive like rolling up your sleeves to solve a difficult challenge.
Recently, my business partner, Ron Yolles, and I have been deeply focused on the troubling rise of anti-Semitism. Ron is Jewish and I am Episcopalian, and we’re working on bringing together local synagogues and parishes across the greater Detroit area to break bread, facilitate honest dialogue, and coordinate joint community service. We’re just getting started with this project, but it’s already deepening our connection to our community.
5. Intentionally Cultivate Multi-Generational Friends
As we age, our social circles naturally shrink if we aren’t careful. To keep your outlook fresh, look for environments where you can connect with people younger than you.
My father did this through sailing; I do it by playing sports with guys who can run circles around me. My daughter is even in a running group filled with men my age. It provides a shared energy that keeps you engaged and connected.
Retire to Something, Not from Something
For many people, a happy retirement isn’t built with a one-time, static plan based solely on your finances. Instead, it often requires regular physical movement, a healthy dose of intellectual curiosity, and above all, the grace to give your spouse some breathing room to figure out exactly who they are at noon on a Tuesday.
We’re here to handle the numbers, allocations, and the nest egg to help ensure your financial foundation is strong. But as your partner in this journey, I challenge you to start planting those human seeds today, too. And if any questions come up along the way, you know where to find us.
If you’re not yet working with us but are contemplating your retirement lifestyle, this is exactly the kind of partnership we build. Let’s talk about your whole life, not just your portfolio, in a complimentary Financial MRI meeting.
