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My favorite part of being a financial planner is getting to know our clients at an intimate level. While we intentionally limit the number of families we work with to ensure meaningful relationships, we’ve discovered something remarkable: our happiest clients share five common characteristics that consistently contribute to their well-being in retirement.
Yes, financial security is one commonality. But it’s far from the only one. After all, people are not just “numbers on a screen,” and a person’s obituary never states when they started Social Security or their 401(k) balance.
Strong Social Connections: The Currency That Matters Most
What’s the point of having wealth if we can’t enjoy it with the people who matter most?
Think about it: many of our clients spent 40 hours a week, for up to 40 years, working alongside colleagues. In some cases, they logged more hours with coworkers than with their own families. These workplace relationships provided genuine friendships and a sense of belonging.
Then retirement arrives. Suddenly, that daily social fabric disappears.
Do you have plans to stay in contact with those colleagues? Will you watch the grandkids regularly? Have you scheduled monthly breakfast dates with friends or your kids?
Losing social interaction and sense of community is one of the greatest dangers retirees face—especially in an era where “connection” often means scrolling through social media.
Our happiest clients don’t leave this to chance. They create deliberate plans to maintain and nurture their relationships.
One client comes to mind immediately. This gentleman has a legendary system for tracking birthdays. His memory is uncanny, but his organizational skills and willingness to care about others are what truly impress. He makes sure nearly everyone he knows is remembered on their special day with either a card, a call, or an in-person visit.
Last I checked, no one has ever been upset about receiving birthday wishes. But here’s the best part: as much as people love receiving his thoughtful greetings, he genuinely enjoys giving them. It keeps him busy and connected—time well spent for everyone involved.
A Purpose Each Morning: The Antidote to the Retirement Blues
One of the most heartbreaking things many retirees face is a sudden lack of purpose. You work somewhere for decades, building skills, contributing, making an impact… then you just stop.
Now what?
We always ensure the people we work with can afford to retire. But affordability is just one factor among several. We know what you’re retiring from, but the more important question is: what are you retiring to?
One of my favorite clients is a perfect example. He held a Senior VP position at a highly successful firm and made excellent money. He could have coasted into a traditional retirement of golf and leisurely mornings. Instead, he was ready for something more, and other passions called his name.
Today, he works as a consultant—not because he needs the money, but because he enjoys the challenge. He also serves as choir director at his church, presides over the board of a nonprofit, is pursuing his master’s degree, and relishes life with his wife and their many animals at home.
He’s financially set, but more importantly, he’s living a life of significance—which is what every retiree (and frankly, every person) is working toward.
Instead of watching The Price is Right every morning, his schedule is intentionally full. As he puts it with a smile, “I’m busier now in retirement than when I was working.”
Busyness isn’t the enemy. Busyness without purpose is. Our happiest clients have figured out the difference, and they’ve filled their calendars with meaning.
A Focus on Health: Your Best Long-Term Care Insurance
One of the biggest fears many retirees harbor is the specter of long-term care costs and end-of-life care. The fear is justified—it’s expensive, it’s scary, and it’s a very real threat.
There are many ways to pay for long-term care, but I believe the most effective and efficient strategy is to avoid needing it in the first place.
Now, don’t get me wrong—you can do everything “right” and still end up requiring care. Genetics, accidents, and plain bad luck happen. But you dramatically decrease the odds when you make health a priority.
One client has elevated organic gardening to an art form. She started the project the year before retiring, and it’s since taken on a life of its own. She credits it with giving her both purpose and improved health. Knowing her garden provides fresh, healthy food each day—while also getting sunshine, fresh air, and physical movement—has created a sustainable habit that supports longevity and vitality.
Other clients have become dedicated gym enthusiasts, diving into Hyrox, a new workout routine that’s taking the world by storm, yoga, or the rapidly growing pickleball phenomenon. The specific activity doesn’t seem to matter. What matters is that our happiest clients love talking about their physical fitness routines with genuine enthusiasm.
After all, who doesn’t feel great after a good workout?
Financial Organization and a Clear Plan: Money with a Mission
Yes, we spend considerable time discussing finances—it’s literally our job. But as much as we enjoy maximizing returns and minimizing taxes, we also want people to give their money a purpose beyond growing it in an account.
Dream vacations to finally take. Helping a child with their first home down payment. A meaningful gift to your church or a cause you believe in. Weekly date nights at your favorite restaurant.
This is why you’ve saved, risked, lost, recovered, then lost again and recovered again over all these years. Not to watch the number grow indefinitely, but to enjoy it when the time is right.
Here’s the challenge: many of our best savers can be our worst “enjoyers” of money. They worry about running out because decades of disciplined saving have trained them to be cautious. That habit served them well during their working years.
We absolutely agree you should spend within reason. The risk of running out of money is real and should be planned for carefully.
But there’s another risk that’s equally concerning: the risk of not utilizing your money. Of never assigning purpose to those dollars you worked so hard to accumulate. Of reaching the end of your life with a healthy bank account but a deficit of meaningful experiences.
In our view, dying with too much money can be every bit as problematic as running out too soon. Our happiest clients have found the balance—they have a clear financial plan that allows them to spend confidently and purposefully.
A Live-for-Today Attitude: Tomorrow Isn’t Guaranteed
You’ve probably heard the phrase “live for today, plan for tomorrow.” We wholeheartedly agree. But in my humble opinion, too many financial planners focus exclusively on tomorrow at the expense of today.
I’m often reminded of one story that will forever be etched in my memory.
We had recently begun working with a couple where the husband had worked a physically demanding job that had taken its toll over the years. He kept telling us he was ready to retire—and financially, he could absolutely afford to do so. Yet something seemed to be holding him back. He seemed hesitant, like he was withholding information.
About a year into our relationship, we learned why. He had a chronic health issue that would likely prove terminal.
I remember the exact moment I heard the news and how our entire planning perspective shifted. But I’ll never forget his simple yet profound request: “I want to enjoy this last year with my grandson, and I’m entrusting you guys to take care of my wife.”
Knock me over with a feather.
What followed was one of the most impactful experiences of my career. He and his wife made a bold decision: they would sell their home, buy an RV, and spend his remaining time traveling and making memories.
On paper, it sounded wonderful. But we also had legitimate concerns. What if you don’t like the RV lifestyle? This represents a massive financial commitment—what if it’s a mistake? Have you ever rented an RV to test it out? Can your health realistically withstand this dramatic change of pace?
We presented our concerns honestly but supportively, affirming that while challenging, it was absolutely possible. Ultimately, we did everything we could to plan for this transition, and this courageous couple took the plunge.
The gentleman passed away about a year later. The meeting with his widow was one of the most difficult—and paradoxically, one of the most rewarding—meetings we’ve ever had.
Through tears, she told us something I’ll carry with me forever: “It was the best decision we ever made. The time my husband got to spend with his grandson was worth more than any dollar he ever earned.”
The power of planning was crystallized for us in that meeting—not planning for the sake of accumulation, but planning for the sake of living fully.
The Bottom Line
We’re not all given an expiration date, but make no mistake—we all have one.
The question we need to ask ourselves is: what are we ultimately after? Strong relationships that feed our souls. Clear purpose that gives meaning to our mornings. Good health that extends our runway. Organized finances that provide security and freedom. And perhaps most importantly, the wisdom and courage to enjoy today while still planning responsibly for tomorrow.
These are the traits we consistently observe in our happiest clients. They’re not the wealthiest by net worth, but they’re undoubtedly the richest in the ways that truly matter.
After all, what’s the point of accumulating wealth if we never give ourselves permission to properly utilize it?