How do you know you’re ready to retire? Three couples, three different paths, and the one question that helped all of them find clarity.
By Ronald M. Yolles, JD, CFA, Diversified Portfolios Inc.
Key Takeaways:
• What if I’m not sure we have enough money to retire? For many of the couples we work with, the answer is yes. But believing that takes time, honest conversations, and a process that moves in small steps rather than one leap.
• Do both spouses need to retire at the same time? Almost never. In our experience, one partner usually goes first, and the other follows once they see how much fuller life becomes.
“Envision yourself in your early 80s, looking back at the person you are right now. If your 81-year-old self could sit down with you today, what would they say?”
I’ve been doing this work for nearly 40 years, and that’s a question I come back to with each of our clients considering retirement.
I call it a righteous trick, because it works almost every time. That reframe cuts through the noise in a way that financial projections alone rarely do. Most people, once they sit with the question honestly, already know the answer. They just needed someone to help them trust it.
How Do You Know When It’s Time to Retire? Start by Listening to the People Around You.
Something we repeat constantly in our work is the idea that money should be a positive force inside a family, not a source of friction. And when one partner has been running at full speed for decades, the entire family can often feel that stress.
No two families are the same, but I’ve noticed something about the timing of when couples tend to reach out to us for the first time. They’re between the ages of 54 and 64, often both doctors, lawyers, or sporting some combination of legal, medical, or business careers. Their youngest child has just gone off to college, and for the first time in decades, the house is quiet.
When the rhythm of parenting slows down, there’s new room to notice that one (or both) of them has been running on fumes. The career that was once energizing has become something closer to an obligation, and it’s creating more stress at the end of most days than positive energy. The family feels it, the spouse feels it, and sometimes even the adult children feel it.
And often, the family is the one to say it first. We don’t need more money. We need more of you.
Scenario #1: When You Know It’s Time, But It Doesn’t Feel Right
I’m thinking of a couple, both attorneys, who came to us not long ago. He had built a successful career, but recently noticed just how much he dreaded practicing law every day. His wife could see it taking a toll, and she was ready for him to step away. But he wasn’t sure they could afford it, and he wasn’t sure who he’d be without the work.
We model scenarios to help you understand how much income may be generated from a portfolio without touching the principal, and in many cases, clients find they are in a stronger position than expected. Still, that gap between knowing and feeling is something we see constantly, and we’ve learned that you can’t close it with a spreadsheet. Building real confidence takes fewer numbers and more conversations.
So instead of pushing this client toward a decision, we started small: could he take seven to ten extra days in Arizona this winter? Let the kids and grandkids come visit and see what it felt like to have a little more space?
He did. And he liked it so much that on December 31st, he retired completely. His whole family is better for it, because he’s happier. We also set up quarterly check-ins and a 12-month comprehensive review, so if at any point it didn’t feel right, he could explore going back. That safety net mattered enormously, even though he never needed it.
Scenario #2: When the Resistance Runs Deeper
Sometimes, though, the resistance runs deeper than practical uncertainty.
I once worked with a gentleman whose own parents had run out of money. That experience never left him. Every financial decision he made was filtered through one question: What if it happens to us, too? He believed the best thing he could do for his wife and children was to give them more financial security than they could ever imagine, even if it meant sacrificing the moments that mattered most.
His family saw it differently. They didn’t want more security; they wanted more time with him.
We brought in a skilled life coach, and that’s when things began to shift. The life coach listened to him, sat with his anxiety, and helped him understand that the fear he was carrying from his parents’ experience was driving him toward the exact opposite of what his own family needed.
That kind of work, the emotional and psychological layer underneath the financial planning, is something we take seriously.
Related: Why Does Spending Feel Harder Than It Should for New Retirees?
Scenario #3: When One Spouse Is Ready (and the Other Isn’t)
I’ve worked with a couple, two doctors, where the wife had been practicing medicine for more than 35 years and was exhausted. Her husband, on the other hand, still loved his work. Medicine gave him energy, identity, purpose. He wasn’t going anywhere.
And that’s completely fine. In our experience, couples almost never retire at the same time. It’s almost always asynchronous; one person tests the waters first, and the other sees how much richer life becomes.
For this couple, the turning point came when we shared stories of other doctors who had retired, what they were doing with their time, and how they’d found new sources of meaning. She immediately started picturing it: trips to New York with girlfriends who had similarly retired, art galleries, plays, a book club, learning to cook. She didn’t need her husband to be in lockstep with these things.
And once she made the transition, something else happened. She leaned into coordinating their life as a couple in ways she hadn’t had the bandwidth for before. She planned the travel, organized their social calendar, made sure time with the kids and grandkids was thoughtful and regular.
In many professional fields, like medicine, law, finance, and business, experience carries a premium. You can be at the very top of your game in your 50s and 60s, and there are plenty of happy, practicing 80-year-old physicians. But there are also plenty of physicians in their 60s who are ready for what comes next, and the freedom to make that choice on your own terms is what real financial planning should support.
Your Kids Are Watching, Too
When a parent finally gives themselves permission to stop working and start living differently, the adult children notice. They see a mother who’s more present, a father who’s less stressed, or a marriage that has more room to breathe. And whether they realize it or not, they’re absorbing a lesson about what money is actually for.
That’s one of the reasons we work with both generations. Many of the adult children we advise are early in their own careers, and watching their parents make this transition well gives them a healthier framework for their own financial decisions down the road. They’re going to inherit a significant amount of money someday, and we want that to be a blessing, not a burden.
What Would Your 81-Year-Old Self Say?
The journey to retirement looks different for every couple we work with. But the pattern I’ve seen, again and again, is that once people give themselves permission to live differently, they discover a version of life they didn’t know was available to them.
If you’re reading this and something resonates, whether it’s the career that’s wearing you down, a spouse who keeps saying they’d rather have you than another year of income, or a question you haven’t been able to answer on your own, my advice is this: talk about it.
Talk to your family. Be transparent, be vulnerable, and know that these conversations don’t have to happen all at once. We work with couples at whatever pace feels right, sometimes moving in small increments over months or even years, because the goal isn’t to rush a decision. It’s to make sure both partners feel comfortable and aligned for the long run.
If you’ve been sitting with a “should I?” question of your own, we’d love to hear what’s on your mind. That conversation is exactly what we’re here for.
Not yet working with Diversified Portfolios? If you’re navigating a career transition, weighing retirement, or just wondering whether the numbers really do support the life you’re imagining, we’d welcome that conversation. We invite you to schedule a complimentary Financial MRI meeting, where we can take a close, confidential look at your full financial picture and help you see what’s possible.
Disclaimer: The couples and individuals mentioned in this article are fictional composite characters created to represent common situations we have encountered with multiple clients over the years. Any resemblance to actual clients is purely coincidental. This article is for informational purposes only and does not constitute investment advice or a recommendation to buy or sell any security.
