Retirement — it’s a word that carries a lot of assumptions. But what if everything we thought we knew about retirement was only part of the picture? That’s exactly the kind of conversation I had with Mitch Anthony, a recognized thought leader in financial life planning, author of numerous books, and someone who’s been challenging the status quo in retirement thinking for over two decades.

We sat down recently to talk about one of his cornerstone works: The New Retirementality. Though originally written in 2001 and now in its fifth edition, the book remains startlingly relevant today. Why? Because the conversation around retirement is still evolving — and Mitch has been at the forefront of that shift.

"Retirement Is an Artificial Finish Line"

Mitch opened our conversation with a powerful idea: “Retirement is an artificial finish line — someone else put it there.” For decades, 65 has been etched into our collective consciousness as the age to retire, largely thanks to Medicare and earlier, Social Security. But Mitch challenges the assumption that everyone should stop working just because they hit a specific birthday.

“Age tells us nothing,” he said. “Some 85-year-olds act like they’re 50. Some 45-year-olds act like they’re 90.” The takeaway? Your vitality, your drive, your purpose — none of these are dictated by the calendar.

From Physical to Intellectual Capital

Mitch drew a fascinating contrast between the Industrial Age and today. Back then, retirement made sense — people traded physical labor for a paycheck, and by 60, their bodies often couldn’t keep up. But today? We’re trading intellectual, relational, and experiential capital. And that doesn’t diminish with age — in fact, it often grows.

He told me about his 88-year-old father who still works in radio, a career he’s loved for 67 years. “If I didn’t have this to do,” his father told him, “I would’ve been dead 20 years ago.” It’s proof that staying engaged in meaningful work can literally be life-sustaining.

"I Tried Retirement — I Flunked"

One of my favorite moments was when Mitch recalled meeting a retiree on a plane who said, “I tried retirement — I flunked.” After a few months of aimless days, he was called back to selectively re-engage with his old job. “Every cell in my being was screaming ‘Hallelujah,’” the man told him. The lesson? Many people walk away from more than a paycheck — they walk away from purpose, relationships, and problems they love solving.

The Dangerous Void: Planning Only the Money

As financial professionals, we often focus solely on the numbers — do you have enough money to retire? But Mitch warned that this leaves out half the equation.

“I’ve done the research. More than 60% of retirees go back to work within a year,” he said. Why? Because they’re not emotionally or mentally prepared. Retirement is often romanticized, but when people suddenly have 168 hours a week to fill — and no plan for how to spend that time — the reality can feel like a vacuum.

To help individuals prepare, Mitch developed tools like My Retirement Reality and exercises such as My Ideal Week in Retirement, where retirees are challenged to fill out 21 blocks of time each week. It quickly becomes clear that golfing every day doesn’t cut it for long.

The Importance of Purpose

Mitch emphasized that financial planning should be built around two core questions:

How do you want to spend your time in retirement?
Do you have the money to pay for it?

You can’t answer the second question until you’ve deeply considered the first. “Money can fund a purpose,” Mitch said, “but it can’t create one.”

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Retirement Coaching: The Missing Piece

One of the most impactful ideas Mitch shared is the growing need for retirement coaching. While we have coaches for everything from business to fitness, few people are coached through what could be a 30-year chapter of life. He’s spent the last several years training advisors to have these conversations, helping clients think not just about retiring from something, but retiring to something.

From “retirement honeymoons” to “reality check” conversations, Mitch recommends a series of check-ins — years ahead of retirement, just before, six months in, and a year later. Retirement is not a one-time decision. It’s a series of choices, pivots, and experiments.

Final Thoughts: The Return on Life

At the end of the day, Mitch reminds us that our ultimate goal isn’t just financial security — it’s about living a rich life. “Return on life,” he calls it: having the best life possible with the money you have. And that begins with having the right conversations, early and often.

If you’re nearing retirement — or guiding clients through that phase — don’t stop at the numbers. Ask the deeper questions. Plan for purpose. And most importantly, realize that retirement isn’t a destination. It’s a new kind of journey.

If you have a question or topic that you’d like to have considered for a future episode/blog post, you can request it by going to www.retirewithryan.com and clicking on ask a question.

As always, have a great day, a better week, and I look forward to talking with you on the next blog post, podcast, YouTube video, or wherever we have the pleasure of connecting!

Written by Ryan Morrissey

Founder & CEO of Morrissey Wealth Management

Host of the Retire with Ryan Podcast

Reframing Your Retirementality With Mitch Anthony

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