Happiness expert Monique Rhodes explains why retirement often feels disorienting at first — and how creating a personal retirement roadmap can turn this transition into one of the most fulfilling stages of life.

Retirement is often marketed as the ultimate reward. After decades of work, deadlines, and responsibility, you finally arrive at a chapter filled with freedom, rest, and happiness.

But for many people, that moment doesn’t feel the way they expected.

In this episode of Retire Today, I sat down with Monique Rhodes, a happiness expert who works with people around the world — especially those approaching or entering retirement — to talk about why this transition can feel unsettling and how to approach it with intention.

Why Retirement Can Feel So Uncomfortable

For years, work provides structure, identity, and a built-in sense of purpose.

Then one day, it’s gone.

Monique explained that retirement often removes all of that at once. “The structure, the identity, the daily sense of purpose — they all fall away at the same time,” she said. What’s left can feel like freedom… or confusion.

In fact, research shows that many people experience lower happiness in the first year of retirement than when they were working. Feelings of restlessness, anxiety, loneliness, and even grief are common — but rarely talked about.

This doesn’t mean retirement was a mistake. It means the transition requires more than financial preparation alone.

Comfort vs. Happiness

One of the most thought-provoking ideas Monique shared is that too much comfort can actually work against happiness.

She described how modern life is designed to remove friction — from climate-controlled homes to effortless entertainment. But living without any “edge” can dull creativity, resilience, and engagement.

“If we’re consistently living in comfort, we lose our ability to adapt,” she explained. Happiness, she argues, comes from a balance — not too tense, not too relaxed.

Monique used powerful metaphors throughout the conversation, from surfing ocean waves to tuning a guitar string. Too loose or too tight, and it doesn’t work. The same is true for life in retirement.

Retirement Is Not a Holiday — It’s a Redesign

Many people enter retirement expecting it to feel like a permanent vacation. Monique sees this expectation create unnecessary disappointment.

“Retirement is sold to us as a never-ending holiday,” she said. “But when that structure disappears overnight, people are suddenly faced with the question of who they are.”

This is where her Retirement Roadmap comes in — a framework designed to help people intentionally rebuild purpose, routines, relationships, and meaning.

Rather than drifting through unstructured time, retirees are encouraged to create days that feel energizing and aligned with who they are now — not who their job required them to be.

Rebuilding Purpose From the Inside Out

One of the most powerful moments in the conversation was when Monique talked about building a new relationship with yourself.

After years of serving careers, businesses, and families, many retirees struggle to answer a simple question: What do I enjoy?

Monique often starts by asking clients to think back to childhood interests — art, music, movement, creativity — and explore those again without pressure. “Your purpose isn’t gone,” she said. “It’s just no longer handed to you by a job description.”

She emphasized that this phase of life offers something rare: the freedom to choose intentionally — where you live, how you spend your time, who you invest energy in, and what brings joy.

Three Questions Worth Asking

Toward the end of our conversation, Monique shared three questions she believes are foundational for a fulfilling retirement:

Where do I want to be that makes me happiest?
What do I want to do that makes me happiest?
Who do I want to be with that makes me happiest?

These questions don’t have one-time answers. They evolve — and that’s part of the beauty of this stage of life.

The Bottom Line

Retirement isn’t just a financial transition. It’s a psychological and emotional one as well.

When approached consciously, it can become one of the most liberating and meaningful chapters of life — not because everything is perfect, but because you’re living with intention.

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About the Author:

Jeremy Keil, CFP^®, CFA^® is a financial advisor in Milwaukee, WI, author of the bestseller Retire Today: Create Your Retirement Master Plan in 5 Simple Steps and host of both the Retire Today Podcast and Mr. Retirement YouTube channel

Additional Links:

Buy Jeremy’s book – Retire Today: Create Your Retirement Master Plan in 5 Simple Steps
Create Your Retirement Master Plan in 5 Simple Steps
Monique Rhodes website
In Your Right Mind Podcast with Monique Rhodes
Monique Rhodes on LinkedIn

Connect With Jeremy Keil:

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Additional Important Disclosures

Designing a Meaningful, Joyful, Purpose-Driven Retirement with Monique Rhodes