Think You're Almost Ready to Retire?

Steve Sandoval, Ph.D.
Aug 15
5 min read

Read This First.

Written by Dr. Steve Sandoval, Founder | The Flourishing Retiree

Most of my writing so far has focused on people who are already retired; folks who’ve made the leap and are trying to figure out what this new life shift actually looks like.

But this post is for a different crowd.

If you’re not retired yet but are thinking about it, planning for it, maybe dreaming about it while sitting through your third sit-‘n-get meeting of the day, then this one's for you.

Maybe retirement still feels a little out of reach. Maybe it feels a little too soon. Maybe you're wondering if you’ll ever really feel ready. Let me offer some perspective, a personal story, and a few nudges before you decide when and how to take the leap.

You Only Get One Chance

I had a past colleague—a sharp, hardworking, dedicated, kind-hearted professional—who spent her entire career giving her best to the system. I had not spoken with her in a couple years, so I assume she had big retirement plans: perhaps travel, grandkids, gardening, sleeping in past 5:30 a.m., who knows? Her last day of work before retiring was to be May 2026. She passed away unexpectedly this summer.

I still think about her. And she never got to enjoy the retirement she spent decades earning.

It’s a story that haunts me not because it’s dramatic, but because it’s real. It’s a reminder that we don’t have an unlimited number of years to play with.

So, when clients ask, “Should I retire early, if I can?” — my response is this: You at least owe it to yourself to find out.

The Case for Retiring Earlier Than “Normal”

Most people follow the traditional retirement formula: start working around age 20, retire around 65. That’s 45 years of work for maybe 20 to 30 years of freedom—if you're lucky.

But here’s the eye-opener: only the first five to ten of those years are what are called go-go years. This is when you still have the energy, drive, and joint mobility to travel, hike, volunteer, play tennis, take on new hobbies, or learn how to salsa—without needing a nap, a heat pad, or both.

After that? Life doesn’t stop—but it does slow down. And that’s not being negative; that's just biology.

In fact, think of retirement as happening in three distinct speeds for many of us:

Go-Go Years (before ~70): You’ve still got the energy, drive, and mobility to do the things you’ve always said you’d do—travel, take up a new hobby, start something meaningful, or just enjoy your days without a calendar full of doctor appointments.
Slow-Go Years (~70–79): You’re still active and engaged, but the pace shifts. Travel becomes more intentional, routines matter more, and recovery takes a little longer. Life is still full—just with fewer moving parts.
No-Go Years (~80+): These years often bring a slower rhythm. Energy is limited, and priorities shift toward comfort, connection, and simplicity. It's very much still life worth living—but it’s less about chasing new adventures and more about being present for what matters most.

So, don’t wait until your go-go years are already behind you to retire.

The earlier you can step away from the grind, the more of those high-energy, high-joy years you actually get to live on your terms, not your boss’s. Because the worst-case scenario isn’t that you retired early and had extra years to enjoy. It’s that you waited too long—and never got the chance.

No, This Isn’t a Finance Blog—But…

Let me be clear: I’m not a financial advisor, and I won’t pretend to be one. But I am a big believer in getting your financial house in order before you take this next big step. So, before you take the leap, meet with a solid financial advisor—preferably someone who talks to you like a human, not a series of numbers.

Ask questions like:

Can I realistically afford to retire when I want to?
How long will my money last based on different spending levels?
What happens if the market dips? Or inflation spikes?
Should I do a Monte Carlo analysis to stress-test my plan?

Monte Carlo simulations might sound fancy, but they’re just a way to run thousands of possible future scenarios using your financial information to see how likely your retirement plan is to hold up. They’re absolutely worth it! My wife and I did one a year ago and it gave us answers to questions we couldn’t possibly answer ourselves.

And no, this doesn't mean you need to have millions stashed away. It just means you should understand what your money can do for your lifestyle, before you leave that paycheck behind.

Start with Reimagining What Retirement Could Look Like

A solid financial plan is necessary for retirement, but it’s nowhere near sufficient. You can have all the money you need and still feel lost the moment you hand in your keys to HR.

I've met plenty of people who retired financially prepared—but found themselves restless, anxious, or surprisingly flat for several months and years. Why? Because they had no vitality plan. They knew how to stop working, but they didn’t know how to start living differently from their professional identity of 20, 30, 40 years plus.

That’s where a retirement vitality plan comes in. It’s about thinking about how you’ll stay engaged, healthy, connected, and purposeful, before you actually retire.

Ask yourself:

What do I actually want my days to look and feel like?
What brings me energy? What interests or passions do I need to uncover?
Which parts of my life—physical health, relationships, creativity, inner life—could use more care and attention?
How can I structure my time in a way that supports who I want to become?

Sketch out a loose schedule. Something that reflects a balance of structure and flexibility. Include movement, connection, learning, rest, and joy. And then—and this is key—expect it to evolve. Your first few months of retirement will teach you a lot. Stay open to adjusting.

Remember, retirement isn’t just about quitting your job. It’s about stepping into a new role—one where you call the shots.

The Takeaway

If you’re still working and retirement is somewhere on the horizon, don’t just focus on your 401(k), pension, or Social Security estimates. Ask yourself bigger, better questions that make spending that money worthwhile from an existential point of view:

What kind of life do I want in my go-go years?
Am I financially and emotionally ready to leave my career behind?
What’s waiting for me on the other side—and how can I prepare myself—the vitality part of me—to embrace it fully?

And most of all: Don’t wait too long. Life doesn’t guarantee you’ll get to enjoy retirement just because you planned for it. I saw that firsthand, and I don’t want that to be your story.

If you’ve got the means, the desire, and the curiosity—retire early. And get busy living as the captain of your own ship.