Why 65 Might Be the Worst Age to Retire

Here's something that might surprise you: after working with over 500 clients, I've learned that 65 is often the worst age to retire.

Not because you'll run out of money. Not because Social Security says otherwise. But because it's a number someone else picked for you—probably decades ago—that has nothing to do with your actual life.

Most people retire at 65 for the same reason their parents did. It's comfortable. It's expected. But here's the reality: nearly half of retirees don't even get to choose their retirement date. The Employee Benefit Research Institute found that 48% leave work earlier than planned due to layoffs, health issues, or burnout. Only 10% retire later than expected.

It's almost a coin flip whether you'll actually get to decide. So banking on "figuring it out at 64" is playing a risky game.

And here's what really should make you think twice: a Transamerica Center study found that among people who delayed retirement, nearly half wish they'd left four years earlier. That's over 1,400 days of alarm clocks, long commutes, and postponing what you actually want to do. These weren't people who retired broke—they were successful professionals who followed every rule except the one that matters most: listening to their own situation.

Think about it like coaching an NBA game. Great coaches don't make substitutions just because the clock says so. They read the court and adjust in real time. Most people just keep staring at the scoreboard, missing what's actually happening in the game.

Here's what separates happy retirees from anxious ones: they don't just ask "Can I afford to retire?" They ask "Can my plan survive the worst-case scenarios?"

Online calculators assume 40 years of smooth growth. When has life ever worked that way?

My client Mark had plenty of money saved but was terrified of retiring during a downturn. So we ran the numbers. We modeled a 2008-style crash. We tested a decade of high inflation. We threw every tough scenario at his plan. Result? It survived 94% of the toughest cases. Even in the worst scenarios, small tweaks let him maintain his lifestyle.

Mark retired two years earlier than planned. Now he says he sleeps better than he did while working.

The tool we use is called the Guardrails Strategy. It's simple:

You need rules that automatically adjust based on what's actually happening, not what you hoped would happen.

Take Adam, a marketing executive making $300,000 a year. He insisted he needed another ten years before retiring at 65. But when we stress-tested his plan, it withstood everything. His real obstacle wasn't math—it was fear of the unknown.

He finally retired at 55. Two years later, he's checked off 12 countries on his travel list and started the photography business he'd always dreamed of. His portfolio has actually grown in retirement.

Even wealthy retirees make this mistake: they ignore their health window until it slams shut.

Here's what the data shows: people in their early 60s spend way more on travel and bucket-list adventures than those in their late 60s. Why? It's not about money. It's about energy.

Would you trade $100,000 for ten extra years of energy and adventure?

Physical capability isn't a forever resource. I've seen clients at 78 with more money than they'll ever spend, but they can't manage the trip to Australia they dreamed about. Your best retirement energy years often peak in your early 60s and fade fast.

If your dream involves hiking, playing with grandkids, or traveling the world, every extra year you work might mean trading time for dollars you'll never use.

Here's the exercise: get brutally honest about your bucket list. Is it active or relaxed? If it's active, the clock isn't just ticking on your finances—it's ticking on your ability to do those things.

One couple dreamed of walking Spain's Camino de Santiago. We compared financing that trip at 63 versus 73. The numbers didn't change much, but the likelihood of enjoying the experience did. They retired at 64 once they realized their health window wouldn't last forever.

Money? Check. Health? Check. But what are you actually retiring to?

Losing your purpose is a silent threat. Suddenly your identity isn't "director of operations"—it's just "retired."

The happiest retirees retire to something, not just from something.

My client Luke had finances and health nailed down but no clear vision for his days after work. I asked him: "If work disappeared tomorrow, would you know what to do with yourself?" He said, "I guess I'll figure it out."

We spent months helping him explore new roles—mentoring, volunteering, trying different activities. Three years later, he's thriving because he built purpose before retiring.

Ask yourself: if you stopped working tomorrow, do you already have activities that will pull you out of bed? Projects, relationships, passions? If not, start building those now, before your last day at work.

Let's recap the three readiness signals:

Financial readiness: Can your plan survive a 2008-style crash and a decade of inflation? Do you have rules for adjusting spending?

Health window: Are you physically capable of your bucket-list dreams today, or are you at risk of waiting until they're out of reach?

Purpose: Are your days filled with things you look forward to—things that use your talents and give you energy?

When these three align, that's your "all systems go" moment. Age is just a number. What matters is your actual readiness, not someone else's timeline.

Here's your action step: lay out your true living expenses and stress-test your finances with tough scenarios. Write out your top retirement dreams and get honest about whether you can do them now or later. If you're not sure what you'd do with unstructured time, start trying new projects now.

Most people discover they're closer than they think—if they just drop the arbitrary milestones and focus on what really matters.

The happiest retirees stop asking "When should I retire?" and start asking "When am I ready?" That shift—from passive to intentional—makes all the difference.

Want to see the full breakdown of these three readiness signals? Visit our website to watch the complete video and learn how to test your own retirement readiness.

Education only, not advice. Consult your professional(s).