Retirement Isn’t Broken. It Was Never Real.
Why chasing freedom at 65 keeps millions stuck—and what actually works
- Sonoran Sunset by yours truly. (It’s a desert, an oasis.)
Worried about money, your job, or whether you’ll ever be able to retire? You’re not alone. Millions of Americans feel trapped—working jobs they don’t love, running businesses that drain them, and quietly worrying about what happens if the paycheck stops.
Let me offer some peace of mind.
Retirement, as most people imagine it, is largely a myth.
Now, if you’re a financial advisor, let me explain myself before you grab the bat.
I’m not saying people don’t retire. Many do. Some love it. But the idea of retirement—the finish line where stress disappears and meaning magically appears—was invented for a different world.
An industrial world. One that no longer exists.
The modern concept of retirement showed up in the late 19th and early 20th centuries, when factory work physically broke people down and life expectancy was much shorter. Retirement was designed as an exit ramp for worn-out bodies, not fulfilled lives.
Fast forward to today. We’re living longer, working less physically demanding jobs, and being sold a dream that fewer and fewer people can afford.
Most Americans are nowhere near financially prepared for retirement. Federal Reserve data makes that clear. And here’s the part that rarely gets talked about: even among those who retire comfortably, many report boredom, loss of identity, depression, or a dull sense of emptiness within a few years.
So they go back to work.
Or they volunteer.
Or they drift.
I know this because I’m 64.5 and living it. And because a hunch I had 30 years ago has now proven itself.
Solving for retirement isn’t the real problem. Finding meaningful, sustainable work is.
Look at people in the so-called Blue Zones. They don’t even have a word for retirement. According to research popularized by Blue Zones, wealth is measured by purpose, not portfolio size. Work doesn’t end. It evolves.
Work isn’t the enemy. Meaningless work is.
I see this every day with my coaching clients—most of whom are half my age. They want purpose and meaning more than money. They want a quality of life that doesn’t grind them down before 50.
I learned this the hard way. Slowly. Over decades.
In my early 30s, I worked as an independent retirement planner and later at Merrill Lynch. I was successful. I built trust. I did right by my clients. I understood sales. I understood systems. I had more hair.
What I didn’t understand was life.
I was working for money and purpose while constantly worrying I wasn’t good enough, rich enough, happy enough, or successful enough. Fear was my fuel.
Being motivated by fear instead of love is a slippery slope into a dark abyss. Unfortunately, fear controls most of us until we wake up.
Most of my clients who wanted to retire didn’t love their work. Many were twice my age. I was helping them prepare for a future I hadn’t lived yet.
The real education came two years after they retired.
The call usually sounded like this:
“Hey, Cliff, we need to come see you. Retirement’s been great… but Johnny’s bored playing golf. He’s sitting around the house pouting. We’ve traveled enough. We need a new plan. Oh—and we could use some more income.”
Those calls fueled my hunch: retirement felt unreal. Like an oasis in a scorching desert—beautiful from afar, but often a mirage up close.
Now, in my mid-60s, I know that hunch was right.
We’re being sold an illusion by a massive wealth-management marketing machine. Fear is profitable. Anxiety sells. The promise is simple: work hard now, suffer through decades you don’t enjoy, and someday you’ll be free.
But free to do what, exactly?
Free to do what you want, when you want, within the limits of your lifestyle. To afford a life you actually enjoy.
If retirement simply means “stop working,” what replaces the structure, identity, social connection, and sense of contribution that work provides?
That’s the question the glossy brochures never answer. Where’s the purpose?
Some of the most successful people alive rejected the idea outright. Actor Clint Eastwood put it plainly: “The idea of retiring is absurd.” Investor Warren Buffett said for years he’d keep doing what he loved as long as he could—and largely did.
This isn’t about glorifying hustle or denying rest. It’s about realism.
If you love your work, why would you stop—unless your health forces the issue or the job physically breaks you down?
The real problem isn’t retirement. It’s a culture that disconnects people from meaningful work. But once you understand the rules of the school of life, you can stop blaming the culture and start choosing differently.
Americans are taught to chase income, attention, fame, and fortune first—purpose later, if ever. This mindset is reinforced by Wall Street, private equity, and financial institutions that profit from fear-based planning.
Here’s a simpler, more durable solution:
Know yourself.
Know your values.
Be aware you have a purpose.
Find work you enjoy and can adapt over time.
Spend less than you make.
Save and invest the difference.
Never stop evolving.
Do that, and retirement anxiety largely disappears.
You’re no longer dependent on politicians or the long-term solvency of the Social Security Trust Fund. You stop counting the days until escape. You build a life that works now—and later.
Real wealth isn’t a number in an account.
It’s knowing yourself.
It’s understanding your unique gifts.
It’s having something meaningful to wake up for.
That’s freedom without illusion.
I’ve lived this way since 1991, when I quit my corporate job at 30.
Retirement isn’t a destination. It’s a story we were sold.
The truth is simpler: retirement promises freedom.
So why wait until you’re old to claim it?
That’s when fear finally loses its grip.
I’m an author, strategic coach, and mentor. Discover the power of the Clarity S.H.I.F.T. Method® for improving yourself, your career, business, and life at www.CliffordJones.com.