Five years ago, I sat in my empty home office, staring at a box of desk supplies I’d cleared out from my corporate cubicle. The company had downsized, and at 62, I found myself “retired.” That word felt like a death sentence rather than freedom. Little did I know that moment would mark the beginning of one of the most transformative chapters of my life.

If you’re reading this and feeling like it’s too late to start over, too late to chase that dream, or too late to become who you really want to be, I’m here to tell you something important: sixty-five isn’t an ending. It’s a plot twist.

The myth of being “too old”

We live in a culture obsessed with youth. Every advertisement, every success story seems to feature someone half our age. But here’s what nobody tells you about starting fresh in your sixties: you’ve got advantages those twenty-somethings can only dream about.

You’ve survived heartbreak, loss, triumph, and everything in between. You’ve probably raised kids (mine are 38, 36, and 33 now), navigated career changes, and learned that most of what we worry about never actually happens. That’s not baggage – that’s wisdom.

When I decided to learn Spanish at 61, my daughter laughed. “Dad, you can barely remember where you put your reading glasses.” But you know what? My son-in-law’s mother cried when I wished her feliz cumpleaños in her native language last month. Sometimes the best moments come from the things we start “too late.”

Embracing the uncomfortable truth about regret

Let me be brutally honest with you. I missed too many school plays. Too many soccer games. I told myself I was providing for my family, but really, I was hiding behind spreadsheets and conference calls. That regret still stings, especially when I watch my five grandkids and realize what I missed.

But here’s what I’ve learned: regret can either paralyze you or propel you forward. At 65, you can’t change the past, but you sure as hell can refuse to repeat it.

Finding purpose when the old one expires

After my early retirement, I went through what I can only describe as a mourning period. For forty years, I knew exactly who I was: the guy with the answers, the problem solver, the provider. Suddenly, I was just another guy in sweatpants watching daytime TV.

That hit hard. Some mornings, I couldn’t see the point of getting out of bed. My wife would find me staring at the wall, and we both knew something had to change.

That’s when I started writing. Not because I thought I was particularly good at it, but because I needed to make sense of this strange new world where my calendar wasn’t packed with meetings.

Five years ago, I started journaling every evening before bed. Those scribbled thoughts eventually became articles, and those articles became a new identity: not the retired executive, but the guy who helps others navigate life’s second acts.

The unexpected gifts of starting over

That pottery class where I met my wife forty years ago? I was terrible at it. My bowls looked like abstract art pieces (and not in a good way). But showing up to that class, being vulnerable enough to fail at something new – that’s where the magic happened.

Starting over at 65 means you get to be bad at things again. You get to ask questions without worrying about looking stupid. You get to explore interests you buried under decades of responsibility.

Practical steps for your own new beginning

So how do you actually do it? How do you begin again when everything in society tells you to slow down?

Start small. Pick one thing you’ve always wanted to try. Not ten things – just one. Maybe it’s painting, maybe it’s learning to code, maybe it’s finally writing that novel. The what doesn’t matter as much as the starting.

Find your people. The biggest surprise of my sixties has been discovering how many of us are going through the same thing. We’re all trying to figure out who we are when we’re no longer defined by our careers or our roles as active parents.

Give yourself permission to suck at it. Whatever “it” is. You’re not competing with anyone. You’re not trying to become the world’s expert. You’re just exploring what lights you up.

Document the journey. That journal I write in every night? It’s become my roadmap for understanding this new chapter. Some entries are one sentence. Others are three pages of rambling thoughts. All of them matter.

The courage to be a beginner

Last week, my fourteen-year-old grandson tried to teach me some video game. I was absolutely terrible. He was patient, explaining the controls for the fifth time while I accidentally walked my character off a cliff again.

“Grandpa,” he said, “you’re really bad at this.”

“I know,” I laughed. “Isn’t it great?”

That’s the secret nobody tells you about being 65: you’ve earned the right to be terrible at new things. You’ve proven yourself in a thousand different ways. Now you get to play.

Final thoughts

Beginning again at 65 isn’t about pretending you’re thirty. It’s about recognizing that you’ve got decades of life experience and, hopefully, a couple more decades to use it in new ways.

Every morning when I wake up, I have a choice: I can mourn the life I’ve left behind, or I can get curious about the life that’s waiting for me.

These days, I choose curiosity. And let me tell you, it makes all the difference.