I Graduated at 63: Lessons About Second Acts
👋 A PERSONAL NOTE FROM CURT
Hey everyone,
This isn't the typical newsletter format. No featured article. No action plan. Just me, wanting to share something personal after an incredible weekend.
Saturday, I crossed the graduation stage at the University of Florida and received my Master of Science in Entrepreneurship.

But that's not really what I want to talk about.
🎓 EIGHTEEN MONTHS AGO
When I told the family I'd been accepted to UF's graduate program, my oldest granddaughter asked:
"Pappy, why are you going back to school? I thought you retired and weren't going to do anything."
Out of the mouths of kids, right?
I told her: For years I'd talked about getting my master's from a prestigious school like the University of Florida. About building a lifestyle online business on my terms. These were "someday" dreams.
Then I retired at 61 and realized: someday is now. Either I do these things, or I keep talking about them forever.
Shari and I decided long ago that we're committed to living life without regrets. That means when we say we're going to do something, we actually do it. Even when it's scary.
This past Saturday, that same granddaughter watched me cross the stage and accept my diploma.
That's what matters.
💡 WHAT I ACTUALLY LEARNED
The straight A's were great. The $10,000 in grants from a business plan competition felt validating. The Entrepreneurial Spirit Award was an honor.
But here's what actually mattered:
The dream was never about the degree — It was about proving to myself that I could do hard things at 63. That "too old" is a story we tell ourselves, not a fact.
Fear doesn't dissipate — I thought it would go away as I got comfortable. It didn't. I just got better at walking through it. That's the actual skill worth developing.
I built a foundation — While in school, I focused on creating value: this newsletter, the FREE Hub, blog content, the podcast. I built a community of 1,800+ people thinking about their second acts.
Now that school is over, I can really focus — Here's the truth: I haven't monetized Retirepreneur yet. That was intentional. While juggling coursework, I needed to build the foundation first.
Now I can do the deeper dive into what's really needed. Create the unique value proposition that makes this genuinely useful—not just another platform promising quick fixes. And I'm doing this in real time. You'll see me figure it out, make mistakes, adjust, and keep building.
🚀 WHAT'S NEXT: BUILDING THE LIFE WE WANT
Here's the thing about living without regrets: it's not just about work.
Starting in January, I'm launching Coffee with Curt — a YouTube Shorts series documenting my journey building Retirepreneur from day one. Not the polished version. The real thing. Strategy sessions. Failures. Pivots. Wins.
I want you to see what building a second-act business at 63 actually looks like. It's messy, uncertain, and absolutely possible.
But here's what else Shari and I are doing:
We've decided to travel to new places in 2026. Not "someday when we have time." Now. The business comes with us. That's the point of building something online.
I'm going to really learn to play guitar. I've owned guitars for years and dabbled just enough to convince myself I could play. But I've never put in the real work to get good. That changes now. I want to pick up an instrument and actually make music, not just fumble through three chords."
And my former partner from the Westmont Homes days keeps trying to talk me into riding another century ride. A hundred miles on a bike at 63? The old me would've said "those days are over." The new me? I'm seriously thinking about it. Or maybe a metric century🤣
🎯 WHAT THIS WEEKEND WAS REALLY ABOUT
This weekend wasn't about checking a box or adding credentials to LinkedIn.
It was about standing in front of my family and proving something I've been preaching: that second acts are real. That you're never too old. That fear is just part of the process, not a stop sign.
But it's also about showing them—and you—that life after 55 can be expansive, not contracting.
Shari and I could've settled into quiet retirement. Nobody would've judged us.
Instead, we're choosing energy. Growth. Adventure. Purpose. Living.
That's what "no regrets" really means. Not being reckless. Just asking yourself: "What do I actually want to do with this time I have?" And then doing it.
💪 WHAT I WANT YOU TO TAKE FROM THIS
If you're thinking "I'm too old to start something new"— you're not!
If you're wondering "Is it too late?"— it is not!
If you're asking "Can I really build something meaningful at this age?"— you can!
I'm not special. I'm a 63-year-old CPA who decided that retirement meant beginning, not ending.
And I'm still figuring it out. You don't need it all figured out before you start. You need to start while you're figuring it out.
The degree on my wall isn't proof that I was ready. It's proof that I was willing to try even when I felt unready.
🎸 THE BIGGER PICTURE
You know what Shari said after the ceremony?
"I'm proud you did this. But I'm more proud that you're not done. That you're still curious. Still wanting to grow. Still willing to be a beginner."
She's right. The degree matters less than the mindset that got me to pursue it. The achievements matter less than the decision to keep learning, keep trying, keep living fully.
So yes, I'll be building Retirepreneur into something valuable and sustainable. But I'll also be learning guitar. Training for that century ride (maybe). Traveling with Shari to places we've never been. Spending time with nine grandkids who now know that Pappy doesn't just "not do anything" in retirement.
This is what second acts look like. They're not just about work. They're about creating a life that's full—of purpose, adventure, growth, and zero regrets.
📅 BACK TO NORMAL NEXT WEEK
Next Tuesday, we'll return to our typical newsletter format with practical strategies for building your expertise-based business.
But I wanted to share this moment first.
Because if even one person reading this decides to finally start that thing they've been putting off, finally take that first scary step, finally choose expansion over contraction—then Saturday was worth every late night and every moment of doubt.
You've got decades of experience. You've got skills that matter. You've got time to build something meaningful.
Keep building. Keep living. No regrets.
Curt
P.S. — Quick funny story. During our celebration BBQ one of the grandkids blurted out with a cute laugh "why did you go to school... to learn? you're like a 100 years old" 🤣
Retirepreneur: Because retirement isn't the end of your story—it's the beginning of your next chapter.