👋 Welcome
Hope everyone had a great week!
This week our main feature focuses on the decision to create memories from unfulfilled dreams.
Take action this week!
🌟 Words to Inspire
“It’s never too late to become who you might have been.”
— George Eliot
📖 Deathbed Regrets
I don’t mean to sound morbid, but I want to discuss what has been motivating me to make some significant changes over the past couple of years... and hopefully provide inspiration if you are in the same place I was.
It started on a long drive this week, just me and my thoughts, when a semi truck roared past me on the highway. I was thinking about this exact story and wondering if “Deathbed Regrets” was too heavy a title for a newsletter. Then I saw it, plastered across the back of the trailer in big bold letters:
"Die with Memories, not Dreams"
I laughed out loud. Sometimes the universe doesn’t whisper - it yells past you at seventy miles per hour.
For as long as I can remember, I carried over year to year a list of dreams:
- Retire early enough to actually enjoy life.
- Earn my master’s degree from a university I could feel proud of.
- Build a flexible online business.
- Get healthy and lose the weight.
- Travel often and meaningfully.
- Become a real guitarist, not just a guy who fiddles around.
But here’s the thing - by age 60, I hadn’t accomplished much of that list.
Don’t get me wrong - I’ve had a vibrant and blessed life. I married the sweetest woman on the planet. We raised four great kids who have blessed us with nine grandkids, whom we absolutely adore. I’ve had business successes and faceplants, joyful seasons and some that tested everything I thought I knew.
In other words, I am simply an ordinary human.
So, why did some dreams get chased while others sat on the shelf? Maybe fear. Maybe timing. Maybe just life getting in the way of living. But here’s what I’ve come to believe:
"The past is just information, it is not a prison sentence. The present is an opportunity. And the future? That’s where the magic happens".
Once I hit 60, those “deathbed regrets” quotes started hitting differently. You know the ones: “What will they say at your funeral?” “Don’t leave your music still inside you.” “Live like you’re dying.”
They stopped sounding like clichés and started feeling like instructions.
I didn’t want to be the “remember when” guy at the bar, or the "armchair quarterback" critiquing other people’s lives. I didn’t want to follow others who succeeded while my own dreams gathered dust.
I wanted to become something else entirely: a quiet example of what’s possible when an ordinary person chooses to fill their life bucket to the brim with memories.
So I started.
- I applied to the University of Florida's Master's program in Entrepreneurship. I got in. I’m graduating in December 2025.
- I faced my fear of public speaking, entered pitch competitions, and even won a few.
- I launched Retirepreneur.com.
- I lost weight. I hike, walk, bike, and do Pilates with Shari.
- I committed to traveling somewhere every month in 2026 and beyond, even if it’s just for a few days.
- And yes, I’m still working on my guitar chops. That one might take a little longer.
If I can accomplish all of this, and still show up as a loving husband, father, and “Pappy”, then I’ll leave this world full of stories, not regrets. I’ll have lived a life of joy, momentum, and meaning. And I’ll be the old man whose grandkids roll their eyes, but hopefully smile, when I start yet another story down memory lane..
Here’s the honest truth:
If I can do it, so can you.
You don’t need to be special. You don’t need permission.
You just need to start filling that bucket with stories, adventures, and choices that feel true to you.
So I’ll ask you, what the truck that flew past me asked:
What’s still sitting in your dream bucket… waiting to become a memory?
🧰 Weekly Resource
Need a roadmap for what’s next? Our Essential Guides, straight from the Retirepreneur blog, share actionable ideas to help you take the next step in building a purposeful and fulfilling second act.
Here’s a quick look at the six core guides:
- Retirement Entrepreneurship - step-by-step advice to turn your experience into a flexible, purpose-driven business.
- Flexible Work Options - remote jobs, freelancing, and part-time roles designed for freedom and simplicity.
- Purposeful Living - find meaningful ways to give back, mentor, or pursue work that matters to you.
- Business Resources - simplify the tech and tools behind your second-act venture—from websites to invoicing.
- Financial Wellness - build income without risking your retirement. Smart tips on budgeting, taxes, and planning.
- Personal Fulfillment - explore hobbies, creative passions, and legacy projects that bring joy to everyday life.
🔗 Browse all 6 Essential Guides: Retirepreneur.com/retirepreneur-guides
📝 Action Challenge
This week, take a 20-minute “life audit” session. Jot down 3 dreams you’ve shelved and write one small step you could take toward each. Action clears regret faster than reflection.
💡 Quick Tip
Take two minutes to explore the Retirepreneur website - you’ll find tools, stories, and ideas designed to spark your next move. Sometimes all it takes is one page to reignite a dream.
🛑 Parting Words
I hope you enjoyed this weeks newsletter and most importantly, you take one action step towards creating "memories" to last a lifetime!
Best wishes!
💁 That’s a Wrap
When you’re ready, here are ways that Retirepreneur can help:
🚀 Explore the Retirepreneur Hub
You don’t have to build your next chapter alone. The Retirepreneur Hub gives you access to step-by-step tools, trusted guidance, and practical resources to turn experience into income... at your pace, on your terms.
📝 Explore the Action Guides
Need help taking that next step? Our free Retirepreneur Action Guides give you simple, proven frameworks to move from dreaming to doing—on your terms and timeline.
📘 Read the Founder Story
Wondering if it’s too late to start? Read Curt’s journey from retirement to reinvention and discover how purpose and freedom are still possible at any age.
