Most people will never know what they’re truly capable of—not because they weren’t good enough, but because they were too afraid to try.
I come from a family that played it safe. Same jobs. Same houses. Same routines. They lived comfortably, but cautiously. And I saw the cost: regret, what-ifs, and untapped potential. No one talked about that part. No one warned me that safety can become a prison.
But I chose a different path.
And yes—it was terrifying.
I married at 23, divorced by 25, and remarried at 27. My first marriage felt like a failure… until I realized it was actually a teacher. That crash landing gave me the insight to choose better next time—and here I am, 48 years later, with a life partner I truly love and a daughter I’m incredibly proud of.
Then there was the business. I walked away from a family business at 30 to build something of my own. I wasn’t fearless—I was determined. I wanted freedom more than I wanted security. I stayed self-employed for 35 years. I stumbled, got back up, and never stopped growing.
And then there were the 3 rental properties I bought at 36. A bust. A stress storm. A “bad investment.” But again, the real return was clarity: real estate wasn’t for me, and now I’ll never live with the itch of “What if I’d tried?”
Here’s what I know:
You can choose your life, or let it choose you.
And if you let it choose you, it will always choose safety over joy.
Thoughts From Others
“Twenty years from now, you’ll be more disappointed by the things you didn’t do than the ones you did.” — Mark Twain
I’d go further: When you’re lying in bed for the last time, it won’t be your failed attempts that haunt you; it’ll be the courage you never summoned. The conversations you never started. The dreams you never chased. The parts of yourself you kept hidden because it felt “too risky.”“The only risk you should avoid is the risk of doing nothing.” — Denis Waitley
My father never pursued his passion for art. Never followed that real estate opportunity that could’ve changed his life. I saw his regret firsthand. And it left a mark. Not a warning to avoid risk—but a call to embrace it.
Let Me Be Clear: Taking Risks Isn’t Reckless. It’s Required. You don’t need to quit your job tomorrow or sell your house. But you do need to stretch. Say the thing. Try the thing. Be the person you’re meant to become, not the one the world pressured you to be.
Start small if you have to—but start.
Try something new. Speak up. Say yes. Say no. Show up differently.
That’s how you build muscle. That’s how you take your life back.
Questions For You
Let’s get real:
If you kept all your “regrets” in one jar and “possibilities” in another, which jar would be more full?
What’s something you secretly want to do, but you keep talking yourself out of it?
What story are you telling yourself about why you “can’t”?
What’s the worst thing that could happen if you tried? Could you survive it?
What’s the best thing that could happen? How would that feel?
What’s one tiny risk you could take this week that moves you one step closer?
Final Thought
This isn’t just about career moves or big investments. It’s about the everyday choices that define who we are. Playing it safe is seductive, but playing it brave is transformative.
I’m 75. I’ve lived through losses, failures, and scary decisions. And I wouldn’t trade them for a safer life—not for one second. Full disclosure: I have to admit that they were difficult times, but I learned a lot of life lessons along the way. Because this life—the messy, uncertain, fully lived one—is the one I chose.
What will you choose?
Explore more insights on Cliff Harwin’s Highly Sensitive Thoughts Blog. Each post offers encouragement, practical wisdom, and real-life reflections to help you live with greater confidence, calm, and self-understanding.
