My heart almost burst out of my chest the day I crash-landed my plane on a remote Atlantic Island. Then there was the time I crashed my motorcycle in Africa. And I’ll never forget being attacked by a bear while hiking in the Tennessee mountains. But those moments have now become some of my most treasured life stories, illustrations that I was willing to take risks and write my own personal prescription for living my life.

 

My wife, Teresa, has lived her life that way too. We sometimes talk about how we wish we’d met 40 years earlier. Then we consider whether we’d have stayed alive this long; two “go for it” risk takers together during the “no fear” years of youth.

 

Earlier this month, we celebrated the Fourth of July, commemorating the independence our forefathers fought to secure. But their vision wasn’t just about creating a free nation, it was about how we, as individuals, should be able to live within that nation. The freedom to choose our own path, to pursue our dreams, to live according to our deepest values rather than the expectations others place upon us.

 

This truth became crystal clear to Bronnie Ware, who spent years caring for people in their final weeks of life. In her powerful book The Top Five Regrets of the Dying, she reveals the most common deathbed regret: “I wish I’d had the courage to live a life true to myself, not the life others expected of me.” Not financial regrets. Not career regrets. The profound sorrow of realizing they had lived someone else’s life.

 

Think about that for a moment. In our final days, when all pretense falls away, the thing we regret most isn’t what we failed to accumulate, but who we failed to become. The dreams we buried beneath other people’s expectations. The adventures we postponed indefinitely. The authentic self we kept hidden to avoid disappointing others.

 

This insight resonates deeply with my own journey. I’ve spent decades building real estate companies that operate differently from industry norms, often facing skepticism from peers who couldn’t understand why I wouldn’t follow the conventional playbook. I’ve flown my Cirrus aircraft across the continent and ridden motorcycles through countries where most tourists never venture. Yes, these choices carried risks, greater risks than typical vacations, conventional travel.

 

But here’s what I’ve learned: the greatest risk isn’t physical danger or professional uncertainty. The greatest risk is reaching the end of your life and realizing you never truly lived it. As my friend Bruce once wisely told me: “Our greatest regrets are the risks we don’t take, the adventures we don’t create.”

 

I don’t interpret living authentically as living selfishly. Some believe “living your way” means abandoning responsibility to others, but that’s a shallow understanding. Multiple studies confirm that those who love deeply and are deeply loved in return don’t just live happier lives, they live longer ones too. The key is understanding that genuine fulfillment comes from aligning your actions with your core values, not from seeking approval or avoiding difficult conversations.

 

When I look back at my seven decades, do I have regrets? Absolutely. But they’re not regrets about the risks I took or the unconventional paths I chose. My regrets center on the times I wasn’t disruptive enough, when I played it too safe, when I allowed others’ expectations to dim my own inner voice. As I often say, “Politicians pander to the polls, while leaders determine the polls.” The same principle applies to life. We can either react to others’ expectations or create our own authentic path.

 

The balance between risk and reward isn’t just about physical adventures or business ventures. It’s about the daily choice to honor what makes you feel alive, proud, satisfied, and excited about each new day. It’s about recognizing that while a doctor might prescribe medicine for your body, you and you alone write the prescription for your life, for how you live, love, adventure, and leave a legacy.

 

This doesn’t mean reckless abandon. It means thoughtful authenticity. It means asking yourself: What makes me feel truly fulfilled? What impact do I want to have on the world? How can I contribute something meaningful while staying true to who I am at my core?

 

In doing so, the beautiful paradox of authentic living is that when we courageously become ourselves, we give others permission to do the same. When we break free from the invisible shackles of external expectations, we create ripples of freedom that extend far beyond our individual lives.

 

Robert Frost captured this truth perfectly: “Freedom lies in being bold.” The boldness to live according to your own values. The courage to pursue what genuinely excites you. The wisdom to understand that changing the world, no matter how big or small that change might be, begins with the radical act of being authentically yourself.

 

So whatever your age, whatever your circumstances, I challenge you to ask yourself: How would I live differently if I felt completely free to live 100% my way? The answer to that question isn’t just about your happiness, it’s about your legacy. It’s about ensuring that when your time comes, you’ll look back not with regret, but with the deep satisfaction of a life courageously lived.

 

Your prescription for life is waiting to be written. The pen is in your hand. The decisions you make today will define a well-lived life tomorrow.