Would You Trade Longevity for Legacy?

As I wrote in my guide Position of Success, I believe success is nothing more than the meeting or exceeding of expectations. However, the problem the guide notes is that most people have allowed others to set their expectations. But what if you could live a life of complete fulfillment, reaching the summit of your dreams, experiencing triumph, respect, admiration, and love all before the age of 50… but that was the end? Your life would come to an end.

Would you take it?

It’s a question that doesn’t come with an easy answer. But it’s one that gnaws at my soul after watching Earnhardt, the powerful four-part documentary on Amazon Prime that traces the life and legacy of NASCAR legend Dale Earnhardt. From his hard-nosed rise through the ranks to becoming The Intimidator, to his longing for his father’s approval, his deep love for his family that grew over time, to his tragic death in the final lap of the 2001 Daytona 500, this series is more than just a biography. It’s a mirror. And if you’re paying attention, it forces you to ask yourself: What would I choose?

Dale Earnhardt didn’t just race. He lived at 180 miles per hour. Every turn, every pass, every risk was calculated, and sometimes not. He chased greatness with a fire that didn’t leave room for mediocrity. He became a seven-time NASCAR Cup champion. He was a cultural icon, a man who walked with grit and dignity both on and off the track. He lived with intensity, driven not by fear of death but by fear of wasting a life.

And yet, death came swiftly.

Fifty years old. A legend sealed in time.

Now here’s where it gets personal, and is the question I asked my family member, Mike “Loodie” Rakestraw, last week as we sat and watched the sun set over the same track where Earnhardt lost his life.

Would you take that deal? Fame, family, fulfillment… then silence. No rocking chair years, no golden retirement. Just a life full of success and then impact, then exit.

Or would you trade the thrill of the summit for the long, quiet security of a life that goes on but never soars? Never provides you with the opportunity to meet or exceed your personally set expectations.

It’s easy to say we want to live long lives. It’s hardwired into us. But longevity is not synonymous with meaning. Dale Earnhardt didn’t live a long life, but he lived a loud one. His fingerprints are all over NASCAR, his influence evident every time a driver climbs into a car or grips the steering wheel with both purpose and poise.

There’s a tension here that every person, regardless of profession, age, or ambition, must wrestle with: Would you rather have a life that is long and safe… or one that is short but significant? One that could change the world or, at the very least, the trajectory of your family for generations.

Most of us won’t be asked to choose so dramatically. But we do make choices every day that lean us toward one direction or the other. We choose comfort over courage. Routine over risk. Preservation over passion. And sometimes, we wonder why we feel stuck.

Earnhardt’s story forces us to recalibrate what success really means. It’s not just about trophies. It’s about impact. It's the influence on family, the lessons passed to children or friends, the way you’re remembered in the hearts of those who knew you best, and even those who never met you at all. The knowledge of knowing you met or exceeded your own expectations.

Living to 90 with no regrets is a beautiful thing. But so is burning bright for 50 years and leaving behind a legacy that outlives you by generations. The truth is, no one really wants to choose between the two. We want both. But life rarely gives us that guarantee.

So we ask again, and this time more personally: If you knew you’d only get 50 years, but they would be your 50 years, defined by dreams fulfilled and a life well-lived, would you say yes? Would you say no?

There’s no right or wrong answer. But the question itself may be the most important part. Because it shines a light on what you truly value.

Maybe it motivates you to take that risk. To say what you’ve been holding back. To chase what you've put off. To love harder, lead braver, and live fuller. Whether you’re 25 or 65, the Earnhardt question still stands:

Would you trade more time… for a life that matters more?

And more importantly, are you living in a way today that would make either answer worthwhile?