Life Advice from a Man Who’s Planning His Death
Let’s get one thing straight: I’m not dying anytime soon. At least, I hope not. But I’ve spent a lot of time thinking about it—probably more than your average 35-year-old startup founder with a mortgage, a podcast, and an app designed to outlive me. And yes, that sounds a bit weird when I say it out loud.
Why? Because planning for death forces you to focus on what really matters. It’s like a brutal spotlight shining on the core of your existence, and spoiler alert: it’s not the number of Instagram followers you have, the car you drive, or how quickly you climbed the corporate ladder. It’s not about the fleeting validation of a like, or the temporary satisfaction of a new acquisition. It’s about something far more lasting, something far more meaningful.
Death strips away all the BS, all the pretense, all the shallow pursuits that we spend so much of our time on. It leaves you with one brutally honest question:
What kind of legacy am I leaving behind?
Lesson #1: Forget Fame—Love Is the Only Legacy That Matters
Let’s face it: society trains us to chase the wrong things. Fame. Fortune. The perfect flat-lay photo of avocado toast. We spend so much of our lives climbing ladders—career ladders, social ladders, even the stairway to a beachfront Airbnb. But when you’re gone, when you’re dust, none of that crap matters. Trust me on this, I’ve seen too many people chase shadows, only to find they’re empty when the light goes out.
Here’s the truth, the raw, unfiltered truth:
- Your followers won’t miss you. They’ll double-tap your vacation pics and forget about you when someone posts a better sunset. They’ll be onto the next influencer, the next viral trend. Your digital imprint will fade quickly, like footprints on the sand at high tide.
- Your LinkedIn network won’t cry at your funeral. Your coworkers might send flowers, but only if HR reminds them. And let’s be real, they will probably just be there to network, not because they truly care. They’ll be back at their desks, chasing their own promotions, before the ink on your obituary is dry.
The only people who will genuinely grieve for you, who will feel your absence down to the marrow of their bones, are the ones you loved deeply and who loved you back—your kids, your partner, your best friend from high school who still remembers your bad haircut phase. Those are the connections that count, the bonds that withstand the test of time.
That’s where your legacy lives: in the love you give, not the stuff you leave behind. Not in the zeros in your bank account, or the accolades on your resume, but in the genuine, heartfelt connections you make and the lives you’ve touched with kindness and compassion.
Lesson #2: Success Is a Moving Target, So Stop Chasing It
If there’s one thing thinking about death teaches you, it’s that success isn’t a destination—it’s a journey. It’s a mirage on the horizon, always just out of reach. You chase it, you grasp for it, but you never truly arrive. There is always some new goal to reach, some new milestone to achieve.
Sure, you can set goals. Build a business. Win awards. But the second you hit one milestone, there’s always another one waiting for you. It’s like trying to finish Netflix—impossible and exhausting. You’ll always be chasing the next episode, the next binge, and never truly satisfied.
Success is about something deeper, something more profound. For me, it’s about creating something that outlasts me. Something that makes life better for the people I love. That’s why I built Wills.com—not to get rich, but to ensure that my kids, my wife, and the people I care about never feel unprepared or unsupported when I’m gone. It’s about creating a framework that will continue to offer them guidance, support, and security, long after I am no longer around.
Lesson #3: Don’t Be Afraid of Failure—It’s the Best Teacher
You know what’s worse than failing? Not trying. Living a life of quiet desperation, wondering what could have been, and what might have been if you had been just a little bit braver. That’s the real tragedy. It’s not the fall, but the fear of falling that keeps you from rising.
I’ve started businesses that flopped. I’ve made decisions that tanked. I’ve screwed up relationships and embarrassed myself more times than I can count. And you know what? Every failure taught me something. Every stumble was a lesson in disguise, and every misstep propelled me forward.
- Mistakes are tuition for wisdom. You pay for the lessons, but they’re worth it. Each mistake is a chance to learn, adapt, and grow. It’s the real-world education that textbooks can’t provide.
- Fear of failure is a prison. It keeps you small, it keeps you timid, and it keeps you from reaching your full potential. It locks you in a cage of “what ifs.” Let it go. Break free from the chains that hold you back, and embrace the unknown with open arms.
When you think about life through the lens of mortality, failure doesn’t seem so scary. Because at the end of the day, you’re going to die whether you succeeded or not. So, you might as well take the risks that matter, the risks that align with your true purpose, and the risks that can provide you with the greatest reward.
Lesson #4: Plan for the Inevitable, but Live for the Now
Here’s the irony of planning your death: it makes you appreciate life more. It’s a paradox of sorts, that by acknowledging your mortality, you become more aware of the preciousness of every moment, and your time on this earth.
I’ve spent hours creating a failsafe for my family—an app that sends them videos, files, and even cash when I’m gone. But those hours also made me realize how precious the present is. I’ve come to understand that the future is uncertain, and the past is gone. So the only real moment we have, is the here and now.
It’s a cliché, but it’s true: the only moment you have is this one. So, put down your phone, the constant source of distraction, and stop living vicariously through other people’s curated lives. Go outside. Feel the sun on your skin. Tell someone you love them. Share a laugh, and a good meal. Eat the carbs. Don’t wait for the perfect moment, because it might never arrive.
Lesson #5: Legacy Isn’t About Stuff. It’s About Stories.
When my dad passed away, he didn’t leave a will or even a letter. He left a void, and my brothers and I were left trying to untangle his life while grieving his death. It sucked. It was a mess, and it was emotionally draining, but it also taught me a hard truth:
The most valuable inheritance isn’t money—it’s the memories, values, and wisdom you leave behind. It’s the stories that shape us, the lessons that guide us, and the love that sustains us.
That’s why my app lets you record videos for your loved ones. Not because I think they need a reminder of what I look like—I’m sure they get enough of that, but because I want them to hear my voice, my stories, my advice. I want them to know that:
- Life is tough, but they’re tougher. They have the inner strength and resilience to navigate anything that comes their way.
- It’s okay to fail, as long as you keep trying, learn from your mistakes, and never give up on your dreams.
- And never, ever trust someone who doesn’t eat carbs. It’s a sign of a serious character flaw, and also a clear sign that they don’t appreciate the finer things in life.
Lesson #6: Don’t Take Yourself Too Seriously
Look, I know all this talk about death and legacy can get heavy. It can feel like a deep dive into the existential void, but here’s the thing: none of us get out of this alive. So, you might as well laugh along the way, embrace the absurdity of it all, and find joy in the ordinary moments that make life worth living.
That’s why my first posthumous video to my kids starts with:
“If you’re watching this, I’m dead. But don’t worry—you’re still stuck with my dad jokes.”
Humor is part of my legacy, too. Because if I can make the people I love smile—even after I’m gone—that’s a win in my book. It’s a way to continue to connect with them, and to show them that even in death, love and laughter can endure.
The Takeaway: Life Is a Gift. Use It Well.
If you take one thing from this article, let it be this: your time is limited, so spend it on what matters. Don’t waste your precious energy on things that don’t fulfill you, or on people who don’t appreciate you. Focus on what truly resonates with you, what makes you feel alive, and what allows you to leave a lasting impact on the world.
Love deeply. Fail gloriously. Share your wisdom. And when the time comes, leave a legacy that’s more than just stuff. Leave behind a tapestry of memories, experiences, and love that will continue to inspire, comfort, and guide those you leave behind.
Because life is short, but love? That’s forever. It transcends time, space, and even death itself.
Are You Ready to Build Your Legacy?
Download the Wills app today and create a failsafe for the people you love. It’s not about immortality—it’s about making every moment count, about living a life that is rich in love, meaning, and purpose, and about extending that love and purpose into the future.
