We’re entering that time of year when people tend to get a bit more reflective. At least I do.

Work slows down, family time picks up, and we’re invited to reconsider what matters most.

Over the years, I’ve explored that question through different frameworks and tools. But none has been as clarifying for me as writing my own eulogy.

Yes—you read that correctly. A eulogy. As in the thing people read when you die.

It might sound morbid, but I found it surprisingly life-giving. Writing down what I hope people will say about me when it’s all said and done—whether that’s next week or fifty years from now—forced me to get honest about the kind of man I’m actually becoming, not just the one I talk about.

It’s the ultimate application of Stephen Covey’s “begin with the end in mind” principle.

I recently revised the version I wrote in 2017 (prompted by Michael Hyatt’s book Living Forward), and I’m sharing it below for two reasons:

1. To encourage a few of you to try the exercise yourself

2. To hold myself accountable to living a life worthy of these words

Here’s what I wrote.

Here lies John—an imperfect man who wouldn’t have wanted anyone to pretend otherwise. He struggled to express his deepest emotions. He battled the fear that he wasn’t enough. And he sometimes failed to prioritize relationships over productivity. But however great his failure, he believed his Savior was greater—and lived with the quiet conviction that God’s grace was always offering him a second chance.

John leaves behind a family who loved him deeply and knew that he would do anything for them. As a husband, he did his best to discern Janell’s heart and help her find outlets for the deep wells of love found within her. As a father, he cherished time with his children and did all he could to help them develop their God-given potential. And as a grandfather, he sought to support his children as they cared for their own.

The line between John’s personal and professional life was blurry, and—though it was messy at times—he liked it that way. He thrived around people who were hungry to grow and consistently found himself in communities that shared this hunger. His family, friends, and business associates all carry stories of moments John created—moments that helped them see more of what they could become—a role he deeply enjoyed.

John was competitive and hated to lose. But somewhere along the way, he decided he’d rather have more losses on his record if it meant fewer regrets when his life was over. To borrow one of his favorite quotes, he strove to be the kind of man “who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.” His hope was that his life might give others the courage to do the same.

Writing this didn’t make me think about death. It made me take stock of my life—honestly and prayerfully.

Increasingly, I believe a life well led is less about what we accomplish and more about whether our actions reflect our values. This exercise helped me see where those are aligned for me, and where there is still work to be done.

If you’re in a reflective season, I dare you to do the same. It won’t be easy. But I can almost guarantee that you—and those you care about—will be better for the trouble. And if you feel called to share it with someone, I’d be honored to read it.

A word from fellow travelers

I suspected that my last newsletter about money would elicit a wide range of responses, and I wasn’t wrong. I’m grateful for the thoughtful conversations that have emerged (and continue) with many of you! While I’ll keep most of those exchanges private, I did want to share a piece of gentle pushback from a reader in Florida, which I thought was spot-on:

“There's an amount of money past which something strange happens. A man may start to hoard it (Smaug), love it (Scrooge McDuck), worship it (golden calf), or use it to get out of human obligations (Troy Chatham; Jayber Crow). Bottom line: a man must remain humble and self-aware about his own vulnerabilities. Even our rosy view of money as a symbol of service has to acknowledge its limitations." 

Very well said—and proof that Florida produces more than just “Florida man” headlines.

Have a Merry Christmas fellow travelers, we’ll talk soon!