Write Your Own Obituary Before Someone Else Writes It For You

I watched a man stare at the program from his father’s funeral like it was a financial statement he didn’t recognize. He wasn’t crying. He was scanning.

He traced the bullet list with his thumb: jobs held, awards earned, organizations served. The kind of list that sounds impressive in a room full of strangers.

Then he said something I can’t shake: “This is what we printed. I don’t know if this is what we lived.”

That line is the reason I keep coming back to the exercise of writing your own obituary.

Not because it’s morbid. Because it’s honest.

It forces you to make a decision: are you building a life that reads well… or a life that leaves people steady when you’re gone?

Your obituary is a leadership tool, not a death exercise

Leaders love scorecards. They love dashboards. They love metrics. I do too.

But you and I both know the problem: what you measure is what you get.

If the only thing you measure is output, you will eventually trade presence for production. You’ll trade your marriage for momentum. You’ll trade your kids’ childhood for “just one more quarter.”

Writing your obituary is the simplest way I know to expand the scoreboard.

It makes you name the outcomes that don’t show up on a P&L.

• What did your wife feel when you walked in the door?
• What did your team believe was acceptable because you modeled it?
• What did your kids learn about God, stress, money, and people by watching you?

When you write it down, you stop hiding behind busyness.

You see the gap between your intentions and your patterns.

And if you’re willing to look at that gap without flinching, you can close it.

The words people say about you are already being written in their nervous systems

Obituaries are polite. They’re edited. They’re curated.

What isn’t curated is what people feel in their body when they think about you.

Some leaders walk into a room and the room tightens. Not because they’re evil. Because they’re unpredictable. Because they bring chaos. Because people don’t know what version of them they’re going to get.

Other leaders walk into a room and shoulders drop. The room steadies. The temperature changes.

That’s legacy.

Legacy isn’t the plaque on the wall. It’s the nervous system you leave in other people.

You don’t get that by having good intentions.

You get it by having a standard.

A standard for how you speak when you’re tired.

A standard for what you do when you’re wrong.

A standard for what you do when nobody is watching.

If you want to know what your obituary will really say, don’t ask what you’ve accomplished.

Ask what your closest people have had to learn to survive you.

That question stings, but it’s clean.

The two obituaries: the one you want and the one your calendar is producing

I’ll give you a pattern I’ve seen with high-performing operators.

They can tell you exactly what they want their obituary to say.

• “He was a man of faith.”
• “He loved his family well.”
• “He built people.”
• “He was generous.”
• “He made everyone around him better.”

Then you look at their calendar and there’s a different story being written.

A calendar full of travel, back-to-back meetings, late-night email, and “I’ll make it up to you.”

This is where the exercise becomes useful.

When you write your obituary, you’re not writing poetry.

You’re writing a target.

Then you test your actual life against that target.

Here are the questions I use when I do this for myself:

1. If my obituary says I was present, where is presence scheduled? If it isn’t scheduled, it isn’t real.
2. If my obituary says I was generous, where is generosity budgeted? If it isn’t budgeted, it isn’t consistent.
3. If my obituary says I was faithful, where is faith protected? If I only pray when I’m scared, I’m not leading from faith.
4. If my obituary says I developed people, where is coaching happening on my calendar? Not “leading meetings.” Developing.

This isn’t guilt. It’s alignment.

Your calendar is your obituary in rough draft form.

The legacy that matters is usually small, repeated, and unsexy

A lot of men secretly want a legacy moment.

A big speech. A big exit. A big recognition.

But the legacy that actually lasts is almost always built in small repetitions.

It’s in the way you speak to your wife when you’re late and frustrated.

It’s in whether your kids feel like an interruption or an inheritance.

It’s in how you treat your assistant when the pressure is on.

It’s in the way you handle conflict: direct and clean, or passive and poisonous.

It’s in whether your team feels safe enough to tell you the truth.

When I think about writing my own obituary, I don’t start with what I hope someone says at a microphone.

I start with what I want my family to feel on a random Tuesday.

Because Tuesday is the real scoreboard.

The obituary reveals what you’ve been outsourcing

There’s a subtle trap ambitious leaders fall into: we outsource the parts of life that don’t yell.

We outsource reflection until something breaks.

We outsource emotional presence because it doesn’t have a deadline.

We outsource spiritual leadership because it feels inefficient compared to “getting things done.”

And then one day you wake up and realize you’ve been living on autopilot with the people you say matter most.

Writing your obituary interrupts the autopilot.

It forces you to answer three uncomfortable questions:

• What have I been assuming will “work out later”?
• What have I been avoiding because it’s messy and relational?
• What have I been calling ‘providing’ that is really just hiding?

When I’m coaching a founder, I can usually tell where they’ve been outsourcing by what keeps surprising them.

If every conflict “comes out of nowhere,” you’ve been outsourcing hard conversations.

If your marriage feels like it changed overnight, you’ve been outsourcing emotional check-ins.

If your faith feels thin, you’ve been outsourcing the daily practices that keep you rooted.

Your obituary doesn’t need to be dramatic. It needs to be diagnostic.

How to actually write it (and not turn it into a Hallmark paragraph)

I’m going to make this painfully practical.

Set a timer for 20 minutes. No music. No phone. Pen and paper if you can.

Start with these prompts and write in complete sentences:

1. “He was known for…” (This is about reputation. Not hype. Not branding. Known for.)
2. “At home, he…” (Be specific. How did you show up on normal days?)
3. “Under pressure, he…” (This is where your real leadership lives.)
4. “He handled money by…” (Stewardship leaves a trail.)
5. “He handled conflict by…” (Avoidance is a legacy too.)
6. “He left people…” (Better? Clearer? Safer? More courageous?)

Then write the last line.

Not a quote you saw on a wall.

A sentence you’d be proud for your wife and kids to sign their names under.

After you write it, do one more thing: circle every adjective.

“Loving.” “Faithful.” “Present.” “Strong.”

Those are not traits.

They’re behaviors.

Translate each adjective into a weekly behavior you can measure.

• “Present” becomes “I’m home by 5:30 four nights a week and my phone stays in the kitchen.”
• “Faithful” becomes “I’m in the Word before email, and I’m in church even when business feels heavy.”
• “Steady” becomes “I don’t vent down the org chart; I process up with mentors and peers.”

That’s how the exercise changes your life: it moves from sentiment to standard.

Your future self is begging you to make one decision this week

If you do the obituary exercise well, you’ll see one decision that keeps showing up.

Not fifty.

One.

For some of you, it’s a relationship decision: apologize, reconcile, name the truth, stop avoiding the hard conversation.

For some of you, it’s a boundary decision: stop letting your calendar be run by other people’s urgency.

For some of you, it’s a faith decision: return to God with humility instead of trying to manage everything with control.

For some of you, it’s a health decision: stop treating sleep and training like a hobby.

And for some of you, it’s a leadership decision: stop asking your people to live with standards you aren’t living with.

Here’s what I know.

If you keep postponing that one decision, your obituary will still get written.

It’ll just be written by the patterns you keep defending.

If you want help doing this work with a small group of operators who will tell you the truth and hold you to a standard, Bridge Builder Mastermind is where this work gets done in a small room of operators.

Action Items From Today

1. Write two obituaries. One you want, and one your current calendar is producing. Don’t edit. Tell the truth.
2. Highlight the three phrases you care about most. “Present father.” “Man of faith.” “Steady leader.” Whatever yours are.
3. Audit your calendar for the next 14 days. Circle what supports those phrases. Box what contradicts them.
4. Make one hard trade. Cancel one thing or say no to one request that is stealing the life you say you want.
5. Have one direct conversation. With your spouse, your business partner, or your team. Name the gap you see and the change you’re making.

Five Bridges Challenges

Internal: Where are you tolerating a standard in private that you would never allow publicly? Name it, then put one constraint in place this week.

Relationships: What would your spouse say your “default mode” is when you’re stressed? Ask them, then listen without defending.

Legacy: If your kids wrote your obituary, what would they emphasize? What would they leave out? Pick one small repetition you’re going to start on Tuesday.

Inspire & Impact,

Josh