What would you do if you knew you had 3000 weeks left to live?

Last month I turned three dozen years old.

My home office was being redesigned at the time - now a double office with my wife, the beautiful Emily Milazzo, who is now back to working part time as a charitable foundation trustee after spending years mostly at home with our young children (who are now all in elementary or pre-school). The office now looks incredible, with ample lighting, space for both our desks, and a glass whiteboard on the wall to doodle on ideas away from screens.

My desk, sitting diagonally across from my wife’s.

A little seating area in the corner between us.

A whiteboard space to come up with ideas.

As happy as I was with the new digs, I did want to add one visual element added for the home office before we wrapped the project.

Choosing projects with my mortality in mind

After I read my friend Chris Anselmo’s post on What Really Matters in the End, which in turn points to the classic Your Life in Weeks concept from Tim Urban, framing and hanging up a Your Life in Weeks poster in my office became important.

It hits different to think about our life as a series of weeks that can be crossed out on a single poster and see how much of my expected life span has been used up already.

As I framed the poster and filled in the weeks already passed, I thought of those who never had the “expected” amount of time. At this point, I’ve already received more time here on Earth than Jesus, and my college roommate Jimmy.

In the next five years, I’ll also pass Martin Luther King Jr. and Kobe Bryant.

Three of my grandparents made it to 80+ years old, while a fourth died of cancer in his 60s. I am fortunate enough to be in good health and have relatively strong genetics, so the John Hancock Life Expectancy Calculator says I can expect to live to 95, but that is by no means a guarantee. Death can come unexpectedly.

¹⁵ As for man, his days are like grass;
he flourishes like a flower of the field;
¹⁶ for the wind passes over it, and it is gone,
and its place knows it no more.

- Psalm 103

Lament from an ancient Hebrew king doesn’t do it for you? Fret not, I have another.

What we do in life echoes in eternity.

- Maximus, “Gladiator”

Let’s say I do get those 95 years. That would leave me with ~3000 weeks left to invest. How will I look back at those weeks I was given to be alive?

Drivers and Constraints

Reflecting on the brevity of life helps me focus on what truly matters. With this in mind, I’ve been reevaluating how I approach my work, guided by both what drives me and the constraints I face.

My first startup taught me that chasing personal growth, validation, and financial freedom often comes at a steep cost. Over eight years, I scratched false expectations off my list, making little money and enduring significant stress. With four children now depending on me, my risk tolerance has shifted dramatically. I’m no longer willing to gamble my family’s security or sacrifice my time and energy chasing shallow goals.

So, within the constraints of providing both time and attention for my family, it raises the bar on the quality of the idea that’s required to take the risk to build again, and lowers the risk tolerance for anything less than ideas that will kill me not to try.

When I do latch onto one of those ideas, I’m aiming to have more validation and less risk in place by the time I make anything a full time focus. Within that framework, I can think of my use of time as investing those 3000 weeks.

Is this project, role, or next full-time startup effort (gasp!) worth the precious investment of my limited time on Earth?

Time investment checklist

• Will I get to spend more time around interesting and enjoyable people?

• Will I look back and know I made some small difference for humanity’s benefit?

• Will I look back and know I made a large difference for my family’s benefit?

• Will I regret not giving this project a shot when I’m on my death bed?

• Will I hear “Well done, my good and faithful servant” from God if my Christian worldview proves true after death?

We all have a finite amount of weeks to expend. Setting the bar at wealth and status for my first startup wasn’t too big a vision; it was too small. For me, it’s now about seeking the right battles, embracing what truly matters, and striving for a life that echoes well in eternity. That’s my new definition of Worthwhile.