How to Live With No Regrets

Jodi Wellman was a senior vice president of operations at a national fitness chain — good money, good title, good parking spot — when her stapler ran out. She walked to the storage room, loaded a fresh row of staples, and made herself a promise as she clicked the lid shut: I’ll be gone before this row is done. She walked back to her office feeling electric. Then she did nothing. A year later, same stapler, same storage room, same promise. It took three rows of staples before she left. She still has the stapler.

Here’s what I didn’t expect from this conversation: the woman who literally counts her remaining Mondays — she had 1,707 left the week we recorded — is not fearless. She calls herself a professional dream-delayer. She has a fiction project she’s terrified to put into the world (so do I, it turns out, and we get into that). The difference between Jodi and the rest of us isn’t courage. It’s that she keeps a skeleton at the door on purpose, because she’s learned that nothing else gets her moving. Her mom died in her late 50s with manuscripts unmailed and businesses unstarted, and Jodi spent days throwing away the evidence. She decided she’d rather be poked in the ribs by the Grim Reaper every Monday than end up there.

We talk about all of it — the mortality math, the eight lessons of people who almost died, the Land of Dormant Intentions, why “find your passion” is the wrong assignment, and what to do before the staples run out.

About Jodi Wellman: Jodi is a speaker, the founder of Four Thousand Mondays, and the author of You Only Die Once: How to Make It to the End with No Regrets — endorsed by Adam Grant, Martha Beck, Daniel H. Pink, and Arthur Brooks. A former fitness-industry executive turned leadership coach, she studied positive psychology in grad school and now speaks and writes about squeezing the most aliveness out of a finite life. Her next book, Ask the Reaper: Advice for People Who Might Die Someday, arrives in fall 2027.

The average life contains about 4,000 Mondays. Jodi checks her remaining count every week — not to spiral, but because of a concept from her research called temporal scarcity: when we see an asset as limited-time-only, we treat it differently. We do this instinctively with money, with sales, with parking meters. We refuse to do it with the only asset that actually can’t be replaced. The count isn’t morbid. It’s a unit of urgency.

“Temporal scarcity is this concept where if we look at any asset and we recognize it’s limited time only, we value it more. And that’s exactly true for life.”

Jodi describes the dream you’re postponing as a key you’re already holding — you just won’t turn it in the lock. And the reason isn’t the laundry, the kids, or the calendar, even though those are the reasons we give. The reason is that turning the key means risking failure and rejection, and it’s more comfortable to keep the dream in mint condition, untested, safe. The busyness is real. It’s just not the cause.

“I think ultimately it comes down to fear. I think it’s scary to live the life you’ve imagined.”

The regret research is remarkably consistent: at the end, people rarely regret what they did. They regret what they didn’t do. Jodi’s move is to get that list out of you while there’s still time on the clock. Imagine tonight’s the night and write down what you’d kick yourself for — the language you never learned, the book you never wrote, the thing you never tried. She calls them pregrets, because unlike the deathbed version, every item on this list is still reversible.

“Most people don’t regret the mistakes they made, the things they did. Most people regret the things they didn’t do.”

The real confession inside the stapler story isn’t procrastination — it’s that Jodi spent those years waiting to be rescued. Her actual dream was that a headhunter would call and hand her a new life, so she’d never have to choose one. I hear this from women constantly, usually dressed up as patience. Jodi’s lesson is that the pride you’re looking for only comes from moving yourself, even if where you land isn’t perfect. Her upgrade now isn’t that she never hesitates — it’s that she’s shrinking the hesitation. What took three years should take one. Progress in the deliberation time still counts.

“I was waiting to be saved. I was waiting to be plucked and headhunted... you’ve gotta actually take action yourself, and then that’s what makes you feel proud of yourself.”

When Jodi’s mom passed, Jodi cleaned out her apartment and found a life’s worth of creative work — stories, drawings, business plans, including a natural dog biscuit business — none of it ever sent, started, or shared. In her book she calls it the Land of Dormant Intentions. Her mom wasn’t blocked by a lack of ideas or talent. She was blocked by the belief that there would be a later. Jodi looked at those boxes and saw her own reflection: a big-idea person letting “what will people think” run the show. Grief made the cost of waiting visible. The rest of us get to learn it secondhand.

“She largely didn’t go ahead with a lot of her plans because she believed that there was a later.”

This one cut both ways in our conversation. I told Jodi about my old baking blog — five years of joy that curdled the moment people started placing orders and I started resenting every brownie. Jodi catches herself doing the same thing: she finishes an art project and immediately hears “how can I monetize this?” Her answer is self-awareness about which side of the line a thing lives on. If creating for its own sake makes you feel alive, that’s a complete outcome. The pressure to make every passion productive isn’t ambition — it’s the culture talking, and it lands especially hard on women.

“Okay, dude, just slow down. What if you just did an art project and had it sit beside you?”

For everyone who hears “light your furnace” and feels nothing: Jodi thinks the passion question itself carries too much pressure. Her method is a buffet. Start with what obsessed you as a kid and blow the dust off it — not the activity itself, but its elements (mine was paper dolls; what I actually loved was inventing characters and worlds). Then try things cheaply, expect to be bad at most of them, and abandon freely. Jodi bailed on bridge after one excruciating lesson and never looked back — and her doodles, which started terribly, became the illustrations in her book. Quitting isn’t flaky. It’s data collection.

“Allow yourself to try it all, and then allow yourself to leave it all... You tried at the buffet the baby corn, and you’re like, I should have known I didn’t like the baby corn. Throw away the baby corn and then move on.”

Jodi’s entire framework rests on one uncomfortable gift: the deadline is real, and pretending otherwise is how a creative, capable woman ends up with boxes of unstarted plans. You don’t need a brush with death to wake up — you can borrow the lessons. Here’s where to start:

1. Do your mortality math. The average life holds about 4,000 Mondays. Look up your life expectancy, subtract your age, and get your number. Write it somewhere you’ll see it on Mondays. The point isn’t panic — it’s converting “someday” into a quantity.

3. Take the second-chance tour. Jodi’s exercise: imagine you were just discharged after six weeks in a coma and you’re seeing your desk, your calendar, your commitments with fresh eyes. Walk through your actual life asking one question of each thing: does this still matter? Notice what you’d drop instantly — and what you’d start.

4. Write five pregrets. If tonight were the night, what would you kick yourself for not doing? Big, small, tiny — Spanish, the dating app, going blonde, the book. Then pick the one you can take a first step on this week, because every item on the list is still cancelable.

5. Set a stapler deadline — and tell someone. Pick a visible, finite marker for the change you keep promising yourself, and attach a real action to it, because Jodi’s own stapler proves the marker alone isn’t enough. If you’re mid-deliberation, don’t demand a decision today; just commit to shrinking the timeline. Three years of stalling becomes one.

6. Resurrect one childhood obsession. What did you do for hours as a kid? Pull out its elements — the making, the performing, the being alone, the world-building — and find one cheap, adult-sized way to try it this month. No talent required, no output owed.

7. Quit something at the buffet. If you’ve been grinding through a hobby, class, or commitment out of sunk cost, give yourself formal permission to abandon it this week. Fast quitting isn’t failure; it’s how you clear the plate for the thing that actually lights you up.

8. Connect with Jodi. Grab You Only Die Once and find her at 4000mondays.com or on Instagram @4000mondays. Tell her you found her through Ladies Get Paid :)