A friend of mine, also part of the FI community, was over at my house the other day. His youngest just moved out, and he’s finally talking about travel. He said it half joking, but it landed harder than he probably meant it to: “Well, I’ve only got another 20 years or so, so I should really start going places.”
He laughed, but I didn’t. Not really. Because I started doing math in my head, and the math was not fun.
I’ve got good genes. Barring anything unexpected, I’m planning on sticking around into my 90s. That gives me somewhere between 30 and 40 more years. That sounds like a lot until you remember that “planning on” and “guaranteed” are two very different things. Life doesn’t care about your spreadsheet. It doesn’t care that you’ve got a 4% withdrawal rate figured out to the decimal. It can throw you a curveball on a random Tuesday, and no amount of index fund diversification will stop it.
That conversation with my friend is the reason you’re reading this. I want to talk about time, about the bucket list you keep saying you’ll get to, and about why “one more year” is one of the most dangerous phrases in the FI world.
The Math Nobody Wants to Do
Here’s an exercise. Grab a piece of paper, or open a fresh note on your phone, and figure out how many years you’ve got left if you live to be 90. (Or pick a realistic number based on your health, your family history, and a little bit of humility.)
Now subtract the years you’ll spend in your 80s dealing with whatever your 80s decide to throw at you: creaky knees, a hip that needs replacing, maybe a spouse who can’t travel as easily anymore. Subtract the years in your 70s where a long flight to Southeast Asia sounds less like an adventure and more like a chore. You start to realize that the window for the big, physical, “climb a mountain” or “backpack through Patagonia” kind of bucket list items is a lot smaller than the number on your life expectancy calculator.
My friend’s “20 years” comment wasn’t really about dying at 75. It was about the years he has left where his body and his energy will cooperate with his ambitions. That’s a much scarier number than the one on the actuarial tables.
This is the part where FI folks tend to get quiet. We’re really good at optimizing tax brackets and building glide paths for our portfolios. We’re less good at admitting that the asset we should be optimizing hardest is time, and that time doesn’t compound. It just runs out.
One More Year Syndrome Isn’t Just About Money
If you’ve spent any time in this community, you’ve heard of One More Year Syndrome, the habit of hitting your FI number and then deciding you need just one more year of income before you actually quit. It’s a money problem on the surface, but underneath it’s really a courage problem. It’s easier to keep collecting a paycheck than to face the uncertainty of what comes next.
But there’s a cousin to that syndrome, and it’s sneakier. Call it One More Year Bucket List Syndrome. It’s the belief that the trip, the reunion with an old friend, the hobby you’ve always wanted to try, or the conversation you’ve been putting off can wait until next year. Until the kids are older. Until work slows down. Until you’ve saved a little more.
The problem is that “next year” is a moving target, and you’re not the only variable in the equation. Health changes. Relationships change. The friend you keep meaning to visit might not be around next year, and neither might you.
What Hospice Doctors Actually Hear
I want to bring in someone who has a much clearer view of this than most of us do: Dr. Jordan Grumet, known to most of the FI world as Doc G, host of the Earn & Invest podcast and author of “The Purpose Code.” Doc G spent years as a hospice medical director, sitting with people in their final days and doing what’s called a life review, a structured conversation about their biggest moments, their regrets, and the people who mattered most.
Here’s the part that should stop you cold. According to Doc G, in all his years doing this work, dying patients almost never bring up money. Nobody says they wish they’d hit a higher net worth. Nobody says they wish they’d worked more nights and weekends. What they say, over and over, is some version of the same sentence: “I really regret that I never had the energy, courage, or time to…” and then they fill in the blank with an experience, a relationship, or a dream they never chased.
Grumet has talked about this pattern showing up so consistently that he built it into a kind of test. He suggests imagining your own deathbed and trying to finish that same sentence right now, while you can still do something about it. If you can fill in the blank, you’ve just found your bucket list item, and you’ve also found your deadline, because none of us know how much runway we actually have.
That’s not meant to be morbid. It’s meant to be useful. A hospice doctor isn’t a doom and gloom guy for a living, he’s someone who has seen, up close, exactly what people wish they’d done differently. That’s about as close to insider information on a life well lived as you’re going to get.
Building a Bucket List That Actually Gets Done
Most bucket lists fail for a boring reason: they’re vague, they’re huge, and they live in your head instead of on paper. “Travel more” is not a bucket list item. It’s a wish. Here’s how to turn wishes into things that actually happen.
Write it down, all of it. Don’t edit yourself yet. Skydiving, learning to make sourdough that doesn’t look like a hockey puck, seeing the northern lights, reconciling with a sibling, running a 5K, whatever it is. Get it out of your head and onto a page where you can see it.
Carl and I did this on a 15-hour roadtrip, where the girls weren’t with us and we had LOTS of uninterrupted time to talk. One idea sparked another. We talked about what some people have on their bucket lists, and how we’d morph that into something we actually wanted to do. Example, we know a lot of people who want to see a baseball game in every stadium in America. That’s awesome if you like baseball, but we don’t. We do, however, love football. So we put this “someone else’s bucket list item modified for our interests” onto our bucket list. We don’t love soccer, but after watching Ted Lasso, flying to England and watching a game in one of those massive stadiums sounds like fun. (We do not want to see a game in ever stadium, because we’re just not that into soccer.)
Sort by expiration date. Some bucket list items have a shelf life. Backpacking across Europe with a 50-pound pack gets harder every decade. A physically demanding trip belongs earlier on your timeline than a museum tour you could do in a wheelchair at 85. Be honest about which dreams are time sensitive and put those first.
Attach a real date, not a vague one. “Someday” isn’t a date. “October of next year” is a date. If it’s not on a calendar, it’s not a plan, it’s a nice thought you’ll have again in five years when you’re feeling nostalgic.
Here’s where Carl and I have a bit of ‘one more year’ syndrome that we can’t really move. We have two daughters, and one of them is still in high school. Our Bucket List trip isn’t going to start until October of 2028, which is after the younger one graduates from high school and is settled in college. We’re still going to make plans (and in fact have started making them already – Hello Camino Hike, 2028) so we’re following this one, but on a modified timeline.
Budget for it like you budget for anything else. This is where the FI part of your brain gets to help instead of hurt. If the item costs money, figure out what it actually costs and build it into your plan the same way you’d build in a house down payment. You’ve spent years getting good at delaying gratification for a number on a screen. Spend a little of that same discipline making sure the number on the screen eventually buys you something other than more screen time.
Do the free stuff now. Not every bucket list item costs a fortune. Reconnect with an old friend. Learn to say “I love you” more often to the people who need to hear it. Sit with your kid and ask about their day without checking your phone. These cost nothing but attention, and they’re the ones people on their deathbeds mention most, according to Doc G’s decades of life reviews.
I wanted to make this easy on you, so I created a fillable PDF for you, with all of this incorporated so you really just have to think about what you want on your list. You can download it from our Resource Library.
The FI Community’s Blind Spot
We are, as a community, exceptionally good at delayed gratification. That’s literally the whole strategy. Save aggressively now, live a little leaner than your coworkers, so that later you get freedom. It works. I’m not here to argue against saving.
But delayed gratification has a shadow side, and it’s this: some of us get so good at delaying that we forget to stop. We hit our number and keep working “just in case.” We build a travel fund and then keep adding to it instead of booking the flight. We tell ourselves the trip will be better once we’ve saved 10% more, once the market recovers, once we’ve paid off the last chunk of the mortgage.
Meanwhile, the knees keep aging. The parents keep aging. The kids keep growing up and leaving, the way my friend’s did. The window doesn’t wait for your spreadsheet to say you’re ready.
Financial independence was never supposed to be the finish line. It’s the tool. The actual goal is a life you don’t regret, and according to the guy who has literally sat with hundreds of people at the end of theirs, regret isn’t about the number in your brokerage account. It’s about the energy, courage, and time you didn’t spend on the things that mattered.
Start the List Today
You don’t need to quit your job tomorrow or book a one way ticket to Bali by Friday. You just need to stop treating your bucket list like a retirement bonus you’ll cash in eventually. Start it now, even in a small way. Write down one thing today. Put a real date next to it. Tell someone about it so you feel a little bit accountable.
My friend’s joke about having “20 years or so” wasn’t really a joke. It was a math problem dressed up as a punchline, and most of us are avoiding the same math. You might have more time than he does, or you might have less. Nobody gets a guarantee, and that’s exactly the point.
So make the list. Put the flight on the calendar. Call the sibling. Sign up for the pottery class that’s been sitting in your bookmarks for two years. Your future self, the one sitting somewhere down the road looking back at this decade of your life, is going to care a lot more about what you did than about how much you had saved while you didn’t do it.
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