What Are We Waiting For?
On time, aging, and the life we keep putting off
I turned another year older in April. My son celebrated his birthday in February. And last week, my daughter turned 10.
We took her and four of her friends to Door County for two nights. A real sleepover trip. My wife’s birthday also fell the day before, so the whole weekend carried a little extra weight. The kind of thing everyone will probably remember. The kind of thing I know I will.
Door County is a place that has followed me through my whole life. I went there as a little kid with my family. I went back as an adult and wrote the majority of my book there, finishing it on one of those trips. It’s also where Spilled Coffee began. Some of the most important moments of my life have happened in that water, those trees, that quiet. And now my daughter is building her own memories there.
Watching her with her friends, I kept thinking, where did the time go?
She is 10. Which means I’ve been a father for 10 years. Which means my parents are 10 years older than they were when she was born. Which means every person I love most in this world has less time ahead of them than they did a decade ago. Including me.
I’ve been sitting with that feeling for a while now.
Sometimes life sends you the same message from multiple directions at once. Lately, a movie, two TV shows, and a podcast I came across all circled the same theme without knowing it. Time. What we are waiting for. How short and precious life actually is.
I don’t think that’s a coincidence. I think I was finally ready to hear it.
In investing, I talk often about the idea that there is always something to worry about. Always.
Think back across just the last decade or so. The debt ceiling. Trade wars. A global pandemic. The fastest rate hikes in modern history. Inflation at levels not seen in 40 years. Bank failures. Russia invading Ukraine and what it meant for energy and inflation. War spreading through the Middle East. Tariffs. Recession fears that seemed certain and then didn’t arrive. More tariff fears. The news cycle has never once run out of reasons to be afraid.
And yet. The market went up. Not in a straight line. Not without pain. But it went up. The people who waited for the all-clear signal, who needed the headlines to calm down before they felt comfortable investing, missed most of the gains. Because the headlines never calmed down. They just changed.
There’s never a perfect moment to invest. There’s always a reason to wait.
That same truth applies to life. And I’m not sure I fully understood that until recently.
We’re always waiting for something.
Waiting until we save a little more. Until the kids are older. Until work settles down. Until we pay off the debt. Until next summer. Until we feel ready. Until the moment feels right. We manage our lives carefully, like we’re holding something fragile, protecting it from risk. And somewhere along the way, the life we were protecting passes us by.
I’ve been guilty of this. I think most of us are.
Whatever number you have saved right now, there’s probably a bigger number in your head that you’re waiting for. And when you get there, there’ll be another one after that. At some point, you have to ask whether the goalpost is ever going to stop moving. Whether you’re chasing a number that will give you permission to live, or whether that permission was always yours to give. The number goes up. The waiting continues. And the years keep passing.
We’ve told ourselves that convenience is optional, something we earn. But somewhere along the way, convenience became the default. Comfort became the plan. Waiting became the strategy. We optimized for safety and called it wisdom.
I’m not sure it is.
Watching my daughter blow out her candles, I thought about the windows we get in life. They’re smaller than we think. The window to take that trip. The window to call that person. The window to start that thing. The window to just be present with the people you love before everyone gets too busy, too old, or too gone.
My parents won’t always be here. My kids won’t always be kids. The friends I have right now won’t always be a short drive away. I know this. But knowing it and feeling it are two different things.
I’m feeling it now.
I write to learn. I write to teach. But sometimes I write because it’s the only way I know how to process something that doesn’t fit neatly into a conversation. This is one of those pieces.
I’m coping with time. With the reality of it. With the strange mix of gratitude and grief that comes from watching a life you love move forward whether you’re ready or not.
It’s not easy. It’s also the most human thing there is.
So here’s what I keep coming back to.
You’ll have as much life as you allow yourself.
Not as much as your schedule permits. Not as much as your bank account unlocks. Not as much as the market cooperates with. As much as you allow.
Make a memory a day. Not a grand one. Not a vacation or a milestone. Just a moment you chose on purpose. A conversation that mattered. A meal you actually sat down for. A walk you didn’t scroll through.
Die living, not existing.
Because the alternative, I think, is the real risk. Not losing money. Not making the wrong call. The real risk is arriving at the end of a life you managed very carefully, realizing you forgot to live it.
We all have a very small window.
I don’t know exactly what I’m waiting for anymore. But I’m trying, right now, to stop.
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