I spend a lot of time writing about things that you ought to do. I share adventures I’ve taken that I think you might enjoy and encourage the choices that make our lives better. After all, my goal, both for myself and for you, dear reader, is to build a life so rich and fulfilling that we no longer crave escape from it.
A life where our bucket list adventures don’t act as brief breaks from monotony, but as extensions of a life we already love.
Seldom do I write about what we shouldn’t do. But as we work toward creating lives worthy of gracing any bucket list, there are habits, beliefs, and quiet mental traps that can drag us down. They don’t announce themselves with flashing lights. They sneak in through our routines, our comparisons, our “shoulds.” And before long, they sap the joy right out of us.
This post kicks off a new mini-series: things to avoid if you want to protect your joy.
The first joy-sucker on our list?
Measuring your life by how it “should” be by now.
The Tyranny of the Timeline
Many of us were handed a script early on.
Go to school.
Get a job.
Meet someone nice.
Get married.
Buy a house.
Have kids.
Work hard.
Retire.
Enjoy your golden years.
It’s tidy, it’s predictable, and for some people, it works. But for many of us, life doesn’t follow that script. We graduate later, or not at all. We change jobs. We move. We fall in and out of love. We skip the house. We skip the kids. Or we find new dreams entirely.
And yet, that little voice in the back of our heads still whispers:
“You should have figured it out by now.”
“You should be married by 30.”
“You should have your dream job by 40.”
As if our lives are meant to unfold like clockwork, all hitting the same milestones at the same time.
And when we don’t? We call ourselves failures.
Not married by 30? Spinster. Might as well get a cat and a cardigan.
Didn’t make partner by 40? A has-been.
Still renting at 50? Must’ve done something wrong.
But let’s pause here. Whose voice is that, really? Society’s? Our parents’? Our own inner critic, parroting what we were taught?
The Myth of “Too Late”
The truth is, there’s no such thing as “too late.”
Colonel Sanders didn’t start Kentucky Fried Chicken until he was 62.
Julia Child didn’t write her first cookbook until she was 50.
Stan Lee didn’t create Spider-Man until his 40s.
Milton Hershey failed with multiple candy shops before founding Hershey’s Chocolate.
And sliced bread? It took over a decade to catch on as an idea people actually wanted.
Even Abraham Lincoln, that pillar of perseverance, lost job after job and election after election before becoming one of the greatest presidents in history.
If any of these people had believed the story that they’d “missed their window,” they would’ve stopped before success ever arrived.
And if that seems like ancient history, look around today. Some of the most interesting, creative, and fulfilled people I know are those who stopped trying to follow the timeline and started following their curiosity instead.
They’re going back to school at 45.
They’re switching careers at 50.
They’re learning to paint or surf or start a business long after the world says they should’ve “settled down.”
You’re Not Late. You’re Just on Your Path.
Julius Caesar once lamented, at age 32, that he hadn’t yet achieved what Alexander the Great had by the same age. At the time, Caesar was a minor administrator with little acclaim. He had no idea that his greatest accomplishments were still ahead of him.
We all have those moments, standing before the metaphorical statue of someone else’s success, feeling small by comparison.
But your path isn’t supposed to look like anyone else’s. You’re not on Alexander’s timeline, or your neighbor’s, or your sibling’s. You’re on yours.
Every detour, every pause, every “failure” teaches you something that smooth sailing never could.
The Cost of “Should”
Spending time lamenting what hasn’t happened yet only keeps us stuck. It traps us in the past, in a cycle of comparison and self-judgment. We get so focused on the shoulds, what we should have done, where we should be, that we miss what’s right in front of us.
It’s like staring at the GPS instead of enjoying the drive. You’ll get to where you’re going, but you’ll have missed all the scenery along the way.
And let’s be honest: nobody builds a bucket list life by following someone else’s map.
Charting a Different Course
Here’s the thing: your “timeline” is just a story. You can rewrite it anytime you want.
Maybe your bucket list includes seeing the Northern Lights, writing a book, starting a garden, or falling in love again. None of those dreams come with an expiration date.
You don’t have to “make it big” to make your life meaningful. Sometimes the best things we build are small, moments of joy, quiet progress, and self-acceptance.
The most extraordinary lives often grow from the most ordinary days, repeated with care and curiosity.
So Let’s Ditch the Clock
Stop measuring yourself by where you should be. Start asking where you want to be—and what small step you can take today to move in that direction.
Because life isn’t a race. It’s not a checklist. It’s a collection of moments that, if we’re lucky, we get to fill with wonder, growth, and connection.
You’re not behind. You’re becoming.
And that, dear reader, is exactly where you’re supposed to be.
Budget Bliss: Bucket List 