One of the greatest shifts in my life happened because of an old typewriter.
Not because it was valuable.
Not because it was rare.
But because of what it revealed about me.
When my wife Dee and I first sailed to the Bahamas decades ago, clearing into the country was a very different experience than today. We anchored the boat, climbed into our dinghy, and went ashore to find customs and immigration.
The office looked like something out of another era.
The officials were using ancient typewriters with sheets of carbon paper layered between forms. They typed slowly. The process took forever. Papers were stamped, shuffled, restamped, and stacked in piles.
I remember standing there becoming increasingly impatient.
My first thought was:
“This is so backwards. We do this so much more efficiently in the United States.”
Then almost immediately another thought hit me:
“If I wanted things done like in the US- I should have stayed home.”
I didn’t sail all the way to the Bahamas to judge these people. I came here to learn from them.
That moment stayed with me for the next 17 years as we sailed around the world through more than 100 countries.
Because I slowly realized something important:
Judgment closes doors.
Observation opens them.
And most of us spend far too much of our lives judging.
We judge other people.
We judge cultures.
We judge generations.
We judge politics.
We judge success.
We judge failure.
And maybe worst of all…
we judge ourselves.
The Hidden Cost of Judgment
What’s fascinating about judgment is that it often disguises itself as intelligence.
We think being critical makes us discerning.
Sophisticated.
Perceptive.
But in reality, constant judgment usually creates something far less useful:
rigidity.
Once we decide we already understand someone, we stop being curious about them.
And curiosity is where growth lives.
Travel taught me this over and over again.
When Dee and I sailed into developing nations, we encountered people whose lives looked completely different from ours. Some lived in grass huts. Some had no electricity. Some survived on incomes that wouldn’t cover a dinner out in America.
Yet many of them radiated joy.
If I had stayed trapped in judgment — “they’re poor,” “they’re backwards,” “they’re less advanced” — I would have completely missed the deeper lesson:
Many of these people understood community, gratitude, family connection, and presence far better than many wealthy Americans.
Observation allowed me to learn that.
Judgment would have prevented it.
The Problem With Having Opinions About Everyone Else’s Life
Recently I saw another example that really struck me.
I’m a huge fan of ski racing, especially the women racers. I think what athletes like Lindsey Vonn and Mikaela Shiffrin have accomplished is extraordinary.
Last year Lindsey Vonn decided to attempt something almost nobody thought possible.
After being retired for six years and enduring enormous pain from years of injuries, she underwent a partial knee replacement. Then at age 41 she decided to try racing again. Competing against girls who were 16, 17, and 18 years old — attempting that takes astonishing courage.
And what stunned me wasn’t the comeback itself.
It was the reaction.
The amount of criticism and hate she received online was unbelievable.
People mocked her.
Criticized her.
Told her she was too old.
Told her she was embarrassing herself.
Told her what she should and shouldn’t do with her own life.
I remember reading those comments and thinking:
Why do people feel such a need to insert themselves into someone else’s dream?
Why not simply observe?
Why not admire the courage it takes to try?
Why not say:
“Good for her. I hope she succeeds.”
Or even:
“That’s not what I would choose for myself, but I respect her willingness to go after it.”
Instead, so many people rushed toward judgment.
And I think I know why.
Because judgment is easier than self-examination.
When someone else dares greatly, it forces us to confront our own fears.
Watching Lindsey Vonn attempt the impossible raises uncomfortable questions:
What dreams have I abandoned?
Where have I played small?
When did I stop risking embarrassment?
When did I stop challenging myself?
Judging her is easier than answering those questions honestly.
Observation Creates Wisdom
One of the greatest gifts of sailing around the world was that it slowly trained me to observe instead of judge.
You can’t spend years crossing oceans and entering foreign countries without eventually realizing how little you actually know.
And that realization is liberating.
You stop needing to be right all the time.
You stop seeing your own culture as the default setting for humanity.
You stop assuming your way is the only way.
You become more interested in understanding than condemning.
And that mindset changes relationships too.
Think about how often conflict starts because we instantly interpret someone else’s behavior through our own lens.
Someone cuts you off in traffic:
“What a jerk.”
Someone doesn’t text back:
“They don’t care about me.”
Someone behaves awkwardly:
“They’re rude.”
But observation asks different questions.
Maybe they’re distracted.
Maybe they’re overwhelmed.
Maybe they’re grieving.
Maybe they’re afraid.
Maybe they simply see the world differently than you do.
Observation creates space.
Judgment creates walls.
And here’s the really important part:
The habit of judging others almost always turns inward eventually.
The Most Dangerous Judgment Is Self-Judgment
For many people, the harshest critic in their life lives inside their own head.
We replay old mistakes.
Old embarrassments.
Old failures.
Old heartbreaks.
We judge ourselves endlessly for things we would instantly forgive in a friend.
One of the most important insights I’ve learned is this:
You can observe your mistakes without turning them into your identity.
That distinction changes everything.
You can say:
“I failed at that business.”
without deciding:
“I’m a failure.”
You can say:
“That relationship ended painfully.”
without deciding:
“I’m unlovable.”
You can say:
“I handled that situation poorly.”
without deciding:
“I’m a bad person.”
Observation allows growth.
Judgment freezes identity.
And frozen identities create frozen lives.
People who constantly judge themselves become afraid to try new things because every setback becomes evidence against their worth.
But people who observe themselves with curiosity become adaptable.
They learn.
Adjust.
Grow.
Move forward.
They think more like sailors.
At sea, judging the wind is useless.
The wind does not care about your opinion.
A sailor doesn’t scream at the storm:
“This shouldn’t be happening!”
A sailor observes conditions honestly and adjusts accordingly.
That mindset works in life too.
Observe reality.
Adjust intelligently.
Keep moving forward.
That’s far more powerful than outrage, blame, or self-condemnation.
What Happens When You Stop Judging
When you stop judging constantly, something remarkable happens.
You become lighter.
More open.
More curious.
More compassionate.
More flexible.
More peaceful.
You begin listening instead of waiting to speak.
Learning instead of defending.
Growing instead of proving.
And perhaps most importantly:
you become free to fully become yourself.
Because people who spend their lives judging others are almost always terrified of being judged themselves.
But once you stop obsessing over what others should do, something shifts.
You stop organizing your life around other people’s opinions.
And that is incredibly freeing.
Years ago someone gave me a piece of advice that permanently changed my life:
“What other people think of you is none of your business.”
That doesn’t mean we shouldn’t care about being kind or ethical or compassionate.
It simply means we cannot build our lives around external approval.
Because if you do, eventually you stop living your life…
and start performing one.
The older I get, the more convinced I am that wisdom begins with replacing judgment with curiosity.
Curiosity about people.
Curiosity about ourselves.
Curiosity about life.
The world doesn’t need more outrage.
It needs more understanding.