I Was Living the Life You See On Instagram… And I Didn’t Know It?
A story of social comparison and a sudden realization

Some of you may be familiar with the story of The Fisherman and the Businessman:
One day a fisherman was lying on a beautiful beach, his fishing pole propped up in the sand, enjoying the warmth of the afternoon sun and the prospect of catching a fish.
A businessman walking by noticed him and asked why he wasn’t working harder to make a better living for himself and his family.
“You aren’t going to catch many fish that way,” said the businessman to the fisherman. “You should be working rather than lying on the beach!”
The fisherman looked up at the businessman, smiled and replied, “And what will my reward be?”
“Well, you can get bigger nets and catch more fish!” was the businessman’s answer.
“And then what will my reward be?” asked the fisherman, still smiling.
The businessman replied, “You’ll make money and be able to buy a boat, leading to larger catches of fish!”
“And then what will my reward be?” asked the fisherman again.
The businessman was beginning to get a little irritated with the fisherman’s questions: “You can buy a bigger boat, and hire some people to work for you!” he said.
“And then what will my reward be?” repeated the fisherman.
The businessman was getting angry. “Don’t you understand? You can build up a fleet of fishing boats, sail all over the world, and let all your employees catch fish for you!”
Once again the fisherman asked, “And then what will my reward be?”
The businessman was red with rage and shouted at the fisherman,
“Don’t you understand that you can become so rich that you will never have to work for your living again! You can spend all the rest of your days sitting on this beach, looking at the sunset. You won’t have a care in the world!”
The fisherman, still smiling, looked up and said, “And what do you think I’m doing right now?”
For Years, I Was Trapped in the Belief That I Didn’t Have Enough
When I was unemployed after finishing my studies, I thought, “I’ll be happy when I get a good job.”
Once I secured a prestigious job in a shiny skyscraper, I thought, “My office job is boring; if only I could travel more.”
When that job introduced remote work within Europe, I thought, “I’ll be happier when I have a fully remote job and can travel anywhere in the world.”
Upon resigning and landing that fully remote job, I thought, “I’ll be happy when I earn more money to travel even more comfortably.”
After getting promoted and improving my salary, I still felt dissatisfied: “It’s not enough—my European salary in a city like New York doesn’t go far. I need to earn more while keeping my flexibility. And being fully asynchronous would be ideal.”
And so the cycle continued.
What I Missed Was the Big Picture
By the time I realized it, I had already achieved most of my goals:
landing a prestigious job after university,
transitioning to fully remote work,
traveling the world, and even
earning a promotion.
Of course, there were trade-offs. For example, I wasn’t fully asynchronous because my company’s clients were mainly in Europe.
Still, I felt trapped in comparison-driven details.
When visiting my partner in New York, for instance, I couldn’t shake the feeling that my salary wasn’t high enough to live comfortably in the city. Yet, I overlooked the fact that none of the New Yorkers I knew had nearly the year-round freedom I did. Additionally, the fact that I needed to spend only two or three months there at a time—while the rest of my time was in more budget-friendly places—wasn’t enough to quiet my self-criticism.
My mind was stuck.
Once I Obtain All the Things I Want “What Will My Reward Be?”
Then, recently, while visiting my parents in Italy, I took a moment to look around.
We were having dinner in the backyard, just a few steps from the beach.
On the table: fish my dad had caught that morning, vegetables from his farmer friend, olive oil from our own family’s harvest.
The setting sun and the gentle breeze completed the painting.
Just like in the tale of The Fisherman and the Businessman, I imagined being asked,
“Once you obtain everything you want, what will your reward be?”
My answer?
“I’d travel part of the year and spend the rest of my time in Italy, enjoying good food with family and friends.”
And then I pictured the fisherman looking at me with a smile and asking,
“And what do you think you’re doing right now?”
Thank you for reading Freedom Focus!
This article was originally written in mid-2023. However, the message still holds true today. In light of this, I’d be curious to know:
Do you struggle with social comparison?
What is something that helps you navigate or overcome it?
Or
for a more intimate experience among like-minded, freedom-seeking folks.
That’s all from me this week. I’ll see you again next week!
Yours,
Caterina
I love this. So often we miss out on the big picture because we're so busy chasing the next thing.
Omg that olive oil !! The fisherman story is spot on! Sometimes I need to pinch myself and remind me I am living the life I wanted and I am where I always dreamt to be. Sure, there are tradeoffs... Such is the life of a migrant/expat