Is NOT settling the root of modern unhappiness?
Here’s Jackie in the 1800s.
His father was a baker. So, he never really thinks of anything other than becoming a baker. Within his 10 mile radius there are a few girls his age and, mostly as a function of family arrangements, he ends up dating one. He proposes and genuinely believes if he doesn’t keep his vow for life, he will burn in eternal hell (pretty compelling commitment device). His neighbors have a new plow, a few chickens, and a nice wood-fire stove. So, he feels he is more than “keeping up with the Joneses”.
Contrast that with Jackie in 2026.
On a daily basis, he sees finance bros, youtube influencers, and entrepreneurs in every industry and product imaginable “living life on their terms” and following their passion. His alma mater alone offered over 200 majors. Similarly, every day he is bombarded with the most beautiful women from around the world on instagram (many of whom are AI) and on the dating apps he sees every possible single woman in all of the Pittsburgh metro. And as for his neighbors, if we go beyond physical neighbors to include people in his orbit on social media, we have sports cars, trips to Fiji, new suits, and every single consumer good or experience imaginable.
So, while we tend to think of abundance and choice as sources of happiness, perhaps we passed over the sweet spot, as it were, sometime between the 1800s and 2026.
While we may call old past Jackie’s life dull, boring, and lacking the wonder of possibility, he was probably pretty content. Sort of like asking someone who is color blind if they are missing out. They wouldn’t even know what you’re talking about.
If we assess present Jackie with a bit of candor, we might call this experience dizzying, disorienting, or infinitely frustrating.
Imagine if you were at a magical buffet with every single possible food in the entire world and you were allowed to only eat one plate without regretting it. It almost wouldn’t even be satisfying. In fact, it may be psychological torture. Now apply this to dating, career, lifestyle, etc., where the stakes are much higher than a meal.
Perhaps by basically expanding the realm of the possible to literal infinity (e.g. I can follow Jeff Bezos on instagram and see his day to day reality quite intimately) we have actually locked ourselves into a psychological torture trap.
As your realm of possible wants expands ad infinitum, no matter what you get or what you choose, you will always be comparing it to something more, and you will always feel it is never enough. You’ll always be settling.
So maybe happiness in 2026 is really the art of learning to settle?
This skill (do we call it a skill?) is more important than ever before. As we covered, 1800s Jackie didn’t have to settle precisely because he didn’t know he was settling.
So here are three ideas that may help you adopt the right kind of settling…
Define “life parameters”.
Sanity check your expectations.
Stop giving a sh*t (in a Zen way).
"Beware of looking for goals: look for a way of life. Decide how you want to live and then see what you can do to make a living within that way of life." — Hunter S. Thompson
How do you know if you’re failing, settling, exceeding expectations, or succeeding beyond your wildest dreams?
You need to define a few parameters to set out a definition of success in building the life you want. You see, I believe part of the reason that it’s so easy for people to get carried away into some ridiculous standard for a partner, career, lifestyle, etc. is because they never defined success in the first place.
If you go through life with some vague idea of “I want to live somewhere nice and make good money and have my dream job” then “nice,” “dream,” and “good” will always flutter off further into the realm of the unrealistic as you engage with social media and increase your present success.
Instead, what if (totally hypothetical) you said, “I want to make a little over six figures, work 30-40 hours per week with about half of it on happiness-nerd learning and teaching, and I want to do so in Western PA with all my friends and family.”
The beauty of parameters like this is that they are sort of variables that allow for many possible solutions to “solving for” your ideal life — e.g. I could win military resilience and wellbeing contracts, I could be a pro-d company for happier schools, I could be an internet happiness beat writer, etc. — or all the above. And now, not to overshare (said immediately before oversharing), I have, finally, hit my parameters in 2026.
So, I’m settling. And I genuinely feel happier than I have over the last 3 years of striving.
This takes me to my second point. Sanity check your expectations.
According to the nonprofit DEEP, about half of the world (~4 billion) live on less than $7 per day.
Are you living on more than $7 per day? If so, then congratulations because you are crushing it by a pretty healthy margin. Median individual income in the US was $46,960 in 2025. Are you making in that general range? Congrats on being a normal person then. If everyone were making way more than the average then it would no longer be the average!
My point is, it’s so easy to get carried away in appearances. But we need to practice some numerical fluency to sanity check ourselves. Your “settling” — from a statistical PoV — may not even be settling. It may be exceeding.
Finally, point three, the great Zen teacher, Suzuki Roshi, once wrote something like “good enough is good enough.”
I know this is starting to sound quite poetic, but what if you just stopped giving so much of a sh*t. Decide what’s important to you and never take it for granted. And just be content with that.
I read in a section from Oliver Burkeman, a story of the teacher Jiddu Krishnamurti. As he was giving a lecture, he paused, leaned forward and said in a whisper, "Do you want to know what my secret is?" The entire room leaned in in anticipation and he said, "You see, I don't mind what happens.”
In other words, can you just be fine with whatever happens? Can you settle for experiencing your life? Can you learn to say that good enough really is good enough?
(More thoughts here.)
So I’ll end with a bit of quotable advice…
Don’t settle for less than you deserve. Actually do, I just want you to be happy.
your happiness nerd,
Jackson K.
