On the money
If I had money, I would…
Money is driving us crazy, so let’s call it out.
What I am about to share comes from a place of knowing, caring and honestly, being a little worn out. I was going to write an article about understanding AI and society (maybe another time), but I think we have all had enough of that lately.
Instead, I decided to write about another equally tired, yet somehow unsolved mystery:
Money 💸.
To be clear - this is not a rant.
This is not commentary on capitalism or greed or ethics.
This is about understanding. This is part of my life’s work.
Calling Out Money
We still don’t talk about money enough.
We joke about it, stress about it, chase it, avoid it, or pretend we don’t care about it.
But all of us - at one point or another - have whispered the most universal sentence of modern humans on Earth:
If I had money, I would <do something>…
You know the rest:
…buy food
…pay bills
...quit my job
…build a school
…start a business
…take a break
...help a friend
…donate to charity
…disappear?
You’ve thought it. Maybe today. Maybe right now. Maybe it caused you a ton of anxiety and worry (if so, I sincerely apologize). Maybe it gave you hope.
Deep breath. Let’s keep going…
Money Isn’t Just a Tool
Here’s the uncomfortable truth:
Money doesn’t just buy things - it shapes what we think is possible.
It influences our choices, dreams, relationships, and even our sense of worth.
If you don’t have enough money, life sucks.
If you have too much, life can also suck - just in different ways.
Money is strange like that - a bit like oil in water.
Necessary, but never quite blending comfortably with life.
And yet, try asking yourself:
If I already had the money, what would I actually do (“spend it” doesn’t count)?
What do I want? What do I actually need?
What would I build? Who would I help? Who would I be?
Money is Overloaded
Humans need food, water, shelter, time, love, health, joy and so much more.
In the year 2025 A.D., whether it’s a need from Maslow’s Hierarchy of Needs 1.0 or 2.0 (2.0 from Manfred Max-Neef in the book Human Scale Development), money has become a placeholder for almost all needs.
You can’t eat money, drink it, wear it, or live inside it…
money doesn’t care, it doesn’t have an opinion, it doesn’t love you or hate you,
and yet you need it to do almost anything.
Money is tired, it has been overworked and underpaid (that’s a joke).
And we’re tired too (that part isn’t funny).
The Worm in My Brain
To prove that I am human (and not a robot), I will definitely say that I need money and I have to think about it, just like we all do, just like we all need air, water, food, shelter, etc.
I dislike having to think so much about it. I’m mad at myself for even writing about it. I also think I cannot find something important to say about it if all I am doing is worrying about it.
There are variations on “money thoughts” and (also) lamentations:
“If I had money, I would...”
“If I had money like they do, I would...”
“I need money to.....”
“It just costs so much money…”
“I don’t have enough money for…”
…I could go on
I recently took a sabbatical - something I planned and feel incredibly fortunate to experience. I recognize the privilege.
Even during sabbatical, money has been in my face every day, sometimes every hour or minute, all the time. It’s like a small persistent worm nibbling through the brain. Cute in cartoons, less cute in real life.
Even when I try to tell the money monsters inside my head (and outside too) to “stop it with the money thing”, they do not go away easily! If for a moment you can stop thinking, wondering, worrying - someone else will likely very soon remind you:
“So… how are you going to make money?”
“Aren’t you worried about money?”
“You need to get rich and win the lottery.”
Or, I am reminded by that bill I need to pay or the prices of things in the grocery store.
Money Won’t Leave Us Alone
One could say that “money just won’t leave us alone” in the sense of the always-present burden that comes with thinking about money, needing it, wanting it, etc. Some may jokingly wish for “money to bother them much more often, especially big boatloads of it”!
Whether we like it or not, we can’t stop talking or worrying about money.
I’ve tried leaving money behind but it keeps finding me. Money, I want to quit you!
The irony that I just made you all think about money… again… is not lost on me.
And yet, our relationship with money is fleeting. It’s almost as if money has a mind of its own - leaving our lives just as fast as it enters.
Those of us who are constantly opening our purses and wallets or pulling out the credit card might feel like our money is constantly fleeing our presence. Every time I open my wallet… money jumps out and flies away 💸. Heck, money flies out of my bank account without me ever even touching it.
Money leaves me alone.
Whether money goes on its own, is given, or is taken - often when it goes we feel a loss or sense of security. It is almost as if “money has left us and now we feel alone”. Empty-pocket syndrome. In some ways, being free of money can be freeing, but we also strongly feel its absence.
Or, more seriously, as I have seen a number of times - those who have enormous amounts of money often find themselves alone and isolated. Having lots of money does not necessarily solve anything.
In this sense, money can feel cruel.
Twenty Questions for Money
Questioning money is like questioning time - neither has existed as long as the universe, but both control how we live inside it. On a geologic time scale, money (e.g. currency) is a pretty small blip on the timeline.
Asking yourself hard questions about money can be quite revealing.
Here are some interesting questions I think we should ask more often:
What would I do if I actually had the money to…?
What would happen if I lost all the money I have, how would I go from there?
I hope you never have to actually answer this question, and I care for those that have or are going through this.
What would I do if I had way too much money? What would I do with it?
Once I have enough money, and I have satisfied essentially all my needs and wants related to it, what am I going to do with it?
This seems like a nice problem to have but from the experiences I have seen with people who encounter it, it actually isn’t that nice of a problem at all.
Do I really need as much money as I thought I did?
How much money do I really need, and do I really need what I can buy with that money?
What if I didn’t think or worry about money first, what would I think of instead?
…and the list goes on here as well.
We Have to Figure This Out
I respect money. I need it. I live in the same world you do. But I’ve never been motivated by money for its own sake.
Maybe that’s foolish. Maybe it’s exactly why I care about this.
You may notice that my Substack isn’t monetized. That’s not a mistake.
I might need money too, but right now, I’m chasing something else:
a way to live, work, and help others without money being the first and last question.
What I’m Working On
I realized that “figuring out money” isn’t just an interesting topic to me - it is part of my vocation.
I am working on it, and I have some thoughts.
The truth is, I want to push myself hard, maybe for the rest of my life, until I figure something out that helps us humans about money.
Money may buy happiness, but there is no guarantee.
This goes towards a fundamental philosophy for me. I want to live a good, reasonable, practical life - have some fun, and as much as possible enjoy the big three: health, wealth and happiness. My happiness comes from the love of my family, my friends, and caring about other humans.
My Own Answer (For Now)
If I had money, I would figure out how to help others first, today.
Breaking it down, I notice several things:
If I had money, I wouldn’t worry about it. So I am searching for a solution that provides money, so that I can not worry about money, so that I can help others first.
If I could do something that would satisfy the need to have money and help others first, then my problem is solved and what I can do to help others can be realized.
If I am subject to analysis paralysis, worrying about having money is preventing me from important and meaningful action. This is bad.
I’d rather figure out how to help others first, without having to worry about having money at all.
I genuinely care about other people - this is important to me.
How amazing can it feel to start from a place of thinking about helping and doing good without worrying about money, even before I have the money to do so?
What would I do if money didn’t decide what was possible?
Your Turn
So here it is - the challenge:
If you had the money, what would you do?
(Really. Think about it. Write it down. Tell someone.)
P.S. If you still want that AI + technology change and society article, let me know in the comments. Honestly, AI might just be another story about money, but that’s something for another day.



You heard how much this is on my mind just today! I think part of it comes from following my dreams in years past, failing, and then finding myself in scary situations. Money has such a hold on me because my loved one's health is intrinsically tied to it. I agree it *shouldn't* be this powerful of a force in my life, but, unfortunately, to follow other dreams- like having kids - it *has* to be ever-present in my decision-making.
Thank you so much for your thoughtful post, Jon! I look forward to becoming closer friends as time goes on 💛