Gratitude, Desire, and a Money Paradox
“Desire is a contract that you make with yourself to be unhappy until you get what you want.” –Naval
I once dated a woman who was building her own jet charter company. She was one hell of a self-made entrepreneur and a beautiful spirit to boot. One late night, we talked about death. She told me that if she had to die the next day, she would do so in peace. She was completely in sync with her life, with who she was and what she wanted to do.
To me, death was frightening. I felt like I hadn’t even begun to live my life. I felt no pride in what I was doing. Whatever gift I had to offer the world, I knew I was not tending to it. Time was a-wasting.
Easy for her to feel at peace, I thought. She was accomplished. Me? I was worrying about money, the future, and my place in the world.
A couple of months ago I pursued a new habit. Every night I pulled out a pad of paper and filled a blank page with answers to the question “What do I want in life?” (This is an exercise based on Jim O’Shaughnessy’s excellent six-part Thinker & Prover thread.) Unearthing my desires was painstaking work.
At first, the pages contained memetic clutter. There were objects, achievements, and other external measurements of success. Things like, “I want to make $500,000 a year” or “I want to be worth $5 million.” Then there was “I want to own my own place in New York, and one in Florida for the winter, and in the Alps, and in Italy, and …” And let’s not forget “I want to write books that sell millions of copies.” Don’t get me wrong, I would not reject any of this if it came my way.
But these ideas were quickly overshadowed by the central tenets that emerged on the pages: Love, a partner, family, community, friendship. And to pursue interesting and creative work, to learn, travel, and explore. Lastly, to be free and secure.
More than anything, I want to follow my own path and share it with a partner, family, community, and the world at large. What I really want in life are experiences, activities, and states of being, not possessions.
And yet, money was always on the page. Sure, some amount of money is needed to live comfortably (and more in an expensive city or if one raises a family). But the numbers I put on paper had no intrinsic meaning and kept changing all the time. There is no specific amount of income or wealth that I’m looking for. Being rich is not actually important to me. Neither is having an investment track record or achieving success as a founder or professional investor.
More often, money showed up implicitly. It was the quicksand on which other desires seemed to rest. Money would provide freedom and security. Money would allow me to travel and pursue whatever work I found rewarding. Money was the wall behind which I could shield myself from the world’s pressures and do as I please.
I realized that my desires require time and attention much more than money. It was a paradox: What I wanted was to not ever have to worry about money again. Instead, all I worried about was money. As Tim Ferris said, “An obsession with security breeds a feeling of insecurity.”
Money was supposed to provide safety. Instead, an obsession with money made me feel anxious and inadequate. I failed to appreciate what I already had. To reach an imagined state of freedom, I focused my time and attention on money. I encaged myself and ended up with neither.
“It turns out that the life of protecting yourself from your problem becomes a perfect reflection of the problem itself. You didn’t solve anything.” –Michael Singer, The Untethered Soul
I was also setting myself up to feel miserable. Because, frankly, I haven’t been very good at money—at making it, compounding it, keeping track of it, and protecting it. Using money as a scorecard was bound to lead to perpetual frustration, especially in a place like New York which, as Paul Graham wrote, “tells you, above all: you should make more money.”
Longtime readers may remember that I fell in love last year before leaving New York for Germany. When I returned in May, I saw this woman again once before she ghosted me. A few months ago, she returned to my life with an apology. My feelings for her were still very real and with a mix of hesitation and excitement I met her for dinner. Over wine and cheese, she lobbed a question at me: Was my house in order?
I tensed up. I desperately wanted her back and was ready to shout “yes, one hundred percent!” But there it was, my inner voice of doubt. Was my house in order? The path I’ve chosen is risky. I have no idea whether writing will lead to financial success. I can’t offer predictability, stability, or comfort. In comparison to her, who had just started at a fabulous and very well-compensated new job, my house seemed shabby.
But I’ve since realized that yes, my house is in order. And it is truly my house. For the first time in my life, I’m feeling a degree of comfort with who I am and with what I’m doing. I don’t know what my path will look like. It’s like one of those long walks through the woods near my hometown. Just me and the crunch of my boots in the snow. The forest is silent. Sometimes a lone branch tugs at my coat. But this time, there is a song in the distance. I know there is no turning back. I must keep walking and follow that feeling of deep emotional resonance. Future me is waving from beyond the trees. “Just keep at it,” he whispers.
“Writing a novel is like driving a car at night. You can see only as far as your headlights, but you can make the whole trip that way.” E. L. Doctorow quoted in Bird by Bird
I can’t see further ahead than a few months. And I have to accept that I can’t expect anyone else to join me on this path. Whether or not they do is not up to me. But I feel grateful for having found a sense of mission that I hope will guide me through life from now on.
Rifling through my notepad made me realize there are many things I want. But none are as important as being true to myself, now that I’ve finally found a trace of who I am. Nothing else worked out when I didn’t know myself—certainly not money.
I’ve finally seen a glimpse of inner peace. Some days it touches my face like sunlight breaking through the clouds. There is no specific accomplishment or milestone that will make my life worthwhile. Walking is the reward. Following my own path is the peace.
“Pick your one overwhelming desire. It’s okay to suffer over that one.” –Naval
I did. It’s beautiful. And I’m incredibly grateful to all of you for being a part of it.
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Really enjoyed reading this! Thank you!
Your writing has truly changed my life. Thank you, Fred!