Money & Me: A Love Story

If you and Money were to walk into a bar, what would it be like? How would you feel in Money’s presence? Does one person talk over the other? Is there a power dynamic? Are you friends?

Wait. I'm in a relationship with Money? My coach's question stopped me cold. Suddenly I was back in highschool, seeing Money for the first time when my little gaming website turned a profit. I was drunk off the idea of earning money, and I was a little shit about it too. I’d brag to my parents, friends, and anyone that would listen. The amount wasn’t even worth bragging about, but Money and I were hopelessly infatuated. That young, rebellious, fogged-up car windows in an abandoned parking lot kind of infatuation.

But now, months into my sabbatical, we looked nothing like that steamy affair. I imagined us sitting across from each other at a dingy dive bar – Money fidgeting, tapping her nails on the table, looking anywhere but at me. I felt restless, worn out, indignant. Our dynamic wasn’t just off, it was broken. How did we even get here?

Well, it started months before when Money and I came to an agreement. I was deep in burnout as Elon was dismantling Twitter, and I needed to get off the hamster wheel and recover. Money and I had a chat and agreed that we had enough savings to justify a sabbatical. So, I quit. With nothing lined up.

Those first months of unemployment were bliss. I’d wake up on a Monday and make myself a 6-course breakfast, waltz over to yoga, call a friend, then take the scenic route to dinner. For months I followed a similar schedule going to museums, taking long walks through Prospect Park, surviving Burning Man, and prepping for my brother’s wedding. My days were all about me.

Meanwhile, Money started to get anxious. I could hear her whimpering in the background, but I wasn’t ready to hear her. I needed–nay, I deserved–a break from capitalism and she wasn’t about to take that away from me.

Over time, her gentle gnawing turned into full-blown anxiety. What used to be a relaxing breakfast became a hollow routine. My yoga studio became an escape from Money’s regular tantrums. I was fidgety and restless in everyday conversations, saying yes to events I didn’t even care about—just to avoid facing Money.

Wtf. I didn’t get it. We had enough savings to be comfortable for a while. Why was she being so panicky? Can’t she see that I’m finally prioritizing myself? Don’t I deserve this? Why can’t she just let me LIVE?!

Exhausted, I broke down. Ignoring her wasn’t working, and I was numbing myself just to avoid the talk. That’s when my coach staged the intervention with those questions about our relationship.

So, I wrote a letter to myself, from Money, and boooooy did she have a lot to say. She was scared that I abandoned her and that our dreams were slipping away. That my tech skills would atrophy, or that we wouldn’t be able to send our (imaginary) kids through college. Or worse–that we’d have to settle for off-brand coconut water (sorry Vita Coco, you’re just not it). It wasn’t just about the numbers - she was exhausted from the uncertainty and wanted to know that she mattered. That the dreams we made together still mattered.

Of course they did. Though, admittedly, I hadn’t thought about them in a minute. It dawned on me that her “nagging” was really just her looking out for us.

So, I spent the next month focusing on her. I created financial projections to plot our way to a single family home. I gave up my in-unit laundry and got roommates to cut my burn rate. And most importantly, I made an iron-clad promise: if we ever got below a number, then I’d drop everything and get a job again.

This was enough to help money feel more secure and start to loosen up. Knowing that we had a plan to hit our goals, she could trust that I wasn’t abandoning our future - I was just taking a different path to get there. Putting those clear lower bounds gave us more room to explore. It’s intuitive when I say it now, but it definitely wasn’t obvious then.

So, explore I did! In the past year, I’ve gotten in the trenches with founders and coached product strategy, birthed a journaling company, and built my first neural network. I also face planted at my improv show, took weekends upstate to learn wilderness survival, heaved through a 10k race with friends, and built nearly a dozen small projects along the way.

And honestly? Nowadays I wouldn’t mind getting a paycheck again. I came to that conclusion on my own, without Money pestering me. It’d be nice to afford nice jackets and not think twice about an Istanbul adventure.

By agreeing to those strong lower bounds, she was able to give me leeway and trust that I would find my way back. I suppose that’s what a secure relationship looks like, huh? The anxiety hasn’t disappeared, but we’ve softened into each other, and we’ve become partners on this roller coaster instead of frenemies.

Of course, Money and I still have our moments – what relationship doesn’t? Though, I’d like to say if we walked into a bar together, we’d shoot the shit about our future over a couple of beers and raunchy jokes.

So, when’s the last time you talked to Money? Not about Money – to Money. What would they say?