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June 9, 2021
My psychologist friend says the most dangerous part about being a gambling addict is that you have hope.
You always maintain the obsessive belief that you’re just one bet away from turning it all around, solving all your problems and getting back on your feet.
That’s right man, after this last big score, it’s smooth sailing from here on out. No more hemorrhaging cash, dragging my family into debt just barely outrunning insanity each day. Back to my peaceful, honest and sober life.
But as with any addiction, just when you get there, there disappears. The hope never cashes out the way you want it to. The dragon is perpetually one step ahead.
Deniro’s warning in the best gambling movie of all time comes to mind:
In the casino, the cardinal rule is to keep people playing, and keep them coming back. The longer they play, the more they lose, and in the end, we get it all.
This is how running a business made me feel. Like any obsession, it started out feeling euphoric. All this attention and approval and money and love, yo, pass that shit, man.
But after a decade of making that daily entrepreneurial gamble, it occurred to me that I was no longer chasing the high, but simply trying to evade catastrophe. It was no longer about seeking pleasure, but avoiding pain.
That wasn’t enjoyable, that was sad. Sitting in my apartment all day, desperately waiting for that one email that would change everything, it just felt pathetic. My hope had stopped paying out.
The story I told myself about being one gig away from turning it all around wasn’t working anymore.
That’s when the idea of retirement started to cross my mind.
What if I could leave behind all the gambling, all the risk, all the unhealthy and obsessive parts of this thing, and move forward in a way that felt more pure and sustainable? What if I could find a day job that underwrote my ability to work on my own creative projects, but without the bottomless need for hope as fuel?
It had to be possible. There had to be a way to shrink the size of my business to fit my reality and keep only the parts that I loved the most.
Sure enough, there was. It took longer than I expected to make that transition. Maybe four years. But dual citizenship, as I’m fond of calling it today, is a better fit for where my life is now.
What I cherish about it is, there’s no more casino. There’s no more being one bet away from turning it all around.
Because screw gambling. Screw risking it all. Screw betting on yourself in the name of getting famous and growing rich and leaving a legacy. It’s not worth it.
If it’s true that love and fame can’t live in the same place, then it’s crystal clear which path is best for me.
Now I can save my hope for when I need it most.
What dangerous situation are you trying to convince yourself is just a phase that will improve?