Fold or Go All In
On knowing when to hold on, when to let go, when to bet on yourself, and where to sit at the steakhouse.
It’s 3 AM on a Wednesday, and I’m coming down off two tabs of acid at a poker table in Palm Springs.
My friend, completely sober, wants to rally and hit the roulette wheel.
I say, let’s do it for the plot.
Can you see how this is shaping up to be a night of well-informed, rational decisions?
Let’s back up. How did I get here?
A few days earlier, I’d landed in Palm Springs for Modernism Week, under the well-intentioned guise of appreciating Richard Neutra’s houses and taking long early morning walking tours around picturesque Vista Las Palmas. But what do I actually remember most fondly?
Roasting in the desert sun, lounging by the zigzag-shaped pool at the Ace.
Steak dinners at Melvyn’s, the kind that compel you to wear a suit even when it’s 90 degrees out.
Taking the cable car up the mountain and sketching out dream houses on the backs of cocktail napkins.
Some fun tidbits and insights I picked up on that trip include but are not limited to:
The corner booth we sat at in the back of Melvyn’s was Sinatra’s favorite, because you can see the whole dining room. And all the exits.
The zigzag pattern of the Ace pool isn’t just aesthetic—it’s designed to create natural gathering points for conversation.
Get the tableside bananas foster. Hell, get the tableside caesar and a steak Diane. Everything is better when it’s lit on fire and made at a rolling cart by your table.
The one lesson that actually stuck with me?
The one that changed how I think about risk, decisions, and life?
I learned that at the poker table at the Agua Caliente casino.
If You’ve Got a Losing Hand, Fold.
Thankfully, I’ve never really been one for casinos. I have literally, never once in my life, walked out of a casino with more money than I came in with. Not once. Whatever I brought was always gone in a flash.
And yet, there I was, staring at a losing hand, convincing myself I could bluff my way through. I knew I should fold. But I didn’t. I liked to let ego and fear of losing keep me in.
So, shocker, I lost — probably harder than I had to.
Looking back, that stuck with me: If you’re holding onto something that isn’t working, stop doubling down. Got shitty cards? Fold ‘em. See what else life hands you.
Folding isn’t failure. Folding is discernment.
And when you do like your hand? Go all in.
You Can’t Half-Ass Two Things.
Here are some ways that going all in on yourself might look:
Dropping out of school to pursue a career you believe in.
Moving to a new city with no backup plan because you know you’re meant to be there.
Starting your business, making your art, publishing your work, even when you’re scared.
Doing it especially when you’re scared.
Prioritizing one thing fully instead of splitting focus across five half-hearted efforts.
Making a deliberate choice to believe in yourself before there’s external validation.
When I was 17, I was fully convinced I was way too cool for school.
I was skipping class to take client meetings, building what would soon become a full-time design career. I was balancing freelance work, client meetings, and pretending to care about how I did high school.
I liked my hand.
My parents and teachers did not.
One day, my mom sat me down and said:
“You need to focus. You can’t half-ass two things, you have to whole-ass one thing.”
That conversation over lunch has always stuck with me.
It was all the permission I needed to take action, make a decision, and drop out— I went all in on myself.
That one decision set the tone for everything. Every time I’ve committed fully to something, I’ve won. Every time I’ve spread myself too thin, I’ve lost.
There is rarely an in-between.
After I dropped out of high school in Oklahoma, I moved to San Francisco because I wanted to be around the people who were doing the damn thing. I thought I wanted to build a startup. I thought I wanted to be a founder. But the truth? I didn’t. I wanted to amplify. I wanted to be around creative energy. I wanted to be the mirror, not the engine.
It took me a while to admit that. I kept doubling down on the wrong hand — focusing on superficial status markers, chasing things that didn’t actually light me up. The smartest thing I ever did was fold. I walked away. That’s what ultimately led me to branding—where I am the amplifier. That’s where I create win/wins for my partners and clients.
What Folding Looks Like When It’s The Right Call
Folding isn’t failure. It’s knowing when to walk away so you can play a better hand.
Here’s what that might look like:
• Leaving a job that drains you instead of doubling down on trying to make it work.
• Ending a relationship that keeps you stagnant instead of waiting for them to change.
• Pulling the plug on a startup idea that isn’t taking off instead of throwing more time and money at it.
• Letting go of an identity you’ve outgrown instead of clinging to it because it’s familiar.
• Canceling a project when you realize you don’t actually care about it instead of forcing yourself to finish it just because you started.
• Accepting a sunk cost instead of trying to recover it.
Momentum Saves Lives.
Sometimes, you get dealt a winning hand—but you play it wrong.
In 2023, I accidentally built a viral empire overnight…
I started HustleGPT, an experiment to see if ChatGPT could build a business from $100. I figured it’d be fun. Instead, it turned into a global phenomenon.
News stations. Podcasts. Suddenly, I’m going on live TV. People are calling me an AI expert. I was being pulled in a million directions.
I burned out—hard.
Quick contextual aside: The Work Is Never Done.
My dad told me around this time that actors have a saying:
“Don’t stop going to class.”
He said it means that even when you think you’ve made it, when the big-break opportunity finally lands in your lap, you keep showing up and putting in the work.
There is no arrival — there’s only What’s Next.
This is the problem with perfectionism, though. We tell ourselves we’ll turn something in when it’s flawless. Or worse, we avoid finishing things at all because we’re afraid they won’t be perfect.
But the reality is that you’ll never get it perfect. You can only get it done.
Back to the burnout:
At first, I thought I just needed rest. Then days turned into weeks, and weeks turned into months. I was spiraling — drinking, numbing out, barely leaving my bed. I was virtually catatonic. I didn’t see or talk to anyone for most of the summer.
I kept waiting for someone to notice, to step in, to save me.
Of course, no one did. I’d been waiting for so long, until it got to this huge physical manifestation, for someone to walk in and whack me over the head with The Big Baseball Bat of Reason and Action. No such baseball bat exists.
I had to trudge through undeserved self pity and isolation to get to the moment. The epiphany.
Here’s what I realized: If I was going to keep waiting for the perfect moment, the perfect motivation, for some external intervention—I was going to stay stuck forever.
So, the next morning, I took one step. I didn’t drink.
I started small. I asked for help. I kept not drinking.
I didn’t have a grand plan. I just started moving, and it felt so unnatural.
And that little momentum, as small as it was — I think that’s what saved my life.
Folding, in this case, wasn’t giving up. It’s realizing I was in a losing game I don’t actually want to play anymore.
At press time, I haven’t had a drink or consumed any self-prescribed mind-altering substances in 485 days.
Play With Conviction, or Fold With Grace
I could have kept half-measuring my way through sobriety — trying to cut back, making excuses, waiting for the right time. But there is no halfway with something like that. Either you fold or you go all in.
And going all in — fully committing to recovery — is what actually changed my life.
So, hey. Maybe you’re at a crossroads. I actually think that feeling like you’re at a crossroads, or in a transitional time, can be an incredibly destructive mindset. It’s easy to feel safe in the in between, in not acting one way or another.
Maybe you’re holding onto something that’s draining you because you’re afraid to walk away. Maybe you’re keeping one foot out the door, afraid to go all in on what you do want.
How To Know Whether to Fold or Go All In
If it’s draining you and you’re only staying because of what might happen if you walk away—fold.
If you really want it and you’re scared of failing — that’s your sign to go all in.
If you don’t know what you want, take one step. Any step. Just move. You can’t screw up so badly that you can’t bounce back having learned something.
Play with conviction or fold with grace. Just don’t sit on your cards.
The scenic route is always worth it. And the view is better anyways.
That’s it for this week.
xo,
Jazzy
100%
My brother the psychic!