My wife has been on me for months.
“You should do a speaking tour,” she says. “You’re great at this. People need to hear it live.”
She’s not wrong. Speaking is how I’ve landed most of my best clients.
And yet, here I am. Writing you an email instead of standing on a stage somewhere. Classic me.
Let me tell you where this one started.
My dad was 35 when he was diagnosed with leukemia. He lived another ten years — but I was only 12 when he passed. Old enough to understand what was happening. Old enough for the lesson to stick.
He wanted to protect us. So he made some big moves. Bought a motel in Kissimmee, Florida — 15 minutes from Disney, where the parking lots are bigger than some countries. It never really took off.
He also bought a farm to develop into office buildings. Then the market tanked.
We got stuck with both properties. Huge mortgages. When my dad passed away at 45, the life insurance didn’t even come close to covering it. My mom — a widow in her 40s — was staring at ten thousand dollars a month in negative cash flow. In the 80s.
They borrowed from family to stay afloat, but it wasn’t enough. She had to sell the house I grew up in. We went from what felt like stability to renting. Just like that.
The message I absorbed wasn’t subtle:
Play it safe. Don’t take risks. Get a job that pays.
If Dad had just worked a regular job and saved, we’d have been fine.
That message is still running. Thirty-plus years later.
I’ve been a financial coach for 15 years, self-employed the whole time, teaching people about their money patterns — and my own pattern still has its hand on the wheel.
I call it the Play It Safe Loop.
It doesn’t announce itself. It’s sneaky. It disguises itself as prudence. As being “responsible.” As “not rushing into anything.”
You might recognize it as:
- The promotion you didn’t ask for because the timing wasn’t perfect.
- The investment you researched for eighteen months and still haven’t made.
- The business idea living in a Google Doc so long it’s practically pickled.
- The raise conversation you keep postponing until you have “more leverage.”
- The emergency fund that’s now so big it could double as a fortress for your fear. 🏰
The Play It Safe Loop feels like wisdom. It sounds like your most sensible self. But underneath, it’s just a story you inherited — probably from someone who got burned once and decided, never again.
Here’s the thing, though. My dad wasn’t running the Play It Safe Loop.
He was running the opposite.
Call it Leap Before You Look.
The pattern that says: move fast, bet big, figure it out later.
The motel and the farm weren’t reckless — he was sick, desperate to provide, and the math really did make sense at the time. But the pattern underneath was: action now, consequences later.
Some of you are running that one. You know who you are.
- The big swing that didn’t pan out.
- The “opportunity” you jumped on before you’d done the math.
- The credit card balance that grew because the moment felt right and the future felt far away. 💳
Two patterns. Opposite expressions. Same root: money doesn’t feel safe.
One responds by freezing. The other by leaping. And sometimes — if you’re really lucky — you marry your opposite, and the two patterns get to fight it out in your kitchen every time a financial decision comes up.
The pattern you’re running probably isn’t the one you chose. It’s the one that got installed — by a parent, a crisis, a story you watched unfold when you were too young to know you were taking notes.
You don’t break it by arguing with it. You break it by catching it mid-sentence. By noticing the moment you’re about to freeze again — or leap again — and doing something different.
For me, that means booking the first speaking gig this week. Before the loop talks me out of it. Again.
(Psst — want me to speak at your workplace? A men’s group? Your book club that’s really just an excuse to drink wine? I’d be honored. Just hit reply.)
What’s your loop? And what would doing something different look like — just once?
CTA:
Wondering what pattern is running your money?
Book a free clarity session and let’s find it together.
Avraham
Your Financial Coach
P.S. My wife is going to read this. So now I actually have to book the speaking gig. Sometimes accountability is just hitting “send.” 📨
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