Fearless, except for money

I need to enter a season of radical financial abundance. As with most things, writing is how I think things out. Maybe you need this to, let's do it together.

Nothing scary I've ever done has lived up to the hype

How many times have you been scared of something, only to do it anyway, and then you were happy you did it.

For me it's 100%. Not 90%, not 99%. 100%

Every single bit of fear I've ever felt in my life has been unfounded once I had the experience I was so scared of.

Joining the Army, becoming a paratrooper, going to Kabul - twice, getting married, buying my first house, my first rental property, going to college, hiking Kilimanjaro, moving cross country to a place where I didn't know anyone with no job lined up (did this one many times), quitting jobs, quitting relationships, going to new gyms, making my first investment, public speaking - literally everything.

Confronting fear works, and over time my brain rewired properly and I now walk the earth without much fear (or stress) about anything. I feel like I'm tough as nails.

but with money I still play scared.

This is not without trying. I spent the last decade aggressively investing in stocks, real estate, and myself. I have lost money along the way, and I have made a LOT more than I've lost. Yet the conditioning around money hasn't had the same effect as all the other adventures - despite that other risks like international travel and jumping out of airplanes and war are real risks while money risk is artificial.

When it comes to money I play way too safe, I don't take big enough risks, I go way too slow, and I am very fucking sick of it.

Facts

1. Life is an adventure, and adventure inherently comes with risk
2. People critically over estimate risk
3. People critically under estimate upside
4. I stress the same about money now, as when I had none

This tells me that I have a neuroticism about money that may never be cured, a frustrating thing to consider, but it also tells me it has nothing to do with money and everything to do with something about the way my brain is wired.

Is this unfixable, or just hard to fix?

The best investors and entrepreneurs I know are constantly put big money behind their ideas and they don't seem to stress much. Maybe they are wired differently, maybe it's biological, but I definitely want to get closer to that. I have been more than safe for this lifetime.

No more saving

I believe in my potential, and I believe in the potential of the quilt shop.

but as I have written before, belief is something you act out - it's not something you say.

So if I really believed in the quilt shop I would dump all the cash I have into marketing. If I really believed in myself as a charming power-networker whose presence and friendship is a blessing to everyone I meet I would dump all my cash into local private communities to become the Austin social staple I want to be.

So what's stopping me, other than a mindset of scarcity?

I'm not rich by any means, and money always feels tight, so it's not like I have infinite money to just throw around at stuff like this.

...but that's exactly my problem. That's the kind of reasonable talk that keeps me playing small. It's not inherently untrue, but it's also true that if I took all my capital and put them into the opportunities I believe in, I would have more than I have now.

This is also the truth: I'm sitting on more cash than I probably need, a decent portfolio of positive cash flowing real estate and broad stock equities, and I have a stable income. Even if I contribute nothing else to it for the rest of my life and just waited for what I have to grow, I will be fine to retire comfortably. Yet instead of leaping eagerly at the grand opportunity in front of me I'm stockpiling resources like chicken little.

If behavior is the measurement of what we believe. My financial behavior would show me to be scared - and I don't like to think of myself as fearful. I need to fix this.