The 5 Monster Trades That Changed My Life
The thing about life is that it comes at you in real time.
"Risk comes from not knowing what you’re doing."
― Warren Buffett
"Every choice you make has an end result."
― Zig Ziglar
"There are no solutions. There are only trade-offs."
― Thomas Sowell
As regular readers know, in another life (and Substack), I am a trader.
Trader (n.) – A risk tactician who weighs reward against ruin, knowing survival depends not on being right every time, but on never being catastrophically wrong.
Trading isn’t just about buying and selling—it’s a mindset, a framework that extends beyond the markets.
I don’t mean this in some mystical, shamanic, Val Kilmer in Thunderheart type of way, but in the way in which the decision-making process in markets mirrors that of life.
It's the way we evaluate risk and reward, time our entries and exits, battle fear, greed, and ego, and ultimately live with the consequences—good or bad.
Recently, I reflected back on five of the more consequential “trades” that shaped the first half of my life. Here they are.
"The Perfect Entry"
My father worked for one company, Campbell Soup, for over 20 years. If my mother had her way, I would have followed his path.
After high school, I would have gone to a good, but reasonably priced, four-year college. Then, just as they handed me my diploma, a pneumatic tube would have sucked me up and inserted me directly into a cubicle at a Fortune 500 company.
My closet would be stocked with blue suits, white shirts, and black wing tips. In at nine, out at five—lather, rinse, repeat for 40 years, until they chucked a gold watch at me as I was shown the door.
Upon graduation there was a lot of pressure to choose a path—one that would decide the direction of the rest of my life—and I was feeling that pressure in spades. Worse yet, it felt as if the window to make that decision was closing rapidly.
So I almost took the "safe" route, but I knew in my bones that college wasn’t for me. Instead, I turned a high school side job into a full-time business.
This early entry into entrepreneurship allowed me to be my own boss and rise or fall on my own merits instead of punching a clock and kissing ass to try and climb the corporate ladder.
It might not have been the right choice for some, but it was the right choice for me.
"Cutting My Losses"
My first serious relationship was with a beautiful Peruvian girl named Maria, whom I fell head over heels for. It was a passionate and volatile relationship, as young love often is.
The first hint that there might be problems surfaced one night while we were having dinner at a Mexican restaurant.
After the waitress took our order and left the table, the conversation went like this:
Maria: I can’t believe the way you were looking at her.
Me: [Honestly puzzled] What are you talking about?
Maria: Oh my God, you looked at her like you wanted to jump all over her.
Me: [Heavy sarcasm] Yeah, in fact, when you go to the restroom, I’m going to ask her for a date.
Fortunately, I have good reflexes, and the salsa bowl hit the wall behind me.
I loved her as much as I could have loved someone at that time, and early on, I thought there was a future for us. But if Leonardo DiCaprio has taught us anything, it’s that love often has an expiration date.
And just one year into our relationship, we were attending weekly counseling sessions, trying to work through the countless issues that made us incompatible.
Then one night, as we were waiting to go into our session, it hit me harder than when Spade cracked Farley with that 2x4 in Tommy Boy.
If we’re only dating and already in counseling, where the fuck is this relationship going?
I hit the eject button right there, joined my friends at a local bar, and though I didn’t have a beer bong with me, I still managed to "get it in" as fast as I could.
"Rolling A Position Forward"
As a young man, I had one mantra that I repeated ad nauseam to every girl I dated:
I am never getting married, but if I do, I am NEVER having kids.
Boy, what a catch I must have seemed like!
After dating my current wife for almost six years, our relationship had reached a decision point—fish or cut bait.
She comes from a large Catholic family, and having children was embedded deep in her DNA.
Of course, that didn’t faze me. I figured I’d lay it on the line: the wonderful me or kids.
It was an offer she couldn’t refuse.
So I asked a friend of mine to help me practice my spiel. She pretended to be my future wife, throwing every argument she could at me to change my mind, but I was solid.
When it was time to have "the talk," we met at an international food court near my office. It was a good place to deliver bad news—it was always crowded, reducing the chances of an ugly scene. Plus, the Italian joint had a great calzone.
We sat down, and I told her straight out that I loved her and wanted to marry her, but under no circumstances would I be having children.
She didn’t bat an eye and simply responded:
Well, then I guess this is the end for us because I want to have kids.
I stared right back at her—having been well prepared for this moment—and said:
Well, baby, if that’s the case… then… well, uh… I guess I’m okay with having kids too.
I’m not a religious guy, but every night, just to cover my bases, I say a prayer to:
God
Mohammed
Buddha
Jimmy Page
Shiva
Vishnu
Mark Zuckerberg
Satan
That guy who keeps predicting the Armageddon
And I thank them for helping me put my ego aside, and letting me turn that losing position into a winning one.
"Learning Not To Chase"
In Southern California, when a baby is born, they give it a bottle and a subscription to the local MLS service. That’s where I grew up, and for as long as I could remember, buying real estate was a simple concept.
All you had to do was buy a house, and it went up in value. By the time I was 25 I had bought and sold three houses, but all for purpose of making money, not laying down roots.
Fast forward to 2002, and SoCal housing prices began to climb even more than normal. By 2004, the home-buying mania was in full swing, and my wife and I considered taking the plunge, to buy our “let’s raise a family here” home.
But we couldn’t agree on what we wanted, so we decided to wait.
By 2005, you couldn’t turn around without knowing someone who had just bought a house. When we went to cocktail parties people bragged about the five or six properties they were flipping.
The pressure to buy was incredible. And since we had a decent amount of cash in the bank, I was tempted to just say, “what the fuck,” and do it.
So I checked interest rates and talked to my mortgage broker friends. They all assured me that now was the best time in the history of the world to buy the house of my family’s dream future.
I resigned myself to doing so. But before meeting with my broker to start the search, I drove through a nearby housing tract and saw a newly listed property.
It was a 40-year-old, five-bedroom, 1,700-square-foot house in a decent but unremarkable neighborhood. It was marketed as a “fixer upper” with a listing price of a cool $1.5 million (about $2.4 million in today’s dollars).
I knew at that moment that the market had gotten away from us. And I canceled my appointment
.Life happens in real-time, and you have to make the best decisions you can with the information you have at the time. I’ve had some good outcomes and some bad ones.
These were five of the good ones.
Some day (soon) I’ll tell you about five of the bad ones.
The average person can read 250 words per minute.
If you made it this far, you took a seven and a half minute break from an increasingly chaotic and unhinged world.
Come back here next week and we’ll do it again—or stay on break and check out The Best of ‘The Anecdote.’
You kept me reading i was expecting something more deep; lol.
it's not easy to keep me glued to text without pictures but YOU DID IT :)