If you’re like me, you didn’t start in sales. You got a regular job, worked a predetermined set of hours, and got paid around the same amount every other week. You held a position at this job, with a title, glamorous or not, and you quickly learned that if you didn’t show up without notice one day, everything would fall into complete chaos for the work day. Not to mention, your coworkers and boss would seriously resent you. If you did this more than once, you were done-cut, fired, let go-and replaced by the next overly qualified resume that looked just like yours.
You then realized you were never going to get rich renting out your time anyway. You’re giving up the best years of your life helping someone else get rich and accomplish their dream. Anyway, you didn’t like the idea of only having the time and money to do something when you’re too old to want to do anything.
After your 3 day couch bender of Million Dollar Listing Los Angeles, you decide you want to get into sales. You were enamored with the idea of selling real estate, getting commission checks on 8M dollar properties. You probably wouldn’t drive a Rolls Royce yourself because you’re not a pretentious a-hole, but you liked the idea of knowing it was possible.
You get your last check in the mail, scoff at those poor suckers you left behind, feeling sorry for them that they’re too scared to leave the endless grind. But a flutter of excitement dances from your chest to your fingers as you type your card number into the online real estate course shopping cart.
Your $260.00 purchase completed, and you feel like a 15th century explorer charting the new horizon.
After months of learning crazy words you never heard of, like encroachments, encumbrances, and other “legalese,” you pay $400 to take the exam and pay for the application fee- a fee that the online course conveniently forgot to mention in their advertising- and you pass.
Letters from brokerages everywhere flood your mailbox. You feel worried for a second because you made a promise to yourself not to ever buy anything from an advertisement that reached out to you for business promising you’ll make big money (that time you got terribly swindled out of $300 for a dropshipping business that didn’t make a dollar, it actually cost you $100).
You choose a brokerage, and suddenly, the cage door flies open. You have total freedom. No clock-in times, no manager breathing down your neck, no mandatory desk hours. It feels liberating for exactly twenty-four hours. Then the psychological shock sets in: if you do nothing, absolutely nothing happens. Your calendar is a blank canvas of terrifying silence.
To fill the void, you volunteer to host an open house. You spend ten brutal hours over Saturday and Sunday standing on polished hardwood, smiling until your jaw aches. Eighty people stream through the front door. Eighty opportunities, you think. Except almost every single one of them walks in with an agent already attached to their hip. You feel like a glorified tour guide, handing buyers to the listing agent on a silver platter.
Later that evening, your phone buzzes. It is a text from the listing agent. Five offers are on the table, and counteroffers are already flying. You type back a congratulatory message, forcing a genuine tone into the screen. You are happy for her, truly. But a cold realization settles in your chest. You just gave up your entire weekend, sweated through your clothes, and worked ten hours for zero dollars, effectively earning someone else a massive commission check off your sweat and tears. Welcome to the 1099 life.
Just as the internal spiral starts, an experienced agent stops by the house before lockup. She sees the exhaustion in your eyes and talks you down from the ledge. She started five years ago and remembers the exact shock of moving from a predictable paycheck to the wild west of independent contracting. She hands you a perspective shift about renting and the grind that sticks: W2 employees can buy a house with 3% down because banks love predictable stagnation. A 1099 entrepreneur has to show up with 20% down because self-employment requires proving your worth upfront. The day will come when you cross that threshold, she promises, but right now, you just have to swallow your pride, put in the work, and hunt for your own leads.
It clicks. It connects deeply with that concept from Naval Ravikant: play long-term games with long-term people. All the real returns in life — whether in wealth, relationships, or knowledge — come from compound interest. Right now, you are just depositing the first, painful rounds of capital into a game that takes years to pay out.
But exactly what skin you have in the game is exactly what you get in return.
“One day your net worth will match your sweat equity.”
