“I will start when…” is the most expensive sentence you can ever say.
Well, maybe other than “Let’s buy a boat.”
But in terms of wanting to grow and make progress, “I will start when” is costing you way more than you can imagine. I know what you are waiting for.
You want to understand just a little bit better, have just a little more time, a little more money, or study one more option before you get started.
I’ve heard every version of this along the way of stepping outside of the comfort zone. Hell, I’ve even said it myself more times than I can count.
The problem here is that NO ONE actually feels ready except for the people who are probably not ready.
I’m not saying preparation doesn’t matter. You should understand what you are doing before you do it. What I am saying is: change your definition of when you should start, because the real opportunity is the time you are missing while waiting to feel confident.
When it comes to the stock market, analysis paralysis, paper trading, and hindsight trading are notorious ways to leave you feeling regret:
- I should have bought Google 20+ years ago.
- I should have sold Moderna at $350 a share.
- I should have bought more shares during the pullback. * Why didn’t I sell more at the top?
I picked those specific examples because those are actually things I did. And can I tell you something? I had no idea what I was doing at the time. What I’ve witnessed—and what you know as well—is that you learn more from actually doing than you’ll ever learn from thinking about hypotheticals and wanting to feel ready.
Have you heard the saying, “Luck is what happens when preparation meets opportunity”? You might say I was lucky to buy Google in college and sell it 20 years later. You might say I was lucky to buy Moderna stock at $20 a share and sell it at $350.
What you didn’t see was the stock I bought that went bankrupt. The stocks I watched triple in the tech bubble only to drop to almost zero. What if I had stopped then?
You never saw how many covered calls I sold on stocks where I got called away way too soon. How many times I watched a stock double or triple after I’d already exited.
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The first time I traded an option, I wasn’t sure I was ready. Even today, decades later, there is still uncertainty. Still a little discomfort.
That feeling NEVER goes away. No amount of research or hours of study are going to make you feel “more ready.” In fact, the more you study, the more complicated you are going to make it—which will make you feel even less ready than you really are.
You learn options by trading options. Small size. Real money. Real feedback. That’s what turns information into knowledge.
Every month you wait is a month of premium you didn’t collect. A month of compound growth that doesn’t start. The market doesn’t pause while you get ready. It just keeps going.
Start smaller than you think you should. One contract on one stock you know well. Risk an amount you could genuinely afford to lose and not lose sleep over. See what happens.
You won’t be ready. Do it anyway.
