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Trading Truths I Learned the Hard Way
Weekly Edition: June 4th, 2025
Market Movements
Weekly Return | Current Level | |
---|---|---|
S&P 500 | 0.757% | 5,970.37 |
NASDAQ | 0.865% | 19,398.96 |
DJIA | 0.506% | 42,519.64 |
VIX | -7.913% | 17.69 |
Russell 2000 | 1.585% | 2,102.98 |
*Weekly Return is calculated as market open of the previous Wednesday, to market close this Tuesday (yesterday); Current Level is Tuesday’s (yesterday’s) close.
Weekly Rollout
The markets kicked off the week with mixed signals: U.S. stocks hovered with cautious optimism while bond yields crept upward, nudging the dollar into a downward spiral. Morgan Stanley sees this as more than a wobble, forecasting a 9% drop for the good ol’ dollar, blaming sluggish U.S. growth and an increasingly skittish global investment mood. Meanwhile, the OECD threw another wet blanket on the party, trimming its U.S. growth forecast again thanks to tariff tensions.
Over in Europe, all eyes are on the European Central Bank, which is widely expected to cut rates on Thursday. And in a headline straight out of a science-fiction-corporate-strategy hybrid, Meta entered into a 20-year deal for nuclear power, seeking to feed its AI ambitions with nuclear fusion—nice.
“Good-To-Know’s”
Selling Naked vs Covered Options — When people start selling options, they come across informational pieces that mention how it’s insanely risky. They tell their friends, who may be vaguely familiar with options, who then share horror stories of “unlimited potential losses.” However, most often they are referencing naked options, or uncovered options, and granted, those can be extremely risky.
For example, selling an uncovered call can open you up to the possibility of an infinite negative return, because, like shorting the stock, you’re agreeing to buy it later. If the stock goes absolutely f*cking ballistic, then buying later might mean buying it at 10x, 20x, or even 100x what it was trading at when you entered the position.
On the other hand, secured options counteract this by incorporating another piece into the strategy. When selling calls, it utilizes the ownership of the stock, so you don’t have to ‘buy it later.’ For selling puts, it secures the cash that you need to buy the stock at the strike price.
Make sure you know the difference.
Quote(s) I Like
"It’s good to learn from your mistakes. It’s better to learn from other people’s mistakes."
"If you don’t make mistakes, you’re not taking enough risk."
Thought Throttle
As the quotes above suggest, there is an immense amount of value that comes via learning from your mistakes, and especially, the mistakes of others. Why not let the people ahead of you on your journey serve as your learning curve?
This is especially true in an endeavor as complex as financial markets and the utilization of options. In this edition, I’ll cover a few key concepts that I wish I had known earlier in my investing and trading journey.
Mostly Purchasing Options > Mostly Selling Options
The natural course of trading development is to begin purchasing high-risk, high-reward (but low probability) call options. Many are drawn in by the allure of unlimited upside, the dream of turning a small sum into a fortune overnight. The image of Redditors going all-in on speculative trades is etched into the public perception of options trading.
The vast majority of options traders start here, but what truly matters? The speed at which you evolve past this stage. Most move on to strategies that involve selling options, or at least begin to incorporate selling into their approach. This introduces a more probability-driven and statistically favorable edge—when executed properly.
As with many things in life, consistency is quite a force to be reckoned with. It becomes invaluable, not just for financial growth through compounding, but for mental clarity and resilience. It keeps us level-headed, discourages reckless behavior, and promotes long-term thinking.
Shift from chasing lottery tickets to building a repeatable, structured process, and watch how you begin to unlock the true potential of your portfolio with options. It’s not a single trade, but the discipline over time.
Check Your Account Value Less
Check your numbers less frequently. This is a tip for 95% of people. There is an important caveat, however. This isn’t meant to be taken as ‘don’t know what is going on’ or ‘set it and forget it,’ but rather to strike a balance between over-monitoring and being unaware of what’s truly going on.
Most people with an interest in options fall into the ‘overly analytical’ category. But, constantly refreshing your portfolio doesn’t make you more informed; in many cases, it just feeds your anxious and impulsive self.
There’s a saying in the grilling and BBQ world: “If you’re looking, it ain’t cooking.” And that sentiment, to an extent, applies to selling options as well. If you're obsessively watching every tiny fluctuation, you’re more likely to make emotionally driven, short-term decisions, often at the expense of your long-term strategy. Not good.
Awareness, however, is still crucial. You do need to understand the state of your portfolio. You should measure performance and risk at regular intervals, with intention and perspective. After all, what gets measured gets managed.
Ultimately, it’s about creating enough distance to let your strategies work, while staying engaged enough to adjust when necessary. Knowing what’s going on, whilst recognizing that measuring too often or without purpose, can be just as damaging as not measuring at all. Time and practice are requisites to finding this balance.
Setting A Realistic Timeline
Understand that building big sh*t takes time. There’s a quote (I can’t remember from who, maybe Alex Hormozi) that essentially says, “it always takes longer and costs more than you think it will.” This is absolutely the case when it comes to investments. Growth is slower than you can bear, until it becomes faster than you can even imagine.
The level of nuance and detail involved in analyzing stocks, let alone options, is incredible. Most new traders underestimate just how much there is to learn. You’ll pay for that gap in knowledge with time, mistakes, frustration, and long nights. That’s the price of reducing ignorance. But believe me, it can be well worth it.
Even if we aim for a solid 2% monthly return—roughly 26.8% annually—building real wealth still takes longer than expected. And you don’t start at 2%. That is the ‘ideal’ for many. You grind, learn, adjust, and slowly work your way there. Consistently hitting the mark is the goal.
All worthwhile things come with a cost, and options trading is no different. Building something meaningful takes time, patience, and a willingness to stick with the process.
Building big sh*t takes time.
Patience, or Cash, is Often a Better Idea Than a Mediocre Trade
Have you ever gone to the fridge, looked in, didn’t see anything appetizing, walked away, only to come back 10 minutes later and do the same thing again? The contents didn’t change. You just lowered your standards out of boredom or habit.
That “persistence by any means” mindset doesn’t serve you, and in options trading, it can be downright dangerous. Lowering your standards in the market almost always leads to the same thing: a lower account value.
Waiting is an active choice. It’s not the same as doing nothing. Doing nothing is easy—being patient is hard. When you're unsure what to do with your “lazy dollars,” reframe the situation.
Putting your capital to work right now assumes you’re on a time crunch. But more often, you’re actually on a capital crunch. Your portfolio has time. What it can’t afford is unnecessary losses.
Cash is underrated. Cash beats a lukewarm trade.
When it comes to mediocrity, make like the anti-drug campaigns of the 80s: “Just say no.”
Work On Self-Control
I'll keep this one brief, because to some extent, every rule that’s come before this one alludes to one thing: self-control. It’s the dividing line between beginners and experienced traders.
The markets will test you. No doubt about it. But your edge comes from staying level-headed and sticking to your plan until the data changes, not when your feelings about the plan or data change.
Discipline creates consistency. And in trading, consistency wins out.
Trade Mechanics
This week’s subject is Ford (F). Ford is a stock that many people begin their option-selling journey using, usually with something like the Wheel Strategy. This is for a variety of reasons, but among these are the comparatively cheaper price per share (~$10) and its relative neutrality and stability.
This is Ford:

Let's say that we thought Ford is a good long-term hold and we would like to purchase the stock at the right price. If the right price were determined to be ~$9.50 (It’s at $10.19 currently), we could enter into a Cash-Secured Put that would cater to our outlook.
The basic function of the trade would go like this: We would sell the 3 July 2025 $9.5 Strike Put for $10 of premium. We would then have to secure $940 for collateral ($950 [Strike * 100 shares] - $10 Premium).
If by July 3rd, Ford falls below the $9.50 strike price, we’ll purchase the shares at an adjusted cost of $9.40 per share. If it remains above $9.50, we would keep the $10 premium.
Even on an underlying as stable as Ford (Stable = less volatile = smaller premiums), 1% in a month is not bad at all. When I started, these were the types of underlyings I would look for to ensure that I understood the basics.
This is the power of selling options.
This is for educational purposes only—not a trade recommendation. Remember to always do your own due diligence and consult a financial advisor before making investment decisions.
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