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How to Achieve Financial Freedom by Selling Covered Calls Every Week  (4/6)

This is already the fourth post in my series. I’ve been reading through all the comments, and many of you asked the same kinds of questions: Which stocks are best for selling covered calls? What Delta should I pick? How far out should I set the DTE?

These are all great questions, but they’re also very technical. The truth is, everyone develops their own preferences. A stock that works well for me may not suit you, and even if two people trade the same stock, the results can be completely different. That’s why my intention with this series isn’t to give step-by-step instructions on which exact stocks to trade or how to trade them. Instead, I want to share the lessons I’ve learned after more than a decade in the market — especially the insights from the last six or seven years, when I’ve focused heavily on selling covered calls. Think of it less as a guidebook and more as me reflecting out loud.

Why Tesla is my go-to stock

Let’s start with the obvious question: which stocks are suitable for covered calls? As I mentioned before, my number one pick is Tesla (TSLA). I sell both calls and puts on it, and I often use puts to intentionally build a larger position.

Now, Tesla isn’t for everyone. Some people feel it’s too volatile — and they’re not wrong. Over the last two or three years, it’s had several explosive rallies. If you’re selling calls, it’s easy to get called away in those moments. But here’s the thing: every stock is different, and you need different strategies for each.

My approach to Tesla is simple: I treat it as a 10-year hold. If I’m holding it long term anyway, why not sell calls along the way? Sure, I won’t catch every monster rally like the run from $100 to $300 in 2023 or $150 to $250 earlier this year. But let’s be honest — very few people actually capture those moves. Selling calls consistently gives me steady, low-stress income. To me, that’s far better than just sitting on the stock and calling myself a “long-term investor.”

The results so far

Here’s what it looks like in practice. I’ve been holding a sizable TSLA position for over three years now. Through covered calls alone, I’ve already collected more than half of my original cost basis back in premiums. At this pace, five years of selling CCs would reduce my effective cost to zero. And in reality, it’s even better — because I can use those premiums to buy more Tesla shares, which then continue to appreciate.

My rocky start in the market

Since many of you are new, let me also share a bit of my personal journey. I entered the stock market in 2007 with $25,000. Very quickly, I discovered options — and how fast the money could come. Within half a year, I’d turned that into over $100,000.

At the time, I was finishing my PhD and struggling with job prospects since I didn’t have a green card. My plan was simple: trade until I made $500,000, then use investment immigration to get my green card.

But then 2008 happened. The financial crisis wiped me out. By early 2009, not only were all my profits gone, but my original capital was completely wiped out too.

From 2009 onward, I got more disciplined. I put my monthly savings into mutual funds, slowly, consistently. But after a few years, I realized mutual funds were only giving me 5–6% annual returns. Eventually, I came back into active trading — short-term trades, long-term investing, buying and selling options, even dabbling in futures and options on futures. Some days I’d make a year’s salary in a single session, only to lose it all the next day. It was exhausting, and my results were mediocre at best.

The lesson that changed everything

Looking back, the most important lesson I’ve learned is the value of constant reflection. Back then, I often felt selling covered calls was just “picking up pennies and missing out on dollars.” But over time, I realized the real power of CCs: when combined with strong fundamentals and an understanding of stock trends, they give you a buffer — more time and more breathing room.

That’s why I say this isn’t about copying my trades. My exact moves won’t work for everyone. What I really want to share is the mindset: it’s better to learn how to fish than to be handed a fish.

In future posts, I’ll go deeper with examples — including how I handle situations when my covered calls go in-the-money. That’s a whole skillset on its own, and definitely not something you can approach mechanically.

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