Today I want to kick off a new series: a look back at how I used covered calls over the past decade to reach financial freedom. This isn’t just about sharing numbers; it’s about offering an example of how a long-term, disciplined approach can change your life.

Ten or so years ago, I was fresh out of school. I had landed a job in a traditional industry, but I was basically starting from scratch—no savings, no family money, nothing. With just an ordinary paycheck, I began putting aside a little each month and investing in the stock market. Over time, I discovered a strategy that truly fit me: selling covered calls. That’s what ultimately allowed me to step off the treadmill and reach financial independence.

The Early Struggles of Covered Calls

If you’ve ever sold covered calls, you know the initial attraction. It feels like “free money” — you’re getting paid just for owning stock. But soon reality sets in: you miss out on big rallies, your stock gets called away, and you start to wonder if the strategy is even worth it.

A lot of people stop there and dismiss covered calls as a “pennies now, dollars lost later” game. But that’s only true if you treat it carelessly. Done right, CCs are not just about clipping coupons—they can be structured to generate consistent income, smooth out volatility, and support long-term wealth building.

That’s what I’ll be exploring in this series: not just the mechanics, but the mindset, techniques, and real-world lessons I’ve learned.

Why I Chose Covered Calls

One of the biggest benefits of covered calls is peace of mind. Unlike speculative trades that keep you glued to your screen, CCs let you make money with time on your side. And time, unlike the market, never stops. Whether stocks go up, down, or sideways, theta keeps ticking, and you’re constantly collecting time value.

About 6–7 years ago, I committed to selling CCs as my primary strategy. Three and a half years ago, I started tracking every single trade in Excel. I wanted to see the real numbers, not just impressions.

Here’s what I found:

• Over 185 weeks, I sold thousands of CCs (with some cash-secured puts mixed in).

• My average weekly income: $6,000 in premiums alone.

• Annualized, that’s around $300,000 per year — not counting stock appreciation.

That’s what I mean by financial freedom. Even if my portfolio value were cut in half tomorrow, I’d still expect to generate around $3,000 a week. That’s still more than enough to cover living expenses.

What’s Next

This first post is just the overview. In the coming entries, I’ll dig into the details: the techniques I use, the trade-offs involved, the mistakes I made early on, and the real-life case studies behind the numbers.

Because while covered calls might look simple from the outside, there’s a whole world of nuance once you commit to doing it for the long run.