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Options Trading: My Journey from Penny Stocks to Passive Income

Chris W.
Author
Chris W.
Owning my financial freedom
Table of Contents
Options Trading - This article is part of a series.
Part 1: This Article
I’ve been trading since I was 20 years old. It started with a tip from a coworker, a penny stock, and every dollar I had in savings. What followed was a rollercoaster that changed my life—and eventually led me to options trading.

How It All Started
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It was at work that a colleague started talking about stocks and penny stocks. He was buzzing about how his purchases had appreciated over the course of a year. I barely knew what stocks were at the time. He told me I should invest in the one stock he highly praised.

So I did. I put in all my savings.

Rookie Mistake

Putting all your savings into a single stock based on someone else’s tip is one of the worst things you can do. Don’t do this.

The first few weeks, it dropped like a stone. I had lost over 40% on paper. I got discouraged and wrote it off mentally. I stopped checking the price altogether.

But a year later, out of curiosity—and because I remembered I still had that stock sitting in my portfolio—I decided to have a look and see what the damage was.

To my surprise, the stock had appreciated over 100%.

The Hook

That’s the day I got hooked. I started researching everything I could about markets, investing, and trading. To this day, I’ve never stopped learning—reading books and articles daily, watching news channels, exploring new ways of passive investment.


The Path to Options
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Early Exploration
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Asset Class What I Learned
Individual Stocks Stock picking is hard; most people underperform the index
ETFs Diversification matters; low costs compound over time
Warrants (European Market) Leverage can work both ways—fast gains, faster losses

I made money. I lost money. But most importantly, I learned.

Expanding Horizons
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Asset Class What I Learned
Forex 24-hour markets are exhausting; leverage is dangerous
More ETFs Index investing works, but I wanted more control
Research Books, courses, articles—I consumed everything

I was profitable, but I felt like something was missing. I wanted a way to generate consistent income without staring at charts all day.

Discovering Options
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After about 10 years of heavily exploring stocks, ETFs, warrants, and forex, I finally decided to jump into options trading.

A New World

Options opened a new world to me. I realized that options (on the US market) are not high risk if employed correctly. On the contrary—they can be highly lucrative and serve as a form of passive investment.

Did I burn my fingers? Yes, absolutely. I learned the hard way more than once. But options transformed my approach, showing me how to trade smarter, not harder.


Why Options?
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Here’s what I’ve learned after years of trading options:

Myth Reality
“Options are gambling” Options can reduce risk when used properly (selling puts, covered calls)
“Options are too complicated” The basics are simpler than you think; complexity is optional
“You need a lot of money” You can start with a few thousand dollars
“Only professionals should trade options” Retail traders have more advantages today than ever
The Key Insight

Options aren’t for everyone. But with knowledge and discipline, they can supercharge your investing. They’ve certainly transformed mine.


What This Series Covers
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I decided to write this Options Series to share everything I’ve learned and show you how you can benefit from options trading too.

Strategies You’ll Learn
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  • Cash Secured Puts - Get paid to buy stocks you want at prices you choose
  • Covered Calls - Generate income from stocks you already own
  • The Wheel Strategy - Combine puts and calls for consistent premium
  • Credit Spreads - Defined risk, defined reward
  • Iron Condors - Profit when markets go nowhere
  • Poor Man’s Covered Call - Capital-efficient income generation

Risk Management Topics
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  • Position sizing that won’t blow up your account
  • When to take profits (and when to cut losses)
  • Rolling positions to manage losing trades
  • The Greeks explained simply
  • Building a diversified options portfolio

Real-World Application
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  • Step-by-step trade examples with actual numbers
  • Entry checklists you can print and use
  • Workflow guides for managing positions
  • What I do daily, weekly, and monthly
  • Mistakes I’ve made (so you don’t have to)

A Word of Caution
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Be Realistic

I’m not going to promise you’ll get rich quick. Options trading requires:

  • Time to learn the fundamentals
  • Capital that you can afford to have at risk
  • Discipline to follow your rules
  • Patience to let strategies play out

If you’re looking for a get-rich-quick scheme, this isn’t it. If you’re looking to build a skill that can generate consistent income over time, keep reading.


Let’s Get Started
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I hope this intro sparks your interest. In the upcoming articles in this series, I’ll dive deeper into strategies, examples, and risk management.

My Goal

My goal is simple: share what I’ve learned so you can avoid the mistakes I made and get to profitability faster. Whether you’re completely new to options or have some experience, there’s something here for you.

Hope you find it useful.

Cheers, Chris

Options Trading - This article is part of a series.
Part 1: This Article

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