By Roi Riddler
Is Options Trading Gambling? Skeptical of Trading
To be honest, I’ve been burned by gambling pretty badly in the past. Losing money chasing highs, not knowing when to stop — it left a mark on me. That’s why I was hesitant at first to dive into stock and options trading. I thought it might just be another form of gambling.
But after seeing it firsthand — my uncle making millions, and my friend consistently pulling profits daily from vertical spreads — I realized there’s a clear difference. Trading options — when done right — is more like running a business than rolling dice in a casino. Specifically, I’m only interested in cash secured puts, vertical spreads, and covered calls.
Trading Options Is Like Running a Business
Think about opening a restaurant. Is that a gamble? In some ways, yes but it’s a calculated gamble. It takes planning, startup capital, and industry knowledge. Without those things, you’re just hoping for the best.
Options trading works the same way. When you treat it like a business — with a solid trading plan, enough capital, and proper knowledge — your chances of success seems probable.
The problem is when people jump in without learning the basics. Maybe these people are too eager to make money and don’t fully grasp the risk or understand what they’re doing.
The Real Stigma: Controlled Risk vs Degenerate Gambling
Gambling itself shouldn’t have a bad stigma — controlled gambling or risk-taking is a part of life and business. The real issue is with unchecked, compulsive gambling — chasing losses and highs without any limits
We’ve all heard the stories — someone hits a massive jackpot, only to lose it all trying to win more. It’s not the win that ruins them, it’s the lack of discipline afterward. The key difference between a disciplined trader and a gambler is:
Having a plan.
Knowing when to cut losses.
Jumping Into Stock Trading Without Knowledge Is Gambling
Jumping into the stock market without proper knowledge or a plan is basically gambling — pure chance with little control over the outcome.
Sure, all of life involves some level of risk. But there’s a massive difference between taking informed risks and blind ones.
Once you actually take time to learn — develop a trading strategy, understand risk management, and make decisions based on data — you’re not gambling anymore. You’re building a skill.
It’s kind of like this: betting on red at a roulette table is one thing. Running a restaurant after months of research and planning? That’s something else entirely.
A good trader thinks like a business owner. They analyze trends, manage risk, and know when to walk away.
Everything Is a Gamble — But Not All Gambles Are Equal
Life is a series of gambles. Taking a 9–5 job is a safe bet — you trade your time for a steady paycheck. Putting everything on a roulette spin? That’s all luck.
Options trading sits somewhere in the middle. It’s riskier than a job but way more controllable than a casino spin — if you treat it like a craft, not a quick win.
The Mindset That Makes All the Difference
Trading isn’t about winning every trade. It’s about winning more than you lose and managing risk so your losses don’t wipe you out.
You have to accept when your trade goes against you, cut it loose, and move on. Holding onto losses hoping for a miracle is the quickest way to lose everything — just like compulsive gambling.
My Plan: Learning, Practicing, Documenting
I’m not blindly diving into options trading. I’m stacking my money on the side while I take the time to properly learn this skill. Why? Because I genuinely believe that if done right, trading can be life-changing. It’s a high-value skill, and fortunately I believe at this point in my life I should be taking calculated risks.
At 25, I want to build something for myself. The thought of being a serial entrepreneur was always enticing to me. Still, I can’t lie… sometimes I wonder if I really have what it takes. But the only way to find out is to at least try.
I’ll be honest, I let emotions take over in the past. I used to be pretty disciplined with money — always thinking ahead, looking for ways to invest and grow it. Real estate was even on my radar as a future move. But somewhere along the way, I let emotions take the wheel. I blew through a big chunk of my savings gambling, and it’s one of my biggest regrets. It set me back more than I’d like to admit.
Still, this isn’t where my story ends. I’m not giving up here. I’m stacking my bread, rebuilding smarter, and making a promise to myself: no more reckless moves. I’ve learned the hard way, and now it’s time to move with purpose.
So here’s what I’m going to do within the couple months/year:
- Start from scratch: learn the basics of options trading.
- Use ThinkorSwim platform and practice paper trading.
- Save and budget consistently
- And documenting this entire journey on this blog so I can grow, reflect, and maybe help someone else along the way
Facing Self-Doubt: Part of the Journey
I won’t lie — I’ve been having a lot of self-doubt about my career choices lately. I’m scared. Stepping into options trading and entrepreneurship feels risky and uncertain, and sometimes I wonder if I’m making the right move. The fear of failing or losing everything can be overwhelming.
But I also understand that these feelings are part of the process. Taking risks and stepping into the unknown almost always comes with fear. What truly matters is that I keep moving forward, learning, and staying disciplined — even when the fear is very real. This is my journey, and I’m committed to seeing where it leads.
I’ve come to realize that almost everyone who has achieved success has faced these same doubts. Maybe it’s just a sign that we care deeply and want to do well. That kind of passion — even in the face of uncertainty — is something worth holding onto.