What Winning Traders Do Differently

The Harsh Truth: It's Not the Strategy

Here's what most new traders believe: "I just need the right strategy."

If I could learn the perfect setup…
If I could find the right indicator…
If I could just hit one big winner…

You know how this ends. The new strategy works for a while. Then a losing streak hits. Suddenly it's time to hunt for the next "better" approach.

Here's the uncomfortable reality: Over time, the gap between winning traders and everyone else has almost nothing to do with what they trade, and everything to do with how they trade.

Two people can run identical strategies, the same Wheel, the same PMCC framework, the same credit spread rules. One grinds out steady, manageable returns. The other blows up, gives up, or stays stuck in the "almost working" phase forever.

This article is about that difference.

Same Strategy, Different Outcome: A Simple Example

Picture two traders: Alex and Jordan.

Both follow the same options income framework:

• Small, high-probability trades

• 30 to 60 days to expiration

• 50 to 75% max profit targets

• Defined position sizing rules

• Focus on the Wheel, PMCCs, and credit spreads

Same tools. Same basic playbook.

Alex (the struggler):

• Doubles position size after a few winners "to speed things up"

• Ignores stop-loss levels because "the stock will bounce"

• Adds trades when emotional instead of when conditions line up

• Checks P&L every five minutes and overrides the plan constantly

• Quits a strategy after a normal drawdown

Jordan (the winner):

• Keeps size fixed and small, no matter how "confident" they feel

• Treats stop-losses and exits as rules, not suggestions

• Only adds trades when they fit a written checklist

• Accepts that no single trade matters, only the long series does

• Stays with a strategy through normal losing streaks, adjusting slowly and logically

Same strategy. Same market. Same opportunities.

The difference is behavior under pressure.

What winning traders do differently isn't glamorous. It's boring. But boring, repeated, rules-based behavior is exactly what lets the math of your edge show up over hundreds of trades instead of being derailed by a handful of emotional decisions.

1. Winning Traders Think in Series, Not Single Trades

Losing traders live and die with every trade.

A winner means, "I'm good at this."
A loser means, "I'm an idiot, this doesn't work."

Winning traders think like statisticians: "This is one trial in a long series. My job is to keep each trial consistent so my edge has a chance to show up."

They understand:

• Even a 70% win-rate strategy will cluster losers

• You can flip heads 5 to 7 times in a row on a fair coin

• The Law of Large Numbers only kicks in when you let it, by running the same process over and over without changing the rules every time you take a hit

So instead of asking, "How do I make this trade work?"

They ask: "How do I design a process I can execute 100, 200, 300 times without blowing up, burning out, or abandoning it?"

That shift, from event to process, is one of the clearest markers of a winning trader.

2. They Obsess Over Risk Per Trade, Not Profit Per Trade

Most traders start by asking: "How much can I make on this?"

Winning traders start with: "How much can I lose on this, and is that acceptable?"

The difference shows up in simple behaviors:

They keep each position small relative to portfolio size.
For most beginners, that might mean 0.5-2.5% of total capital at risk per trade, depending on the structure.

They structure trades so max loss is known and survivable:
Defined-risk spreads instead of huge naked positions. Cash-secured puts that fit the account instead of oversized leverage.

They assume bad luck will eventually show up:
A gap down. A surprise headline. A fast market. Instead of trying to "avoid" risk, they budget for it.

Losing traders lean hard on conviction: "This trade can't lose, the setup is perfect."

Winning traders lean hard on math and humility: "Even if this is a great setup, it's still just one trade. Size it like any other."

3. They Use Written Rules (Not Vague Mental Notes)

Ask a struggling trader for their rules and you'll get something like:

"I try to take profits around 50-70%."
"I usually cut losers if it gets too painful."
"I sort of wait for things to be overbought or oversold."

Ask a winning trader and you'll get specifics:

On credit spreads, I typically:

• Enter with 30-60 days to expiration (DTE)

• Target 0.20-0.35 delta short strikes

• Take profits at 50-75% of max credit

• Have a clear exit for adverse moves (breach of short strike, % of max loss, or specific technical level)

For the Wheel, I use:

• Only names I'd be comfortable owning

• CSPs with a certain delta range

• A maximum allocation per ticker

• Pre-defined assignment and covered-call rules

Written rules create three advantages:

Consistency - Your trades are repeatable.
Accountability - You can tell when you broke your own rules.
Improvement - You can tweak one variable at a time and see what actually helps.

Without rules, every trade becomes improvisation. Improv might be fun in comedy, but in trading it's just a fancy word for gambling.

4. They Respect Boredom and Avoid Drama

Losing traders often crave excitement:

• They trade too often because "nothing is happening"

• They take oversized bets to feel something

• They chase headlines, earnings, and meme spikes without a plan

Winning traders are comfortable with boredom:

• They repeat the same core setups again and again

• They sit in cash or stay small when conditions aren't right

• They accept that most of trading is waiting, for the right setups, for time decay to work, for the next high-quality opportunity

Options income strategies, when done correctly, are not supposed to feel like a casino. They're supposed to feel like running a small, repeatable business:

• You know your costs (risk per trade)

• You know your product (your strategies)

• You know your process (checklists and rules)

• You know that some weeks are slow and some weeks are busy, and both are normal

If your trading feels constantly dramatic, urgent, or exhausting, that's a signal something is off in your process.

5. They Treat Losses as Data, Not Identity

Everyone takes losses. Not everyone handles them well.

Losing traders:

• Take it personally: "I knew I shouldn't have traded this, I'm terrible at this"

• Immediately change strategies after a normal drawdown

• Double down to "make it back quickly"

Winning traders:

• Log the loss, calmly

• Ask, "Did I follow my rules?"

  • If yes, they record it as the cost of doing business

  • If no, they adjust their behavior, not the market

• Look at losses in context:

  • "Is this an outlier?"

  • "Is this a cluster that happens regularly?"

  • "Is the strategy broken, or is this just variance?"

Instead of reacting emotionally, they use losses as feedback:

"Is my position sizing appropriate?"
"Did I respect my exits?"
"Did I enter in line with my checklist?"

That mindset keeps them in the game long enough to benefit from the Law of Large Numbers. It also preserves the most important asset in trading: mental capital.

6. They Connect Every Trade to a Bigger Plan

Winning traders don't see trades as isolated bets. Each trade has a job within the larger portfolio.

For example:

Core positions (PMCCs, long LEAPS):
Provide stock-like exposure with defined capital, forming the backbone of long-term growth.

Income overlays (covered calls, short calls against LEAPS, the Wheel):
Harvest premium, reduce basis, and smooth returns over time.

Opportunistic spreads (earnings iron condors, short strangles, short-term credit spreads):
Take advantage of specific volatility or expected-move setups, always within a risk-defined framework.

Instead of "this trade will save my year," the thinking becomes: "This trade is one tile in a mosaic. My edge comes from how the whole mosaic is built."

Losing traders often have no such structure. Their portfolio is a random patchwork:

• A few long calls bought on impulse

• A naked put here, a strangle there

• No real idea of how much downside a cluster of bad outcomes might create

Winning traders know:

• Which trades are core

• Which trades are income

• Which trades are opportunistic

• And how much capital each bucket is allowed to use

7. They Respect Volatility Instead of Ignoring It

New traders often focus only on direction:

"I think this stock will go up."
"I think volatility will drop."

Winning traders focus on direction and volatility and time:

"Implied volatility is elevated; selling premium might make sense here, but size must stay conservative."

"IV is cheap, so buying premium might be more attractive, but I still need a clear exit and realistic expectations."

They pay attention to metrics like:

• Implied volatility (IV) and IV Rank

• Expected move around earnings

• How volatile their underlying tends to be historically

And they use that information to shape their position sizing, structures, and expectations, not as a crystal ball.

A Simple Framework You Can Start Applying Now

You don't have to become a different person overnight. But you can start acting more like a winning trader by building a few simple habits into your process:

Write your rules.

• How much will you risk per trade?

• What DTE range do you like?

• What deltas do you target for short options?

• When do you take profits?

• When do you cut losses?

Track your trades, but judge them by process, not outcome.

• Did you follow your rules? Yes/No

• If not, why? Emotion? Impulse? Overconfidence?

Think in batches of 50 to 100 trades.

• Don't rewrite your entire playbook after 3 losers in a row

• Look at the bigger picture: win rate, average win, average loss, drawdowns

Shrink size until you're bored.

• If every trade feels emotionally charged, your size is probably too big

• Winning traders often sound boring when they talk about their positions. That's a feature, not a bug

Always tie trades back to a portfolio-level plan.

• Which bucket is this? Core, income, or opportunistic?

• How much total capital is allocated to each bucket?

The Quiet Edge That Actually Matters

There's no shortage of strategies out there.

You can run PMCCs, the Wheel, iron condors, vertical spreads, collars, synthetic dividends with LEAPS, the menu is long. Plenty of these approaches are statistically sound when used with appropriate sizing and discipline.

The real question is: Will you run your strategy like a casino, structured, rules-based, emotionally neutral, or like a gambler, reacting to every outcome as if it's a verdict on your intelligence?

Winning traders don't have magic indicators or secret order flow. What they have is rarer:

• Respect for risk

• Patience with the process

• Commitment to written rules

• A willingness to be bored

• And the humility to let math, not ego, drive the long-term results

Those are the things most traders never quite adopt. Which is exactly why they work.

Want to Go Deeper?

If you're serious about moving from "strategy-hopping" to running a calm, rules-based options process, that's exactly what I focus on each week in The Option Premium.

I walk through real model portfolios, explain the why behind every trade, and show you how concepts like position sizing, volatility, and the Law of Large Numbers tie together in practice, not just in theory.

If this article resonated with you, the next step is simple: start acting like a winning trader on your very next trade, small size, clear rules, long view. Then repeat that a few hundred times.

Probabilities over predictions,

Andy Crowder

If you want a deeper dive into the live execution of these mechanics, consider our focused services: Wealth Without Shares (PMCC portfolios), The Income Foundation (Wheel/CSP strategies), and The Implied Perspective (credit spreads (verticals, condors) and tactical hedges).

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Disclaimer: This is educational content only. Not investment, tax, or legal advice. Options involve risk and aren't suitable for all investors. Examples are illustrative. Real results will vary. Talk to professionals before you risk real money