What Asking A Girl Out Taught Me About Trading

Good morning, traders…

Back in High School, I finally worked up the courage to approach the girl I liked. 

She said no.

It hurt. I was embarrassed. Discouraged. It was the kind of rejection that makes you hesitant to put yourself out there again.

For a while, I didn’t. I let that fear of hearing “no” stop me from taking shots. 

Then it hit me. I had to practice.

So I practiced courage. I rehearsed mentally until I figured out how to approach women successfully. 

Not by being someone I wasn’t, but by being genuinely myself. 

So I asked again. This time with more confidence. 

And she said yes.

That “yes” restored my confidence. 

Years later, when I met my wife, I didn’t hesitate. I asked for her number the first time I saw her. I didn’t let the fear of rejection stop me. 

Sure enough, she didn’t say yes immediately. But I kept shooting my shot. I now had the confidence to do so. 

Last month, Shannon and I celebrated our 20-year wedding anniversary. Two decades and three beautiful children later have passed, and I owe it all to confidence.

And the same principle applies to trading.

If you’ve been struggling to find your niche — the types of trades that perfectly fit your style — it’s time to pay attention…

Your Shot Must Fit You

You have to be yourself in the markets. 

What works for anyone else and what fits your personality may be two completely different strategies. 

Start matching your trading style to who you are:

  • If you can’t sleep well with overnight risk, don’t make huge swing trades.
  • If you’re impatient, don’t take long-dated positions. 
  • If you can’t handle volatility, don’t trade when the VIX is above 20.
  • If you tend to overtrade, limit your number of trades per day. 
  • If you don’t have time to watch charts in the middle of the day, don’t day trade.

And if you’re tired of staring at charts all day.

Stop constantly babysitting volatile day trades…

Start making some “Chill Trades” with me…

Your confidence grows from your own positive outcomes. Not from watching someone else win.

When you take a trade that fits your style and it works, that builds real confidence. 

When you copy someone else’s trade without understanding why they took it or how they’re managing it, you’re just along for the ride. 

And if it doesn’t work, you have no idea what went wrong.

The Dangers of Copying Trades

I see this all the time…

Someone posts a screenshot of big gains on a Reddit forum. 

Minutes later, other traders post matching positions, following this faceless guy on the internet into a highly speculative trade. 

But they aren’t thinking about whether the setup fits their strategy.

They just see the big gains and want in … now.

Then the stock pulls back. Or takes longer to break out. Or trades sideways for hours. Or requires adjustments they don’t understand. 

They panic sell. The stock starts tanking. Capitulation unleashes. The trade gets destroyed. 

This gets worse during major market-moving catalysts

Social media explodes with traders sharing their bets. Everyone has an opinion, trying to convince you their trade is a sure bet. 

But blindly copying trades is a recipe for disaster. 

You don’t know their full strategy. You don’t know their risk tolerance. You don’t know their exit plan. You don’t even know who these people are. 

And if too many people pile into the same trade, it becomes overcrowded — setting up the perfect conditions for a short attack or stop-loss hunt. 

(Just look at yesterday’s big dip in quantum stocks for evidence of this.)

Trust your own research. If you don’t understand a trade inside and out, don’t take it.

Your trades should match your mindset, your account size, and your risk tolerance. 

How to Shoot Your Shot

Just like the fear of rejection kept me from asking girls out, the fear of losing money can keep you from entering a great setup. 

But one rejection doesn’t equal total failure. One losing trade doesn’t mean you’re a bad trader.

What matters is that you keep shooting. That you learn from what didn’t work. That you refine your approach. That you stay authentic to who you are instead of trying to be someone else.

Getting rejected is uncomfortable.

But real progress comes from pushing through that discomfort repeatedly, learning what went wrong, and fixing those mistakes for next time

You don’t have to be smooth. You don’t have to be perfect. You don’t have to trade like me or anyone else in our community. 

You just have to show up as yourself, execute trades that fit your style, and keep shooting your shot. 

So, tell me…

Will you keep playing guessing games in the options market?

Or will you start weaponizing the 1 strategy that works in 80% of market conditions?*

I’m talking about the same approach I used to turn $50 into $1,260 in just 2 months while stocks struggled with trade war uncertainty.*

This single strategy recently delivered my team 64 winning trades in a row.* 

I’m about to reveal exactly how to use this strategy to your advantage during my Simpler Options 2-Day Virtual Bootcamp.

I’ll show you:

  • The only strategy you should focus on right now. The same approach that helped my students catch 123 doubles in the past 12 months.*
  • The 3 simple rules that keep you out of trouble. The guidelines that helped one student go from $600 to $3,000 in his third week.*
  • My personal checklist for every trade. The systematic process that removes guesswork and emotional decisions.
  • Why this approach feels just like trading stocks (but with significantly more leverage and precision).

If you’ve been wanting to understand how options really work, now is the time…

The market won’t wait for you to figure this out on your own.

Join Me at the SIMPLER OPTIONS 2-Day Virtual Bootcamp on October 28-29 @ 12 p.m. ET/9 a.m. PT

Happy trading, 

Ben Sturgill

*Past performance does not indicate future results. Not Typical.

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