Why the Market’s ‘Pain Trade’ Is Still Higher — and How I’m Playing It

by | May 14, 2025

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The market doesn’t care about logic — it cares about pain. And right now, that pain is pressing higher.

If you’ve been cautious, bearish or just waiting for a pullback, this melt-up has been brutal. The S&P 500 blew through key levels, and we’re now up nearly 3% above a solid symmetry projection. It’s been a classic pain trade — not because it makes sense, but because it forces the most people to be wrong.

That’s exactly what we’re seeing now. Eleven straight weeks of extreme bearish sentiment in the AAII Investor Sentiment Survey? That’s fuel for this squeeze.

When everybody’s positioned for a recession that hasn’t shown up, the market punishes them — and that’s what it’s been doing.

How I’ve Been Trading It

I didn’t chase this thing — I positioned myself early. I was long back when SPY was selling off hard. I sold premium, sold puts and leaned bullish when things felt the worst.

And that’s what’s paying off now.

At this point, though, I’m not piling in. I’m sitting at fresh highs in my portfolio and holding more cash. Now it’s about income. Covered calls across the board — IBIT, Snapchat (SNAP), Pfizer (PFE), Silver (SLV), Baidu (BIDU), JD (JD)…

All designed to let me get paid while avoiding assignment. If any do get called away, fine — I’ll just reset.

But I’m also realistic. I can’t justify buying here unless we get a pullback. That’s the only way I’ll add new positions — not at highs, but on dips. Until then, I’m rolling calls, booking profits and watching for signs of a reversal.

What Happens Next

I’m watching the 6,000 to 6,100 zone on the S&P for a possible pause. We’ve got gaps to fill and backfill zones to test. If this thing pulls back, I’ll be ready.

But if it keeps pushing to 6,500 or even 6,900, I’ll look for a low-cost hedge — something that risks $500 to make $4,000 or more.

This isn’t the time to call a top. It’s the time to be smart, stay patient and let the market tell you what’s next. Right now, that story is one of disbelief, bad positioning and a relentless grind higher — in other words, the pain trade.

And I’m playing it for all it’s worth.

I’ll see you in the markets.

Chris Pulver
Chris Pulver Trading

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*This is for informational and educational purposes only. There is inherent risk in trading, so trade at your own risk. 

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