“When The Grind Works (And When It Doesn’t)”

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The Core Truth:

This is the game when you’re trying to grind it out.

You’re not trying to hit home runs. You’re not trying to capture every dollar of every move.

You’re trying to generate consistent, predictable income while managing risk.

Some stocks cooperate. Some don’t.

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Why PFE Worked:

PFE: +$4,532 profit on $16,514 deployed = 27.4% in 6 weeks

What Made It Grindable:

1. Range-bound movement
   • PFE traded $26.50-$28.00 for 6 weeks
   • Narrow $1.50 range
   • Perfect for selling $28 calls, collecting premium, rinse and repeat
2. No earnings surprises
   • Moved $0.80 on last earnings
   • No gap risk
   • Predictable, boring
3. Low volatility
   • IV stayed stable 18-22%
   • Premium consistent week to week
   • No wild swings
4. Strikes stayed valid
   • Sold $28 calls week after week
   • Stock never blew through them
   • Never had to roll at a loss
   • Just collected, expired worthless, repeat

Result: The grind machine hummed along perfectly.

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Why VZ Didn’t Work:

VZ: +$815 profit on $29,332 deployed = 2.8% in 6 weeks

What Broke The Grind:

1. Trending movement
   • VZ went from $42 → $49 in 3 weeks
   • $7 directional move
   • You can’t grind a trend
2. Earnings gap
   • Gapped $5 overnight
   • Blew through multiple strike levels
   • Made weekly management impossible
3. Volatility spike then crush
   • IV pumped into earnings
   • Crashed after
   • Your $48.50 LEAPS got IV crushed (-$1,083)
   • Premium inconsistent
4. Strikes kept getting violated
   • Sold $39.50 calls → blown through
   • Rolled to $42 → blown through
   • Rolled to $47 → blown through
   • Paid $18,907 in roll costs fighting it

Result: The grind machine got caught in a trend and shredded itself trying to adapt.

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The Real Lesson: Know Which Game You’re Playing

The Grind (What You’re Doing):

Goal: Generate 20-30% annualized returns with consistency and low stress

Requires:

• Range-bound stocks
• Low volatility
• Predictable movement
• No major catalysts

Works on: PFE, T, utilities, boring dividend stocks

Fails on: Anything that trends hard (up or down)

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The Momentum Play (What VZ Became):

Goal: Capture directional moves, maximize gains

Requires:

• Directional conviction
• Willingness to let winners run
• Wide strikes or no short calls
• Accept volatility

Works on: Stocks in strong trends

Fails when: You try to grind it with tight strikes

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You Mixed Strategies:

You brought a grind strategy (tight strikes, weekly premium) to a momentum stock (VZ rallying on earnings).

That’s like:

• Bringing a singles hitter to a home run derby
• Bringing a marathon strategy to a sprint
• Bringing a fixed income mindset to a growth stock

It’s not that you did it wrong. You used the right strategy on the wrong stock at the wrong time.

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The Framework: Match Strategy To Stock Behavior

For Range-Bound Stocks (PFE):

✅ Tight strikes ($1-2 OTM)
✅ Weekly expirations
✅ Aggressive premium collection
✅ Roll aggressively to stay in range
✅ Max out the grind

Expected return: 25-40% annualized
Risk: Stock breaks out of range (up or down)
Management: If it trends, close and move on

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For Trending Stocks (VZ post-earnings):

✅ Wide strikes ($5-7 OTM)
✅ Monthly expirations
✅ Conservative premium (accept less)
✅ NEVER roll at a loss—take assignment
✅ Let the LEAPS do the work

Expected return: 15-25% annualized
Risk: Give up upside, but avoid roll disasters
Management: Accept the cap, collect modest premium, sleep well

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For Volatile/Uncertain Stocks:

✅ Don’t trade them with this strategy at all
✅ Or use VERY wide strikes ($10+ OTM)
✅ Or skip options, just own LEAPS naked

Expected return: Unpredictable
Risk: Everything
Management: Don’t

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The Revised VZ Story:

“I Made $815 On VZ. Here’s Why That’s Actually Fine.”

VZ rallied from $42 to $49 in 6 weeks. I made $815 on $29,332 deployed.

That’s a 2.8% return while the stock did 16.7%.

Disappointing? Yes.

A failure? No.

Here’s why:

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1. I Was Playing The Wrong Game

I brought a grind strategy to a trending stock.

The grind works when:

• Stock stays in a $1-2 range
• You collect weekly premium
• Strikes never get violated
• You compound the gains

VZ was NOT cooperating:

• Moved $7 in 3 weeks
• Gapped through multiple strikes
• Made the grind impossible

I should have recognized this after the earnings gap and switched strategies:

• Close the tight strikes
• Accept I’m in a trend
• Sell $55 calls and let the LEAPS ride

Instead, I kept grinding. Tried to roll. Fought the trend.

That’s like trying to bunt for singles when you should be swinging for the fences.

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2. The $815 Includes Paying Tuition

My $815 net is AFTER paying $18,907 in bad roll costs.

If I’d just taken assignment on the first blown strike:

• Made $4.50/share spread = $18,000
• Plus premium collected = $1,200
• Total: $19,200

Then restarted fresh with proper strikes:

• New LEAPS at $47
• Sell $52 calls
• Collect another $2,000-3,000 over next 3 weeks

Total if I’d played it right: $21,000-22,000

What I actually made: $815

Tuition paid: $20,000+

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3. But I’m Still In The Position

My current open position is +$4,665.

If I close it today:

• Total VZ return: $815 + $4,665 = $5,480
• Return on $29,332: 18.7%
• Time period: 6 weeks
• Annualized: 162%

So the story isn’t over.

The $815 realized is just the tuition I paid learning. The $4,665 unrealized is me applying what I learned.

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4. PFE Showed Me It Works (On The Right Stock)

PFE: +$4,532 on $16,514 = 27.4% in 6 weeks = 238% annualized

The strategy isn’t broken.

I just applied it to the wrong stock at the wrong time.

PFE was grindable. VZ wasn’t. Simple as that.

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The Chapter Conclusion: “That’s The Game”

When you’re grinding it out:

Some weeks, you make $400-600 and everything works.

Some weeks, the stock gaps through your strikes and you pay $6,000 to roll.

Some months, you’re up 27% and feeling like a genius.

Some months, you’re up 2.8% and wondering why you bother.

That’s the game.

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The Key Is Knowing When To Grind And When To Step Back:

PFE at $27.60, stable, post-earnings, range-bound?

• GRIND IT: Sell $28 calls every week, collect $1,200, repeat.

VZ at $49, fresh off a $7 rally, momentum strong?

• STEP BACK: Sell $52 or $55 calls for less premium, let the LEAPS work, don’t fight it.

VZ at $42, earnings next week?

• SIT OUT: Skip the week, don’t risk the gap.

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The Honest Assessment:

“I made $815 on VZ when I could have made $4,870 if I’d bought stock.”

“I made $4,532 on PFE when stock would have made $1,600.”

“Combined: +$5,347 vs. +$6,470 if I’d just bought shares.”

“So I underperformed by $1,123 despite using leverage and actively managing for 6 weeks.”

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“But here’s what stock holders didn’t get:

1. I controlled $340,000 of exposure with $45,000 deployed (7.5:1 leverage)
2. I collected $8,000+ in weekly premium (cash flow stock doesn’t provide)
3. I learned $20,000 worth of lessons (about strike selection and roll management)
4. I’m protected on PFE (stock holders have unlimited downside, I’m capped at $6,400 loss)

“Was it worth it?”

“For PFE: Absolutely. 27.4% in 6 weeks, smooth, easy, repeatable.”

“For VZ: Not really. 2.8% return for that much stress and capital.”

“But that’s the game. You don’t know which stocks will cooperate until you’re in them.”

“PFE worked. VZ didn’t. I made money on both anyway.”

“Next quarter, it might flip. VZ might be the grind. PFE might trend.”

“The strategy is sound. The execution on VZ was rough. But I survived, I learned, and I’m still here grinding.”

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The Final Framework:

When The Grind Works:

• Range-bound stock
• Post-earnings (no catalyst)
• Tight strikes
• Weekly cycles
• Collect 20-40% annualized effortlessly

When The Grind Doesn’t Work:

• Trending stock
• Pre/post-earnings gap
• Your strikes get blown through
• You pay to roll
• Make 0-5% annualized with maximum stress

How To Know The Difference:

You don’t. Not ahead of time.

You just:

1. Start with the grind strategy
2. If it’s working (PFE), keep grinding
3. If it’s not working (VZ), adapt or exit
4. Take your lumps
5. Move on

That’s the game.

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