Financial Freedom Friday is for people serious about financial freedom. Every Friday I share what 28+ years of trading taught me. My mistakes. My systems. The lessons that got me out of Corp IT by 40. Learn from someone already doing it.
The first is a guy I talked to recently. Smart. Successful. Has some cash sitting on the sidelines. And he told me, flat out: "The stock market doesn't interest me."
I didn't argue with him. But I can't let it go... Not because he isn't sharp, but because he doesn't know what this decision is costing him. He'll never see the bill for it. He could buy back his time using math based options... I hope you know just how powerful the market is and you're making money with the Good Kids!
The second is a woman I "met" in a book I finished recently: Die With Zero by Bill Perkins.
Perkins' argument is simple and a little uncomfortable. Every dollar you die with is life energy you traded away and never got back. You worked for it, stressed over it, gave up mornings and weekends for it.. Then never turned it into anything. Not time. Not experiences. Not freedom.
Which brings me to Anne Scheiber. She was an IRS auditor. Never got promoted. Never made more than a modest salary. She took about $5,000 in the 1940s and turned it into $22 million in dividend stocks over fifty years. Coca-Cola, pharma, the classics. Textbook buy and hold. Who says dividend stocks are boring :)
Here's the rest of the story. She lived alone in the same rent-controlled studio for decades. Wore the same coat. Skipped meals to save money. She died at 101 and gave it all to a university. It was a beautiful gift. But she never spent a dime of it on her own life or saw what her money did for others.
Here's what gets me: she and my friend made the exact same mistake, from opposite ends. He won't touch the market, so his money isn't working for his freedom. She never touched her winnings, so the work never paid off. Both forgot that money is a tool for freedom.. Not a thing you avoid, and not a scoreboard you die holding.
Now.. Before the buy-and-hold dividend crowd nods along and deletes this email, there's a second uncomfortable truth in here, and this one has a ticker on it.
Yield is not always a strategy.
I posted this in our Discord this week about ConAgra (CAG):
I don't care what your dividend yield is. If you bought a stock at $40 a few years ago and it trades at $14 today, that's no good. The "yield" didn't protect you. It's a distraction while the stock fell apart. Now CAG is missing guidance and the headlines are floating dividend cuts. I didn't sell puts on it either. I'd rather trade better companies.
Anne Scheiber's mistake was never selling anything.. Including her own time. The CAG holder's mistake is never selling the wrong thing. Which raises the question nobody teaches:
When do you actually sell a stock?
Perfect week to ask. PayPal popped 17% on Tuesday when word got out that Stripe and Advent put in a $60.50-a-share buyout bid. Our Inner Circle chat lit up, and my answer surprised some people: I encouraged folks to sell it.
Here's my logic. We trade stocks because they're good companies. When a stock jumps because of other news... A rumor, a bid the board hasn't even accepted?? That's a sell in my mind. The deal might close. It might not. You're risking a real drop to squeeze out the last few dollars of a maybe. So even if you miss out on a little upside: take the gift, then go sell some premium in a good company for $3.00 and make up the difference in a quality trade.
That's not a hunch. It's the same math as everything else we do... Take the high-probability money, skip the coin flip.
The Inner Circle broke down exit decisions on ETSY and S. I walked through looking at what we know and what we can see to decide when or if we should sell: weekly/daily moving averages, support and resistance, a dive into the options chain skew.
If you want to see that breakdown... you have to be in the Inner Circle. :)
One last thought to close the loop on Perkins.
The reason I sell premium instead of just holding and hoping isn't only the math. It's that income shows up now!!! While I'm young enough to kayak at sunrise, lift heavy weights, take trips, and enjoy this journey called life.
Dying rich is "easy". Living free takes a system and some courage.
Somewhere between the guy who won't play and the woman who never cashed out, there's a third way: build the machine, take the income, live on it now. That's the whole game. Die with zero regrets. Money is a tool, it's not your goal.
Turning knowledge into wealth,
$Maxwell
P.S. Know someone sitting on a dividend stock that's down 30+% "because the yield is great"? Forward them this email. And if someone forwarded it to you subscribe here so you get one every Friday.
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Financial Freedom Friday is for people serious about financial freedom. Every Friday I share what 28+ years of trading taught me. My mistakes. My systems. The lessons that got me out of Corp IT by 40. Learn from someone already doing it.