Dear Financial Samurai,
I’m not usually one for technical analysis, but I was trading stocks on November 7 before our parent-teacher conference. A 3-month T-bill expired October 31, and I’d been waiting for a dip to buy back in, and it came.
According to Challenger, October saw 153,000 job cuts, the most for any October since the 2000 Dot-Com bust. The news spooked investors, and stocks fell fast.
But by Friday’s close, we got a bullish signal — a hammer formation. Stocks dropped in the morning, then rallied hard to erase losses. Sellers were exhausted, and buyers took over. I love that kind of price action.
Buying when the labor market is weakening might sound counterintuitive, but here’s how I see it:
1) We’re entering a historically strong period for stocks
2) A weaker job market increases the odds of a Fed rate cut in December
3) The NY Fed President said the Fed could soon resume expanding its balance sheet
4) There’s a high chance the government reopens before Nov 21.
With this setup, I can’t help but buy the dip. Timing tops and bottoms is nearly impossible — odds are, the bull market keeps going. Of course, there are never guarantees and I am worried about valuations. Just look at Meta get crushed recently. Notice the hammer shape of the last green candle.
A Lack Of A Paycheck
If you’ve got a good job, especially one that pays well, cherish it. I’d love to have a juicy bi-weekly paycheck smacking me in the face right now. If I did, I’d invest at least half of it because investing feels so much better than spending!
After 13 years in equities, I’m wired to invest first and maybe spend later. But when you’re jobless like me, not being able to invest aggressively when you’re bullish feels like deprivation.
If you enjoy a good dose of investing FOMO, you’ll like my latest post: FIRE Confessional: Not Having A Big Paycheck During A Bull Market Stinks.
Below are some of my investments I made on Friday, November 7 before our parent-teacher conference started at 10 am PST. Notice how the cash balance ran dry. Note: I have a margin account, but didn't buy stocks on margin. It's just a classification. I stop when my cash runs out.
Housing Insecurity In Retirement — NYC Edition
After managing a relative’s portfolio for the past year, I’ve realized another reason to own instead of rent: housing security when you’re older.
Since 2003, I’ve taken that security for granted because I bought. But my NYC relative is facing a major rent hike in 2026. At nearly 60, with limited earning power, being forced to move is the last thing she needs.
As an economist, I understand market forces. Renters often say they’ll invest the difference, but few actually do so consistently over the long term. And as her portfolio manager, despite her best intentions, I see her cash flow going toward plenty of other things besides investments.
Her housing stress has transferred over to me. I wish we’d talked about her finances a decade ago.
Read: Please Don't Rent Your Entire Life: Housing Security Is Vital
It’s Hard To See What’s In Front Of You
We all have blind spots. Even after 1.5 hours writing this newsletter, I’ll still miss errors — like when I forgot to delete a duplicate passage a few issues ago. Our minds skip details to move faster. That’s why it’s smart to get second opinions, especially on finances.
I learned this again recently with my current home. Despite being in escrow for nearly three months, I missed something obvious — a $1,000 mistake that could end up costing $15,000+.
If you're in the market for a home, check out my post: Paying For A Home Inspection Is Worth It: Don’t Skip Out
The Surprise Of Giving
During our meetings with our kids’ science and music teachers, they thanked me for my book Millionaire Milestones. I’d forgotten I dropped off copies before summer break. I was also surprised because this was the first time meeting them. My children and I only gave books to about six individual people.
Apparently, several teachers have been discussing personal finance topics this school year, to my delight. It feels great knowing we’ve created a small educational partnership. Nothing makes me happier than helping others reach financial freedom sooner—so they can live with more courage and do more of what they love.
If you’d like to gift copies of my USA TODAY bestseller to your community — and get some personal finance advice from me — visit my personal finance consulting page. As the year ends, a review session could help you start 2026 on stronger financial footing. With seven weeks left in the year, I'm limiting the session to seven spots.
To your financial freedom,
Sam
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