Dennis Friedman

Managing money well isn’t about always making the right move. It’s about avoiding the wrong ones—and knowing when to wait.  humbledollar.com/2026/02/value-…

I know a lot of people are worried right now. Prices are higher, jobs feel less secure, and businesses are cutting back. Seeing that only reinforces what I’ve come to believe: humbledollar.com/forum/someday-…

Rachel and I are not exchanging gifts this Christmas. We already have the best gift an older couple can have—that is each other. humbledollar.com/forum/someday-…

Jonathan's final book, Money and Me, is now available for pre-order.  If you enjoyed his @HumbleDollar articles, you'll surely like this.  humbledollar.com/forum/one-last…

Retirement Is Wonderful — But No One Warned Me About These Four Fears: humbledollar.com/forum/whats-re…

Farewell Friends - HumbleDollar humbledollar.com/forum/farewell…

Three ways people sabotage their own retirement: humbledollar.com/forum/retireme…

AI vs. Urgent Care: Guess Who Got It Right? humbledollar.com/forum/ai-vs-ur…

Should we help my stepson? humbledollar.com/forum/why-mone…

I’m not qualified to carry this anymore. humbledollar.com/forum/not-qual…

I’m not the same person I was when I retired. But the biggest change is this: I cry more easily. humbledollar.com/forum/i-cry-mo…

I gave a college grad two gifts: cash—and a newspaper subscription. Here's why that second one might matter more. humbledollar.com/forum/a-gift-w…

“Going it Alone” I realize that getting older isn’t easy — and losing someone you love is even harder. dennisfriedman.medium.com/going-it-alone…

When I think about what life would be like without my wife, I realize that getting older isn’t easy — and losing someone you love is even harder. humbledollar.com/forum/going-it…

Who Will Care for Us? humbledollar.com/forum/who-will…

“The Little Things That Scare Me Now” dennisfriedman.medium.com/the-little-thi…

The Wrong-Sided Man - He won’t move over. Not for me, an elderly man. But I watched him step aside without hesitation for someone his age. humbledollar.com/forum/the-wron…

At 74, It’s the Little Things That Scare Me Now. dennisfriedman.medium.com/at-74-its-the-…

My Investment Portfolio is Like a Cruise Ship. dennisfriedman.medium.com/my-investment-…