So I walk into my elevator. And there’s Taylor. Taylor is my neighbor. My wife thinks she’s so cool. Always smiling. Always has something going on. Today she’s wearing a pink hat. With furry moose antlers on top. I look at the antlers. I look at Taylor. “Nice antlers.” She laughs. “It’s a Jays thing. Vladdy ears.” I nod like...
I’m standing in a professional organizer’s basement. Seven kids live here. Seven. This is the playroom. You know, the room you’re supposed to shut when guests come over. But here I am. In the playroom. Door wide open. The books are color-coded. The boxes are labeled — not just “toys,” but dolls, Lego, Playmobil, art supplies, dress-up clothes. One box...
I was nine years old. My mother had finally had enough. Cleaning my room was a constant battle growing up. She’d ask. I’d “clean.” And by clean, I mean I’d grab everything in sight and stuff it into the closet. Problem solved. Looks fine. Don’t open that door. But she always opened the door. My mother would inspect. She’d look...
She was exhausted. A client. Just back from a hard trip overseas to see her mother. Batteries low. The kind of tired that doesn’t go away with sleep. Or coffee. Or a weekend. She told me she’d fallen behind on her numbers. The spreadsheet she usually keeps up with? Untouched. The tracking? Slipped. A few years ago, that would’ve sent...
She saved $70,000 by the time she was 17. I’ll say that again. Seventy thousand dollars. Age seventeen. No trust fund. No inheritance. Just a kid who saved. It was instinctive. Easy. The way some people are naturally athletic or can carry a tune without thinking about it — she could save money without it feeling like a sacrifice. She...
When I was a kid in Toronto, we watched hockey on TSN. And whenever the game shifted — the moment everything changed — the announcer would call it the TSN Turning Point. We all knew the phrase. My friends and I used it constantly. Something would happen at school, at home, on the street, and someone would say, “That’s the...
Transitions are torture for me. Finishing one task and starting another? It sounds simple. It’s not. At least not for me. My wife can attest. Years ago, when our daughter was little, we were driving home close to bedtime. My wife turned around and said, “Okay, just so you know — we’re heading home, then supper, then bath, then bed.”...
Kari’s clutch blew out on the way to Colorado. It was 2017. Starting over. Moving to a new state. And somewhere on the highway, her Subaru gave up. She burned through her savings to fix it. Then a boyfriend talked her into living way beyond their means — and funding his business venture. (She got rid of him eventually.) By...
Some of you have been reading my emails for years. I offer a free session at the end of almost every email. I’ve had amazing conversations because of it. But some of you have never booked one. I WONDER WHY A reader named Holly wrote me this week: “I know where I could probably change but I’m far too embarrassed...
My friend Sruli said something the other day that stuck with me.He was talking about potential — how sometimes, everything you want is already there, just waiting. You just have to turn the dial. Like a bubblegum machine.You know the ones: a glass globe filled with colorful gumballs. You drop in a quarter, turn the dial, and out comes a...
