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Camp costs $2,000. That’s what’s on the invoice. That’s the number in my head. That’s the number I told myself when my daughter asks to go. $2,000. Fine. We can swing that. And then my wife gets “The List” from a friend. The shirts. (Plural. Not one shirt. Shirts.) The skirts. The tights. The slippers. The water sandals. (Different from...

My daughter’s at sleepaway camp in the Catskills. First time. Eight-hour drive from Toronto. She called home. Told my wife it was POOOOOOOOURING.☔ I knew. I’d been checking the weather there every day since she left. Not because I could do anything about it. Just… checking. Imagining how much fun she was having. Or not having. Here’s a weird thing...

My daughter looked at my sneakers and said, “Tatty. No.” (That’s “Dad” in my house.) That’s it. That’s all I got. “Tatty. No.” I’m wearing Nikes. NIKES! I grew up in the era of Bo Jackson. “Bo Knows.” The Slam Dunk Contest. Nike wasn’t just a brand — it was THE brand. My Nikes? Cross trainers from the 00’s. They...

Fractured ribs. Autoimmune illness. Half her savings — gone. Fraudulent startup. Expensive executive coaches who changed nothing. Clothes she never wore. Business ideas she never started. Stuff in every corner. Can’t sleep. Can’t think. “I cannot recognize my place.” “I try to organize a part, and it’s completely scattered the next day.” That sums up an email I got from...

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...

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...

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.”...

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...