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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 I just discovered about myself: I assume sunny days mean everything is okay. If the weather is good, she’s fine. I checked the weather: flash flood warnings. 89% chance of rain. She must not be having fun. And here’s the weird thing: every time the weather’s bad, the same thought shows up uninvited. I wonder what the weather is in San Diego. Like clockwork. For years. Because San Diego is considered the best place to live in the U.S. for weather. 266 sunny days a year. I Googled it. So I checked the weather in San Diego, and my wife caught me checking. Again. “Why do you do that to yourself?” It’s an obsession. She used to get nervous about it — not that I was secretly planning to move us to California. More like how she gets nervous when […]

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 call them “vintage” now. Apparently, On Cloud is the thing now. The split soles. The cool kids. The whole vibe. She has a pair. She loves them. Their “heaven”. “Everyone has them, Tatty.” So I went to the store. The On Clouds were right there. Front and center. On display like museum pieces. Everyone was trying them on. Looking at themselves in the little mirrors. Nodding approvingly at their own feet. Social proof everywhere. So I tried them on too. Felt pretty good about myself. Then I saw the Hokas. They looked comfortable. Maybe I’ll try those too. “Tatty. No. Hoka is for old people.” (I Googled it later. The Hoka demographic is “individuals aged 25–45.” I’m over 45. Apparently too old for the old people shoes. Teenagers.) 🙄 “On Cloud is cooler. By far.” So apparently my choices are: […]

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 a reader last week. BUT A FEW YEARS AGO? None of this was happening. In fact, everything in her life was awesome. Last week I told you about the cascade up. Seven kids. Immaculate playroom. One success leading to another. This is the cascade down. Get in the DeLorean. We’re going back to see how all this happened. WHEN EVERYTHING WORKED “I knew where everything was. I hosted fun dinner parties and loved having people over. They could come at any time.” She did the whole KonMari thing. She read the book. Followed the method. Organized every drawer, every closet, every corner. And it worked. (If you missed it: the KonMari method is where you hold each item and ask if it “sparks joy.” I got through half a drawer before giving up and eating my kids’ cheese strings straight […]

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 probably said, “tiny things that hurt when you step on them.” (It didn’t. But it should have.) Not a single toy on the floor. NOT ONE. I ask the obvious question: Were you always like this? She laughs. Not a polite laugh. The kind that says oh, you have no idea. “Actually,” she says, “not at all.” THE BEFORE She wasn’t born organized. Not even close. “I craved schedules, calm spaces, an uncluttered mind — but it felt elusive.” She tried systems. They didn’t stick. She tried solutions. She couldn’t carry through. She was always catching up. Always reactive instead of proactive. “I knew there was a better way. I just couldn’t get there.” Sound familiar? THE UNEXPECTED PART Here’s where I expected her to say she found the right organizer. Or read the right book. Or finally bought enough […]

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 her into a shame spiral. But here’s what struck me: she wasn’t beating herself up about it. She told me she’s learned to have discernment with herself. To know when to push forward and when to pull back. She’s proud of that. It took work to get there. Then she said something that stopped me: “Self-compassion allows self-esteem to grow.” I wrote it down. ✍️ THE NEXT TWO CALLS Different clients. Different situations. Same territory. Both were beating themselves up over choices they’d made in the past. Spending decisions. Career moves. Things they couldn’t undo. The shame was loud. And the shame was leading to more spending — the spiral I’ve seen a hundred times. I told them about the first client. I shared the quote. They wrote it down too. THE CONNECTION Here’s what I’ve learned after 15 years: […]

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 TSN Turning Point.” The fulcrum. The turn. The moment before and after became different. I’ve been thinking about that phrase a lot lately. THE LIE When people come to me, they usually want one thing: Show me the numbers. Give me the tactics. Let me see the spreadsheet. I get it. Numbers feel concrete. Actionable. Like if you just see the problem clearly enough, you’ll fix it. But here’s what 15 years has taught me: In all that time, I can count on one hand the people who looked at their numbers and then made the pivot. Maybe two. For everyone else — the numbers didn’t unlock them. The numbers alarmed them. ALARM VS. UNLOCK There’s a difference. Alarm is seeing the credit card balance and feeling your chest tighten. Alarm is running the retirement calculator and wanting to close […]

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.” I asked what she was doing. “Helping her with her transitions.” I’d never even heard the concept before. My wife understood something I wouldn’t figure out for years. THE STUCK Classic ADHD brain. Once I’m in the zone, I’m in. But switching? Moving from one thing to the next? It’s like my brain needs a full reboot. I finish an email. I know I need to do some online banking next. But instead of doing it, I’ll grab a drink. Check my phone. Wander around. Open the fridge. Close the fridge. Open it again like something new appeared. An hour later, I still haven’t started. THE PRAYER This one tortured me for years. I’m a religious guy. So I prayed for an answer. Nothing fancy came. No burning bush. No ten-step system. Just a small idea. THE PIVOT Here’s what […]