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I was on a Zoom call when it started. A loud pinging off my office window. Sounded like somebody was throwing frozen meatballs at the glass. I wasn’t far off. They said the hail was the size of golf balls. Some bigger. Then the sky went black in about four minutes. The rain came down so hard you couldn’t see the end of the street, and trees started snapping. At the trunk. And I’m on a call, being a professional, while approximately one thousand percent of my brain went: the kids. So I sent the fastest text of my life… Me: Get inside My wife: That’s an understatementThe hail were like ice cubes (There is a natural disaster occurring. Ice is falling from the sky. And my wife’s contribution to the moment is a light editorial note on my word choice. This is also why she edits my emails. It’s also why they’re any good.) Toronto looked like a disaster movie. People sprinting into Tim Hortons for cover. (Which is the most Canadian sentence I have ever written). ☕️🇨🇦 And with all of it — the whole city, that much damage — nobody was seriously hurt. I’m still not over […]

A client of mine lives on a mountain. Like, a MOUNTAIN mountain. So far up that her cell phone runs on satellite. No Starlink, no signal. I’m pretty sure there are mountain cats up there. Last month, construction workers knocked the Starlink off her roof. No internet. No phone. No way to make our call. So she drove half an hour down the mountain just to get cell service… Just to reschedule. 🤯 (I would’ve gone back to drinking my Orange Pekoe tea and explained it next time we chatted. But that’s me.) And in the meantime? She’d already: All before we even talked. She showed up anyway. — BOMB SHELTER Another client — a couple — lives in a conflict zone. We had a call scheduled. Ten seconds before we started, he said: “Just got out of the bomb shelter.” (I’m sorry, WHAT?) His wife had already rushed downstairs with both kids. He came back, changed a wet diaper — because parenting doesn’t pause for war — and joined the call. Halfway through, their phones buzzed. A warning. If there’s a siren, it’ll be in two minutes. Sure enough — sirens. They had to end the call, wake the […]

In 2013, I was Calendly’s first paying customer. Sort of. The product was free. I sent a check anyway. That’s how much I believed in it. They never cashed it. (It’s probably framed in the founder’s office by now. Okay, maybe not. But I like to think so.) Tope Awotona — the guy who started Calendly — called to thank me. I was in my office in downtown Toronto. He just picked up the phone — no Calendly link, ironically — and we talked for 45 minutes. He told me his story: There was a scheduling tool he loved when he was in sales. It went out of business. So he decided to build his own. He wasn’t even a coder — he hired a team in Kyiv to build it. Ruby on Rails, I think? Honestly, I’m not a techie. I just nodded like I knew what that meant. Cool as a cucumber, this guy. Talking about his little startup like it was obvious it would work. I told him about my app. I was building one too — a 12-month financial projection tool. Something that looked forward instead of backward. I’d tried Mint, Quicken, iBank, YNAB — none […]

She and her sister each had piggy banks. Ceramic. The real kind. One day she walks into the dining room. There on the sideboard — her piggy bank. Open. Empty. She’s looking at the piggy bank. She’s looking at her parents. They’re counting out the money. She could tell — they were desperate. (Why else would they go into their kids’ piggy bank?) “What’s going on?” “Oh, sorry. We just needed some money to pay the bills. But you’ll get it back.” (They never got it back.) She felt outrage. Like something got stolen. Taken. A violation. “This is MY money. Why are you taking it?” This was Germany. Before she was eleven. It was 80 Marks. Maybe less. (For a kid in the eighties? That was a lot of money. That was everything she had.) — AND THEN IT GOT WORSE There was more. Before things fell apart, her parents had started savings accounts for the kids. For school. For the future. Then her father made an investment. A gamble. Lost everything. Sold the house. Savings accounts: emptied. Piggy banks: gone. “As a kid, I never even thought about spending that money. I didn’t need to. It was just… […]

My client is standing in a health food store in Kīhei, Maui, looking at her receipt. On the conveyor belt: a bunch of small chocolate bars. She buys them in variety, puts them in little brown paper bags, writes Mahalo Nui Loa on the outside — that’s “thank you very much” in Hawaiian — along with Thank you for your service and You are appreciated. She gives them to flight attendants and pilots. (It’s sooo her.) She’s also picking up dinner from the deli, but you pay first and then go grab it. So she’s standing there. Receipt in hand. Dinner waiting. Chocolate bars bagged. And something’s off. She has this discount card she bought from the local elementary school, good for a year at over 30 restaurants and businesses in town. Save money where you’d go anyway. Support local kids. Everybody wins. She remembered showing the card. The cashier was scanning the chocolate bars. She held it up right there. But the discount isn’t on the receipt. Huh. That’s weird. Let me check. What’s the harm in checking? Maybe it’s there and I missed it? (It wasn’t there. She didn’t miss it.) — Now. Here’s where it gets interesting. […]

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 asked 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 sandals. (Different from the slippers. Apparently.) The nosh boxes. 🍬 (That’s Yiddish for “candy boxes you fill so your kid can trade snacks like it’s the stock exchange.”) The bus ticket. The camp bags. (Also plural.) The camp fan. (Because the Catskills in July is apparently a furnace?) I’m staring at this list like she just handed me a NASA launch checklist. “Uh… what is all this?” My wife? Cool as a cucumber. Ice in her veins. Zero panic. “Yeah. This is normal. This is what camp costs.” I’M SORRY, WHAT? 😳 I haven’t had a daughter in camp for a few years. I forgot all of this existed. My wife didn’t forget. My wife never forgets. She’s the one who’s naturally wired to see the whole picture. Born with savings instincts. Probably budgeted her allowance as a kid. Me? I saw the $2,000 […]

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 […]