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October 2011. Steve Jobs had just died. Apple held a memorial at their campus. I watched it. Tim Cook spoke. Jony Ive spoke. Then this guy got up. I didn’t know who he was. But I could tell — from the way people leaned in, from the way Tim introduced him — that he was close. Really close. “He is...

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...

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...

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...

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...

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...

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...

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...