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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 […]

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 to show you.” Maybe that’s it. The fear of being judged. The fear of being seen as irresponsible. You’re good at what you do. You earn well. You should have this figured out by now. And the thought of sitting down with someone and admitting you don’t? That feels like failure. It’s not. YOU’RE NOT ALONE You know who calls me? C-level execs at Fortune 500 companies. Doctors. Lawyers. Developers. TV personalities. University professors. Tech professionals. These are people who are brilliant at what they do. Leaders. Decision-makers. People who “should” have it all figured out. They don’t. That’s exactly why they call. HERE’S A THING THAT HAPPENS Financial advisors and portfolio managers call me all the time. “I have a client in mind — tell me about what you do.” We talk. I explain the work. And at the […]

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 gumball. The gumballs were always there. You just had to turn the dial. I’M STEALING THIS Sruli called it The Bubblegum Effect. It’s mine now. The idea is simple: the potential is already there. Waiting. But nothing happens until you turn the dial. TWO SESSIONS Here’s something that surprises my clients:Within two sessions — about three hours of actual work — they gain clarity on their numbers. Income. Expenses. The flow of their money. Something they’ve been avoiding for months. Years. Sometimes forever. Three hours.And they always say the same thing: “That was nothing.” I DO THIS EVERY YEAR I’ll be honest — I hate doing taxes.Every year, I push it off. Every year, it sits on my to-do list, getting heavier. And every year, when I finally sit down and do it? Same thought: Wow. That was nothing. But this year? […]

The other day, my wife said something I can’t stop thinking about:“Desire got you to eat the first chip. Guilt made you finish the bag.” She’s right. She usually is. 🤓 I KNOW THIS PATTERN WELL Twelve years ago, I joined a men’s weight loss program. I was all in—tracking everything, following the rules, and I lost 49 pounds in a year.I looked great. Felt even better. That kind of energy you get when everything’s clicking? I had it. Then came Purim. If you’re not familiar, Purim is a Jewish holiday where kids dress up in costumes and collect mountains of candy. It ends up everywhere.One day, a chocolate bar mysteriously ended up in my mouth. I don’t remember picking it up. I don’t remember unwrapping it. But suddenly—sugar rush. That old, familiar kryptonite hit me hard.Oh. I remember this. ONE CHIP BECAME THE WHOLE BAG It didn’t happen all at once. It never does.A little nosh here. A piece of candy there. “Just this once” on repeat. Eventually, I gained it all back. Not because of one chocolate bar. But because of what came after.Guilt. “Well, I already blew it.”“What’s the point now?”“I’ll start fresh on Monday.” Sound familiar? […]

The other day, I got a message from a reader named Akiva: “Yours is one of the few emails I get that I have to go back to later on my computer because I don’t have a browser on my phone. Always a good read.” Akiva built a system to avoid distractions — no browser on his phone. And somehow, my emails made the cut for “worth coming back to.” That message? It made my day. It reminded me why I write these emails in the first place. It also got me thinking: why do people like my emails? HERE’S MY SECRET (HINT: IT’S ABOUT NOT HAVING SECRETS) I wasn’t born with good money genes. I’ve bounced checks. I’ve spent emergency money on beer in Jamaica. I’ve felt that sinking feeling when I logged into my bank account and saw less than I expected. So when I write these emails, I’m not writing from a pedestal. I’m writing as someone who’s been through it. HOW THESE EMAILS HAPPEN I listen. Clients say things that stop me cold. I write them down. Readers send emails that stick with me. Conversations with family and friends spark ideas. I steal from everywhere. From […]

I was 19. Jamaica. I was traveling with an older friend, Rino. My mom was a flight attendant, so I was flying standby on her employee pass. Free flight — if there was a seat. No seat, no flight. A few days before heading home, I checked the flight. Looked wide open. It’ll be fine. So, naturally, I did what any 19-year-old would do: I spent my emergency money. More Red Stripe. Souvenirs. Whatever else seemed like a good idea at the time. Then I got to the airport. Overbooked. That means I’m not getting on the flight. ZERO My brain went into a spiral. Avraham, you’re so stupid. Why did you do that? Then the panic: What am I going to do? I’m all alone in Jamaica. Where am I going to sleep? The resort might not even take me back. What is my mother going to think? And finally: Those pilots better say yes. I’ll beg if I have to. I had zero money. Not “low on cash” — zero. And I was stuck in a foreign country with no way home. Rino? He had a confirmed ticket. Paid in full. He shrugged. “I’m sure it’ll be fine.” […]