Jun
24
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 […]
Jun
19
I was nine years old. My mother had finally had enough. Cleaning my room was a constant battle growing up. She’d ask. I’d “clean.” And by clean, I mean I’d grab everything in sight and stuff it into the closet. Problem solved. Looks fine. Don’t open that door. But she always opened the door. My mother would inspect. She’d look around the room, nod, and then walk straight to the closet. I’d hold my breath. Please don’t. Not the closet. She’d open it. Everything would tumble out. And she’d say: “This is not organized.” She was right. It wasn’t clean. It was contained chaos. But this time, she did something different. She went in herself. Organized the whole thing — actually organized it. Not my version. Hers. The shelves made sense. The floor breathed. And so did I. I walked into that room and felt something I hadn’t felt before. Not just cleanliness. Something deeper. Like I could finally take a full breath. Like the room was actually mine. Like I had arrived somewhere. THE MOMENT A few days later, my best friend Shawn came over. We were playing with a remote control car — just doing what boys do, […]
Jun
12
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: […]
May
19
She saved $70,000 by the time she was 17. I’ll say that again. Seventy thousand dollars. Age seventeen. No trust fund. No inheritance. Just a kid who saved. It was instinctive. Easy. The way some people are naturally athletic or can carry a tune without thinking about it — she could save money without it feeling like a sacrifice. She used to bring her little bank passbook to the teller — you know those booklets they’d stick in the machine and print out all your transactions? She’d watch the numbers climb. That was her — a natural born saver. And then she wasn’t. THE SHIFT By the time I met her, she was ordering takeout every night. Picking up every tab. Hosting that left her feeling broke afterward. Saying “don’t worry about it” anytime someone offered to chip in. I asked her once: “What happened?” She got married. And somewhere in that marriage, she forgot who she was. She adopted someone else’s way of showing love — through spending, through gifts, through being the one who always pays. His pattern became her pattern. His language became her language. The problem is, it was never hers. Here’s the thing about adopting […]
May
14
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 […]
May
07
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 […]
Apr
30
Kari’s clutch blew out on the way to Colorado. It was 2017. Starting over. Moving to a new state. And somewhere on the highway, her Subaru gave up. She burned through her savings to fix it. Then a boyfriend talked her into living way beyond their means — and funding his business venture. (She got rid of him eventually.) By the time she reached out to me, she was carrying almost $20K in high-interest credit card debt. THE YO-YO Kari had been on the debt yo-yo for years. Overspend. Feel bad. Pay it off. Repeat. She told me: “The years of living with credit card debt that had accumulated was making me feel like a bad person — like I wasn’t to be trusted with money.” She thought she needed to “atone” for the debt. Like she had to earn her way out through hard-work-grind. ONE CONVERSATION Last November, Kari booked a free call. She thought she was calling to ask what to do with some money from a real estate sale — a joint venture spec home build with her parents. But that’s not what we talked about. She was afraid there would be strings attached. Expectations. Family pressure. […]
Apr
24
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 […]
Mar
24
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? […]
Mar
23
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? […]
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