You earn more than enough—so why doesn’t it feel that way? Join 1,000+ high earners reclaiming control over their money. Real stories and simple insights from me and my clients that will change the way you feel about money—every Thursday.
I hope you get your wish ASAP
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Hello, and welcome to another edition of me writing to you on a Friday evening and choosing to ignore the fact that I could schedule this to send at a time you're more likely to read it. But as usual, I’d rather send it out while the thought is fresh. If this is not your jam, I give you guilt-free permission to swiftly and liberally smash the UN-subscribe link (https://preview.convertkit-mail2.com/unsubscribe). Recently, I’ve been reflecting on the challenge of knowing what you truly want—something you can’t quite confirm until you actually achieve it. A line from Stephen Sondheim’s Into the Woods captures this perfectly: “How can you know what you want till you get what you want and you see if you like it?” In the musical’s first act, we see each character pursue their most precious desires, doing whatever it takes to reach their goals. They appear to find their “happily ever after.” But the second act pulls back the curtain, revealing that not everyone truly wanted what they initially wished for, or that what they attained wasn’t as fulfilling as they expected—or worse, that the price they paid to achieve their wish was far too high. This theme of elusive desire also plays out in Gone with the Wind. Scarlett spends most of her life believing happiness depends on being with a man she's loved since her youth. Yet, when he finally becomes available, she realizes she can't be with him. It’s a powerful moment of clarity—tragic, even—as she confronts the fact that what she spent her life whole chasing wasn't truly right for her. And so, my greatest wish for you is this: May you realize your deepest desire as soon as possible, so you can test your hypothesis. Is it truly what you want? Or is it a distraction from something you might value more deeply? The quicker you take steps toward your dreams, the closer you’ll come to understanding yourself. The more you learn, the better you’ll shape your character and live life the most in tune with yourself. Here’s to finding clarity, fulfillment, and unearthing the most surprising things about ourselves. Cheers, Tyler ❤️ Bips and Bobs📺 Video - I did a truly impulsive thing. 🎵 Album - Once Upon a Time in the West. Iconic opening track. Transport yourself to the Old West with this one. 🎬 Show - Just finished Season 2 of Rings of Power, and I'm not afraid to say I liked it. A lot. 📚 Book - Only a few hundred pages to go until I finish Gulag Archipelago... 🎙️ Podcast - A Train Wreck of Email. This one's real nerdy. ✍️ Quote Of The WeekThis is by far the most important thing to realize about that fear of creating: it doesn’t go away. You just get used to it. But that can only happen if you start making things. From How To Get Over The Fear Of Creating Things by Nat Eliason. Resurfaced by Readwise. Please consider inviting someone you know to subscribe. ❤️ |
Stop Feeling Broke.
You earn more than enough—so why doesn’t it feel that way? Join 1,000+ high earners reclaiming control over their money. Real stories and simple insights from me and my clients that will change the way you feel about money—every Thursday.
Last week, I asked: What would you do with $5 million? And wow. Your responses were incredible. Some of you mapped out every dollar down to the cent like one reader who planned everything from their exact mortgage payoff amount and finishing the basement to funding a sidewalk for their neighborhood. Others had a simpler plan: Half in Bitcoin, half in VOO. But the most fascinating part? No one said they’d buy a mansion or a fleet of luxury cars. Instead, I noticed four big patterns: Financial...
I’ve been watching Beast Games. Go ahead. Judge me. As I watched contestants fight for a life-changing prize, I started wondering: What would I do with $5 million? It’s more money than most people will ever see or earn. To put it in perspective, you’d have to make $125,000 a year (after taxes!) for 40 years to reach that number. So here’s my question for you: If I handed you $5 million right now, would you know exactly how to use it? Most people think a sudden windfall would solve all their...
Ever check your bank account and think, Wait… where did all my money go? You’re not alone. Most people assume their big expenses—rent, mortgage, car payments—are what define their financial situation. But often, it’s the invisible spending that’s actually draining your money. What I see most often among those I speak with isn’t reckless splurging on luxury items—it’s frequent, forgettable spending at places like Amazon, Target, and Walmart. It’s convenience food delivery. It’s random Venmo...