Level Up Financial Coaching

🗓️ I used to think time freedom meant “no schedule.”
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Then I left the corporate grind.
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And almost immediately, I started craving structure.
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😳 Not the performative kind. Not the calendar-stacked, back-to-back meetings, prove-your-worth with trackable hours kind.
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I had 15 years of that. I left it on purpose.
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The kind I crave now is different. It’s the kind that says: this is what matters to me, and this is when I’m doing it.
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Here’s what I’ve learned:
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When I have no plan for the day, I feel listless. Like I’m that American Beauty plastic bag floating in the breeze. Around 6pm, I look back and wonder where the time went.
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But when I tell my time what to do? It’s actually MORE freeing.
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💸 Think of it like a budget.
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When you don’t tell your money where to go, it goes wherever. You’re left feeling out of alignment, wondering how there’s nothing left for the things that matter.
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Time works the exact same way.
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Here’s roughly what my days look like now:
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🌅 A couple hours of creative work each morning. Writing. Building cool stuff for clients.
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☀️ A long midday block for “self care.” Exercise. A healthy lunch. Time outside with Jamie and Mili.
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💻 An afternoon window for client sessions, with a clear shutdown time.
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🌙 Evenings completely off. No mental drag. No anxiety about tomorrow.
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I’m not rigid about it. The structure is loose. But it’s THERE.
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And that’s the magic: when the bones of the day are decided ahead of time, the meat of life gets to be spontaneous.
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Structure IS freedom.
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It helps me accomplish big things AND enjoy this intentional little life I’ve built with Jamie.
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The two aren’t in conflict. They never were.
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💬 Tell me below: are you a structure craver, or does the word “schedule” make you twitchy?
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📍 Lisbon, Portugal
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She smiled. Nodded. Changed the subject. Every. Single. Time. 😏
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My wife Jamie had over $100k sitting in a high-yield savings account.
Every month, a little more landed. The balance ticked up. The machine hummed quietly in the background.
No alarms. No pain. No reason to change a thing.
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So every month or so, we’d sit down and review her numbers.
Her financial dashboard (yes, I made one for her ❤️), her account balances, her cash position.
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And every single time, without fail, I would say the same two words.
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“Cash drag.”
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Jamie would smile. Nod with a subtle side-eye. And smoothly, expertly, change the subject.
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I want to be clear: I was not helping.
Telling your partner the same thing over and over, expecting a different result, is not a sound financial strategy.
It’s just annoying. 😂
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But the cost of that growing balance sitting still was adding up in a way that only I could see.
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Next week I’m sharing where the story goes… and why “cash drag” finally stopped being something she rolled her eyes at.
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💬 Have you ever had someone in your corner who could see something in your finances that you couldn’t? Tell me about it below.
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😮‍💨 If you’re reading this on a Monday morning and rest still feels uncomfortable, you are not alone.
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This is me last Tuesday in the Alentejo countryside. On a swing hanging from a cork tree, in the middle of a vineyard, reminding myself that rest is okay.
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Out loud. To my own face. Because I needed to hear it.
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Resting is HARD for me. Always has been.
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Not the kind of hard where I don’t know how. The kind of hard where my body and brain feel like I’m doing something wrong.
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I know exactly where this comes from.
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Perfect attendance. Straight A’s. Captain of this, president of that. As a kid, that was the metric of how “good” I was. How worthy.
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So I kept going. 🎯
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Through college. Through 15 years in medical devices. Through every milestone I checked off.
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The story I told myself? “I’ll rest when I get there.”
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Then I got there. And I still couldn’t sit still.
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🧠 There’s actually a name for this.
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Psychologists call it “contingent self-worth.”
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The short version? When approval was tied to performance growing up, you learn that worth has to be EARNED. Over and over.
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And the wiring sticks long after the report cards stop coming. 📚
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The nervous system learns to associate stillness with danger. So even when you EARN the rest, you can’t access it.
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That’s not a willpower problem. That’s a wiring problem. And it can be rewired.
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Slowly. Imperfectly. On purpose.
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On a rope swing in the middle of a Tuesday if that’s what it takes. 🌱
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So here’s your Monday permission slip:
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You don’t have to earn rest. You’re already worthy of it.
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💬 Drop a ❤️ if rest feels hard for you too.
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📍 Herdade da Rocha, Portugal
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