Level Up Financial Coaching

🌳 I sat in the park last Friday and watched something that’s stuck with me.
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A mother and her two grown daughters laid out a full lunch spread on a blanket.
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They ate slowly. Talked for over an hour. Cleaned up without checking the time.
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Then, they did something I didn’t expect:
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They stayed.
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🌞 One did a crossword. Another napped on the grass. They laughed at inside jokes. Together. They didn’t go anywhere.
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No phones. No rush. Nowhere else to be.
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For at least another two hours.
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Lisbon keeps subtly reminding me:
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The walking is FAST. Especially up these hills.
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But the moment people arrive somewhere? The rush is gone.
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Time stops being something to manage.
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It just is.
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⏳ My “productive” spirit got really loud after 15 years of corporate. The voice that says even rest needs an output. Even the outdoors became somewhere I “go to recharge for later.”
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Lisbon is gently calming that voice.
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It’s teaching me that being right here, right now, with the people you love, IS the thing.
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Not a means to the thing. THE thing.
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🌳 Drop a 🌞 if you needed this reminder today.
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📍 Lisbon, Portugal
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Everybody told Jamie to buy a house. 🏠
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Her dad said real estate was smart.
Her friends were all buying.
It was the next logical step once you had enough saved.
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So she saved. And saved. And saved.

$100,000 sitting in cash, building toward something she couldn’t quite name.
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When I finally asked her, “Why do YOU want to buy a house?” she had a smart answer for everything else we’d ever discussed.

But not that.
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Because nobody had ever asked her to separate what she wanted from what she’d been told to want.
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That’s the “should” trap.

It doesn’t look like a mistake from the outside.
It looks like a responsible plan. A growing balance. A life checking all the right boxes.
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But underneath it is a question nobody thought to ask you.

What do you actually want?

Not what your parents wanted for you.
Not what your peers are doing.
Not what the next logical step is supposed to be.
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What do YOU want? 👇Not what you “should”, but what feels true to you.
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💬 Drop it in the comments.
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🗓️ 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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