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Level Up Financial Coaching

I'm an adventurer and food lover who values time freedom. I retired at 36 and now I teach overworked high-achievers how to design a life they love. Subscribe to my newsletter for a kind and supportive approach to personal finance, small business growth, and early retirement.

Time freedom and expat life for early retirees
Featured Post

Rena turned down the promotion. Four times.

The view from coffee with me 😜 My friend Rena couldn’t stop laughing. Not because it was funny. More because she couldn’t believe her management team was back again with the same tired request... We were having coffee when she told me the latest. Her hospital had come to her four times now with the same pitch: slide into the charge nurse role. It meant more responsibility and a title bump. “It’ll look great on your resume!” they kept saying. But she’d watched what the role did to the people...

Going from good to great with your finances.

After two years of dashboard reviews, loving side-eyes, and the same two words on repeat, Jamie moved the money from her HYSA. Not all at once. Not in one dramatic moment. The first chunk only took minutes and a few clicks. Done. She told me afterward what struck her most. “The mechanics. It was so simple it felt like a trick. A few clicks and it was done.” She wasn’t wrong. We’ve been conditioned to believe that investing is complicated. That you need a financial advisor, a managed account,...

Retire early and travel the world with Level Up Joe

Last week I told you about the question that changed everything for Jamie. Not “what should we do with your cash?” Simply: “What do you actually want?” Once Jamie could answer that question, I mean really know the answer, something shifted between us. Our money reviews stopped feeling like an ambush. “Cash drag” stopped feeling like nagging from an annoying partner. And for the first time in two years, sitting across from each other with her financial dashboard open, Jamie said something...

Financial Independence Retire Early with Joe Maddux

Last week I told you about Jamie’s cash piling up in her HYSA. The balance that kept growing. The machine that was fully functioning, as designed. And the two little words I kept saying every time we sat down to review her numbers. “Cash drag.” She’d smile. She’d nod. She’d give me a sweet little side-eye. And she would change the subject. And I’d tell myself that next time, she’d finally hear it. She didn’t. Because I was trying to solve the wrong problem. I kept showing up to have a...

Financial independence retire early with someone who's actually done it

My wife Jamie does not need anyone to figure things out for her. She’s organized, intentional, and hard-working in a way that makes me look like an absolute slacker by comparison. When she decides to do something, you better watch out because it is getting d-o-n-e. Done. So early in our relationship when we started conversations about combining our finances, when she finally became comfortable sharing the nitty gritty details, I wasn’t surprised by what I found. She had over $100,000 sitting...

Build a money making machine

In 2014 I came back from three weeks in Vietnam absolutely transformed. Pure culture shock had hit me like a freight train in Ho Chi Minh City the moment I stepped out of the airport. The food, the culture, the people. Strangers who had so little by comparison but seemed so much lighter than me. Happier. More alive. I found something new in myself on that trip. Something that felt real and true in a way not much had before. Then my PTO was over, and within my first hour back in the office my...

Day one is all it takes

I opened my habit tracker yesterday and saw two numbers sitting next to each other. 925 days of reading. 6 days of journaling. My first thought? Gotta start somewhere. My second thought? I’d be lying if I said that big number wasn’t a little intimidating. 925 days is over two and a half years of not missing a single day. It doesn’t even feel like a habit anymore. It’s just part of who I am now. But 6 days ago, “WRITE IN JOURNAL” was exactly what “READ A BOOK” was on day one. Nothing. Just a...

The Myth of Work Life Balance

My sister called me last week with big news. She just landed a new job. New role, fresh energy, a real opportunity. I was thrilled for her. And within the first five minutes, before we even got to what she'd actually be doing, she said it. "I just really hope I can find work/life balance." I smiled. Because I spent the better part of my 20s and 30s saying the exact same thing. Grinding through a career in mechanical engineering. Doing good work. Checking the boxes. Growing a net worth on a...

Financial independence in real life

In case you're wondering where I've been the last six months, the short answer is: living out of a suitcase in 9 states, from Montana to North Carolina, and 3 countries. It's been the most disorienting, exciting, terrifying six months of my life. And if you're wondering why you haven't heard much from me during all this excitement, it's because the fear took over. I didn't post curated photos of the adventure or send my usual email updates along the way because this whole time I've been...

What happens when a high-achiever can't control the outcome?

Last week Jamie and I accomplished something we'd been working toward all year. We completed our Portugal visa application interview! Smiles of relief and accomplishment! Documents gathered. Appointment scheduled. Interview finished. Box checked. This one major step toward our bigger life plan is "officially" done. We've done our part. We've put forth all our best effort and energy. And now, we wait. I'm going to be honest with you. All the documents, navigating the bureaucracy of a foreign...