A few months ago, our 10-year-old daughter, Dylan, sat us down and said something I wasn't expecting.
"I don't want to go back to school this fall."
She wasn't upset. She wasn't being dramatic. She just said, calmly and clearly, that she was bored and ready for something different.
Honestly? She wasn't wrong.
Traditional school had become seven hours a day of memorizing facts she'd forget in a week. She was acing the tests but learning less. And meanwhile, her real education was happening outside the classroom. She'd launched a hot cocoa stand and made $100 in an hour. She'd started a dog-walking business in the neighborhood. She'd been coding mobile apps, not in theory but by building real things people can use. She has her own stock account. If you stopped her on the street and asked about the four ways to make money, she'd rattle them off: employee, self-employed, business owner, investor. Then she'd tell you which ones she's done and which ones she wants to master next.
We said yes. Yes to homeschooling. Yes to curiosity. Yes to letting her learn by doing.
This article is about that decision. But it's also about a much bigger decision that made it possible. The one we made 13 years earlier, when we were sitting at a totally different crossroads.
The decision behind the decision
Back in 2012, my husband and I had a conversation that ended up shaping the next decade of our lives.
We were either going to take a year off and travel the world, or we were going to buckle down and buy as many rentals as we could and bust our butts so he could retire early.
This was around the time I read Tim Ferriss's The Four-Hour Workweek. The tactical advice in that book is fine. The mindset piece was the real shift for me. Specifically the idea that the goal isn't to take a year off. The goal is to build a business that doesn't require you to be in any one place to keep running.
We chose portfolio growth mode. We didn't take the gap year. We worked 10 to 15 hour days, then nights and weekends doing the renovation work ourselves. There was a lot of blood, sweat, and tears in those years. We were obsessed with the goal and we just kept going.
Six years later we hit our financial freedom number. The portfolio was producing more than enough to live on. We could've stopped working entirely.
And then it took me almost two years to slow down enough to actually choose to work 15 to 25 hours a week. That's a story for another day. The relevant point is this: by the time Dylan asked to skip fifth grade, the decision wasn't a financial one. The financial decision had been made years earlier when we said no to the gap year and yes to the rentals.
The freedom to say yes to her now was bought with the no we said back then.
What this lifestyle actually looks like
If you're reading this and trying to figure out whether the picture in your head is realistic, here's what it actually looks like in practice for us right now.
We've done two month-long Europe trips this year. The August one was Athens and a month of Greek island hopping for my husband Travis's 40th birthday. We just got back from a week in Belize. Waterfall hikes, swimming through a sacred Maya cave in an underground river, staying in an actual treehouse. Earlier in the year we did a 3-week trip with a 5-month-old baby, mid-app launch, while managing a new build. Total chaos in theory. In practice, I opened my laptop once in 3 weeks.
A few years before that, we did 10 weeks in Southeast Asia with a toddler. Beijing, Phuket, Krabi, Phi Phi Island, Chiang Mai, Bangkok, Siem Reap, Hanoi, Hoi An, Da Nang, Bali, Kuala Lumpur, Singapore. Self-managing 16 rental units the entire time. Total work hours over those 8 weeks (we calculated): about two. Two repair requests came in. Both got routed to our handyman. The income kept coming in.
I'm not saying any of this to flex. I'm saying it because most people who hear "real estate investor who travels with the family" assume the person has either (a) sold the portfolio and is living on savings or (b) hired a property management company that's eating most of the cash flow. Neither is true for us.
What's true is more boring and more durable. We built systems. We hired the right people. We did the unsexy work of writing SOPs and training operators so the business runs whether we're in Phoenix or in Seminyak. If you want to see how that scales down to a few hours a week, I laid out the system in build a rental portfolio in 5 hours a week. The freedom isn't a vacation from the work. It's the result of a different kind of work, done years earlier, that compounds.
What worldschooling looks like for a kid
I want to be specific about what we're actually doing with Dylan, because "homeschooling" can mean a lot of different things and most of them aren't what we're doing.
We're not recreating a classroom at the kitchen table. We're not sitting through textbook lessons together at 9 a.m. The whole point of saying no to school was to opt out of that model entirely.
What we are doing: letting her learn through real projects, real businesses, and real travel. The hot cocoa stand wasn't a hypothetical exercise from a kid's entrepreneurship book. She bought the supplies, set the price, marketed to neighbors, made the cocoa, took payment, and counted the profit. That's a unit on economics, marketing, operations, and arithmetic compressed into one afternoon. The dog-walking business is a unit on customer service, scheduling, and pricing. The mobile apps she's coding are a unit on logic, design, and shipping a finished product to real users. The stock account is a unit on long-term thinking, compounding, and risk. When the work is for our own business, we put her on payroll the right way, which I walk through in how to pay your kids from your real estate business and built Kids Payroll to handle.
We're using a curriculum to make sure she covers the academic basics. But the curriculum is a structure, not the spine. The spine is the businesses and the projects. A year in, I wrote up what actually worked and what flopped in our first year of homeschooling.
In Raising Mentally Strong Kids, Dr. Amen makes the point that traditional models of education can actually stifle mental strength because they strip away autonomy, creativity, and problem-solving. We're not interested in raising rule-followers. We're interested in raising thinkers. Builders. Children who aren't afraid to take initiative and make mistakes.
The honest version of why we said yes is this: the cost of putting Dylan back in a system that was making her bored, when she was already showing us she could thrive in a different model, started to feel higher than the cost of figuring out the alternative.
The five things long travel teaches you that no book can
I've talked to a lot of investors who say they want this lifestyle but they can't figure out how to start. The honest answer is: take a longer trip than feels reasonable, with the family, while the business is still running. You'll learn things in three weeks of being 5,000 miles from home that you wouldn't learn in five years at your desk.
Here are five lessons that have stuck with me from our trips.
You learn to be decisive, fast. The day before our flight home from a recent trip, London Heathrow shut down due to a fire. British Airways offered to rebook, but that would've wrecked the rest of our plans. I paused, ran through the best and worst case, and decided to wait it out. It worked. Business owners make hundreds of micro-decisions a day. Learning to trust your gut and act quickly is a muscle worth strengthening, and travel forces the reps.
Stress is a choice. We missed two trains to Disneyland Paris on the same trip. After an overnight flight. With two kids. On a few hours of sleep. Total recipe for a meltdown. Instead, we cracked jokes and made friends with another stranded family. You can't control what happens. You can control how you respond. Same goes for business when a launch flops or a deal falls through.
Control the controllables. Portugal was beautiful but the weather was awful. Rain, wind, the works. Instead of sulking, we found indoor spots and watched the radar like pros for sun breaks. When you hit roadblocks in business (bad hires, slow sales, broken systems) the question isn't "why is this happening to me." It's "what's actually in my control here." That's where progress lives.
Don't wait for the perfect time. We did our March trip with a 5-month-old, mid-app launch, while managing a new build. Chaos. But everything kept moving forward. There's never a perfect time to live your dream life. There's just the version of life you're choosing right now. The business is the vehicle for freedom, not the reason to stay stuck.
Discomfort is the best growth hack. Finding your way around a new country without speaking the language is instant humility. You get creative. You rely on body language. You laugh at your mistakes. It's a useful reminder of what your customers feel like when they're stepping into something new. Get comfortable being uncomfortable. That's where the real breakthroughs live.
The system that makes it work
The lifestyle requires a system. Here's the short version of ours.
Income that arrives regardless of where I am. Rental income from a portfolio I no longer have to actively manage. App revenue from products I built once. Both are cash-flowing assets that perform whether I'm at my desk or asleep on a different continent.
Operations run by someone else. Our Director of Operations, Stefan, manages the entire portfolio remotely from Eastern Europe. He handles vendor management, lease renewals, insurance shopping, property tax appeals, and weekly profit and loss reporting. The business moves forward whether I'm paying attention or not.
Travel funded by points, not cash. Most of our long-haul flights are booked with credit card points and miles. Strategic card sign-ups, business spend that earns rewards, and patience with redemptions have meant our family has flown business class to Europe and Asia multiple times a year for years, paying mostly in points and small fees rather than five-figure ticket prices. One recent trip we booked $42,000 worth of flights for $725 out of pocket. If you want the mechanics, I break it down in travel hacking for real estate investors.
A self-managed daily routine I actually want to live. I work somewhere between 15 and 25 hours a week. I pick up Dylan from her activities. I'm home for dinner. I'm not white-knuckling through "balance." I designed my time on purpose.
The pieces aren't secret. The willingness to spend years building them is the rare part.
What this doesn't work for
I don't want to oversell this. Here's where worldschooling and the freedom-path lifestyle don't work.
You haven't built the income side yet. If your business or portfolio still requires you to be physically present every day to keep producing, this lifestyle is on the other side of work you haven't done yet. That's okay. It's also not a reason to stay stuck. It's a reason to start building the asset side now.
You don't have a partner who's aligned. This is a team sport. If one parent is committed to the freedom path and the other is committed to the conventional path, you're going to spend most of your energy negotiating instead of building. Get aligned first.
Your kid isn't asking for it. Some kids genuinely thrive in traditional school. Some kids find their best friends, their first crushes, their favorite teachers, their path forward inside the building. We didn't pull Dylan out because we were anti-school. We pulled her out because she was clearly ready for a different model and we had the flexibility to give it to her. Force a kid into worldschooling who doesn't want it and you'll create a different kind of stuck.
You think it's an escape. Long travel with kids is not a vacation. It's a different shape of normal life, with the bills still coming in, the apps still needing updates, the duplex permits still needing review. If you're hoping a year of family travel will fix something that's broken at home, it won't. It'll just relocate it.
The question worth sitting with
When Dylan asked to skip school, I had a moment where I wanted to default to "well, of course you go to school, that's what kids do."
What stopped me was the realization that we'd spent 13 years building a life that was specifically designed to give us the option to say something other than the default. If we said no to her now, what was all that work for?
Most of the people I talk to about this kind of lifestyle assume they can't have it because the math doesn't work. The math is solvable. The harder part is the question underneath the math.
What are you building toward? And when the moment arrives, are you actually willing to choose it, or are you going to default to whatever's easier to explain to your neighbors?
We said yes when our daughter asked. The reason we could say yes is that we'd already said no to a lot of other things, for a long time, with a specific outcome in mind.
If there's a voice in your head whispering that there's a different version of your life on the other side of some hard choices, listen to it.
You might be raising a kid who's already thinking like an entrepreneur. Or you might be one yourself, finally ready to stop asking permission to live the life you've been building toward.
Either way, the no you say to the wrong things is what funds the yes you'll say to the right ones.
