Finances

Financing a Life of Family Travel,
Freedom, and Fulfillment

(Note: This page was written in 2019 and is now outdated. I have since sold my business, and bought and sold another that I 10x’d in two years.)

How did we finance this travel lifestyle of ours?

The short answer is that I own a 1-hour workweek business that has supported us on our travels since 2009 (yes, I work literally one hour per week on this business, as I recently hired a CEO. Back when we started traveling, I was spending 4 to 8 hours per week on it.) This has also enabled us to create more passion projects that we feel made a positive difference in the world, like the Family Adventure Summit, Family Adventure Academy, and At Home in the World Family Retreats.

But it didn’t start out this way, and it’s taken years to reach the point we’re at now.

Below is a quick summary of how we got to where we are today, financially. For a more thorough version, check out some of the interviews linked below, or on our About page.

Becoming an Entrepreneur

When I was young, I dreamed of growing up to either be a music teacher like my dad, or a computer programmer. Eventually, I became both, and realized that I didn’t want to do either one permanently. I started programming when I was 12 years old, and began teaching piano at age 16.

By the time I was 23, I had ten piano students and several web design clients. I was also struggling to make $10/hour doing Internet technical support, going to college part-time for a Computer Science degree, and taking care of a wife and new baby. This was around 2003.

Entrepreneurship never crossed my mind as a career path. But as a side project to be more efficient with my piano students, I created a website to help me track scheduling and payments.

In 2004, I made this available to other teachers, started charging a monthly fee, and called it Music Teacher’s Helper. After four years of dedicated effort and 70-80 hour weeks, I was earning just enough to quit my job ($1,500/month) and focus full-time on my business.

By 2009, it had grown grew to the point where I could hire some help, live wherever I want, and enjoy a “4 hour work week” lifestyle with my family (around $10,000/month). Today, the business revenue is in the high six figures and employs an international team who work to serve our thousands of customers around the globe.

Building a Business

When I look back on how I did it, I didn’t have a magic formula. And I can’t guarantee that anyone could have the same success that I did. Yet through step by step, day by day focus and determination, along with a bit of luck and good timing, I’ve created a successful business. It feels good to know that the product I’ve created is helping so many music teachers be more organized, efficient, and communicate better with their students.

Of course, there are things I’ve learned in over 15 years as a business owner. I’m no longer a lone entrepreneur, no longer a manager or CEO, but the owner of a company with a fantastic team. My lifestyle didn’t happen by accident.

I’d like to share with you some of the things I’ve learned to help you start your own business or create a career that enables you to live the life of your dreams, and enjoy the process every step of the way. You can download my free guide to Enjoying Life Now below. Thanks for reading, and best wishes on your own entrepreneurial journey.

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Hidden Content

If you’re interested in learning more about my story and my process, check out some of the interviews and blog posts below.

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Entrepreneurship Blog Posts

Marketing Yourself While Maintaining Authenticity

I had an interesting realization while on a brunch date with my oldest daughter, Emily (15). Over some delicious Indian food, we talked about our purpose, what feels meaningful, and what we enjoy working on. And some questions she asked brought up some revelatory insights that I’ve been pondering. Mainly, I realized that I don’t necessarily want to be the spokesperson for the brands I’m…

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Raising Entrepreneurs

It’s exciting to see my kids learning important life skills at a much younger age than I did, and actually earning money with these skills! I suppose when I was around 14 years old, I did start doing random work for people, including typing documents, computer repair, or consulting people on computer purchases, just because there were people who insisted on paying me to do…

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Dream Achievement Blueprint

Do you have a dream you’ve been putting off because you think you don’t have time for it? What would you need to do to create time for it? One of my goals for a while has been to create an online course. You may already know that I’ve been working on a course to help families who want to travel the world long-term. I’ve…

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Our Secret Project, Revealed!

For the past six months, our family has been working on a secret project and we are so excited to finally be able to share our news with you! We are working with an amazing group of people to create a new documentary film, Into The Wind! In this film, we will be telling the stories of several families who have set out on their…

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The Family Travel Event That Everyone Is Talking About!

You may have noticed that lately, we haven’t written on this blog as often as we used to. The reason? We’ve been busy preparing for the most awesome, epic event of our lives! Our team has been working so hard for over a year to put on this event. But even though it was our first year, it turned out to be everything we dreamed…

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5 Tips To Save Money On Accommodation

Traveling with your family doesn’t have to break the bank! One of the biggest expenses of family travel (after airfare) is the price of accommodation. But there are easy ways to save thousands of dollars on family accommodation AND stay in places that are much more enjoyable than a hotel room! How do we save money on accommodation? We Book Houses Or Apartments – Not…

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3 Things to Consider Before Starting a Lifestyle Business

I recently received an email from a young man just setting out on his own path. He’s questioning conventional education and conventional career choices. He’s looking to create a business that would allow him to travel and pursue his passions without succumbing to the daily grind and instability of traditional jobs. I was moved to answer his questions in my latest video. I know there…

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Income On The Go – 7 Ways To Fund A Travel Lifestyle

While many people would love to travel long-term with their families, the task of figuring out to how to fund a traveling lifestyle can seem daunting. It is hard to figure out where to even begin, when all you have known your whole life is how to create a conventional life with a conventional 9-5 job. I made this video to help you brainstorm ideas on…

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Time Mastery Trio – 3 Ways to Track Your Time for Improved Productivity

Many people struggle with not having enough time to do what they truly love, or even accomplish their most basic goals for the day. As an entrepreneur and business owner with a staff of over 20 employees, it’s been essential for me to master my time in order to keep up with my projects on the road. In this week’s video, I’d like to share…

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Practical Tips for Living in Bali

In my latest video, I share practical tips for living in Bali. If it’s your first visit, you may be wondering how to obtain a visa, where to find accommodation, what medical care is available, and how to use the local currency. I cover all of this, and more. I hope after watching, you’ll understand that travel doesn’t need to be intimidating. There are people…

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5 Steps to Begin Traveling Long-term with Your Family

Summary I’m excited to share 5 steps to help your family begin traveling long-term. These are things I’ve done myself that helped create a lifestyle that allows me and my family to travel the world indefinitely. In the past 7 years, we’ve traveled to and lived in over 32 different countries, and our lives have been deeply enriched because of it. We’ve grown closer together…

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A Victorian December

Have you noticed we keep coming back to Victoria? This time we settled in for the month of December, curious to see if its winter season was really as mild as cold-phobic people like ourselves tend to prefer. This is Canada we’re talking about, after all. Wouldn’t you know, we discovered it really does live up to its reputation! It’s in a sub-Mediterranean zone, not…

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Living Your Life Purpose

“It’s messing people up, this social pressure to ‘find your passion’ and ‘know what it is you want to do’. It’s perfectly fine to just live your moments fully, and marvel as many small and large passions, many small and large purposes enter and leave your life. For many people there is no realization, no bliss to follow, no discovery of your life’s purpose. This…

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Making Work Meaningful

When I created Music Teacher’s Helper ten years ago, it was to solve a need that I had in my own life — to better organize my student lesson schedules and payments. I decided to turn it into a “business” for two reasons. One, because other teachers expressed interest in it. And two, to provide for my family without being dependent on an employer. I’ve learned a lot since…

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The Why of Happiness

Despite having stated that I no longer offer business consulting, I occasionally get emails asking me if I can make an exception. Sometimes I’ll write back asking what they hope to get out of consulting, and it usually turns out they want advice on what they should do, or instructions for how they should do it. One of the reasons I stopped offering consulting is that…

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Do you want a portable piano?

It’s exciting to see the progress on the Groove digital piano I’ve been working on for the past several months. The first prototype should be finished very soon! We decided not to make it fold after all, but it will separate neatly into three sections that can fit inside carry-on luggage. The prototype was pieced together from existing keyboard parts and the case is bigger…

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Beach Clubs, Projects, and Kids

Recently, thanks to some friends, we discovered the wonders of beach clubs. Typically, I’m not a big fan of beaches. I do love looking at them, feeling the sand under my feet, and playing in the water and waves can be fun, too. But I have trouble enjoying the aftermath of sandy clothes and a sticky body, and if there’s no shade or food around,…

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Creative Projects and Productivity

When we came back to Bali a few weeks ago, we really hit the ground running. We’ve been very busy, but also creative and productive, and have been enjoying our time immensely. Within one week, we found a house we wanted to live in. It’s a small 3-bedroom house near Ubud, but it’s completely unfurnished and needs some renovation. We signed a lease for 13…

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Playing in the Philippines

For the past several years, I’ve employed people in the Philippines to help me run my business, including programmers, customer support staff, marketers, content writers, and virtual assistants. But I had never met any of them in person, or even spoken to them on the phone. All our correspondence was via email or chat, and lately, via managers I’ve hired. I was looking forward to finally…

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Codependent in Hong Kong

It’s been another intense month for me, digging through the recesses of my soul, questioning what I want in life and relationships, and breaking through more barriers that have been holding me back from being myself. I also took a solo business trip to Hong Kong for a few days, and have been working more on building my business structure and systems to handle new…

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How to Choose a Winning Business Idea

Recently, thanks to some articles I was highlighted in, I’ve been getting more consulting requests than usual. I’ve turned down many of these, partly because I only want to spend so much time on the phone and email each day, and also because the majority of the requests had the same difficult question: How do I choose a winning business idea? I wrote an article about…

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From Entrepreneur to CEO

When I started my online business, I did everything myself. The planning, programming, graphics design, database management, server maintenance, marketing, customer support, billing, accounting, taxes — everything! Most of it I learned as I went along. It was a lot of work and took every spare moment of my time for several years. As the business grew, I realized that I didn’t have to do it all…

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Living the Good Life

I love my life! It’s a lifestyle I’ve created by choice and through persistent hard work, creativity, a bit of luck, and a lot of help from others. Not everyone would enjoy living like I do. Some people don’t like to travel. Others prefer the comfort of a steady paycheck, or are satisfied enough with their life as it is. And that’s awesome! But there are…

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Planning for the Moment

Do you ever find yourself stuck between the balance of enjoying whatever it is you’re doing in the moment, and being lost in hopes or fears about the future? This game seems to play out constantly in my own mind. When I’m not enjoying the moment, the wonders of life tend to pass me by unappreciated. But if I live without structure and planning, little gets…

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Birthdays, Books, and Consulting

My birthday is coming up next week. I don’t usually do much to celebrate. I try to see every day of my life as a celebration, and I already have everything I need. But this year, there is something exciting happening on May 8: Chris Guillebeau is launching his new book, “The $100 Startup: Reinvent the Way You Make a Living, Do What You Love,…

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A Different Kind of Christmas

Christmas has been very different for us since we moved abroad, in more ways than just being far from extended family. Even before we left, we became disenchanted with certain aspects of the holiday, particularly surrounding gift giving. Actually, I love giving and receiving gifts, but it’s not always as satisfying as I’d like. I think giving is most enjoyable for both sides when the…

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Without Internet in a Costa Rican Rainforest

Last week we went with some friends to the Osa Peninsula — a very remote part of Costa Rica accessible only by boat where there is no Internet access, no cell phone service, and no electricity unless you have your own power source. And we had a fabulous time! Below, I’ll be sharing some photos and videos highlighting our trip. But first I’d like to…

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The Global American Dream

Recently, American Family Insurance conducted a survey to determine if the American Dream is still alive. They discovered that 90% of Americans still believe in the American Dream, but only 14% feel like they’re living it. It’s no surprise. The most common dreams chosen by respondents were having money and owning a nice car. And the icon used for “living the dream” was a man…

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5 Tips for Hiring a Programmer

I’ve answered many questions recently from entrepreneurs looking to start their own online business. Most of the people who’ve contacted me aren’t programmers themselves, so a frequent question has been, “How do I find a good programmer to create my website or web application?”. I wanted to give some tips to help with this common question. Don’t Hire a Programmer for Non-Programming Tasks First, if…

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The Art of Non-Conformity

I’ve put off reading Chris Guillebeau’s book, The Art of Non-Conformity, for far too long. I won a copy of the book in a writing contest several months ago, and I figured now would be a good time to finish it, so I don’t have to carry it around to our next location. Fortunately, this book was interesting enough to me that I finished it…

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From On-line Business to… Farming?

Recently, I’ve been entertaining the idea of starting up a farm. For an entrepreneur with a successful on-line business, you might wonder why I’d want to consider tying myself down to a location-dependent business in an industry I know almost nothing about, especially when I said I plan to be leaving Costa Rica later this year. I have two main reasons: I believe it’s wise…

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How I Spend My Time Now

Update: In April, 2009, I wrote a post entitled How I Spend My Time, where I tracked what I was doing every minute of every day for one whole week, to help me visualize how much time I was spending on what really mattered to me. In March, 2011, I did it again and wrote this post below. In January 2013, Tim Ferriss asked if he could…

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Travels, Japan, and Book Progress

We spent the last week in Salt Lake City, visiting our family and friends who live there. It was great to see so many of our loved ones, and have a chance to talk with them in person. Thanks to everyone for your hospitality! We arrived the day after a big snowstorm, so the kids enjoyed playing in the snow (in their dresses and flip…

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77 Things I Did in 2010

2010 was really a landmark year for my family and me. It’s hard to believe how much our lives have changed in these short 12 months, how much we have grown, and how much we have been able to do. After reading a great post by Dragos Roua about 77 things he did in 2010, I decided to follow suit and write about some things…

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Planning 2 Months in South America and How I Outsourced it

Recently, we decided that we’re ready to get out of the rainy season here in Costa Rica, which is usually fine in the mornings, but very rainy, foggy, and cold in the afternoons – at least up in the mountains where we live. So, we’re going to be spending September and October in South America this year, followed by a couple weeks in the States…

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Is Money the Root of All Evil?

I recently received a comment in response to a Twitter/Facebook post I made about considering the possibility of buying a rental condo in Costa Rica. (Lately, I’ve been thinking about the importance of diversifying my investments rather than keeping what little money I have in U.S. based mutual funds). The comment went like this: “hey i may not know you very well or seen you…

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Interviewed by JetSetCitizen

Last week, I was contacted by John Bardos from JetSetCitizen.com, the popular blog showcasing those trying to live their lives to the fullest. I’ve been a fan of John’s blog for a long time, and especially enjoy his interviews with perpetual travelers, international volunteers, entrepreneurs, and others. I was honored when he asked me for an interview, and am pleased to announce that it’s now…

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Tips for Marketing Your On-line Business

Note: This is the fourth in a series of posts about starting your own on-line business. To see other posts in this series, see the Entrepreneurship category of this blog. Not too long ago, I received an e-mail from someone looking to grow their business, and he wanted to know what kind of marketing I’ve done, and what I’ve found effective in getting new customers….

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Handling Customer Support

Note: This post is the third in a series of posts about starting your own on-line business. To see other posts in this series, see the Entrepreneurship category of this blog. In this post, I’ll talk about how to interact with customers, either potential or active, to make sure you are providing enough value that they’ll actually want to pay you for your product or…

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Pick a Need and Fill It

Note: This post is the second in a series of posts about starting your own on-line business. To see other posts in this series, see the Entrepreneurship category of this blog. One important aspect of starting a successful business is picking a product or service that fills a need. Yes, it is possible to create something for which there is little or no interest, then…

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Finding Your Driving Force

Note: This post is the first in a series of posts about starting your own on-line business. To see other posts in this series, see the Entrepreneurship category of this blog. One of the first and most important points I want to make for anyone endeavoring to start a business, is that you must have what I call a “Driving Force” to keep you motivated to…

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How to create a self-sustaining on-line business

Have you ever dreamed about owning a business that continues to bring in a steady stream of income each month, regardless of how much you work? Are you tired of having to depend upon your employer for your livelihood? Do you fear being laid off from your job because the company you work for is downsizing? Maybe you’ve taken a pay cut or two in…

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How I Spend My Time

Update: This post was written in April of 2009, so I have written an update to this post showing How I Spend My Time Now. I like being productive. And I like being able to look back at how I spend my time and see how closely it aligns with my ideals. That’s why I track my time while I’m working. Because I run my…

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The Easy Way to Read Blogs

Do you read a lot of blogs? Or are there just a handful that you like to check up on regularly? I know that a lot of my readers aren’t the “techy” type, but even those who are, I’m surprised to learn, aren’t taking advantage of a great time-saving tool related to reading blogs. I’m talking about RSS Readers. Don’t let this name scare you….

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Being Home

This vacation was truly like no other I’ve experienced. Usually, we spend our vacations running from one activity to another, and come back to a mess of things to do, making us even more stressed than before we left. We usually need a vacation from our vacation. This time, however, we really felt rejuvenated, and have a renewed energy to get back into life. I…

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I lived a 4-Hour work week

As many of you know, I keep track of all my time at the computer. I use a free on-line tool called Slim Timer, that lets me track what I’m doing every second, and run reports to see where I’m spending most of my time. I looked at my reports today, and realized that for the past few weeks, I have been living the four…

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Balancing Work and Life

Automation and Leverage I’ve always loved the idea of automation. I remember when I was about twelve years old, I loved dreaming about how, in the “future”, we’d simply press a button, and we’d have our food. We’d press another button, and we’d be dressed. We’d press another button and we’d be clear across the world. Well, that hasn’t really happened, and arguments could be…

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