Financing a Life of Family Travel, Freedom, and Fulfillment

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 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, Enjoying Life Now. Thanks for reading, and best wishes on your own entrepreneurial journey.

If you're interested in learning more about my story and my process, check out some of the interviews and blog posts below. (Sorry, some of these podcasts are no longer available online)

All Entrepreneurship posts

Jun 2019 · 4 min read

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.

Jun 2019 · 3 min read

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!

Dec 2017 · 2 min read

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?

Sep 2017 · 2 min read

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!

Sep 2017 · 3 min read

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!

Oct 2016 · 6 min read

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!

Aug 2016 · 5 min read

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…

Aug 2016 · 6 min read

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.

Jun 2016 · 11 min read

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.

May 2016 · 12 min read

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.

Apr 2016 · 14 min read

5 Steps to Begin Traveling Long-term with Your Family

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.

Feb 2016 · 11 min read

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…

Sep 2015 · 2 min read

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…

Oct 2014 · 4 min read

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…

May 2014 · 6 min read

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…

Mar 2014 · 1 min read

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!

Nov 2013 · 4 min read

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…

Oct 2013 · 6 min read

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…

May 2013 · 5 min read

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…

Apr 2013 · 4 min read

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…

Mar 2013 · 4 min read

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…

Oct 2012 · 4 min read

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…

Sep 2012 · 11 min read

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…

Jun 2012 · 5 min read

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…

May 2012 · 2 min read

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…

Dec 2011 · 4 min read

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.

Oct 2011 · 5 min read

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!

Sep 2011 · 5 min read

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…

Jul 2011 · 6 min read

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…

May 2011 · 3 min read

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…

May 2011 · 4 min read

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…

Mar 2011 · 8 min read

How I Spend My Time Now

::: note 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…

Mar 2011 · 4 min read

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!

Jan 2011 · 5 min read

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…

Aug 2010 · 5 min read

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…

Aug 2010 · 8 min read

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…

May 2010 · 1 min read

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…

Sep 2009 · 9 min read

Tips for Marketing Your On-line Business

::: note 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. :::

Jun 2009 · 8 min read

Handling Customer Support

::: note 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. :::

Jun 2009 · 7 min read

Pick a Need and Fill It

::: note 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. :::

Jun 2009 · 10 min read

Finding Your Driving Force

::: note 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. :::

Jun 2009 · 4 min read

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…

Apr 2009 · 10 min read

How I Spend My Time

::: note 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. :::

Mar 2009 · 3 min read

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.

Mar 2009 · 4 min read

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.

Feb 2009 · 3 min read

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.

Jan 2009 · 4 min read

Balancing Work and Life

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.…