Making the Decision to Upgrade Your Life!

Step out of the history that is holding you back. Step into the new story you are willing to create.” - Oprah Winfrey


For many, living a suburban life and working extra hard to save money is the the "American Dream".

I fell into this trap, like many of us, and, after living in New York for 12 years, moved to Silicon Valley in California to pursue the riches of start-up life. I lived in a quaint town of 30,000 people with good public schools and lived the typical suburban life. We lived in a modest three-bedroom house with a yard, had two cars and two jobs, I worked 10 to 12 hours days and I saw my kids mainly on the weekend, when I was exhausted, trying to recover from the work week. I was making a six-figure income, but after taxes and with mounting monthly expenses to cover rent, bills, and food for an average life, we weren’t saving anything. We were just surviving, not living.

While we were living the American Dream, I was hurting. I spent most of my days at work and not with the people I love. I was stressed, unhealthy and living on a drug – the drug of false hope that financial success would carry me to a better life, though I knew that the odds of that happening were very slim. But I kept living off this drug and the years kept passing by. Consequently, I was not happy with my life, but I kept dragging on. It was easier to keep suffering quietly than to face change and its uncertainties.

We finally asked ourselves the questions that had been whispering at the back of our minds. Why do we keep living in this rat race when it doesn’t lead to a meaningful life? Why are we trying to live for retirement, when our bodies will be too old and frail to enjoy the activities we love, instead of living our lives now?

With this newly acquired perspective on life, we decided to change course. We decided to stop racing to nowhere and win our lives back. We decided to do the thing we both wanted to do when we were retired – travel the world – but instead of waiting for retirement to fulfil our dream, we decided to make it a reality now!

Why was traveling our dream? Michelle and I met in New York and, while we enjoyed the big city, we also loved traveling. Two weeks into our relationship, we took an overnight camping trip to upstate New York and discovered that we shared a passion for travel in foreign countries. I traveled for nine months in South America and Michelle traveled for fourth months in Europe after college by herself. If you travel, you'll need a medical and travel insurance. We recommend a cost-effective travel and medical insurance. It's just $37/month and the best part, kids under 10 are free!



When our first child was just two months old, we rented a motorhome and took our son on a cross-country road trip 6,000 miles from New York to Los Angeles. (Surprisingly, he says he doesn’t remember much of it.) Throughout our kids’ childhood, we traveled with them to Belize, Mexico, Israel and 9 U.S states. Both Michelle and I had plans to travel around the world when we retired, but it always seemed so far off.

Suddenly, with the understanding that we were wasting our lives chasing dreams of riches we didn’t need or want, traveling seemed less like a fantasy and more like a necessity. “If we don’t do it now,” we said, “we might never be able to do it.” We asked ourselves, “If this is the thing we love doing most, why aren’t we doing it now?”

“Just do it!” - Someone smart on Nike’s marketing team

As we started mulling over the idea, we talked about the obvious reasons we shouldn’t do it (see post 5: Adding Kids into the Mix! Family Consideration), but we found many more meaningful reasons why we should do it now and not wait for later! Our oldest son was nine and we feared that as a pre-teen he wouldn’t want to spend time with us later. We also knew that, as kids get older, maintaining their school friends becomes more important. Separating our kids from their lives for an adventure around the world would be harder and harder as they got older.

We realized that there was a narrow window of opportunity to make our dream of traveling around the world a reality. “If we want to ever do it,” we said, “now is the time, before it becomes too late.”

Not wanting to feel totally crazy, we sat down to write a list of all the reasons FOR a trip and all the possible reasons we could think of AGAINST the idea. Just for fun!

“Once you make the decision, everything becomes easy!” – me

We started with a simple list of pros and cons about leaving our life behind and changing course to explore the world. We poured everything into it, from high-level strategic items (such as, “It will improve the relationship between the kids and strengthen their bond.”) to small administrative items (such as, “We need to find a digital library so the kids can continue to read since we can’t carry too many books.”). As we spent more time on the road, many rows were added, so we created a spreadsheet with all the items you’ll need to consider if you are serious about making this life change. You can download it: Detailed Preparation List.

We quickly realized that the pros list, while shorter, was much more powerful than the cons list. Being the ultimate optimist, I also noted possible solutions to each one of the cons on our list which made them suddenly look very, very manageable.

Once we made the decision to do it, every item on the cons list was put in perspective and became easy. Even the decision to eliminate mail and transition all our mail to a scanning service which allows us to see our mail scanned online (we recommend TravelingMailbox). It was a stepping stone on the way to achieving our ultimate dream - leaving the rat race behind and traveling around the world as a family!

Once you start planning and committing to a date of departure, everything falls into place. It’s like a magical secret that everyone knows but is afraid to say. Making the decision to change your life is, in actuality, much simpler than you think it is and you, most probably, could make it now and, within the next seven days, start lining things up so you can commit commit to a departure date. It's that easy.

If you need any additional guidance to work through your personal circumstances (every person, couple and family situation is different), I’m happy to help. just pick a time to chat.

So, what do you say? Are you joining us? To learn how to get a more balanced and fulfilling life, get the Ultimate Guide To Moving to Bali below:

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