Michael and Melissa Harlow had it all. High-paying jobs. A $1 million house. Watercraft. Luxury cars. They also had a big mortgage and spending habits that left them with too little time and too little money for the things that mattered. They decided to remake their lives to fit their goals. In the process they created a playbook that you can follow to live your dream life too.
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The Harlows knew what they wanted — to sail around the world, with no financial worries or work responsibilities. But, with high-paying corporate jobs and two young kids, they put sailing the world on the back burner.
In the meantime, they had plenty of money to buy whatever they wanted. And they did. As Michael puts it, they’d walk into Costco intending to buy batteries and come out with $1,000 worth of stuff.
When the great recession hit in 2008, things changed. The couple suddenly had trouble keeping up with their obligations. And they realized their lifestyle was hindering their long-term goal.
Define your dream
It had been years since they’d articulated and agreed on their dream life. But they’d also never put any definition or specifics to precisely what they wanted.
When did they want to do this? And how? What kind of boat would they need? What kind of training? Would they take the kids or wait until the kids were out on their own? How much money did they need to make this dream come true?
To live your dream, you need a plan. And there’s no way to create a viable plan when the goal lacks specifics. You need to put both a price tag and a timeline on anything that’s required to live your dream life.
Identify the hurdles
Hurdles to the Harlows plan were easy to see. They had two kids with college aspirations, a pile of debt, and thousands of possessions that they needed to get rid of to make a break. They also needed to learn new skills and safety procedures to sail over open ocean for weeks at a time. Not insignificantly, they also needed a boat.
Break down big goals
To reach their dream life, they needed to achieve five smaller goals. And each of these smaller goals were daunting by themselves.
1. Get rid of most of their stuff.
2. Pay off all of their debts.
3. Save enough to send the kids to college, finance their own future retirement, and create a $100,000 nest-egg to pay for the round-the-world adventure.
4. Buy a boat that could withstand the journey, without adding debt.
5. Learn what they needed to know to sail safely.
Big goals like these are necessary to live your dream. But they can also be demoralizing. Why? It feels like you’re making progress in inches when you need to go miles. That can look so hopeless that many people give up.
The Harlows took a smarter approach. They broke each big goal into multiple “micro goals,” Melissa said. With each small achievement, they got both encouragement and a step closer to the big goal they were shooting for.
For instance, a micro-goal would be to sell their luxury cars and use the proceeds to buy an inexpensive car with cash. Sell the wave runner and use the proceeds to pay off debts. Set and stick to a budget. Stop buying things they didn’t need. With each little success, they got a pat on the back and more cash to feed the long-term goal.
Set a timeline
The Harlow’s timeline had to balance several competing factors. They wanted to sail the world when they were still young and athletic enough to handle the substantial physical demands of their dream life. Yet, the job of revamping their financial lives was massive and would take time. Moreover, they didn’t want to upend their children’s lives. So, ideally, they wanted to set sail shortly after the kids both moved out for college.
That gave them eight years.
The benefit of setting a timeline when you’re going after a big goal is that you can now work backwards. Take the gap between what you have and what you need and divide by the number of months to the goal. That gives you a rough idea of how much you have to save each month.
Unrealistic figure? Realize that invested money usually does grow, so you are likely to get some help from compound investment returns. However, since investment returns are rarely guaranteed, you should also consider what happens if your savings fall short.
Postponing the transition for an extra year can make a big difference. So can scaling back the elegance of what it takes to live your dream life. Figure out what compromises you’re willing to accept.
Get family buy-in
The Harlows knew they couldn’t manage a massive lifestyle change if their kids were fighting them every step of the way. To get the kids on board, they called a family meeting, explained their vision, the spending restrictions it demanded, and their aim to divest themselves of their costly possessions.
“We needed to make it clear that this was a conscious choice to get rid of the things that were holding us back,” says Melissa.
They turned budgeting into something of a game, giving the kids the ability to buy luxuries by earning the money. When Michael and Melissa held garage sales to get rid of their stuff, the kids were able to sell their own possessions and keep the cash.
Live your dream
By 2016, as planned, they had a well-equipped boat, no house or cars to worry about. The kids were in college, and the couple had the savings they needed to live for an extended period on their boat.
They set sail.
But dreams change….
At first, sailing the world gave them everything they wished for. No timelines. No financial worries. They sailed to Mexico and then across to French Polynesia. They sent their kids plane tickets so they could spend the holidays together in the Islands.
But the hard work and isolation of life on a boat eventually began to wear on them. They still wanted the freedom that was at the heart of their dream life. But they longed for land and family.
Listening to a podcast one night, they heard someone discussing life in an RV. It was the impetus for a new goal. Sail home; sell the boat; buy an RV with cash. Travel like before, but on land. And, importantly, live closer to all of the people they love.
Side hustle for freedom
But this presented a new challenge. Living in the U.S. is far more expensive than living abroad. And the Harlows are still in their 50s — far too young to comfortably live on retirement accounts without any other income. How could they make ends meet while still maintaining the freedom to travel?
Their answer was to cobble together a series of flexible side hustles that they could do part-time and even on the road. They still live frugally, but earn nearly six figures while retaining the ability to take long trips, Michael says.
Match skills, interests and resources
To find the right mix of side jobs, they took a look at their skills, interests and resources.
Melissa, who has a background in broadcasting, does voiceover work through Fiverr. Fiverr is a broad-based work platform that allows you to list your ability to perform a variety of services, from house cleaning to consulting. Melissa earns an average of $4,000 to $5,000 a month with voiceover work that she charges for by the word. (You can sign up with Fiverr here.)
Michael offers himself out as a boat captain, advertising this service on the couple’s website, TheAdventureTravelers. Several boat rental sites, including BoatSetter and GetMyBoat, also allow captains to list their availability to work online.
It’s irregular work. But when he snags a gig, it pays generously. He also manages the couple’s website, which brings in about $1,000 a month from advertising and affiliate commissions.
Finally, they rent out their RV when they’re not using it to travel. The couple lists their RV on Outdoorsy, RVShare and RVezy. The RV is rented nearly full-time for six months of the year, delivering roughly $5,000 in monthly income, Michael say. In the meantime, they live in a small guest house near Melissa’s family.
“This is all about freedom,” Melissa says. “It gave me back my life.”
Adds Michael: “Not that many people take off and drop everything. But you can do it. You can leave the 9-to-5 world and live your dream.”