The typical way to recharge your batteries after months of hard work is to take a vacation — a week (or, if you’re lucky, two weeks) off to take a breath of someplace new. This can be a lot of fun, but ultimately, these “week-short” vacations don’t really offer us what they’re intended to simulate, which is a genuine change of pace in our lives.

Imagine, instead, a hiatus from full-time work lasting somewhere between a month and a year. What would you do? Where would you go? How would it change you? The concept of such a long vacation probably seems like something reserved for the super-rich, but with the right outlook and planning, most members of the American middle class can not only dream it but do it. In fact, we’ve done it — on a teacher’s salary.

Rather than get into the details of how to do it, which you can find elsewhere on this site, let’s consider why you’d want to. Why do one-week vacations suck, and why would you want to do something different instead?

They Contain Too Much Unenjoyable Travel

Ever planned a week-long trip to the other side of the country? Driving is not an option, and when you go to book the flights, you’ll immediately sink in your seat as you realize that two or more of your seven free days are gobbled up by miserable flights in crowded commercial planes. That leaves just 70% of your available days for relaxation.

Photo of a crowded Grand Central Station
Crowds of tourists zig and zag across the floor of Grand Central Station in New York City to get to their destinations.

Even if you choose a destination within driving distance, you’ll probably still spend a day or two on the road in total. For those who enjoy road trips, this probably sounds a lot more fun than flying — I know it does to me. But the trouble with road trips is that they’re better when you can take your time savoring them, seeing and doing cool stuff along the way. If your vacation is a week long, you may find yourself too fixated on having enough time at your destination to really enjoy the journey.

They Trick You into Believing You Want to Go Home

Because travel time eats into shorter vacations so much, it’s unlikely you’ll plan to visit several dramatically different locations on the same trip. Most people stay in one area for the most part, which makes sense, but it also leads to a sense of boredom or “doneness” by the time the week is over. In reality, you may not be bored of travel or time away from work — you’re probably just tired of that one destination.

There’s another force at play, too: a fixation on relaxation. When you get a week off from work, you might take that time to just chill out — you need it! But humans are meant to do stuff, and relaxing gets pretty old to everyone after just a few days. You might conclude that you want to go back to work, but consider what you’d do if you didn’t have to go back. Is there anything exciting you’d finally have the motivation to do, try, or see?

If you’re not the type of person who does nothing during a one-week vacation, you might be a planner who packs every moment of your precious week off with activities. This can lead you to think you need a “vacation from your vacation” and to get back to the more routine lifestyle you had at home. In reality, this may just be a symptom of overbooking your vacation schedule because you only had a week off in the first place.

They’re Too Expensive

Wait…How can a one-week vacation be more expensive than a six-month vacation?

Let me start with an example from the supermarket: When buying (non-perishable) groceries, it’s smart to consider the “unit price” of your food instead of the sticker price.

Photo of bulk rice

Buying food in bulk is typically cheaper per unit than buying in smaller quantities, and this saves you money over the long run. Travel should be no different.

When we took our 6-month honeymoon in Hawaii, we rented a beachside apartment for $965 per month ($31.70 per day). We bought a used car and recovered all of our money when we resold it at the end (~$0 per day). We bought most of our food and necessities at Costco, cooking at home every day. Also, the cost of our plane tickets to and from Hawaii at the beginning and end of the trip were amortized over a 6-month period.

When some friends of ours took a one-week vacation to Hawaii, they incurred hotel costs of around $200 per day, rental car costs of about $40 per day, and were mostly forced to eat in restaurants because their hotel didn’t have a kitchen. They had to fly the same distance as we did, but those same tickets only afforded them a single week of travel (a much higher cost per unit time).

Even more important than the low “unit price” of slower travel is the fact that you may actually find yourself wanting to work a little when on such a long trip. You can take on a part-time job or freelance work to offset the cost of your trip along the way. While full-time work can be draining, part-time work alongside the daily dose of an exciting new place can give your life a welcome sense of variety. Actually, using this exact technique, we paid for our entire 6-month Hawaii honeymoon without dipping into our savings at all!

They’re Too Short to Change You

Now let’s forget, for a minute, all the practical stuff we just discussed. The real reason to turn your travel into a lifestyle change isn’t because it’s cheaper, or even because it’s more fun. The main reason to do it is that it can give you a completely different perspective on your own life.

In order to take a long trip, you’ll have to alter your life in a big way. You’ll have to save a lot of money, quit your job or arrange a sabbatical, and spend a lot of time away from friends and family (at least the ones you’re used to living near). This very act itself will force you to think differently. You’ll begin to realize that you have agency over the everyday; you have a choice in how you spend your life.

Photo of a Hawaiian beach
Spending a peaceful Christmas Eve on Hawaii’s La’aloa Bay. This photo is available in our online art shop.

When you have a full-time job, it can feel impossible to muster up the motivation to do things you’re passionate about outside of work. When you take a long period away, you immediately find time to pursue your dreams. By taking months at a time away from a busy 9-to-5 lifestyle, I was able to dive deeper into my artistic passion of photography than I could ever find time to before. Rather than stagnate as an artist, I had time to spend learning and growing — and I got better as a result. Actually, the freedom of thought afforded by one of our trips (and some great conversations on long car rides) is exactly what inspired the idea for this blog. You never know what you’ll find within yourself when you take the time to look.

The financial work needed to make this happen is no small feat. In fact, there’s an entire section of this website dedicated to it. But once you get the mindset right, you can make it work on a middle-class income. We hope you’ll join us on the ride.

— Steven

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