“We just got back from an 81-day vacation.”
When people hear this, they pretty much always leap to the same two conclusions: The first is that it was a once-in-a-lifetime experience for us, and the second is that we must have spent a huge amount of our savings to make it happen.
But those totally understandable assumptions are actually the exact opposite of the truth. In fact, we take at least one of these types of trips every year, and so far, we’ve come home from every single one of our extended sabbaticals with more money than when we set out!
During our time on the road this summer, we got about $39,000 richer.
That sounds so ludicrous that most people dismiss it as some fantasy, which is why I want to stop and explain exactly how we’ve made our “endless adventure” lifestyle a reality — and how you can make it happen for yourself if you want to.
Here are the four strategies we’ve used to escape our employers, design money-making sabbaticals, and truly take unlimited vacation time. If you can master just two or three of these, you’ll be set for life!
1. Build Your Savings & Investments
2. Make Your Boss Give You Whatever You Want
3. Create a Business That Runs Itself
4. Travel Cheaper So You Can Travel Longer
1. Build Your Savings & Investments
The very first thing that keeps most people from even considering long-term travel is their job. If your boss won’t let you take 3 months off work, then you’re doomed from the start, right?
Not at all! But to solve this problem, we have to consider why you even show up for work in the first place: money.
To escape the office, you first need to demonstrate to yourself that you have some way to pay your bills without relying on your job, if necessary (at least for a little while). This will give you the courage, confidence, and negotiating leverage you need to begin the process.
For example, if you have just enough money in your savings account to pay your bills for 3 months, you could technically tell your boss to kick rocks, quit your job, and take a 3-month vacation. But to actually do that that would be pretty short-sighted because by the end, you’d be completely broke and jobless. We’re not suggesting that. You need to think bigger…
When we took our very first 6-month sabbatical to Hawaii at age 24, we had nearly 7 years of our regular living expenses saved up. The prospect of quitting our jobs wasn’t scary at all because we knew that we could easily support ourselves for a long time while looking for new work opportunities after the break was over.
The key to obtaining such freedom at a young age was living frugally and saving the majority of our incomes. Because we intentionally kept our expenses low, the amount we needed to save actually wasn’t much at all. At the time, just $150,000 represented 7 years worth of living expenses for us because our spending was minimal ($22,000 per year combined in 2015).
We shared a used car, shared a one-bedroom apartment in an inexpensive city, skipped TV subscriptions, and cooked our food at home. Those choices armed us with immense financial power in a very short period of time. After just 2 years of intense saving, we were ready to take our first sabbatical with total confidence.
Because we were so practiced in living cheaply, that 6-month vacation in Hawaii cost us under $1,900 per month. And since we were able to make more than that with a few part-time gigs on the island, we didn’t have to spend any of our savings on vacation!
The numbers may be higher today, but the principles remain exactly the same: Spend less than you earn, and you will set yourself free.
As time went on, we took more sabbaticals, and we kept banking even more money — but not in a savings account. By shoveling all of our excess income into passive stock and bond market index funds, we eventually grew a seven-figure investment portfolio that now pays us a substantial income to do nothing.
According to the 4% rule for financial independence, you actually have the option to stop working forever once these types of investments have exceeded 25× your annual expenses. We surpassed that threshold years ago, so at this point, we don’t actually need a job ever again, and we automatically get richer almost every single year.
But remember: You don’t need nearly that much money to take your first sabbatical! Having just a few years of living expenses saved can give you the courage you need to step away from work when you feel like you need (or just want) to — and passive income from a smaller investment portfolio* can still help support you while you’re out on the road enjoying some temporary leave from work.
2. Make Your Boss Give You Whatever You Want
Now, you might be thinking, “I have a good job, and I don’t want to throw it away just to take a long vacation.” Well, that’s totally fine, because you probably won’t have to.
Once you have enough money to leave your job for a while if needed, you can use your savings as negotiating leverage to get extended time off from your employer instead. Rather than simply quitting to take a sabbatical, make it clear that you are willing and able to quit if your employer doesn’t give you the time off that you want.
Here’s what I said to my boss when we took yet another sabbatical back in 2019:
“My wife and I have this crazy idea to visit every National Park in the United States, and we’ve decided to actually do it. It’s gonna take about 7 months, and we’re heading out in the camper van we just bought sometime within the next year. I wanted to give you a heads up so we can leave at a time that’s less impactful to the company. I’m also open to doing some part-time remote work while I’m gone and returning when I get back…or, if I have to quit, I wanted to at least give you lots of advance notice.”
While I was flexible about timing and considerate of the impact it would have on the company, I was also extremely firm about my intentions, and I absolutely did NOT ask for permission to leave. Crucially, there was an implied threat as well: Work with me on this, or I will quit, and you will lose a good employee forever.
My boss didn’t even have to think about it. He immediately saw that I was serious and started discussing timing and a part-time remote work plan with me. I ended up working about ten hours per week on vacation (doing only the most critical parts of my job), in exchange for more than half of my full-time pay — giving me an hourly rate more than twice as high as before!
Needless to say, Lauren and I really did visit every National Park in the United States that year. I returned to work full-time for a little while after the trip, but pretty soon I phased back into part-time contract work again as I eased into early retirement in 2020.
Actually, I still do just a few (very high-paying) days of work per year for that company now! In fact, some pretty significant income from just a tiny remnant of my old job helped make this year’s 81-day vacation profitable.
Having the courage and financial leverage to “tell your boss who’s boss” can give you immense freedom and a more flexible source of income, but it’s worth noting that I had plenty of other ways to make money back in 2019, even if my boss said “no” and I was forced to quit to take that National Parks trip.
I had a thriving photography side hustle, a part-time tutoring side gig, and a knack for buying and selling things on eBay — among other money-making skills. Sometimes, the best way to take a sabbatical is just to quit your job altogether and rely on yourself for an income. There are so many different ways to make this work!
3. Create A Business That Runs Itself
One of the best ways of creating an income that’s independent from an employer didn’t even occur to us until pretty recently. In 2023, we teamed up with a friend and founded a college test prep and tutoring company called CramBetter.
Since we’d already been retired from our jobs for several years at that time, and we didn’t really need the extra money, we had one important condition for starting this new business: It had to be able to run itself — at least eventually.
Founding a startup is always a ton of work, and we were up for a new challenge, but we also didn’t want to create permanent jobs for ourselves. Using principles similar to those found in The 4-Hour Workweek by Tim Ferriss, we set out to create a business that could eventually become a source of passive income. We didn’t want to “sell our time” in perpetuity.
So, instead of relying on live tutoring sessions paid by the hour, CramBetter is built on an asynchronous, subscription-based online learning platform where students access study guides, practice tests, and video lessons on their own.
While our students are learning, we can be traveling, walking on the beach, or even sleeping! As a result of this intentional business design, our customers get dramatically lower prices than traditional tutoring sessions, along with the convenience of 24-hour access. It’s a win-win.
As we drove to and from Alaska, we barely gave any thought to our online business this summer, yet it continued to generate significant income — paying for our whole trip and then some on its own!
With that said, CramBetter still isn’t 100% passive yet. In fact, this blog post is being published a bit late because immediately after our summer trip, we spent 5 solid weeks doing marketing for our company! Still, the important work comes in small spurts, and the payoff has been massive. Overall, it’s been a huge success and a lot of fun.
If you’re interested in creating a business like this, stop and think to yourself: How do I design a genuinely useful product that doesn’t require additional work from me each time someone wants to buy it? Often, these types of ideas come in the form of a digital product, something that can be mass-produced, or a service that can be fully automated.
4. Travel Cheaper So You Can Travel Longer
Multiple streams of income are wonderful, but one central trait has truly underpinned all of our financial successes in life: frugality.
Learning to enjoy life without high spending is what’s allowed us to save more of our earnings and make those savings last longer — both on sabbatical and in early retirement.
Put simply, when you spend less per month having fun, you can afford more months of fun! Here’s exactly how much 81 days of good times cost us this summer:
There are tons of ways to travel cheaply, so you definitely don’t have to copy ours, but let’s go through some of these expense categories and point out a few ways we saved money on our most recent trip — plus a few ways we didn’t…
Most people’s largest vacation expense, lodging, is barely even present on this chart. Even at a low hypothetical rate of $100 per night, you’d expect to spend a minimum of $8,100 on hotels during an 81-day trip. We saved a whopping 80% in that category by sleeping at free campsites in our van whenever the weather was comfortable enough to do so.
But the van comes with its own set of expenses, and on this trip, we had some unusually bad luck. In addition to vehicle depreciation*** and normal maintenance like oil changes, we had to pay for two emergency tire patches, a whole set of 4 new tires, two new tire pressure sensors, a new AC compressor, and a replacement headlight assembly! Fortunately, with a little DIY work ethic, we were able to keep those expenses to a minimum.
Unlike most RVers, our camper van is our only vehicle, so we don’t have to pay for any additional cars back home. Minimizing our ownership of vehicles keeps more of our money invested — working for us and producing additional passive income. Since our van also serves as our daily driver, we chose one with good fuel efficiency (26 MPG, or 9 L / 100 km), making the “Gas” category about as small as it could be for a 15,800-mile trip all the way to the Arctic Ocean. 😅
In the food categories, our portable propane burner (affiliate link) did a lot of work, allowing us to cook groceries on the road. But truthfully, we ate out a lot! To keep restaurant costs down, we did a bit of clever menu hacking and generally just chose casual places with lower price tags.
The “Other” category is where all the entertainment costs of this trip are hiding. We squeezed in a 3-day Magic: The Gathering convention in Las Vegas (which paid for itself because we did well in tournaments), a 2-day trip to Disneyland (which we made cheap with our favorite Disney hacks), a one-year National Parks pass, tickets to a concert we never even got to attend, a couple of bicycle rentals, and a night of bowling with a friend…but the vast majority of our fun was free, courtesy of Mother Nature.
Ultimately, we became $39,000 richer on vacation this year because the cost of the trip was exactly that much less than our income. If we’d booked a series of decadent luxury cruises and fancy hotels instead of an outdoorsy vanlife adventure****, we could have easily outspent our earnings (in a lot less than 81 days!).
No matter how much you make, controlling your spending is what will truly keep you untethered and free. 💸
— Steven
Interested in how long-term travel fits into a larger financial plan? Taking a big break from full-time work to go on an adventure like this is Step 4 of our Financial Roadmap — check it out!
* One additional way you can generate “investment income” to fund your adventures is to rent out your house while you’re gone! We didn’t do that this year, but we’ve done it successfully in the past on our US National Parks trip and our tour of Australia.
** The $12,091 cost of this summer’s trip was calculated using “vacation-related” expenses only, so it doesn’t include “back home” expenses like our existing health insurance plan, condo association dues, etc.
*** To calculate our vehicle depreciation, we took the Kelley Blue Book “private party” value of our van before the trip, and subtracted its value afterward (with nearly 16,000 more miles on it). The “Van” category includes this in addition to all the maintenance, mishaps, and repairs.
**** If vanlife doesn’t interest you, I have great news: It’s not a prerequisite for cheap travel! Check out the financial details of our extended trips to Hawaii, Australia, and Iceland for some affordable travel inspo without any camping at all.
