Best Thing Money Can Buy Haleakala Sunrise
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The Best Thing Money Can Buy

What is your favorite thing to buy? This is such a personal question, and the answers are as unique as each individual. It may be a brand new car, a new piece of furniture, delicious meal, skydiving trip, sarcastic bumper sticker, or a gift for a friend or stranger. Some answers may be surprising or ridiculous to those who don’t agree, but I’d say each answer is a glimpse into what makes that person happy. So, what is our favorite thing to buy? Freedom!

By far, the most commonly asked question we heard (by those bold enough to ask) when discussing our plans to travel around the world for an extended period was how we were going to pay for it. The idea of saving enough money to live for two years without jobs is crazy to some, impossible to others, but in reality, it is neither of these things. In order to address this question and provide some insight into how we are living our dream of travel, we are beginning a series on finance. We will feature our story, resources, big ideas, and little tips. Here is how we came to buy our freedom.

Best Thing Money Can Buy Flight
Our First Flight of our New Life – DC to Seattle! 

Even before we began dating in 2008, both of us wanted to avoid debt with a vengeance. We had seen firsthand that living paycheck to paycheck is very stressful, and we were determined to avoid that life. Each of us made conscious decisions to avoid that stress as we left college. At times, this meant that we couldn’t buy what we wanted or even going without things others may consider necessary, like furnishing an apartment, until we had saved up enough cash for it. We made plenty of mistakes starting out and we didn’t know much except that we needed to start saving for retirement and of course stay away from debt. Since we both went to the Naval Academy where everyone earns a full academic scholarship, we graduated without any student debt and had immediate employment as military officers, which certainly aided our financial goals. Chance and luck played a role as well, as it does for all lives, and we are grateful for the good things that have come our way. Life is still about choices, though, so don’t let your current situation dictate where you end up! You don’t need our life path to experience the same financial freedoms, and our path doesn’t guarantee the opportunities we created since not all of our peers are able to not work for a while and live off their savings (at least not yet!).

Finances are generally taboo in everyday discussions, and you may already be thinking this is boring. However, we believe frank and open conversations regarding money and the various approaches to it are what enable people to make positive life changes. Not everyone desires to make changes, but for those who do, knowledge is power! Money is one of the more easily adapted facts of life that can bring about real and lasting improvements. Imagine life where you have thousands of dollars saved. Imagine not owing money to anyone so that each month is an opportunity to put your hard earned income to work however you see fit. Do you want to take a golfing class? Go for it! See that offer for a tour through the countryside, sampling the local fare with beautiful scenery? Book it for this weekend! We could go on and on with this exercise, but my possibly random examples won’t be as meaningful as what you’re already imagining. We, too, had these thoughts, so when we were unhappy with our situation our main feeling was, “There has to be a better way.” But, what did that look like?

Best Thing Money Can Buy Paris Sunset
Sunset Over the Seine, Paris, France, 2012, from our trip between two deployments.

Graduation from the Naval Academy in May 2009 began our separate training schedules. After we took a celebratory trip to Scotland and Hawaii, I began my Marine Corps training in Virginia and Kathryn began her Naval Flight School in Florida. For the four years between June 2009 and June 2013, we were together for about 18 months in total. The first two years were filled with us living in different cities and visiting on weekends, while training exercises and deployments consumed the last two years resulting in longer stretches of separation and togetherness; the longest uninterrupted stretch together was three and a half months, which happened between two of our six month long deployments. This isn’t an uncommon lifestyle for military families, especially not for dual military couples, and plenty of people choose to live that way for decades whether it is with the military or a different career. In addition to all our separations, neither of us wanted to continue our military careers for various reasons. For us, this time made us realize that neither a lifestyle of many forced separations or a job in the military was something either of us wanted to continue. And so we decided to try to take lessons from our time and move on. We started to think of ways to improve. So, we began putting aside money each month, following the general guidance of saving 10-20% for retirement, or the future, or something…

A helpful concept in life is to focus on what you can control instead of what you can’t. We had decided to join the military and had signed contracts to pay back our college degrees through our service, so we were going to honor that commitment; we couldn’t control being in the military. We could, however, manage our mindsets and affect our small sphere of influence, so we committed to being the positive examples we had imagined in the ways we felt were most important. We also largely couldn’t control the fact we were generally in different cities or at least vastly different deployment schedules. We could, though, control our effort to see one another. This meant several all-night drives to spend 36 hours together (one through a snowstorm after a cancelled flight), or flights from Hawaii to the east coast for a three-day visit, or immediately booking a flight to Italy that left that night once both of our leave requests got approved during one of Kathryn’s deployments, all of which wouldn’t have been possible had we not already been saving. A new marriage is hard enough when you’re together all the time, so for these first few years of ours (we got married October 10th, 2010), our money was largely spent in order to see each other. What didn’t go towards those trips largely went into savings. We had taken control of the immediate situation as much as we could and it greatly improved our outlook, but it certainly wasn’t a long term solution.

Best Thing Money Can Buy Homemade Thai curry
Homemade Thai Curry and Craft Cocktail. Life is Good.

Kathryn was a Naval Flight Officer on P-3 Orion aircraft. Her flights were frequently long so she got to know her crew very well. One of her pilots is a miles and points enthusiast, which means he collects frequent-flier miles and hotel/bank points, largely through credit card bonuses, to be used for free travel. A wealth of information exists on this subject, and Kathryn mentioned one of the resources to me during one of our separations. Million Mile Secrets is probably one of the original blogs on the subject and features a guest blogger interview every Friday. The first interview I saw was with Mad FIentist, who specializes in Financial Independence – the idea you can essentially “retire” long before the traditional “retirement age” of 65, hence becoming Financially Independent. Sock me sideways! This quickly led us both down the internet rabbit holes on both of these subjects and they seemed to be exactly what we were looking for. (Mr. Money Mustache is our absolute favorite, and a full list of our recommended blogs on these subjects is below this article. Enjoy!) Travel is a shared love for us, so using miles and points to save money on travel was exciting, to say the least, and we have subsequently saved thousands of dollars through their use. We were also largely unhappy with our jobs and what came with them, so an excellent solution was to not have one! By eliminating what we felt was the main negative aspect of our lives, we figured we would greatly improve our happiness and fulfillment by being able to pursue other interests. Now that we had found our way out, we just needed to complete our military commitments and we would be free to make the life we wanted.

Best Thing Money Can Buy Biking in the Snow
Cycling Through the Winter Wonderland of DC!

At the time we discovered the idea of Financial Independence in 2012 we each still owed time for our military contracts – I had two and a half years remaining and Kathryn four and a half years, with the additional commitment due to her flight training. This left plenty of time to prepare for our lifestyle change, and we often found our discussions going towards miles, points, and Financial Independence. Although we had committed to achieving our goals, we often wondered what it would be for. We didn’t like our current jobs, but that didn’t necessarily mean there were no jobs that we would enjoy. So maybe our independence, our freedom, wasn’t completely dependent on not working. Maybe, and more likely, it was being able to choose what we wanted to do with our time based on our passions and desires instead of on the money that would come from our actions. It is a common question from guidance counselors and life coaches, after all, to consider what you would do with your days if money wasn’t an issue. During one of these discussions, Kathryn brought up our love of travel and our desire to see what lay beyond our own borders, what life in other places is like. Her proposal to take six months between the end of her military commitment and starting our next jobs was intriguing and needless to say we quickly agreed it was a worthwhile endeavor! And so it was that during one of our many financial discussions the idea of the ‘World Tour’ was born.

Best Thing Money Can Buy Kailua Sunset
Kailua Bay, Oahu, Hawaii – Most of our discussions were during walks on this beach near our home.

The combination of wanting to change our lives and learning about Financial Independence pushed us to begin saving in earnest, and gave birth to an interest in finances, from saving to investing, in general. We began tracking every single expenditure down to the penny (we still do), creating budgets for each month and year and evaluating them often, and saving, not 10-20% but 50% of our incomes. We established habits of thoughtful and conscious spending that are still with us and are now second nature. This required effort and restraint, but it was also incredibly fulfilling to watch that savings number go up and realize that a lot of the things we were “giving up” never really brought us happiness anyway. And no, those years were not terrible either, we still cooked delicious meals, went out with friends, and took many lovely trips to explore our region and celebrate milestones. Yes, we both were well paid at our jobs making more than the average American salary. However, these practices will make anyone more financially independent at any income level. Everyone’s situation is different, and if you are saying to yourself, “Yeah, but…I have kids/student debt/I don’t make that much,” you don’t have to take our word for it. The blogs listed below are written by people with kids, jobs that don’t pay as well as ours did, people from different walks of life who we learned from. By no means are we a perfect example, we could have saved much more in hindsight, but we take the lessons we have learned and keep moving forward.

Best Thing Money Can Buy Hawaii Christmas
Hawaiian Christmas, The Cheers Life Style (Wedding China is to be used not boxed up!)

Today, five years after our enlightenment, if you will, we are in the midst of two weeks in a rented studio apartment in Tahiti. Our view across the shimmering swimming pool is of the surrounding hills and the Pacific Ocean, and just around the corner, we can watch the sunset over the island of Moorea. We have been traveling full time for five months now with plans to do so for about two years (it has consistently lengthened from our original six months and keeps extending), and a lot of our activity is what most people do once in their lifetimes on their honeymoon or other bucket list trip. That fact isn’t lost on us and we often reflect that this whole idea was our best decision, but we also realize it is made possible by our actions and decisions years ago.

Our situation made us feel there had to be a better way to live, but we weren’t exactly sure what it looked like, how to get there, or how we would feel after we made the adjustments. As soon as we learned of people doing things we hadn’t even considered, we were enamored with the possibilities that existed and dedicated to making our life however we wanted it to be. Through months of discussions, we decided this period of nonstop travel was the first step in our post-military lives, and it has proven to be all we imagined and more. (It is hard to imagine going from three months in South America to three and a half months island-hopping in the South Pacific when you’ve had no more than two weeks at a time off work for years. That’s what we did last week, and it was even more amazing than you think!) What does financial freedom look like? Not everyone’s freedom looks like ours. The freedom we all long for is unique, whether it be from crushing medical debt, juggling bills, fear of not being able to pay your rent or mortgage, deciding between medicine or food, the ability to leave that job you hate, or just longing to not worry financially about unexpected life events and the chance to live more of the life you dream about. Right now, our freedom is traveling around the world. We haven’t decided what is next, but we know that whatever we choose we have the ability to make happen because of our decision to pursue Financial Independence. It’s the most valuable purchase we have ever made.

So that’s our story. Now, how exactly did we manage it? Stay tuned to find out!

Using Miles and Points for Travel Savings (aka Travel Hacking)

  • Travel Is Free – Drew and Carrie have been traveling the world since 2011 on $25,000/year while staying in 4- and 5-star hotels.
  • Mile Value – Scott travels for nine months out of the year using points and geographic arbitrage to stretch his money.
  • The Points Guy – Brian is quite the businessman and has built his blog into a thriving lifestyle brand.
  • Million Mile Secrets – Daraius and Emily both worked for Fortune 500 companies and now use their skills to travel for free.

Financial Independence

  • Mr. Money Mustache – Our personal favorite, MMM is a hilarious software engineer/carpenter who “retired” in 2005 while in his early 30s.
  • JL Collins – Jim has been following his simple path to wealth for decades, and the link is to one of my favorite articles, “Why You Need F-You Money.”
  • Go Curry Cracker – A financially independent family of three, with plans to have a second child.
  • Afford Anything – Paula took time off to travel for months like us, and then built seven rental units that financially support her in addition to her online businesses.
  • Mad FIentist – This was our introduction to Financial Independence; he recently gave his two weeks notice and was instead offered a raise to work the same job remotely.

© Cheers Life Partners 2017

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The Cheers Life

We make every day worthy of a toast! We quit our jobs in October 2016 to travel the world full time.


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