Sri Lanken Rupees next to coconuts

The Making of a Money Mindset (Part 1): Learning the Value of Money

I’m often asked how I’m able to travel the way I do. Despite many attempts at an answer and even a few blog posts (none which ever made it to being published), a satisfying answer has eluded me. It’s a question that, in all its many forms, I’ve been gnawing on everyday since I left on that otherwise regular spring day over 16 months ago. Why don’t more people do this? Why didn’t I start sooner? What was it really that sparked me off on this journey? What was it really that’s allowed me to do this? To keep doing this?

Of course, what anyone asking the question usually wants to know is how they might be able to travel too. And that’s what makes answering it so hard: it’s a devilishly personal question. Even just trying to answer the financial, quantifiable part of the question quickly branches off in all sorts of odd directions and one quickly risks finding himself caught out on a shaky limb. The most obvious one being would you even want to travel like me? The truth is few probably would. How and where I travel is guided by my values, my reasons for traveling, my comfort zone and circumstance—which all remain, like travel itself, in flux.

Although the financial aspect of the question is as good as any place to start, it’s really only the toe of the elephant. What are you willing to give up? I had the money to travel for years before I actually did—that wasn’t what was really stopping me although I often fooled myself into thinking it was. Before I traveled I had to let go of furniture, relationships, a business, identities, not to mention my need for control and certainty.

And that brings up another question: what are you willing to do for travel? There are many—probably infinite—ways to travel if you truly want to. There are plenty of ways to subsidize your travels (housesitting, exchange programs like WWOOF, volunteer programs, simple living, etc) and even more ways to sponsor them altogether (savings, teaching English, bartending stints, running an online business, freelancing, etc.). I know people who have traveled on $100/month and people who’ve traveled on $300,000/year. How you travel, as well as if you travel at all, depends more on the lifestyle you are willing to live and the lifestyle you are willing to leave.

Putting the what questions aside for a moment there’s also a question of when should my answer start? I can plainly see now that things I began doing years earlier significantly influenced my decision as well as my ability to travel: managing a business, zen, stoic philosophy, regaining my health, walking away from my business, just to name a few. And although there was indeed a lightning-strike moment where I decided, then and there, that I would travel the world and take those first, heart-pounding steps off the jet bridge and into the unknown, even that had really been the culmination of years, if not a lifetime, of experiences leading up to it.

And there’s at least one more question to answer which is why? Why bother trying to answer the question at all?

The answer for me, the reason it’s worth the countless dead ends and boobytraps involved in hazarding my own answer, has very little to do with travel at all. It’s because how I’ve answered the question of travel is also, in part, my answer to a much larger, more significant and universal question we all face:

How do we create more freedom in our lives?

Because it’s only when we’ve begun to answer this question, that we can begin our real life’s work of answering the question that lies beyond it:

What will you do with it?

Looking out over the Himalayas in Nepal.
The Himalayas in Nepal.

And while I don’t think the answers to these lofty questions begin with money, I’ve realized it is where the story of my answer begins. And strangely enough, that story began with an answer.

I had responded to some questions from a close friend who had emailed me after reading my blog. In response to that (stick with me here) he sent this:

While I’m not sure if you share the same money mindset beliefs as I (I don’t think it matters) it’s clear that your focus towards it has allowed you to create a lot at one point, save and use it in your best way. That all being said I would like to hear more about how you do this.

What follows is the story of where that answer begins.


I was 6 when I was initiated into the world of money and its power. It was the early days of Nintendo. Gaming consoles were just beginning to leave the arcades en masse and infiltrate the inner sanctum of the family living room. More than anything else in my six-year old world, I wanted a Nintendo. Beg as I might, my parents refused to entertain the idea of having one in the house. My only way to play Super Mario remained to hope that my neighbor was home and in the mood to play. Simultaneous two player games had yet to arrive on the scene so even when the stars aligned I still had to wait—excruciatingly so—for my turn at virtual glory.

At the time my parents were giving me a small weekly allowance—a few dollars a week—to start teaching me about money. For the first time I can remember doing so in my life, I began to save it. When I had saved up $1081 my parents drove me down to the local Toys ‘R Us store. I handed over my entire life’s savings and walked out of the store with a Super Nintendo under my arms. It had been a revelation.

Entrance of Kharigandentenphelling Monastery in Thamo, Nepal.
Above the entrance to Kharigandentenphelling Monastery in Thamo, Nepal.

From my seven-year-old perspective Mom and Dad were the Gods of the Universe—everything went through them. Hadn’t they openly resisted the idea of me having a Nintendo? Yet with money I had been able to buy it for myself. Money had given me the ability to do something I hadn’t been able to do. It opened a door that would have otherwise remained closed to me.

I wasn’t much older when I invested in my first company. Dad would act as my broker and “sell” me shares of Disney’s stock which I bought with my savings. Every week or so we’d check the price of the stock together. Over time the value of the stock appreciated and I sold my shares back to Dad for more money than I had paid for them a month earlier. I didn’t have a clue how the stock market worked2 but money I invested in it had grown all on its own. Money had magical powers.

At first I mainly used these powers to acquire more video games. Besides Christmas and birthdays, saving my money was the most reliable way to get hold of new games. But my appetite had grown insatiable. By saving my allowance I could usually score a new game every couple months but there were countless video games I was dying to play and ever better ones hit the shelves each week.


I pestered my parents for jobs around the house cleaning bathrooms, floors and windows. I picked up odd jobs around the neighborhood too, tutoring a younger student, weeding the neighbor’s yards and feeding the McFessel’s dogs on weekends (a particularly lucrative gig if I could swing it). I foraged under the pillows of the living room couch for coins and held garage sales, trading my old books, toys and eventually, even my Super Nintendo for cold cash. I didn’t just have to wait for my allowance to arrive. I could make money come in. Money had begun to motivate me.

Not much later I started my first business. I raided my parents’ garage for cleaning supplies and convinced a few friends to help me wash cars. I led my gang around the neighborhood, soliciting car washes door-to-door for $4 a pop not including the roof which none of us could yet reach. Soon we had our regulars. But managing morale among my new workforce had been harder than expected—it turned out some of my friends didn’t want to spend Saturday afternoons working. I couldn’t understand it. I didn’t particularly enjoy the work either; I loved my free time as much as the next kid. But cash could buy us the things we were all waiting until Christmas for…NOW.

The reason to work had always seemed obvious. A typical video game cost anywhere from $30 – $60 or 5 – 20 hours of work depending on the job. A single video game had the potential to secure weeks or even months of childhood bliss. Giving up some of our free time now could disproportionately increase the quality of our free time later. It was a good investment. Life as a kid was simple.

By high school I was no longer a novice in the art of the hustle. I umpired baseball games for my former little league in the evenings and on weekends. I bid off my mom’s sandwiches in the school cafeteria. I even found a way to merge my love for video games with money by gambling illegally online (I was underage). I turned $5 a friend loaned me on a poker site into a couple thousand. Real paychecks in my name—my first ever—began arriving in the mail. Now my time hunched over a computer screen screaming could also be profitable. I started playing more online poker and less video games. This was paying off in another way too. I was running poker games in my parent’s garage on the weekends.

My interest in video games also began to wane as my social life grew; other things like music, shoes, a state of the art hand held camcorder (it was the era of the TV show Jackass) began to compete for my dollars. But despite my continued interest in the things money could buy, I never considered getting a “real job.” I might have made more money if I had but selling my free time had never appealed to me. Figuring out ways to make money had always been voluntary. I usually found it a satisfying way in itself to pass the time, if for no other reason than because it brought me closer to my goals. A dollar earned on my own terms was worth more to me than a dollar earned on someone else’s.


As a high school graduation gift my grandparents opened up a brokerage account in my name and gifted me a large amount of stock. When I left home for college in San Diego my parents provided me with a monthly allowance, which as long as I was careful, was more than enough to cover my living expenses. All of a sudden I had more money than I knew how to spend. I didn’t know what to do with it. Instincts kicked in and I began squirreling it away.

Grandpa and I
My late Grandpa Al and I. I have fond memories sitting around the living room table in his house playing poker. Probably in part because he usually let me win.

During my freshman year it dawned on me what a huge gift my parents and grandparents had given me. I lived with a close friend who had to take a part time job to cover much of his living expenses. Student jobs weren’t easy to come by as a freshman and he ended up taking a graveyard shift at a bookstore off campus stocking merchandise. Although we were good friends he often didn’t have the time to hang out. It made me sad to see him miss out on so many memorable moments my friends and I were having. Over time we saw less and less of him.

I watched other friends blow away substantial savings and inheritances on food and partying. Inevitably the well would one day run dry. Not only would they no longer be able to afford their excessive lifestyle, but they would miss out on amazing experiences that unexpectedly came up because they didn’t have the money. I never understood their shortsightedness. I had played enough poker by then to know that money gave you a seat at the table.

Everest basecamp.
Everest basecamp. It costs about $30,000 for a seat at this table which affords a climber one shot at the top. (The mountain over the pass in the left corner is Tibet. Mountaineers head up the glacier that climbs behind the tents into the top right of the picture which leads Camp 1).

In my third year at college I discovered a program that offered students the chance to spend a summer studying at Oxford University in England. I hadn’t considered studying abroad before but the idea instantly took hold in my heart. Few things had sparked such enthusiasm in me before. Suddenly it became as clear as Nintendo. I knew what I wanted to do. I sold my shares of stock and pooled my life’s savings together to reserve a spot in the program.

That summer was extraordinary. My world expanded and I with it. It was packed full of the type of wild and raw experiences money can never buy. But money had made it all possible. And the way I had managed money…that had made it a reality—a reality that a few short months earlier I had never imagined possible, let alone realizable. But I hadn’t had to imagine it. It had been enough just to be ready for it.

After completing the course at Oxford I traveled with my girlfriend through Europe for over a month. Along the way I ran out of money and my mom loaned me a large lump sum to keep me going. I returned to San Diego at the end of that summer with my heart full and my wallet empty. It was worth it.

Greased Lightning, my ’96 Ford Taurus station wagon which a family friend had donated to me the previous year, welcomed me back with a freshly cracked transmission. I took a second loan out, this time with my Dad, to have the transmission replaced. I was a year away from graduation and for the first time in my life, I was in debt.

It looked like I was going to need a job.

Read Part 2: Early Experiences in the “Real World”.

*Featured photo is of Sri Lankan rupees and coconuts.

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  1. The Nintendo was only $100 but the sales tax was $8 which I remember feeling was outrageous and grossly unfair.
  2. I still don’t.

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Hello. I’m Alasdair.

Hello. I’m Alasdair.

I believe that being aware of who I am and mindful of who I am becoming is the best investment I can make in my life —and that when we focus our efforts within, the rewards naturally flow outward to those we love and through the communities we belong to.