Part One (Labors 1-3)

Part Two (Labors 4-6)

“If you have built castles in the air, your work need not be lost; that is where they should be. Now put the foundations under them.”

–Henry David Thoreau, Walden

7. Charting the Sea of Frugality

A long life doesn’t promise an interesting one.

Similarly, total time spent on the road does not equate to a journey rich with experience.

We travelers often forget this simple truth.

I once knew a country bumpkin whose dream was to see the world. 

This dream served as his North Star for two long years. During that time, he threw himself headfirst into any profession that paid: waiter, mover, construction laborer, salesman, freelancer, plasma donor. None of these hustles sparked his interest, but that didn’t matter. The world awaited. When his vagabonding departure date drew near, he made one final rally to collect some coin and sold his possessions.

It’s important to note that slogging through monotonous jobs wasn’t his sole sacrifice. Throughout those two years, he decided to forego experiences–almost all of the ones requiring money–in exchange for future experiences on the road. Or rather, the “promise” of future experiences on the road. Nothing was guaranteed.

We were sharing a room in Florence, Italy, one of his first stops abroad. And for the three days we were there, I witnessed a glorious spectacle of idleness that would make even a sloth raise a brow.

He rarely went out. 

When he did, it was only to buy the staple groceries everyone could find at their neighborhood’s corner store, or perhaps, if he was feeling ritzy, a morning coffee and pastry.

One evening, his friend asked if he’d like to join a night of dinner and drinks. “Economizing” was his excuse for staying-in. 

This lad was social, brimming with vitality, and yet snared by a scarcity mindset that restrained him from experiencing the dream he had worked so hard to create.

What good is the money you save if finally, when the adventure starts, all you do is lurk in dark hostel hallways eating stale crackers and off-brand ramen like some deranged traveling zombie simply because you are too tight-fisted to shell out for new experiences?

It doesn’t make sense.

Not until you realize this traveler lived in a world where there was no extra money coming in, the savings from his seasonal gig were dwindling, and there wasn’t a promise of a job (money!) at the end of his ride. 

Amidst the perilous tides of the Sea of Frugality, this is the boat many dirtbags find a seat in. 

Dismissing interesting opportunities in the present in order to extend the journey into the uncertain future is a mistake only a low-level vagabonding grunt could make. 

And one I’ve made several times.

The country bumpkin was me.

My redemption came in the form of a writing workshop in Paris taught by Rolf Potts: author of Vagabonding (the modern Bible of long-term travel), a level 95+ rogue, and one of the biggest inspirations for my current lifestyle.

All together, it was going to be a $2,000 week, which is a hard number to swallow when you know the same amount could afford you 3-4 months in many other countries.

To navigate these waters, I devised the following two questions:

1. Will this investment provide me with skills, knowledge, or health benefits that will enhance my day-to-day life for the foreseeable future?

2. AND, is it a unique experience–one I can’t replicate for cheaper?

If the answer is yes to both of these questions, the experience is likely worth the investment.

For example, the workshop was going to be an intimate and accelerated masterclass in storytelling (one of the most practical and underdeveloped skills). The class was capped at 12 attendees. All of which were older than me, and most had legit writing backgrounds. There would be round table discussions on how to improve each other's essays and stories. Direct feedback from this caliber of group would’ve been extremely hard to replicate. Being surrounded by high-level vagabonds also meant I could expect an upgrade in my traveler’s eye (which is essentially the third eye, providing sight into patterns and themes that most travelers miss). 

The week in Paris may have “cost” me 3-4 months elsewhere, but by sharpening my storytelling skills and traveler’s eye, that investment enriched my time everywhere since.

Additional example: paying to maintain health. 

As discussed in Labor 6, this is an area most rogues cut costs on as soon as we get out of dodge. The problem is if you don’t feel good, it will be harder to immerse yourself totally into the journey. 

If you have a sore throat, you won’t be thinking about how amazing the souks of Cairo are, you’ll be thinking about how miserable your throat feels.

Paying for vitamins, gym passes, clean food, and an occasional private room to catch up on sleep, may extend your journey while increasing the quality of your day-to-day life.

Reversal: There is a deranged beauty in choosing to prolong your voyage in the Sea of Frugality.

One that's charm is lost on those who’ve yet to embark on this particular path. Things mean more when you have less. And having less often forces creativity, which can lead to interesting experiences. Experiences that can’t be purchased. 

You might be forced to ask a farmer if he has an extra bed because the ones in town don’t fit your budget. After a cautionary up-down look, he waves you to follow him through a field and into an old barn. You make yourself comfortable on a stack of hay. There’s a knock on the door and the farmer comes back in. This time, with a steaming bowl of goulash and a loaf of soft white bread. The sheep look blankly up at you while you happily munch on the unexpected dinner. In the morning, if your luck continues, he will invite you in to meet his wife. She will share the tales of the land while you soak in a pot of black coffee and a few tumblers of rakija. After restocking your supply of apples and sausage, they send you back into the sea. 

A sea full of possibility and adventure. 

There’s a lesson in all of that, but one you’ll never learn sleeping at the Hilton.

8. Solving the Riddle of Questions

“Judge a man by his questions rather than his answers.”

- Voltaire

If you find yourself at that table with the farmer and his wife, who are both full of folklore and knowledge, and you don’t know the right question to unlock those stories (or worse, sit there and only share your stories), you have effectively learned just as much as the Hilton traveler who is presently trying to order a decaf, pistachio cream latte and gluten-free pancakes from room service instead of walking a block to the bakery with a line of locals outside.

Until you know how to ask the right questions, you will continue to leave value on the table. The “right” questions are questions that lead to insightful, and ideally empathetic conversations.

Here are some personal favorites (notice who the focus is on): 

1. What did your parents do here?

   • Opens the door to their familial background, how the ended up there, how they were raised, what type of business they were in (which will likely teach you about the local economy)

2. Tell me about your childhood. How has this place changed since then?

   • Most biography questions will open multiple portals to explore their past through. When someone shares a shocking story, don’t respond with “wow”, ask, “what was that like?” or “what changed after that?”. This keeps the portal open and allows you to jump deeper. 

3. Where do you eat? 

   • Not, “where do you recommend I eat”. Two different questions. One focuses on them, the other on you. Bourdain taught drilled that one in.

4. What do you love about your country/city?

   • This will lead to what they don’t love about their country. Ask this question enough to different groups in a country/city, and you’ll start to develop a mental map of the social fabric.

5. What’s a goon to a goblin? 

   • If you find an answer, let me know.

The magic key after you ask the questions: shut up. 

This is the hard part.

Let’s use a hostel lounge room as our setting. 

Level One:

In the first hostels I stayed at, contributing in a meaningful way to group discussions was an impossible task. There were other guys (who we will refer to as Joe) who had been traveling for more than a month–a novel idea back then–and had seen places I’d never heard of. 

How could I, a meer vacationer, have anything remotely sophisticated to add to the conversation? 

So I didn’t say much.

And when I could muster the courage, a boorish excuse of a question tripped out of my mouth along the lines of: “How long have you been traveling, Joe?”

Or, “How many countries have you visited?”

These hierarchical-discovery questions travelers ask each other are equivalent to “where do you work?” and “what car do you drive?”

In other words, these questions are reserved as the final refuge for minds completely void of imagination. 

You might as well go on and probe Joe for his thoughts on today’s weather. 

Level Two:

As my repertoire of experiences grew, so did my contributions to the conversation. I felt more comfortable interjecting and offering an opinion or question:

“You’ve visited 100 countries? How did you pay for that Joe?”

Rather than responding to Joe’s incredible tales with simple “cool man” or “wow,” I’d ask a related follow-up question. This kept the conversations flowing and opened the door to new insights.

Level Three:

After several months of amassing my own set of misadventures, I slowly assumed the role of the hostel lounge storyteller (this is definitely a head of the Hydra, and can be dangerous if not checked).

Joe was still around, and there will always be a Joe around who is more traveled than me, but as Matthew McConaughey said in his book Green Lights, I’d become “less impressed and more involved”. 

The shift was reflected in my questions:

“Out of the 100 countries you’ve been to, which city would you return to tomorrow? Why?”

Because this is a focused question, it will be easier to answer and expand on. There might be a slight pause while Joe thinks, but that’s a good sign. Anything is better than the blunt and overused, “what is your favorite country?” (the snooze button of travel queries).

Level Three comes with a catch: although my storytelling and question-posing skills improved, my ability to listen tanked. The frequency of my questions dwindled, and when I did ask one, Joe's response often slipped past me.

My mind was digging through its chest of tales, trying to find a comparable experience even before Joe had finished sharing his.

The egocentric mindset of thinking “I” have the most to contribute to the group is inexhaustibly obnoxious, and also extremely detrimental on the road because it depletes curiosity. 

And traveling without curiosity is like eating strawberry yogurt if the yogurt was gravel and the strawberries were razor blades.

Level Four:

Can Level Three get worse? Unfortunately.

The over-traveled narcissistic spiral of doom ends in a closed mindset, which is the antithesis to every true traveler’s ethos. 

This realization shook me awake and returned me to a natural state of curiosity.

“Hey Joe, you’ve traveled so much. What keeps you going?”

This was my question to a Joe who’d been around the world several times on a five year solo-stint.

He’s the only traveler to date who’s made it look like I was overpacking.

The group around him were offering the usual “wows!” and asking how he financed everything, so when I asked my question, it caught him by surprise. His answer:

“I still haven’t found what I’m looking for”.

That was all he said. And that’s all he needed to say for me to recognize he was opening a portal directly into his center. 

It would have been fascinating to pursue. It’s an extremely small percentage of the world that could travel like Joe if they wanted to. And an even smaller percentage of that group who actually go and travel like Joe.

He’s an absurd rarity. 

Like with the farmer and his wife, you’d be remiss not to ask the questions that would unlock the treasure chest of knowledge before you.

Unfortunately, when multiple people are present, the deeper and far more interesting portals shut quickly. His profound yearning remained unnoticed by the rest of the group; they couldn’t recognize the scars borne by a soul that had experienced more of life than many ever do.

And so, Joe resumed his stories–the same stories he told countless times to countless faces of the forever awestruck and eternally blind. 

***

The keys to asking a good question:

• Aim for intimate or small group settings

• Focus on the other

• Shut up and listen

Note: None of this will work without genuine curiosity. Be like Sherlock Holmes.

9. Navigating the Virtual Labyrinth

Some people travel to show others they travel. 

Some people travel purely for their own curiosity and passion.

The rest of us fall in between. 

It’s natural that when you do something cool, you want to tell people about it. 

However, pre-Internet, there was a loading time between that cool action and the subsequent storytelling. 

For example, while following the Hippie Trail back in the ‘60s, you might have sent a couple letters back home. Those were the previews of the stories to come, the teasers. You would eventually come home, likely donning a new set of eclectic clothes and long hair, and then you’d share your stories.

The difference today is that you can share stories in the same moment you create them. 

And as you tell stories, you get feedback (likes, comments, followers). When you get feedback, you start to learn what people like. When you learn what people like, you start pandering to people’s expectations. When you pander to expectations, you risk sidelining your own curiosity and passion, to eventually find yourself in Paris at a cafe, full of everyone but Parisians, snapping dozens of pictures of a croissant in portrait mode with the Eiffel Tower in the background, just like the people at the neighboring tables.

“In the City of Love! #thisisparis”

This is not Paris, you are not interested in the cafe, and you probably won’t even eat the rest of that 12 € croissant because all you really came for was the perceived notoriety and status that attracted by that image.

Between an overload of feedback and the unchecked comparisons social media presents, we end up lost in the Virtual Labyrinth.

Ibn Battuta, a famous explorer and writer whose journey spanned across 75,000 miles in the 1300s, wrote:

"Traveling – it leaves you speechless, then turns you into a storyteller." 

When we are speechless, we are listening. When we are listening, we are learning (or at least trying to).

This is the critical period for growth.

When we transition to storytelling prematurely, we skip the listening stage and thereby stump any prospect of development.

It’s like sharing stories from an adventure tour. 

First off, the words “adventure” and “tour” don’t belong in the same sentence unless the sentence is, “We bailed from the tour as soon as it started because we wanted a real adventure”. 

There is nothing adventurous about an organized safari tour that costs more than what you’d need to circle the globe.

The question is, can you have a real story without a real adventure? 

No. Inauthenticity holds no value. At least not to knowing eyes.

Yet, it’s easier to book a tour. And to everyone who wasn’t there, the tour appears to be authentic. Even adventurous. Of course, the pictures don’t show the cage we were sitting behind. Nor the gunman hanging outside of the cage hired to protect us. They only show the lion under the tree, the hippos in the water, and the cheetah stalking gazelle. But this is enough to secure validation and praise from others, which will motivate us to continue projecting false stories until we slowly forget why we sought out real adventure in the first place.

Once again, lost and confused in the Labyrinth like everyone else.

This labor doesn’t have a specific example simply because there were numerous occasions when I slipped into storytelling mode before the story was over. Every time, I thought my knowledge of the downsides would immunize me to them. 

Every time, I was wrong.

Theseus, the young Athenian hero who was the first to navigate the labyrinth, didn’t complete the mission without help. He was gifted a ball of thread which he unraveled as he entered the maze, and after slaying the Minotaur caged in the center, he simply followed the thread back to the entrance. 

(Why no one thought of this solution before Theseus beats me)

Now, fast-forward into the present day, and embrace the Ball of Thread I am offering you. 

It will help you remember that original path of your curiosity and passion, and assist you in your battle against the Minotaur of conformist thinking hidden in the Virtual Labyrinth of groupthink.

For it holds the power to rediscover the path of your initial curiosity and passion.

It will guide you through the Virtual Labyrinth of conformist thinking, and aid you in your battle against the Minotaur (portrait mode, croissant influencer).

The Ball of Thread:

1. Post only non-current content (feed lags by a week or even a month behind reality)

2. Turn off comments and likes (limit the influence of unthoughtful feedback)

3. Don’t travel with a SIM card (less phone time overall)

I also like applying the full power of Labor 8 here, by asking a lethal question: 

“If I couldn’t tell anyone else about this, would I still do it?”

Remember, the most interesting people are rarely the ones telling others how interesting they are. 

As Walt Withman, one of the most influential American poets, wrote:

“I swear I see what is better than to tell the best—it is always to leave the best untold.” 

The highest-level vagabonds I've met can't be found on social media. They're indifferent to inflating their perceived social worth. They are the purists, untouched and unswayed by the world's applause.

They optimized for personal growth, rather than account growth.

That’s why they are the most revered and inspiring.

Which is true beyond the small realm of long-term travelers. 

We never draw inspiration by the myriad of blurred voices lost within the labyrinth. It is always the resolute few, who carve superior paths with swords of curiosity and passion, that reawaken our dormant dreams of a better life.

***

“All men dream, but not equally. Those who dream by night in the dusty recesses of their minds, wake in the day to find that it was vanity: but the dreamers of the day are dangerous men, for they may act on their dreams with open eyes, to make them possible.”

- T. E. Lawrence

To be Concluded…