We shall not cease from exploration
And the end of all our exploring
Will be to arrive where we started
And know the place for the first time.
— T.S. Eliot, Little Gidding

The entire study of of Machine Learning could be described as trying to find the tallest peak in a vast mountain range, but without the benefit of an existing map, and without the sense of sight. Let’s say you were dropped off by a helicopter in the middle of the mountains, and are tasked with finding that highest peak.

What would you do?

Maybe you’d start walking a random direction. Maybe you’d eventually stop when you get tired, and say “this is good enough” and call it a day. That strategy is called a “Random Walk”.

Or maybe, instead of walking randomly, you’d try to find what feels like “uphill” from wherever you are, and only head in that direction. That’d be called “Hill Climbing”.

There’s lots more alternative strategies, some which are geared towards parallel computing, and some which are geared towards quantum computing. But they all suffer from the same shortfall.

How do you know when you’ve found the highest peak?

You may have kept heading uphill until there was no more uphill, but is that really the “global maximum” of the mountain range?

Or, more likely, is it just one of many “local maxima”, like how K2 is the second-highest mountain on Earth. Imagine climbing K2, without the sense of sight, and getting to the top, and declaring “This is the top of the World!” only to be told later that sorry, you were only at the second-top.

When we’re super success-oriented, we often worry about this possibility. We look at our choices in our DAG and we worry — what if I end up on K2, instead of Everest?

This is why so many religions and worldviews and modern psychology and pretty much everything except Western Culture tries to instill in us that “it’s about the journey, not the destination”. Because in Life, we’re all climbing hills and exploring possibilities without any map, and without any way to know we’ll find the top.

There’s one last algorithm which I’ve always found poetic. It’s called Simulated Annealing. The term is borrowed from the Japanese art of crafting katanas, where they heat and cool the sword over and over until they end up with something extremely strong — nearly unbreakable.

Imagine that you are dropped off in the mountains, and start climbing uphill, but this time, the helicopter comes and picks you up after a few days, and drops you off again at a different part of the mountain range. As you learn more, and explore more, you can sometimes return to some places and pick up where you left off. Or you can sometimes choose new places to explore, just to see what’s around that riverbend.

The reality of Life is that you can never be sure you've found the “global maximum”. Every “best life” you create and build and sweat and suffer for, may just be one of many “local maxima”. You may realize one day that you’ve “only” reached K2.

But so what?

If it’s mathematically impossible to know when we’ve reach the highest peak, why bother? Why make that an ultimate goal? Why not instead look for a way to live Life where we find the places and the people and the things that make us happy — but then shake things up every once in a while to try something new? Not to diminish those we love, but to get the most satisfaction out of Life?

We’ve all got our own mountain ranges to explore. Each ridge, and peak, and valley has something unique and interesting to experience. Who cares about perfection when the whole point is to enjoy the hike?

"Hay Más Tiempo Que Vida"
— Mexican proverb

I've been thinking a lot about Timing lately.

I've heard multiple people (a couple generations older than me) talking about looking back on their lives and realizing that — even though they did the right things, their Timing was off, so they missed the opportunities that they were hoping for. It’s not that their actions and outcomes weren’t enjoyable — it’s that they knew that they could be more, and they just… weren’t.

I’m a beginner surfer. I’ve never stood up on a board, but according to my gracious surf instructor, I still surfed 😁 And it was wicked fun. In surfing, it’s all about Timing.

First off, you’ve got to be in the right place, at the right time. You’ve got to have favorable winds, and have timed the off-shore swells just right. The swells come from hundreds of miles — multiple weeks — out in the ocean; they’re meteorologically predictable. But the winds can vary from day-to-day, and can change the surf forecast on an hour-by-hour basis.

Yeah, not complicated, right?

So let’s just say you’re in the right place, at the right time. You’ve figured out the surf forecast, you’ve paddled out there, you’ve sat and watched the timing of the sets, and you’re ready to catch one.

Well, the hardest part is choosing your wave.

Choosing is a form of gambling. It’s trying to predict not just a “winner”, but something you personally can “win”. It means paddling out into the center, choosing the correct timing, and paddling like hell. It means bracing yourself as the sheer force of the wave starts to overtake you. It means keeping your balance in multiple dimensions or risking a wipeout.

So in one sense, it's better to take your time and catch the right wave than it is to rush and catch the wrong wave. But then again, you can’t just let all the waves go by you, or else you’ll definitely never catch one.

And in another sense, you've got to be ready to paddle your damnedest to catch that wave at the right time if you're sure it's the one you want to ride, or else you’ll have let a perfect wave pass you by.

Damn, no pressure, right?

Well, no, not really. Because we all have, like, infinite-many waves to catch!

There are these defining moments in life — these hair-split moments in time — where everything seems to be riding on what we say or do next. We feel, deep in our guts, that our lives are going to split, all based on our next decision.

That’s the time when we need to paddle like hell.

And yeah, OK, sure, fine, we won’t always make it. We’ll mess up. We’ll miss-time things. We’ll not paddle fast enough. We’ll lose our balance.

But did you know that in a typical two-hour surfing session, catching “a couple” waves is considered normal? I’ve asked so many experienced surfers, “how’d it go out there today?” and the’ve all been ecstatic — not to have done things perfectly — but to have just gone out and enjoyed their experience.

The phrase “Hay más tiempo que vida” literally means "there's more time than life", but culturally means both “Chill out, there's time" but also, "The defining moments in life might catch us off guard, and opportunities might pass us by, so don't delay decisions." (source)

What's the solution to correct timing? Well, I can’t answer that for you. I can only answer that for me. And for me, it's a matter of following my intuition, and taking actions towards those things in my life which are bringing me the most joy at the moment — which seem most “light”. I'd rather pursue my dreams now, at whatever scale I can, than defer them to some hypothetical, theoretical, idealistic future.

"Unfortunately there can be no doubt that man is, on the whole, less good than he imagines himself or wants to be. Everyone carries a shadow, and the less it is embodied in the individual’s conscious life, the blacker and denser it is."
— Carl Jung

As much of life is an Upward Spiral, it's sometimes frustrating to find myself in such similar circumstances. Like — haven’t I learned this lesson by now?

Well, no, I guess not.

But still!

I guess, if I were to frame things in a more optimistic light, that frustration can become “interesting” — an opportunity to re-experience my past through a new frame of reference.

But still!

Frustrating because I obviously haven't let-go-of and moved-on-from a number of things which I would have preferred to have. Or at least would have preferred to have believed that I have.

Oh well.

These frustrating aspects are what Carl Jung called the Shadow Self. They’re the parts of ourselves which we avoid, deflect, project, and deny. They’re the parts of ourselves that we don’t want to face. The archetypes which are definitely a part of who we are, but not the “best” parts of who we are.

The problem with avoidance, deflection, projection, and denial is: “that which we resist persists”. It’s another one of Jung’s phrases which is a description of Magick, Law of Attraction, Buddhism, and a million other ways of describing the fact that it doesn’t matter our intention, any energy we give to something makes it stronger.

All of these theories (including modern psychology) agree on the same remedy:

Just accept it.

Imagine you are in third grade, in a schoolyard fight, where you have been called out by the school bully. You meet in the playground at 2:50pm, and all your classmates have formed a circle and are chanting “fight, fight, fight!”

The way we’ve been raised (philosophically termed “Western Thought”) is that this kid across from us is “Other”, and to keep our concept of “self”, we must oppose it, aggress it, defeat it. Only once we have emerged victorious can we have any sense of safety.

As adults, we can see how silly this is. They’re just kids! They don’t know any better! They don’t know the context behind why the bully is mean. They don’t know how insignificant this particular conflict is in the grand scheme of Life. They don’t know that we shouldn’t try to fight with each other, but try to find Common Ground.

OK, well, fast-forward to the present. And instead of third-grade you, you’re you-you. And instead of a bully, you’re facing your feelings of insecurity, addiction, loneliness, and mortality. Jung is like that school teacher interrupting the fight and telling you to be friends.

We don’t necessarily know why we have our own personal bullies — our Shadow Selves. It’s much easier to hate those parts of ourselves than it is to accept them. But only by letting down our guard, and being willing to make friends with the parts of ourselves that we’re not proud of, can we ever really progress as humans.

Easier said than done, though, right? How do we do that?

Well, therapy is a good starting point. No, seriously. Forget the stigmas, forget the Victim Mentality. Find a therapist who is willing to dig into some of those thoughts and emotions that we all have and really explore them. Because just like in that “Dark Thoughts” podcast, we only by discovering, understanding, and accepting the worst and scariest parts of ourselves can we ever change.

Accept first, change later.

But trying to change without accepting? That just makes it stronger.

"You only are free when you realize you belong no place — you belong every place — no place at all. The price is high, the reward is great. More and more, I belong to myself. I’m very proud of that."

-- Maya Angelou

As I was doing my taxes today, this beautiful assassin bug kept wandering around the picnic table where I was working.

I'm no entomologist, but I can hazard a guess as to what its goal was: find bugs to suck, and find bugs to fuck. #sorrynotsorry

But as it explored every surface and every edge of the tabletop, it found everything except what it was looking for. Because it was looking in the exact wrong places. Because it wasn't willing (or able) to break from its current paradigm and look somewhere new.

Damn, little bug, I feel you.

The ego-narratives I tell myself; my avoidance of things which challenge my worldview; hell, even my own antisociality —

These all trap me in my own picnic-table flatland, where I wander around feeling like I'm exploring, but where in reality, I'm a prisoner of my own self, and of my own selfishness.

I'm beginning to think that this may be why I've programmed myself to reflexively avoid comfort and familiarity: it's not necessarily an avoidance of routine; or a seeking-out of novelty; but rather a fear that, while I may feel like I'm making progress, in reality I'm actually quite trapped.

One of my core fears is that I'm a prisoner who feels that they are free. One of my primary motivations (and why I'm traveling) is to define my sense of Home. And I can't help but feel like the two are connected.

❤️ Conrad

“I saw my earlier selves as different people, acquaintances I had outgrown. I wondered how I could ever have been some of them."

-- Roger Zelazny, "The Chronicles of Amber"

We’ve all heard someone say “Version 2.0” to mean “New and Improved”. Sometimes it's about software; sometimes it's about a product “As Seen on TV”; but we've also heard it said about people, like “Jacki 2.0”.

In software, “version x.y.z” represents “[major].[minor].[patch]” (respectively). “Patches” are bug fixes or style changes almost indistinguishable to from the previous version. “Minor” versions include additional features or design improvements. But “Major” updates are reserved for breaking changes, incompatibilities, and redesigns -- things which are worth the effort to upgrade to, and from which you can not easily go back to the way things were before.

Which is why it's so interesting when we use the “2.0” to refer to versions of people. What does it mean to have “breaking changes” or “incompatibilities” with our previous selves?

What comes to mind for me are beliefs, relationships, careers, and locations. They're often transformations which might take place over months, years, or even decades. But at some point, we look back and realize just how different we've become from the people we were previously.

Just how incompatible.

Today, I “randomly” passed by the street dog in this photo, who is the spitting image of Clavo, the street dog I brought back from Perú eight years ago.

This past weekend, I “randomly” met up with a friend and video chatted with another, both of whom are from that same time in Perú eight years ago.

The other night, I "randomly" found a restaurant here in Guatemala which serves beers from the brewery nearest my apartment in NYC eight years ago, right before I went to Perú.

I mean, I know life's an upward spiral and all, but damn! That's a lot of significant re-memories packed into a single week!

It got me thinking:

What version am I on now?

In what ways am I a better version of myself?

In what ways am I the same? (or, dare I ask, worse?)

Which versions of myself have I outgrown?

Which versions can I hardly believe I ever was?

Which versions will I yet still become?

❤️ Conroy v18.9.3

Dreams are the seedlings of reality.

Awake, arise, and assert yourself, you dreamers of the world.

Your star is now in the ascendancy.

-- Napoleon Hill

This weekend, I achieved the top item on my bucket list: to see lava.

It was spectacular.

After a 7 hour hike to 13,000 feet, I was beyond exhausted. Yet when heard the rumblings of the volcano, and the guide yelling, "Come quickly!", my pain was replaced with excitement; my trudging replaced with jogging; and my complaining with joy.

Before I hiked Acatenango, I spoke with at least a dozen people who'd done it already. Each of them expressed some variation of this sentiment: "It was both the most-amazing and the most-difficult thing that I've ever done."

By the time that I rounded the corner and took this photo of my first-ever volcanic eruption, I knew exactly what they had all meant.

One of my favourite authors (and personal heroes), @markmanson, has a saying:

"What's your favourite flavour of Shit Sandwich? and does it come with an Olive?"

By that he means: everything in life has its trade-offs -- its pros and its cons. The secret is to find those things (and people) which are net-positives to you personally: which make you feel alive; which make you forget how exhausted you are; which make you so excited that you find a well of energy within yourself that you never knew existed.

Which you've had along; but which maybe you'd forgotten about.

❤️ Xuxo

I must not fear. Fear is the mind-killer. Fear is the little-death that brings total obliteration. I will face my fear. I will permit it to pass over me and through me. And when it has gone past I will turn the inner eye to see its path. Where the fear has gone there will be nothing. Only I will remain.

— Bene Gesserit Litany on Fear

Every night at midnight, they shut off the generators here to save diesel. So every night at midnight, I sit on my balcony as the entire resort goes dark. I feel the warm sea-breeze and I listen to the crashing waves. I look up at the stars and I marvel at how the moon casts moving shadows on the blueish-white sand in the shape of passing clouds and waving palm trees.

I also watch as the half-dozen security guards patrol the grounds below me, interrupting the otherwise-serene scenery with their artificial-yellow flashlights, squawking walkie-talkies, and crackling tasers. I think about the myriad of potentialities that those security guards are guarding against and let Fear run amok in my imagination. I peer into the darkest of dark patches where the moon doesn’t shine through at all and I remember that quote from J.R.R. Tolkien’s The Hobbit:

"We like the dark," said all the dwarves. "Dark for dark business! There are many hours before dawn.”

But then I catch myself, realizing that this broken record of anxious thought isn’t helpful. I instead think of the quote by comedic-philosopher Bill Hicks:

It’s just a choice, right now, between Fear and Love. The eyes of Fear want you to put bigger locks on your doors, buy guns, close yourself off. The eyes of Love instead see all of us as one.

Even though Bill shared this Truth almost thirty years ago (just a couple years before his death from pancreatic cancer at age 32 — a year younger than me) I’m sure that if he could amend his quote today, he would likely put something in there about hoarding toilet paper.

We do very strange things when we act out of Fear.

Saturday, I was offered a ride up to Cancún to go to Costco. My eyes got wide at the mere mention of that name. I didn’t know there were any Costco’s in Mexico. And of course, Costco is synonymous with stocking up in bulk, which, at the moment, has the tantalizing promise of giving me the illusion of control over the future — that stability and consistently that I crave.

I was very, very, very tempted to go. But in the end, I didn’t, and here’s why:

When I am trying to make a decision, instead of a two-column “Pros vs. Cons" list, I make a quadrant with "Fear vs. Love" on one axis and “Do the Thing” vs. “Don’t Do the Thing” on the other. In a normal “Pros vs. Cons” list, you are measuring the outcomes of a decision; by adding in “Fear vs. Love”, you are measuring your motivations for making that decision.

Here was my quadrant for the choice today:

I kept flip-flopping back-and-forth. And then it hit me: this was a War of Fears; there were no Love-based motivations for going. I was scared to go, and I was scared to stay. And in a War of Fears, there is no winning — you lose as soon as you remove Love from the equation.

Fear and Love are like Yin and Yang. They are non-dualistic. They seem like they are opposites, but just like black and white, you can’t have one without the other — they are two sides of the same coin. Each decision that I make out of either Love or Fear is a building block in my day, and each day is a building block in my life. If I consistently chose Fear over Love, my life would look a lot different than it does today.

It’s not that Fear doesn’t raise valid concerns. It’s just that I need to be aware of how much control I’m giving Fear in my life. Fear is a useful servant but a terrible master. So while I try to listen to what Fear has to say, I don’t let it decide for me.

Because moment after moment, “it’s just a choice, right now, between Fear and Love.”

❤️ Conroy

Que será, será
Whatever will be, will be
The future's not ours to see
Que será, será

— Doris Day in The Man Who Knew Too Much

I apologize for my last post. I'm not proud of it — it definitely didn't reflect my best self. And more than that, I spread negativity in an already-stressful time. I've deleted the post online but I can't take the email back out of your inbox. So I'm sorry; I hope you will forgive me.

Yesterday afternoon, I moved an hour south down to Tulum, Mexico. Being here, I can't help but feel like I am seriously one of the most fortunate people in the world right now. I'm in a beautiful place with supportive friends and still have my well-paying job. This is honestly one of the most amazing periods in my life.

It's also one of the most uncertain periods.

For example: I don't know how long I will be able to stay here or if I'll have to move again next week; I don't know how long I'll have my current client or if I'll have to look for work next week; I don't know how long there will still be flights out of the country or if they'll close the border next week; I don't know how long there will still be peace here or if I will get kidnapped next week; I don't know how long I'll still be healthy or if I'll get sick next week.

See the pattern?

Life is amazing today, but I can't scry even a week into the future. I mean, I get that sometimes there are forks in the road of life that are difficult to see past — that's sort of part of the fun of it. But to have so many foundational aspects of life be so completely upended so quickly for so many people on such a global scale — it's not only difficult to predict what's next, it's been driving me downright nutty just trying.

Last week, an elderly Greek gentleman opened a restaurant next door to where I was living. (Talk about timing, eh?) I asked him what he thought of “things”, and he used a phrase that I'd never heard before:

"Qué pase lo que tenga que pasar."

A literal translation would be "What will happen is what should happen." At first glance it seems similar to "Qué será, será" (“What will be will be”), but there's a subtle significance about how the future unfolds. It's a sentiment of accepting our situation as is because as is is how it needs to be.

If you've ever floated on your back in the ocean, then you know that it takes a certain frame of mind to keep from sinking — a mental lightness, if you will. As soon as you start worrying about floating, you stop floating. But if you relax, and just let go, you become a part of the ocean and ride up and over the waves rather than have them overwhelm you and — worst of all — get water up your nose.

All that to say, from here on out, I'm going to do my best to stop wasting energy trying to figure out what the future holds; to accept things as they are regardless of what's to come; and to relax into the waves of change rather than struggle against them. I figure these are all skills that take a lifetime of practice, but seriously — could you imagine a more perfect opportunity to learn and grow?

❤️ Conroy

Close your eyes, have no fear
The monster's gone, he's on the run

Before you go to sleep, say a little prayer
Every day in every way, it's getting better and better

Before you cross the street, take my hand
Life is what happens to you while you're busy making other plans

— John Lennon

In some alternate universe, I’m on a plane to Brazil right now. But in this timeline, I’m staying in Mexico. I really wrestled with this decision. On the one hand, I’m just one person — how could my traveling really make things any worse than they already are? But then on the other hand, the exponential spread of the coronavirus has only been possible because a bunch of people like me have thought that exact same thing.

Pandemics and toilet paper shortages come about when people feel their individual actions don’t matter; but when the aggregate effects of everyone’s actions really add up. There’s a positive version of this phenomenon, too, though. If you ever wonder if you are making a difference by —

Donating to charities, volunteering, eating vegan, recycling, bicycling, teaching, writing, planting trees, buying only as much toilet paper as you need, being excellent to each other, or a million other things to make this world a better place today and tomorrow…

— The answer is: Yes, you are making a difference. Keep doing those things.

Just like the concept that “we overestimate what we can do in a day, and underestimate what we can do in a year”, we also overestimate what we can do as individuals, and underestimate what we can do together.

❤️

** The photo translates to “Believe in yourself and everything will be possible.”

You only are free when you realize you belong no place — you belong every place — no place at all. More and more I belong to myself. I’m very proud of that.

— Maya Angelou

This weekend I went down to a town called Tulum to attend a “Full Moon Party” which I’d heard about ever since I first arrived here in Mexico. It has quite a reputation, a sort of Mexican "Burning Man". The point isn’t so much what you experience at the festival, as it is being able to post on Instagram that you went. You think I’m exaggerating, but trust me — the entire town of Tulum is littered with purpose-built, inspirational quote selfie stations which were only created so that a given store's logo would be posted thousands of times on social media.

Tulum as a town has its own strange sense of style which separates the "Tuluminati" from the rest of us. And ain’t none of it cheap. I saw a plain silver anklet in a display case for $120 and assumed it was pesos (about $6 USD) but nope, $120 USD. All of this combined gives the whole town an aire of exclusivity. The entire time I was there, I felt an overwhelming sense that I didn’t fit in; that I didn’t belong. 

This got me thinking about what it means to belong — to places, to people, or to yourself. There are places I’ve lived for years which have fond memories, but are still just points on a map, while some (like Juneau) felt like home from day one. Same with people — there are some that I’ve known for years but don’t have have an affinity for, and then there are others (like this WiFi Tribe) who immediately felt like family.

If I were to try to define home or family, I’d say that (like love), they are both just a choice — not to make people or places “yours”, but instead to become theirs. It involves accepting them for who/what they are without requiring them to change; being authentic and vulnerable at the risk of being hurt; giving without expecting anything in return.

But you do get something in return: a sense of belonging.

Belonging isn’t an action verb; it's not something you make happen; and there are no shortcuts. I feel like cultures like the Tuluminati offer a false sense of belonging for a price. But belonging can’t be bought, only given. It’s one of those funny things in life: the more you struggle to fit in, the less you do.

True belonging — when people become family and places become home — happens when we stop focusing on ourselves and start focusing on others.

❤️

I'm late! I'm late! For a very important date! No time to say hello, goodbye! I'm late! I'm late! I'm late!

— The White Rabbit

Last night as I was walking home, I did something unusual for me: I slowed down. I did it as an experiment to see what it's like to walk the same speed as everyone else (aka sooooo sloooooow). Usually I walk very fast, with a destination in mind. Point A to Point B — that's me. Doing that on the touristy Fifth Avenue here can be annoying as I'm barraged by hawkers who just won't leave me be.

But tonight was different. I'd been given a bunch of coins as change today ranging from 1 to 10 pesos ($0.05 to $0.50). I made a goal that I would give out a coin to anyone who asked. I only maybe gave out a max of $5, but rather than ignoring the buskers and hoping they'd go away, I was able to interact with them, saying "I know it's not much, but good luck."

Even with the people asking if I want to buy drugs or get a message or whatever, rather than them calling after me like "Hey, buddy! Amigo!" I was able to make eye contact, smile, and say "No thanks". And lo and behold, in return, I got a smile and a "Have a good night". I could hardly believe it.

That touristy street is entirely different at that pace and with that level of connection. Rather than it being a nuisance on my way to and from the coworking space every day, it was an immersive, unique, and very human experience.

I listened to someone play the harp in an otherwise silent restaurant. I watched some bored teenagers working in a tourist shop just killing time until their shift ended. I became enthralled by some art and spoke with the artist. I petted lots of good-dogs.

But the craziest thing was, before I knew it, I was home. Usually I'm counting down the the blocks until I can get out of the mayhem and onto my quiet side street. But this time, I was actually a little sad that it was over. It seemed like it ended too soon. I kinda wanted to keep going.

The last person I gave money to couldn't've been more than two years old. The boy's dad was playing a Spanish version of The Battlehymn of the Republic on the guitar. His mom was smiling and holding out a hat for donations. And the little boy himself was running around laughing and collecting money from people. Say what you want about the ethics of using your kid to busk, but I was smiling and whistling Battlehymn the rest of the way home.

But as if I needed one more experience as a juxtaposition, I passed a woman closing up her shop who had no fewer than four padlocks up and down the door she was securing. She looked like she spoke English, so as I passed, I jokingly said “Wow that's a lot of locks”. The look she gave me was withering. I felt like I'd just made an enemy — like she straight up hated me for some reason. And in that moment I wondered if that's the face I make at all of the hundreds of people just doing their job on Fifth Avenue.

That walk was exactly what I've been needing all week. I've felt so anxious about the future — thinking of all the things I need to do, and worrying about what next month will be like. I tried and tried to get out of my head but just couldn't seem to do it until tonight; until I slowed down and melded back into the present and once again became a part of — not separate from — the people and places around me.

Sometimes I can get so intent on where I'm going that I lose sight of that saying that it's not about the destination, it's about the jorurney. I think that cliché applies at every scale, from a 30 minute walk home, to the next 30 years of my life.

I don't want to get to the end and feel like I'd just been living with a scowl on my face (also know as RBF) and counting down until it's over. I want to slow down and connect with the people and places around me. I want to be so in the moment, that when the end does come, I'll be able to say, “What, so soon?”

Remind me of that once in a while, will you?

❤️

what is the greatest lesson a woman should learn

that since day one

she's already had everything she needs within herself

it's the world that convinced her she did not

— Rupi Kaur

I had lunch today with one of my favourite fellow WiFi Tribe members. We were a couple stories up, there was a nice strong breeze, and we could see the turquoise blue ocean beyond a sea of palm trees and fuscia flowers. It was such a good reminder of how absolutely, incredibly, mind-blowingly fortunate I am to be living here in this tropical paradise.

As we were watching the ocean, we saw one of the bright orange ferries to Cozumel dangerously close to shore, struggling against the strong wind. The waves were choppy, and each volley pushed the huge vessel closer onto the reefs. Its engines were at full bore and you could see huge jets of white, frothy water being thrown into the air. And yet it seemed to be losing the battle

Dang if that's not how I've felt these past couple weeks. Besides an overbooked professional and social calendar, there's also just an unlimited number of experiences to have here, and a very limited time in which to have them. The FOMO is real, people! Not to mention this amazing chapter has already started to disband (we love you Gabby!) I myself leave in just over a week which is nuts.

As much as I was hesitant to join this chapter, I'm even moreso to leave these people and this town which I've come to love; and to join another group of strangers in a new place. I have no doubt that I will find a new normal there, but I feel like I am still struggling to find that here.

But maybe that's it, though: maybe it doesn't need to be a struggle.

I was listening to the WiFi Tribe Podcast today and the guest said something interesting: at some point early on in his travels, he was in Morocco, and was talking to another tribe member about how he was struggling to achieve freedom and to be able to live the life he wanted. The other member replied: "Look around you. You're in Morocco. Aren't you already free?"

I've been going back and re-listening to Alan Watts lectures. One recently resonated with me, he said: people feel like they need to seek out whatever it is that they are looking for -- when in fact, the paradox is, you've already got it; and the harder you seek, the harder it is to find.

Stoicism echos this with the concept that as long as we are seeking happiness, we will never find it, because happiness is not "out there" as some goal to achieve, it's "in here" as a state of mind and a way of accepting our circumstances.

Or in the metaphor of New Age, as long as we are focused on our present as "lacking" something, we are not attracting abundance, but more lack.

They're all different ways of saying the same thing: we are best able to live a rich, joyful, abundant life by being grateful for our present and accepting whatever comes our way -- both the "good" and the "bad".

I personally need this reminder like, all freaking the time. I spend 80% of my energy focusing on the 20% of my life that I wish I could change, rather than on the 80% of my life that's already absolutely perfect.

Because it is perfect. Just as it is, warts and all. Right here, right now. Everything is as it should be.

So say we all. ❤️

While walking along the road, a man came across a monk carrying a heavy burden. “Oh wise one, please, spare me a moment to help me understand: what is Enlightenment?”

The monk looked up at the man, set his burden down, and stretched. As the man watched, a look of joyful comprehension crossed his face.

“Thank you, wise one. I see now; everything is so much clearer. But then, what do we do once we have achieved Enlightenment?”

The monk picked up his burden and continued walking.

After five days away, it is ridiculously good to be back home in Playa and to re-connect with everyone in the WiFi Tribe chapter. It's mind-blowing to me how quickly this place has become home and these people have become family.

As I walked down Fifth Avenue tonite, I got so much joy from weaving through the crowds of tourists and dodging the hawkers selling everything from cell phone cases to erotic massages.

In a brief moment of what I can only describe as Enlightenment, it felt like I was intimately and inextricably connected with everyone and everything in the city; that we were all just players on a stage — individual participants in a global game.

At one point, one of the hawkers I passed by tried to get my attention by jokingly calling after me using a Spanish insult. With a grin on my face and all the love in the world, I flipped him the bird over my shoulder without looking back. I could hear him and his friends as their laughter shrank into the distance and they went on with their night as I went on with mine.

Somehow, in that moment, that gesture — which usually signifies anger, loathing, and malice — formed a bond of shared humanity. Rather than drive us apart, it connected us in a unique and lasting way.

It's an immensely powerful thing when you feel a sense of agency — yet also of belonging in, of, and to this world. When you have a solid foundation of who you are and what you believe — but are empathic towards others' perspectives. When you pursue your dreams — but don't neglect to balance your responsibilities. And when you set your will in a specific direction — but are open to all the unexpected side trips along the way.

In other words, when you somehow — however briefly — recognize and reconcile some of the key paradoxes of the Human Experience.

For me, moments of clarity like tonight are few and far between. But just knowing that such simple beauty lies beneath, behind, and beyond the complexities of life helps me to keep walking when the night gets dark and the path gets difficult.

I know that one day I will lay down my burdens for good and exit stage left. But until then —

Arriba, abajo, al centro, pa dentro

I took a bus to Cancún this evening as a roundabout way of getting back home to Playa del Carmen. My hostel is near their Carnivál celebration which, to put it mildly, is a little bit different than the one in the tiny island town of Holbox where I spent the weekend. This one in Cancún has amusement park rides, a whole city block of food vendors, and professional dancers complete with crowd going wild.

I realized from the moment I left the hostel that I felt on guard here more than I did in Holbox or even in Playa. Just like Mexico City, I've heard rumours of Cancún as a place where bad things not only happen, but regularly happen. Organ harvesting types of bad things. And I don't mean "heard" like on sensationalist news. I mean I've heard first hand accounts of people I personally know talking about being robbed here while having a gun in their mouth.

And it's not just street gangs to watch out for. On a dive trip the other week, I met someone who had been robbed, kidnapped, and left for dead by police. And just this weekend I met someone who was stabbed multiple times by a taxi driver who wanted to steal their camera bag; and they were lucky to have gotten away with only scars.

Imagine what it would be like to not know if the next time you get pulled over by a cop might be the last minutes of your life. To wonder if that taxi is slowing down to ask you if you want a ride, or to pull a gun on you and force you into the car. When the people and institutions that are purportedly there to help you are the ones you learn to mistrust the most.

Being here has helped make these "what if" fears a lot more palpable. But I can't help but feel the people who constantly live this waking nightmare especially in the United States. Anytime I want, I can retreat back home to my comfort zone and breathe a sigh of relief. But what if home was the place where I felt the most unsafe, and there was nothing I could do about it?

Con mucho amor por todo el mundo ❤️

One day a farmer's horse runs away. "How unfortunate," says his neighbor. "We'll see," says the farmer. The farmer's son returns from searching for the lost horse with two more horses. "How fortunate," says the neighbor. "We'll see," says the farmer. While training the new horses, the farmer's son breaks his leg. "How unfortunate," says the neighbor. "We'll see," says the farmer. Soon thereafter, military officials come through town conscripting young soldiers; the farmer's son is excused due to his broken leg. "How fortunate," says the neighbor. "Well see," says the farmer.

— Ancient Taoist Proverb

This weekend, I went to Holbox (pronounced “whole-bosh”) with the 2020 Playa del Carmen WiFi Tribe chapter. Holbox is literally the island paradise that you think of when you picture white, sandy beaches with hammocks suspended above sparkling, turquoise water. This weekend also happened to be Carnivál which meant that the whole town was brimming with energy all day and well into the wee hours of the morning. The streets were clogged with exotically-costumed dancers, live bands dancing salsa while playing brass instruments, and food vendors occupying every square inch of available real estate around the town square. This was an absolutely perfect weekend in every way, including — no, especially — because of its imperfections.

My subjective experience of this weekend was like two threads weaving in and out through the the fabric of the island festivities. One thread was the concept of group travel and what it means to be part of an entity which can single-handedly start a dance party anywhere we go just by the quality and quantity of our energy. The other thread was the concept of solo-travel as a way of exploring a place, meeting people, and feeling a sense of agency.

I'm not gonna lie, I didn't always do a great job of balancing these two threads. There was one time when I took some much-needed time for myself — but could have done a better job of communicating what I needed. Another time, I went along with the group's decisions because it was easier and more social — when I would have benefitted more from thinking through what I really wanted or needed in that moment. Or, in the worst of all of the times, I was out of contact while the group's travel plans changed which caused unnecessary inconvenience and concern for others — but which also highlighted how amazing it is to have so many people who've got my back and my best interests at heart.

In the Tao (as I understand it anyway), there's the concept that however things are is the way they are supposed to be. It's an extreme form of acceptance which helps me to cope in situations like the above where I feel like I have "messed up". Just like in the story of the farmer's son, it's impossible to know what will come of something — especially "mistakes". The only thing I can do is just accept, learn, and move on.

Onward and upward mis cariños ❤️

“You see this goblet? For me, this glass is already broken. I enjoy it; I drink out of it. It holds my water admirably, sometimes even reflecting the sun in beautiful patterns. If I should tap it, it has a lovely ring to it. But when I put this glass on a shelf and the wind knocks it over or my elbow brushes it off the table and it falls to the ground and shatters, I say, ‘Of course.’ But when I understand that this glass is already broken, every moment with it is precious.” — Achaan Chaa

Tonight, about a dozen of us from our WiFi Tribe chapter had a picnic on the beach at sunset. We laid out towels, ate all sorts of exotic flavours of chips, and sang along to the most eclectic mix of songs — everything from Aqua’s “Barbie Girl” to Queen’s “Bohemian Rhapsody.”

There was a moment where I was laying there and was just struck with how perfect it all was — how magical of an experience — and how fortunate I was to be experiencing it. Not everybody can work and travel simultaneously like we do, and even then, for those who can, not everybody finds a tribe like this that they can belong to. And in that moment, I realized just how unique and precious of a phenomenon we are co-creating this month.

Tomorrow marks the end of the first week of our February 2020 Playa del Carmen WiFi Tribe chapter. One down, three to go. Just a few days ago, I was blown away that we’d only known each other for 100 hours. And now I can’t believe that we’re 25% of the way through our time together. It won’t be much longer before this group will disband and go our separate ways. Given the relatively small size of the community, it’s likely many of us will see each other again in other locations. But never again exactly like this.

All of these thoughts and emotions struck me all at once, and as you can imagine, it was a bit overwhelming. We all know the bitter-sweet feeling when something ends — one of those “you don’t know what you’ve got till it’s gone” sort of situations. But how often do we connect the dots at the beginning? Usually I’m so excited about the start that I don’t really internalize that the ending is a go-with — a necessary part of the balance. Nor do I do a great job of realizing and enjoying the in-between until the end is in sight.

The above story of the glass comes to mind whenever I feel like I want to hold on to the present. Life is impermanent, and resisting that fact only leads to suffering. Times change. People change. Accepting that something or someone won’t be around forever helps me disfrutar* my time with them all the more. And sometimes I need reminders like tonight to help keep things in perspective so that I can make the most of the time I have remaining.

Con mucho amor ❤️

* P.S. disfrutar is one of my favourite Spanish words because it has so much depth and nuance: “to enjoy, bask, delight, or take pleasure in.” How lovely is that?

[Day 33/???] Even though it only took a few minutes to click the buttons and tap the keys which resulted in me getting the above email, it nevertheless represents what might turn out to be perhaps years of my future.

I’m currently in Playa del Carmen, Mexico on Day 33 of what was originally intended to be 99 days of travel. My plan was to go back home to Juneau, Alaska in April 2020. However, even as I booked my chapters with WiFi Tribe and Hacker Paradise, part of me knew it was a 50/50 coin toss of whether — come April — I’d be craving being back home in my own bed, or I’d be energized for more travel.

Rather than booking a return ticket from Florianópolis, Brazil, I hatched a crazy, secret plan that I wouldn’t admit even to myself until I was already well out the door: what would it be like to travel around the world with each of the different digital nomad groups?

And so here I am. Instead of flying from Brazil back to the USA, I will be sailing with Nomad Cruise from Cartagena, Colombia to Lisbon, Portugal. (Jeez, even saying that kinda made my stomach flip a little bit.) The details get a little bit fuzzy thereafter, but I’ll likely take the Nomad Train across Russia, then hopefully join Remote Year in their Asian locations. And then…?

Typically, this is the point at which I would be second-guessing myself. After all (I mean, let’s be honest here) that itinerary is kinda nuts. Especially for someone who is only on Day 5 of their very first nomad group experience.

However, a few things give me confidence that I am on the right path:

First, I am a big fan of following my inner voice. It’s rarely easy, but time after time I’ve found that it’s led me to such unexpected (yet positive) experiences, that when it speaks, I do my best to listen. And it’s definitely confirming this is the right choice.

Second, I am extremely curious. Not only about the world and my place in it, but about the different digital nomad groups and their cultures, values, and experiences. In just these last few days, I have come to feel like I know and love this group of twenty practical-strangers, and the general consensus is that it’s because of the shared values we each do our best to embody. I don’t expect to be able to reproduce this experience or these connections, but I am very much looking forward to seeing inside the different groups and getting to know more people in the digital nomad community.

And last but not least, my first day here in Playa del Carmen, I was working in a café where a woman about my age was giving tarot card readings. Now, I’ve only experienced tarot a few times in my life, but I believe that — spirituality aside — tarot is a great way to (as Paulo Coelho puts it in The Alchemist) “reach through to the Soul of the World.” Kind of like flipping a coin to make a decision, as soon as the coin is in the air, you realize which outcome you are hoping for the most.

My question for the cards was whether I should head back home to Juneau in April, or continue traveling. What I took away from my session is that if I go back, I will no doubt be happy to be home, and I will see it with new eyes; but unfortunately, my world will shrink back down again, as it has done every time I’ve returned to Juneau.

However, if I keep traveling, I will have experiences which will help me to break through The Illusion and see The World as One. When I do decide to make a home, it will be completely different for having had the experiences which are yet to come.

And so I’m going to give it a shot. Because (as many smart people in my life have pointed out) if I don’t like it, I can always just go back home. But if I don’t give it a shot, this will no doubt be one of those “What If?” scenarios that I will wonder about for the rest of my life. And who knows if I will have a chance like this ever again.

So, Nomad Cruise, ready or not, here I come!

You know that phenomenon where time seems to speed up as you get older? I've heard it explained as each year being a smaller and smaller percentage of your overall life, so each year seems to pass more and more quickly.

I personally find that explanation disheartening, because if that's the case, then there's nothing you can do to counterbalance that sensation — you've just got to deal with it.

But I've heard an alternate explanation which is thankfully both more encouraging and more actionable: that the key to pumping the breaks on the passage of time is to seek out and experience novel situations, much like a child does naturally as they move through everyday life.

Routine is often enshrined as a pillar of adulting. Besides being an efficient way to allocate time, there's also a certain comfort in Saturday Night Pizza-and-a-Movie.

But if the novelty theory is true, then it is our routines which are to blame for why one week seems to blend into the next. The same commute. The same weekly meetings at work. The same grocery items in purchased at the same grocery store. And so on and so on, seemingly ad infinitum.

I can chart the decline of my physical, mental, emotional, and spiritual well-being when my weeks start to become indistinguishable from one another. In my experience, this is often a sign that my life is seriously out of balance in some way.

I've found that — as simple as it sounds — going for a walk is *the* most effective way to restore that balance. Besides getting away from whatever is bothering me and letting endorphins trickle-charge my mood, being out and about exploring, taking photos, and people watching, helps me to regain not only my perspective of Life, but of my place in this World.

We can't help but be changed when we connect with the people and places around us. But first we've got to get ourselves out there and be open to connection — which is much easier said than done.

Today was my first work day in the new (to me) city of Playa del Carmen with this chapter of WiFi Tribe. Someone in the group suggested working from a coworking space slash hostel called Selina. We had a nice walk through the touristy 5th Avenue, getting to know each other better while vendors tried to sell us anything and everything. I went on a scavenger hunt to find "la abuela que se vende la desayuna" who ended up being at the end of a colourful pedestrian street. The breakfast was delicious, nutritious, and shockingly inexpensive. We got to use the air conditioned coworking space for free for a couple of hours, then we had some fresh fruit and vegetable juices on the patio. On the walk back home, I found the perfect present and I'm *so* excited to send it back to the States. I got to work from home the rest of the afternoon, then went out for dinner with three of my tribemates at a wonderful little Italian restaurant with the most interesting owner. The weather was perfect and breezy on the walk back home, and I'm now lying in my comfy bed about to go to sleep as the clock hits 00:00.

Today was my first work day in Playa with @wifitribe.co. Someone suggested a coworking space, but it was like a 20 minute walk through the touristy area where vendors bug you every ten steps. I was sweaty by the time we got there. Nobody else was hungry so I went on a wild goose chase to find a restaurant and ate alone. The coworking space was crowded, and I felt unproductive, so I went home. By then it was so hot it was unbearable. I got a present to send back to the States but feel like I got ripped off. I was so miserable I didn't want to see anyone so I holed up in my room the rest of the afternoon. I'm so behind on work that I feel like I'm drowning. I went out for dinner with some people, but I felt awkward like I either talked too much or too little I'm not sure. I'm so tired but I can't stop thinking about how much this week is going to suck. Just wake me up when it's all over.

This weekend, I went up to Teotihuacán (The Temple of the Sun) for a music festival. During my 36 hour trip, not only did I not actually go see the temple, but I also spent less than 90 minutes at the festival. The rest of the time was spent getting to know amazing people who not only added joy to my trip, but to be honest, they all played a crucial role in my safety as well.

There was the lovely elderly couple who ran the "hotel" I booked online which was actually a Michoacán indigenous cultural center. The Señor insisted that he drive me to the festival and that he'd pick me up whenever I called, no matter how late.

There was the young, optimistic, and ridiculously-in-love couple who who run an outdoor restaurant on a plot of land they plan to turn into a community garden to feed the most food-insecure people in their town. They let me use their phone and kept me company while I waited to be picked up that night.

And there was the group of also-lost festival goers (we only had lat/long coordinates to find this place) who gave me a sense of peace and belonging even as we navigated back alleys, rode hanging out of a stranger's SUV with the tailgate up, and wove through giant cacti in the pitch black desert.

During the festival, I had a series of insights which I'll write about another time. But the most beautiful thing for me was realizing:

How I could not have made it there alone.

How when we connect with each other, things like not being able to find where we're trying to go can morph from being frustrating, to being part of our shared journey.

And how when we trust each other and let ourselves be vulnerable enough to rely on each other, we can go so much further than we can on our own.

Eventually, I felt my inner voice tell me it was time to go. I'm glad I left when I did because honestly I don't want to think what might have happened if I'd not run into that lovely couple who let me use their phone, but (and I'm not trying to be be dramatic or anything here guys but) I feel very strongly that it would not have ended well.

tl;dr — be excellent to each other and listen to that still small voice inside.