Only On the Road

Quick note before we get into it. We have moved to a biweekly cadence. Life got super busy this summer and producing something worth reading every single week started competing with actually living the experiences worth writing about. You will hear from me every two weeks.

Now. On to the good stuff.

I travel a lot. Fifty weeks a year, give or take. And for the most part I have it down to a science.

But every once in a while something happens out there that stops you in your tracks. Sometimes it makes you smile or sometimes it makes you laugh or sometimes it makes you cringe or roll your eyes. And sometimes, for whatever reason, it randomly triggers an emotion or a feeling or a sense of the past that has you welling up with tears on a random Tuesday afternoon all by yourself in an airport terminal.

There is science behind why people get emotional and tend to cry more often while flying 35,000 feet up in the air. The cabin pressure at cruising altitude lowers oxygen levels in the blood, which research suggests makes us more emotionally vulnerable and less able to regulate our feelings the way we normally would. Add in the fatigue, the isolation, and the strange suspended reality of being 6 miles up above the ground with nowhere to be for the next few hours, and you have an ideal environment for genuine human emotion. Airlines know this. Which is not surprising that there are so many romantic comedies to choose from in your backseat entertainment system. So without completely divulging how many times this has happened to me - It happens often and I’m always surprised when it does but I usually just roll with it !

This issue is about those moments- well maybe less about the crying episodes and more about the random experiences.

The Dog

A number of weeks back I came across a small pup in an airport terminal who was missing both of his hind legs. He had an outfit with two wheels on the back of his torso — rolling around that terminal like he was in his own personal chariot, owning the place.

He was zipping around effortlessly. Cute little smile on his face. His rear end bouncing up and down with every lap around the gate area. He did not have a care in the world and he made sure everyone around him knew that too.

Probably one of the cutest things I have ever seen while traveling.

Shalom

Earlier this summer a super pleasant gentleman with an orthodox Jewish large brim hat walked up to me, said shalom, and simply asked me if I was Jewish. As soon as I answered pleasantly that I was not, he tipped his head, said thank you, and was on his way.

I am still curious about what he wanted to ask or how he wanted to engage. But that interaction left me with a genuine sense of curiosity and also generated more of a desire to understand the togetherness that the Jewish culture brings — that sense of family that can exist between complete strangers.

The Regulars

One of the really cool things to observe is the random people you come across working out at a gym in the early morning hours mid week.

At the Toronto Equinox there is an awesome woman covered head to toe in tattoos who is on her spin bike nearly every single day, every single week, turning away without a care in the world for the last 2 years that I’ve frequented that gym. And then there is a focused gentleman who is relentless with his strength training, phone constantly recording video — clearly doing some sort of social media thing and generating a whole bunch of followers.

Some of these people I come across once and never expect to see again. Others show up week over week. Either way they always trigger a sense of curiosity in me. What do they do professionally? What are their families like? What motivates them to maintain the routines that they do?

In most cases I just like the idea of curiosity and never actually approaching them or learning the real story. There is something a little extra exciting about the unknown. About just creating the imaginary stories in my head as to what the answers to those questions actually are. This tends to be particularly useful on mornings that I don’t feel terribly motivated to do a hard workout and I’d rather make up stories in my head and watch the time fly by!

Red Wine. White Blouse.

On one particular business class flight across the country these two lovely ladies in front of me struck up a friendship. In the midst of spilling secrets and speaking loudly enough for most of us in business class to hear, the poor flight attendant spilled an entire glass of red wine over one of the women’s white blouses.

Without missing a beat her newfound friend offered a change of clothes she happened to have packed in her carry-on. Right there on the plane. Two random strangers wearing each other’s clothes halfway across the country.

Needless to say both women ended up having a pretty good time for the remainder of that flight. It was quite entertaining to eavesdrop and I was witnessing what will inevitably be a very funny story that will stay with both of them for a very long time. If not forever.

Cupcaked

Earlier this year I got cupcaked.

If you are not familiar with the term — and I was not until a former boss of mine used it nearly 20 years ago — it refers to being stuck in the middle seat on a flight with two large passengers on your left and right, both spilling over into your armrests.

I do not really need to say more to describe exactly the scenario.

In this case it was just between Toronto and New York so it went by rather quickly. But it had me snickering to myself the entire flight thinking about my old boss telling this exact story in exactly this way. A term that is admittedly offensive but one that made me laugh and triggered memories of the past that I had not thought about in a really long time.

Memory is funny that way.

Why I Am Sharing All of This

The point of these stories is simple.

When you travel you come across things you would never have an opportunity to see otherwise. You can put your head down and ignore all of it. Or you can pay attention.

As we have talked about throughout this newsletter, maintaining the energy, the focus, the motivation and the inspiration on the road means drawing from sometimes the most random places. Those places might be fun, curious, quirky or just completely unexpected. But they are there if you are looking.

Sometimes when I am overly tired or stressed I become that grumpy traveler. But then something happens — a dog in a chariot, a stranger tipping his hat, two women swapping clothes at thirty thousand feet — and it reminds me pretty quickly of the privilege I have and the experiences I have been fortunate enough to come upon. It corrects the mindset faster than almost anything else.

I am grateful for all of it. The random interactions. The acts of kindness that catch you off guard. The reminders of how important that character attribute really is.

Keep your eyes open out there. You never know what will put a smile on your face when you need it the most.

— JE

50 Weeks publishes every two weeks. Forward this to someone who needs it.

Issue #013: The Worst Travel Mistake I Ever Made.

I have been doing this for quite a long time. And you forget how many lessons you have learned over the years and the mistakes that you make along the way. And yet I have also managed to forget critical documents, abandon expensive technology, board twelve hour trains, and nearly recreate scenes from the movie “Taken” in Paris. This issue is a bit of a trip down memory lane, those mistakes that jumped out and what you learn along the way.

The mistakes are real, some of them are quite funny upon reflection, some of them were genuinely terrifying in the moment. All of them taught me something though!

The Notarized Letter I Did Not Have

If you travel internationally with a minor child without the other parent present, most countries require a notarized letter of consent from the absent parent. Canada is one of them.

I knew this and I had been really good about doing it before. And on one particular trip across the border with my daughter, I did not have it.

As we approached the immigration desk, the officer asked my daughter directly whether her mother knew she was here.

My daughter, without missing a beat, looked the officer in the eye and said: “absolutely, and I can text her on my Apple Watch right now if you would like to talk to her?”

She was calm and confident. She was only 8. We were waved through but I have never forgotten that experience.

The lesson here is that your child will bail you out haaa, though apparently Alessandra will. It is that a minor administrative oversight, something as simple as a piece of paper, can turn into a serious situation very quickly at an international border. In a worst case scenario it could mean separation from your child in a foreign country.

The notarized letter now lives in my travel folder permanently, alongside my international work permit and other very important documents.

The Sleepy Hollow Cemetery of Forgotten Things

Somewhere out there there is a super high end bougie hotel lost and found containing my Apple Watch charger. Possibly two of them. There is also a plane seat pocket over the Atlantic that once held a pair of Bose noise cancelling headphones that I will never see again. And a 3rd floor at an office in St Pauls’ with a dead laptop in a desk drawer.

I have left things behind in hotels, on planes, in trains, in cars, and in lounges. Sometimes it is the small stuff, chargers, cables, a jacket (my favorite rain jacket on National Rail in Northern England!) Sometimes it is the expensive stuff (the jacket was!). The laptop situation was a genuinely costly lesson. The QC3 headphones still sting.

OF all these, the most egregiously annoying is the charger. It gets me every time. You would think a hotel could locate a small white charging cable. Nope… gone like it never existed.

The lesson here is simple. The most important items, technology, documents, anything that disrupts your ability to work or travel, need a system. Not a mental note or string around your finger. A system. I now do a full sweep of every hotel room before I leave. Looking under the bed, opening every drawer. I once had housekeeping put my personal belongings in the hotel room drawers (I never unpack my suitcase, worth an article on that itself).. and I was astonished when I opened the drawer when checking out to find a bunch of my crap. Check everything… It takes ninety seconds and is worth every nickel as my best pal loves to say.

The Twelve Hour Train

There are obviously direct flights from New York to Montreal. It takes approximately one hour. Early on in my youth I once chose to take the train instead. The journey clocked in at just under twelve hours.

I will not go into the full details of what possessed us to make this decision (cats out of the bag, it was my bachelor party with 8 other guys). Probably curiosity, overconfidence, and a fundamental misreading of the Amtrak schedule. The scenery was admittedly beautiful but the remaining eleven and a half hours were long. Passing through immigration cross border was a bit of a nightmare...

I would not recommend it unless the circumstances are truly extreme. In our case, they were not extreme, just poor decision making and travel inexperience.

The lesson here is to never romanticize the journey when you have somewhere to be. The road warrior ‘ethos’ is not about adventure for its own sake. It is about being where you need to be, in the best possible condition, ready to do either do the work or start your leisure . A twelve hour train ride when a one hour flight exists is not adventure. While I agree that life needs to be about the journey and not the destination, I would argue that most times you want to get the travel out of the way so you can actually enjoy the destination.

Paris. Late. No Cash. No Plan

We arrived in Paris late at night via Eurorail. Pre-Uber, no cash. No clear plan for how to get from the station to the hotel. The city was loud, unfamiliar, and within minutes we had been surrounded by a group of men who had clearly identified us as tourists. We were out of our element, tired, confused and this group intended to take full advantage of that fact.

I will overdramatize it because it was dramatic… Genuinely scary, particularly for my partner at the time. It was unsettling. The aggression was real, the disorientation was real. The feeling of being completely unprepared in an unfamiliar environment at an hour when everything feels more dangerous than it probably is, was very real.

We got out of it. But a moment not forgotten. (even the sleezy cab driver double charged us that evening)

The lesson here is not about Paris. Paris is magnificent. The lesson is about preparation. Being out of your element in an unfamiliar city, in a foreign country, late at night, with no local currency and no clear plan is a scenario that can be avoided. Know how you are getting from the station or airport to your hotel. Have some local cash. Understand the neighborhood. And if something feels wrong, trust that instinct immediately.

Every one of these stories has a version of the same lesson underneath it.

The infrastructure matters. Not the glamorous parts. The notarized letter in the travel folder. The ninety second hotel room sweep. The thirty minutes of pre-arrival research. The local cash in your pocket.

The road warrior who has it mastered is not the one who never makes mistakes. It is the one who has built enough systems and habits that the mistakes get smaller and less frequent over time. And when something unexpected does happen, a flight diversion, a closed border, a late night arrival in an unfamiliar city, they are prepared enough to handle it without panic.

You cannot control everything on the road. You can control your preparation. That is enough.

In 2 weeks: Ads that hit hard

— JE

50 Weeks publishes every other Tuesday. Forward this to someone who needs it

The Story So Far.

Eleven issues in total. Some of you have been here since Issue 001. Some of you are brand new to the series. This issue is all about the recap of the past eleven.

I’ve had readers ask me what 50 weeks means - its simple metaphor to the number of weeks a year I am typically on the road. Before we head into the next set of articles I wanted to look back at the themes thus far, and give anyone who has missed an issue, or anyone just joining, a clean way in. It took me a bit to create the direct links below to each article but hopefully its easy for you!

Where it all started. The origin of this series and the case for why heavy corporate travel deserves some space and an honest storyline.

The economics and pitfalls of getting to and from the airport. Also random acts of kindness.

The Moves Most (Canadian) Road Warriors Never Make But Absolutely Should

Two moves that improved my travels.

This one was not really about running at all.

A phrase I learned from a colleagues farewell in Kingston, Jamaica.

Sleep debt. Love debt. Friendship debt. Specific guidance about addressing each.

A case for building a credit card stack that makes sense for you.

Señor Wilson. And more…

The lounge stack rank. A reflection on what lounges are actually for and what we miss when we move through the world with our heads down and our assumptions intact.

A real day. Worth the read.

The most personal issue I have written to date.

What This Series Is All About

Fifty weeks is the number of weeks (give or take) I spend on the road in a given year. This newsletter exists for the people living that life or perhaps those interested.

The infrastructure is the theme. The habits, the relationships, the sources of energy and meaning that make it possible to do this at a high level for a long time without losing yourself in the process.

Next week: We keep going.

— JE

50 Weeks publishes every Tuesday. Forward this to someone who needs it.

50 Weeks Issue #011

Inspiration.

Toronto. This past week. A townhall with some of the best colleagues I have worked with over the past 2 years. Someone asked me what keeps me inspired on the road and what motivates the articles.

I thought about answering that question - and what better way than in an article. This issue is my attempt.

It is a little different from what I usually write. Probably too personal. But some things are worth saying out loud.

One thing before we get into it. This list is not definitive. It never could be. The people and ideas that inspire us change constantly throughout the course of a life and a career. New people enter your world. Perspectives shift. Something triggers a reminder of what someone you had not thought about in years said. That is the nature of inspiration. It moves.

What follows are the ones that jump out at me right now. The ones I keep coming back to. The ones that have shown up consistently enough that I know they belong here, at least for today.

Theme One: Authors, CEOs, and Business Leaders Who Tell the Truth

The business world is full of people with opinions. It is considerably less full of people with genuine perspective, the kind that comes from having lived something rather than just studied it.

The voices I keep coming back to are the ones who do not perform wisdom. They just have it.

Gary Burnison on love, hope and leadership. Adam Grant on generosity, rethinking and the value of being wrong. Brené Brown on vulnerability and what it actually means to dare to lead. Scott Galloway, occasionally vulgar, always honest, saying things that need to be said in ways that make you uncomfortable enough to actually think. Kara Swisher, who does not soften things, does not perform neutrality, and calls what she sees with a clarity and courage that I find genuinely rare in a media landscape that has largely stopped doing either.

These are not people I agree with on everything. They are people who make me think harder about everything. That is the better standard.

Theme Two: Powerful, Independent, and Strong Women

The most consistent source of inspiration in my life has been women. Specifically, women who carry things quietly, persist without performance, and build lives of genuine meaning without asking for permission or recognition.

My grandmother, Jean Hoglund, had a huge hand in raising me. What she gave me was not just love. It was a masterclass in what good actually looks like. The balance of support and discipline. The grace under pressure. The empathy that never tipped into softness and the resilience that never tipped into hardness. The infectious laughter, love and joy she brought into every room she entered. She showed me what it looks like to hold things together without making a show of it. I carry that with me every day.

My partner, Christina Cuarón, is the most independent and strongest woman I have ever known. She has taught me more about resilience, self-sufficiency, and what it looks like to move through the world on your own terms than anyone else in my life. I am a better person for knowing her.

Patricia Pacheco pursues what she believes in with a relentlessness that is impossible not to be moved by. There is no other person I know who does not take no for an answer the way she does. The persistence, the ambition, the aspiration. She is singular.

And then there is my daughter, Alessandra. She is still young, 10, but she teaches me something every single day. The kindness she shows without being asked. The joy she brings to ordinary moments. The way she loves her mom and her dad with everything she has. There is no leadership book that has ever hit me the way watching her move through the world does. It is no surprise her mom is exactly the same way, and her mom is another woman that has taught me so much over the years, particularly the kindness and selfless approach at life just because.

These women are not inspirational in the way that word gets used carelessly. They are inspirational in the original sense. They put something into you. They fill something up. And when I think about the person I want to be — not just as a professional but as a human being — it is this group I come back to every time.

Theme Three: The Leaders Who Shaped How I Think

I have been fortunate in my career to work alongside and learn from exceptional people. Current and former bosses. Peers. Leaders in technology, cybersecurity and financial services who have shaped not just how I work but how I think about what leadership actually means. this section probably needs its own article and maybe well go deep in a future one.

For now, I’ll name them specifically along with their LinkedIn because they deserve the recognition and because if you follow them you will be inspired or minimally challenged. In no particular order:

David Reilly. Tony Kerrison. Duncan McInnes. Howard Boville. Phil Hordle. Steve Sparkes. Tim Clark. Cathy Bessant. Aditya Bhasin. Afwa Kandawire. Peter Richards. Lou Riccio. Scott Thomson. Guillermo Diaz Jr (G) Marcelo DeSantis

What I have learned from these leaders covers the full spectrum of what exceptional leadership looks like in practice. Each of them has shaped how I think, how I lead, and how I show up. Their styles and attributes are not always the ones I would choose for myself. But that is precisely the point. Great leadership does not come in one form. What these individuals share is an extraordinary ability to drive outcomes, achieve remarkable things, and leave a lasting mark on the people and organizations around them. Watching that up close, in all its different forms, has been one of the greatest educations of my career.

Theme Four: My siblings

There is a category of inspiration that does not come from books or boardrooms or LinkedIn feeds. It comes from people who share your blood, your history, and your childhood bedroom (at one point all 3 of us were in fact in the same attic bedroom!). People who have no obligation to inspire you and do it anyway simply by living their lives.

My sister, Kristen, carries burdens with a courage and resilience that I find genuinely humbling. She has made choices in her life that required a level of conviction that most people never have to find in themselves. She does not seek recognition for it. She simply does it. That is the most inspiring kind of strength there is.

My brother, Paul, has given me something different. Something harder to name but impossible to ignore. Paul spent years full time caring for our disabled grandfather at a point in his own life when he was still searching for his footing. He struggled. He fought. He found his purpose through faith. And today he has a beautiful family and a life built entirely on his own terms.

There is no more powerful source of inspiration than a rebound story. The one with the years of difficulty and the quiet daily choices that nobody sees and the moment when something finally shifts. Paul has lived that story.

I did not expect this issue to go where it went. But that is the thing about inspiration. When you actually sit with it long enough to write it down, it has a way of reminding you what matters most.

Your Turn

I have never written this list down before. Not like this. Putting names to it, being specific about why each person matters, sitting with the full weight of how much of who I am has been shaped by other people — that is not something I do enough.

Write down your four themes. They do not have to look anything like mine. They probably should not. But write them down. Get specific. Put names to them. And then ask yourself when you last told any of those people what they mean to you.

Inspiration is not a passive thing. It does not just happen to you. You have to build it, tend to it, and every once in a while acknowledge it out loud.

That is what this issue was for me. I hope it is something like that for you too.

Next week: Back to some fun, a little less intensity and some cool travel hacks… !

— JE

50 Weeks publishes every Tuesday. Forward this to someone who needs it.

A Day in the Life.

Writing this from Toronto. 5am run in the pouring rain is already done. The CN Tower got hit by lightning at least three times while I was out there. Admittedly a little dangerous. Absolutely beautiful.

How This Issue Started

I’ll be honest — I was stuck this week.

Ten issues in and for the first time I sat down to write and nothing came.

Last night over a beer and dinner with colleagues it served as a reminder of why I started writing in the first place.

We ended up talking about the newsletter over the meal — and what continues to surprise me was how many of them were reading it and had genuine feedback or compliments . Teammates I work with every day who had never mentioned it. Questions about future topics. Suggestions. Encouragement to keep going.

It was one of those moments that reminds you why you started something. And it gave me exactly what I needed — not just the motivation to write, but the idea for what to write about.

One of them asked a simple question: “Does your actual stories really happen like that when you’re on the road?”

So here it is. A real one. Yesterday, unedited, unglamorous, and exactly what it sounds like to be a road warrior

3:30am

The alarm goes off.

Not a gentle fade in. The full thing. I am up.

Yesterday was a departure from a different New York area airport than my arrival airport — which meant I had to do something I genuinely hate and almost never do: take an Uber. I did not take my own advice from Issue #002 I couldn’t drive to the airport this time so had to stomach an Uber, which luckily the gentleman was pleasant,

The ride was fine. The driver was quiet. I was grateful for both.

The Airport

I got there early enough to do the things that actually matter before a flight.

Phone charged. Water. I carry a large canteen everywhere I go — one of the most unglamorous but genuinely important pieces of road warrior infrastructure I own. I filled it before security. I will fill it again on the other side. Hydration on travel days is one of the things most people get completely wrong and then wonder why they feel terrible by 2pm.

First flight out. Always, when I can. The first flight out is the most reliable flight of the day. Everything that can go wrong with the rest of the schedule hasn’t happened yet. Delays cascade — the first flight doesn’t inherit anyone else’s problems.

Toronto City Airport

Landed. Moving.

I had a full day of meetings starting almost immediately upon arrival. No time to check into a hotel. No time to decompress.

I did have time for one thing — and this is the kind of detail that sounds absurd until you’ve needed it.

I got dropped off a block from the office. Found a park bench. Opened my carry-on. Swapped my travel shoes for dress shoes. Stood up. Walked in.

Nobody in that meeting room knew I had been awake since 3:30am. Nobody needed to.

That is infrastructure. Not the dramatic kind. The quiet kind that nobody sees and that makes everything else possible.

The Day

Full day of meetings. The kind that require genuine presence — not just physical attendance but actual engagement. Conversation that goes deep. Decisions that matter. The emotional register that comes with a room full of people working through something real together.

I loaded up on caffeine in the morning. Switched to tea in the afternoon — a small but meaningful shift that keeps the energy steady without the crash. Kept the canteen moving all day. Water is not optional on days like this. It is the difference between being sharp at 4pm and not being sharp at 4pm.

Not once did I yawn. Not once did I feel the 3:30am wake up catching up with me.

That is not luck. That is what the infrastructure is for.

The Evening

After a long day of intense discussion and emotional engagement — the kind that fills you up and empties you out simultaneously — I went for a very long walk.

No agenda. No destination. Just movement and air and the particular decompression that only comes from putting one foot in front of the other with nowhere to be.

On that walk I called my family. I caught up with a few friends. I spoke to a pal I hadn’t talked to in longer than I should have — one of those calls that reminds you why the friendship debt we talked about in Issue #006 is worth paying attention to.

By the time I got back I felt genuinely restored. Not just rested. Restored. The walk did what the walk always does — it held the day without judgment and gave it back to me in a form I could actually process.

That is the evening infrastructure. Underrated. Underused. Worth protecting.

5am. Pouring Rain. Lightning.

I set the alarm for 5am.

It was raining hard when it went off. The kind of rain that makes a reasonable person reconsider. I looked at the weather. I looked at my running shoes.

I went anyway.

The CN Tower got hit by lightning at least three times while I was out there. The streets were empty and dark and completely alive in the way that cities only are in extreme weather at extreme hours. It was admittedly a little dangerous. It was absolutely beautiful.

I got back soaked, energized, and completely ready for whatever today was going to bring.

That is what fuels me. That is what keeps the road from winning.

The Point of All of This

I shared those details — the park bench, the canteen, the shoe swap, the 3:30am Uber I didn’t want to take — because they are the unglamorous reality of what road warriors actually looks like up close.

It is not always elegant. It is not always optimized. Sometimes you take the Uber because you have no choice. Sometimes you change your shoes on a park bench because that is what the morning requires.

But here is what I want you to take from yesterday: not once during that entire day — despite the early start, the travel, the intensity of the meetings, the long walk, the late evening — did I feel depleted. Did I underperform. Did I give anything less than my best.

That is the infrastructure working. The canteen. The first flight. The walk. The run in the rain. The phone call to the old friend. The tea in the afternoon instead of the third coffee.

None of these things are dramatic. All of them are intentional.

Figure out what your version of this looks like. Build it. Protect it. And then show up — to the meeting, to the relationship, to the 5am run in the lightning — as the best version of yourself.

That is what this newsletter has always been about.

Do This This Week

Map out a typical travel day — from alarm to evening. Look at where the energy leaks are. The moments where you default to the easy choice instead of the right one.

Pick one to fix.

Just one. This week.

Next week: TBD !!!!

— JE

50 Weeks publishes every Tuesday. If this one resonated — forward it to someone who thinks the road warrior life is glamorous. It will set them straight !

Provincial.

“We Become Much More Provincial When We Travel”

I came across that line on a podcast called Y We Travel — spotted, appropriately enough, on a wall at Toronto Pearson (The twist in the podcast name, of course, ties back to the airport codes across Canada which all largely begin with the letter Y). One of those moments where you’re moving through a terminal you’ve walked through many times over, see a cute ad, and actually download the podcast!

The podcast explores the deeper psychology of why we travel — not the logistics, not the points, not the lounge rankings — but the fundamental human impulse underneath all of it. Why we go. What we’re looking for. What we actually find.

We think travel broadens us. And sometimes it does. But more often we move through the world in a bubble of our own habits, preferences, and assumptions — the same hotel brands, the same cuisine, the same lounge chair in the same corner of the same terminal we’ve been using for years.

Provincial. Not in spite of the travel. Because of it.

And nowhere is it more true than in airport lounges — the space that sometimes feels like it exists outside of time, outside of weather, outside of the city you’re in and the city you’re going to, populated by people who are technically in motion but seemingly not.

This issue is about lounges. But it’s really about what happens when you slow down enough to notice where you actually are.

The Lounge as Idea

In my view airport lounges are not nearly as good as the travel internet makes them out to be.

They are, however, considerably better than the alternative. And on the right day, in the right lounge, with the right amount of time before your flight — they are something close to genuinely pleasant.

The key is to set expectations - never expect too much. The lounge that disappoints you is the one you walked into with an agenda. The lounge that surprises you is the one you walked into with thirty minutes and no particular plan.

The best thing a lounge can give you is not the food or the drinks or the wifi. It is permission to slow down in a context that is otherwise relentless. To sit. To watch. To be somewhere without immediately having to do something.

The People

Lounges are extraordinary for people watching precisely because the usual bustle of travel is suspended for a moment. Nobody is rushing. Nobody is competing for overhead bin space. The armor comes down slightly. And what you see, if you’re paying attention, is people being remarkably human in the in-between spaces of their lives.

The executive on the phone managing a crisis with one hand and a glass of wine with the other. The couple who haven’t spoken in twenty minutes but are clearly fine with each other in a way that can only be explained by their long relationships. The solo traveler with a book they’re actually reading. The first-time business class passenger trying to look like they’ve done this before.

I have been all of these people at different points. I recognize them all.

The lounge is where the provincial traveler has a chance to catch themselves. To put the phone down for ten minutes. To look up. To remember that everyone in this room is going somewhere too — and that can be genuinely interesting if you allow it.

The Stack Rank

One more thing before the list — and this is genuinely one of the most underutilized pieces of knowledge in travel:

The best lounges in the world are almost always accessible via a business class ticket. Not a card. A ticket.

This sounds obvious until you realize how poorly airlines communicate it. When you purchase a business class fare — even a deeply discounted one booked last minute — lounge access at the departing airport is almost always included. Sometimes at the destination too. It is buried in the fine print, never highlighted at checkout, and rarely mentioned by anyone at the gate.

I found this out by accident many years back flying British.

Last March, I booked a last minute discounted business class ticket on ANA returning home from Tokyo for the marathon. I had no particular expectation about the lounge — I assumed I’d be in a Priority Pass situation and had adjusted accordingly. Someone at the airport mentioned almost in passing that I had access to the ANA lounge.

What followed was one of the best lounge experiences of my life. I almost missed it entirely because nobody told me it was there.

Before every international business class flight — check what lounge access your ticket includes. Don’t assume. Don’t guess. Look it up or ask at check in. The answer is almost always better than you expect.

1. ANA Lounge, Tokyo Narita. The best lounge I have ever been in. Full stop. The food is extraordinary — real Japanese cuisine prepared with the kind of attention to detail that makes you reconsider everything you thought you knew about airport food. The space is large, calm, and beautifully designed. The drink selection is serious. The service is exceptional in that specifically Japanese way — present without being intrusive, attentive without being performative.

If you have a connection through Tokyo and access to this lounge, rearrange your itinerary if necessary. It is worth it.

2. British Airways Lounge, Heathrow. Consistently good. Decent breakfast that actually tastes like breakfast. A setup that rewards the early morning traveler who wants something real before a long flight. Heathrow is a complicated airport to navigate and the BA lounge makes the experience meaningfully better. Not transcendent. Reliably excellent — which at Heathrow is its own achievement.

3. Centurion Lounges. Better than the internet hype when they’re quiet. Worse than the internet hype when they’re not. The food is decent, the bar is reliably stocked, and on the right afternoon they are genuinely pleasant places to spend an hour. The World Cup martini stations were a nice touch — someone at Amex is paying attention to the experience in a way that not everyone does.

The crowding at peak hours is a genuine problem. Arrive early or adjust your expectations accordingly.

4. American Airlines Lounges — International. More dated than they should be for an airline of this size. The Admirals Club is fine. The international business class lounges are a step up and worth seeking out specifically when connecting through a major American hub on a long haul itinerary. Not a destination. A reliable option.

5. United Club, Terminal 2, Heathrow. The somewhat newer location at the Queen’s Terminal is genuinely good — a significant upgrade on what United has historically offered. Nicer than you’d expect. Worth mentioning specifically because most people assume United lounges are uniformly mediocre and this one is the exception.

6. Priority Pass Lounges — Generally. The range here is so extreme that a single ranking is almost unfair. I have been in Priority Pass lounges that were genuinely excellent and Priority Pass lounges that were a windowless room with a bowl of pretzels and a coffee machine from 2011.

What they reliably offer — and this is not nothing — is a place to sit, log in, download your Netflix shows, and avoid the genuinely terrible food options at airports like Pearson. As a floor they are useful. As a destination they are not.

Check the app before you commit. The ratings are usually accurate.

That is my list. Lounge rankings are deeply personal, occasionally irrational, and almost always contested. Everyone who travels has their own version of this.

These are mine. Debate me as I would love to hear yours. And whatever you eat in the lounge — proceed with appropriate caution.

Leisure vs. Business

One more thing worth saying about lounges — and about travel generally.

The experience of moving through an airport lounge as a leisure traveler is a fundamentally different thing from moving through one as a business traveler. I do both often and the difference is more significant than it might appear.

The leisure traveler is anticipating something. They are on their way to a place they chose, with people they love, for a reason that has nothing to do with a deliverable. The lounge is the beginning of an experience. There is lightness in it.

The business traveler — at least the honest ones — is often managing something. The inbox that followed them to the gate. The call they need to make before wheels up. The meeting on the other end of the flight. The lounge is a brief pause between obligations.

I am more often the second kind of traveler. Which is why I have learned to treat the lounge as something deliberate rather than incidental — a conscious decision to slow down for thirty minutes before the next thing begins.

We are all provincial travelers to some degree. The lounge is one of the few places on the road where we have the chance to catch ourselves being that — and choose something different. To look up from the screen. To notice the room. To remember that travel, even the grinding relentless business kind, is still one of the more remarkable things a human being gets to do.

Your Turn

Reply and tell me your single best lounge experience and your single worst. The most interesting submissions — good and bad — will feature in a future issue. I hope we get some fun stories out of this!

— JE

50 Weeks publishes every Tuesday. If this one made you slow down for a moment — good. Forward it to someone who needs permission to do the same.

Bogotá.

Writing this from a different return flight on a holiday trip with the family - rebuilding in my head the play by play of the quick but memorable trip to Colombia a few weeks back. This one was special - and some trips stay with you longer than others.

The initial impressions and preconceived sentiment

Bogotá has a reputation. The statistics are a bit scary — it has historically ranked among the more dangerous capital cities in Latin America, with kidnapping and petty crime that show up in every travel advisory. The U.S. State Department has opinions, and I many others do too.

I postponed this trip three times. One of those times was tied directly to a U.S. government travel advisory.

But we have a large corporate office in Bogotá and a pretty sizeable presence. Colleagues I’d never met in person. A city that kept coming up in conversations and that I kept pushing to the next quarter. At some point the postponing itself becomes a decision — a choice to let the reputation win.

So I finally got the schedule to work and went.

And what I found bore almost no resemblance to what I’d been told to expect.

A city that is warm, a tad chaotic, alive, and genuinely welcoming in a way that caught me off guard. Food that deserves its own newsletter. And as luck would have it — a World Cup energy that made the timing of this long-overdue first visit something I’ll always remember.

This issue is about Bogotá. But it’s also about something bigger — the instinct to let worry make your travel decisions for you, and why that instinct, when it isn’t backed by real data, is almost always wrong.

Señor Wilson

Every trip has a character who sets the tone. In Bogotá that character was my driver.

I’ll call him Señor Wilson — because that is what he called himself, with a formality and warmth that immediately told me everything I needed to know about Colombian hospitality.

He was waiting for me at the airport with a sign, a firm handshake, and an opinion about the World Cup that he was not keeping to himself. By the time we reached the hotel I knew about his family, his predictions for Colombia’s performance, and his strong views on where to find the best bowl of ajiaco in the city — the traditional Colombian chicken soup that locals will tell you, correctly, you cannot leave Bogotá without trying. Rich, hearty, made with three kinds of potato and served with cream and capers on the side. The kind of dish that makes you understand a culture through a single bowl.

My Spanish is functional at best - I’ve struggled most of my life but I try. The kind that gets you through a menu and a basic negotiation but starts to struggle under real conversation. I am self conscious about it — acutely aware of the gap between what I wanted to say and what I could actually produce.

Señor Wilson didn’t care. He embraced it completely. When I stumbled he waited. When I got something right he acknowledged it with genuine encouragement. And when the conversation pushed past the limits of either of our vocabularies he simply pulled out his phone, opened his translation app, and kept going. Two people determined to actually talk to each other — one in broken Spanish, one in translated English — moving through the streets of Bogotá like it was the most natural thing in the world.

It was one of the warmest exchanges I’ve had with anyone on the road in years.

Over the course of two days Señor Wilson became something between a driver, a guide, and a local contact I genuinely trusted. That relationship didn’t happen by accident. It happened because I made the effort — imperfect and self conscious as it was — to meet him in his language rather than defaulting to my comfort zone.

He would prove essential the next day when I needed to get somewhere most visitors never go.

The Emerald

I learned last minute through a quick Claude search that Colombia produces some of the most extraordinary emeralds in the world. The Muzo and Chivor mines have been yielding stones of exceptional quality for centuries — the deep, vivid green that Colombian emeralds are known for is genuinely unlike anything produced anywhere else on earth. And you certainly won’t pay the egregious prices of the infamous NYC diamond district.

I had wanted to get my niece a special gift for her high school graduation - and this seemed to be a perfect opportunity. She was with us at the St. Regis Toronto for Father’s Day — the “Royal Suite” weekend from Issue #007. The emerald earrings was the other part of that celebration.

Getting there required Señor Wilson’s judgment and local knowledge. The emerald district — a concentrated stretch of jewelers and dealers in a specific part of the city — is legitimate, established, and well protected. The surrounding area required more awareness than a tourist street. But with the right driver and the right local contact it was entirely navigable.

Señor Wilson knew exactly where to take me. The “joyería” he recommended had been in the district for years — the kind of establishment that exists because of word of mouth and repeat business, not foot traffic. The stones laid out in front of me were remarkable. The earrings I chose for my niece were a deep, vivid green that photographs cannot do justice.

She was so visibly happy when she opened it. The kind of reaction that becomes a story she’ll tell forever — a Colombian emerald from a city I almost didn’t visit, found in a district I almost didn’t enter, made possible by a driver I almost didn’t get to know.

The same instinct that got me to that joyería — trust your preparation, trust your people — would be tested again before the trip was over.

The Political March

I did not plan to drive through a political campaign rally.

Apparently these things happen quite often in Bogotá.

Señor Wilson and I were moving through the city when the street ahead filled with people. Signs, chants, music, the particular energy of a crowd that believes in something (that weekend were the main government elections). The march spilled across the road and we were in the middle of it before either of us fully understood what was happening.

It was alive and colorful and I did what any curious traveler does — I held my phone out the window to capture it.

Señor Wilson shut that down immediately.

Quickly, assertively, no room for debate: Cierra la ventana. Guarda el teléfono. ¡Ahora!

Cell phone theft in Bogotá is not a minor issue. It is pervasive — phones snatched from open windows, from hands on sidewalks, disappeared into crowds before you’ve registered what happened. The parts reselling market is sophisticated and fast. Your brand new iPhone is worth considerably more to someone in that ecosystem than the inconvenience of reaching through a car window to take it.

I closed the window. I put the phone away.

The march rolled past us — peaceful, joyful, full of civic energy — and we continued on our way. I watched it through the glass instead. A slightly different experience. A considerably smarter one. Señor Wilson didn’t hesitate.

The phone stayed in my pocket for the rest of the drive. Colombia won their opening World Cup match that next day. The city had been building toward something all day — I just hadn’t known it yet.

The Welcome

I want to tell you about my colleagues.

We have a large team in Bogotá. People I had emailed, called, worked alongside across time zones for months — in some cases years — without ever being in the same room. I was sort of expecting a first visit to go like : Senior executive arrives from head office. The obligatory welcome. The polite handshakes. The careful, slightly formal energy of people who aren’t sure yet what kind of leader you are.

That is not what happened.

They built a welcome sign. They organized our town hall onsite— because they genuinely wanted to be there. They filmed the entire experience. They wanted to learn. Wanted to connect with the person behind the emails. The energy in that room was not the energy of people fulfilling an obligation. It was the energy of people who chose to show up. A culture of the company and our department they deeply believe in and find a way to give back.

That distinction matters enormously to me. You can feel the difference instantly and you never forget it.

Colombian hospitality is not a cultural cliché. It is something I experienced firsthand. The warmth that Señor Wilson showed me from the moment he held up that sign at the airport — it runs through everything there. The people, the culture, the city itself.

I left that town hall energized in a way that had nothing to do with the agenda and everything to do with the people in the room.

On Fear and Infrastructure

I’ll be honest — I almost didn’t come. Three postponements. A government advisory. Plenty of reasons to keep pushing it to next quarter.

I am glad I stopped postponing.

The infrastructure that allowed me to move through Bogotá with confidence wasn’t complicated. Know your driver. Know your hotel. Have local contacts established before you arrive. Know enough of the language to show respect even when you can’t sustain a conversation - this is age old travel advice but really does makes a difference. People in the service industries, especially in less developed countries, really appreciate when you try. It puts you in their world for even just a moment. And then trust your instincts, which are sharper than you think when they’re informed rather than just anxious.

Bogotá rewarded every bit of that preparation with something I didn’t expect: genuine warmth. The kind that makes you want to come back.

The Departure

Leaving for an early flight back to the states happened at 3am.

Señor Wilson picked me up for my departure flight. I expected him alone. Instead his wife was in the passenger seat — sweet, warm, and clearly happy to be there despite the hour. I still don’t know exactly why she came. Maybe he wanted her to meet the person he’d been telling her about. Maybe it was just the way they do things. Maybe both.

Whatever the reason, the three of us drove through a sleeping Bogotá in the early dark and it felt like exactly the right way to leave a city that had surprised me at every turn.

I’ve already told him I’m coming back.

Do This Before Your Next International Trip

Identify one city you have been curious about but talked yourself out of visiting because of reputation or unfamiliarity.

Do thirty minutes of actual research — not news headlines, not secondhand warnings. Talk to someone who has been. Read about the neighborhoods. Find a driver with strong reviews. Book a hotel that knows its city.

Then go.

Next week: The lounge stack. Every lounge I’ve actually been in, ranked honestly, with no regard for brand relationships or travel influencer diplomacy. Tuesday.

— JE

50 Weeks publishes every Tuesday. If this one made you want to book a flight somewhere that scares you a little — good. Forward it to someone who needs the push.

A $7,000 Hotel Suite. A $75 Annual Fee.

This issue is about cards and loyalty but as always it’s also about the infrastructure. Some people get emotionally invested in their cards but I stick to the basics so here we are. The card stack. Finally.

How I Think About Cards

Most people treat credit cards the way they treat airline seats — they take whatever they’re given, assume it’s fine, and never think about whether they’re leaving something on the table.

Road warriors cannot afford that approach.

Your card stack is infrastructure. It is the financial layer underneath everything else we talk about in this newsletter — the lounge access, the hotel status, the trusted traveler reimbursements, the points that turn a brutal travel schedule into something that occasionally produces a Father’s Day weekend in a Royal Suite.

More on that below.

The goal is not to collect cards or get run over by crazy annual fees. The goal is to be intentional — to build a small, deliberate stack where every card has a specific job and nothing is redundant. Here is mine.

Card One: Chase Marriott Bonvoy Premier The one that started everything.

I have had this card for nearly twenty years. I want to put that in perspective — I got this card when the annual fee was around $75 and the signup bonus was a lump sum of Marriott points that felt significant at the time. I had no idea what I was actually starting.

The card gave you nights toward elite status. Back then Silver, Gold and Platinum felt like the pinnacle — upgrades, late checkout, bonus points. I was genuinely excited. What I didn’t know yet was that the real benefits don’t start until Titanium and Ambassador level. The suite upgrades. The dedicated Ambassador who knows your preferences. The relationships with general managers that this newsletter has already talked about at length.

But you have to start somewhere. And this card started it.

Twenty years of loyalty to one brand compounds. I am now a Lifetime Platinum member — meaning that status is permanent regardless of how many nights I stay going forward — and an Ambassador, which is the top tier of the Marriott Bonvoy program. Those of you that know, know - lifetime Platinum gets you quite a few perks with Marriott, my favorite is generally the breakfasts and concierge lounge but there are many. Maybe we’ll get into that in a future issue.

Most recently, here is what that actually looks like in practice.

Father’s Day weekend — my daughter, niece, partner and I stayed at the St. Regis Toronto. Celebrating a high school graduation and just being together, we were upgraded, at no charge, to a two bedroom Royal Suite. A room that retails for approximately $7,000 per night during World Cup weekend in Toronto. We paid in points.

That upgrade didn’t happen because of a booking algorithm. It happened because of two decades of consistent loyalty, genuine relationships with hotel staff, and the kind of quiet preferential treatment that loyalty status enables at properties that know how to use it.

That is what a $75 annual fee started twenty years ago.

The card has evolved since then — the fee is higher now, the benefits more sophisticated — but the principle remains the same. Concentrate your hotel spend on one brand. Build the relationship. Let the loyalty compound. Pretty simple - I’m always genuinely surprised when people bounce around hotel chains especially when your company is reimbursing your corporate travel.

Card Two: Chase Aeroplan The one that solved the Air Canada problem.

If you’ve been reading since Issue #002 you already know part of this story. It’s the card I think about least and use the most in the first few months of each year to get the Air Canada status.

Preferred boarding on Air Canada as a standard card benefit — not a status challenge, not something you earn over time. Zone 2 from day one. Overhead bins still available. Gate agents who won’t make you check your carry on. For anyone who moves through Canadian airports with regularity this alone justifies the card.

Add the Aeroplan points that transfer across the Star Alliance network and the NEXUS fee reimbursement we covered in Issue #003 and this card is doing three jobs simultaneously.

One card. Three problems solved.

Card Three: Bank of America Preferred Rewards Cash Back Everybody should have one like it.

Here is the unglamorous truth about card strategy that most travel content ignores: after you’ve met your spend obligations on your primary cards, every additional dollar you put on a points card is often earning at a rate that cash back frequently beats.

The Bank of America Preferred Rewards Cash Back card is what I use for everything that doesn’t belong on the other cards. But here is what makes it genuinely powerful for me specifically — and potentially for you:

Because I am based in the U.S. I’m not able to have my Primary financial accounts with the Bank I work for based in Canada. So my primary accounts are with Bank of America and Merrill Lynch - checking, savings, brokerage, IRA — I qualify for their Preferred Rewards program at the highest tier. That means my cash back rate is boosted significantly above the standard rate. Years of loyalty to one financial institution compounds the same way years of loyalty to one hotel brand does.

No category restrictions. No points to manage. No redemption strategy. Just cash — deposited automatically, accumulated quietly, and meaningful in a way that surprises people when they actually run the numbers. Given my spending patterns on the road I get thousands of dollars back each year. Not points. Not miles. Actual money.

The travel world is obsessed with points optimization. The Preferred Rewards cash back is the play that quietly outperforms for high spenders who bank with BofA and Merrill. If that’s you and you’re not using this card or one like it, you’re leaving real money on the table.

Card Four: American Express Platinum The one with a twist.

Here is where it gets interesting.

I don’t pay the full Amex Platinum annual fee. My partner holds the primary card — and has kindly extended an additional card to me for a nominal fee.

The additional cardholder model is an underused strategy that gets you the majority of the benefits at a fraction of the cost. Here is what those benefits actually look like in practice:

Centurion Lounge access. I’ll be honest — the Centurion Lounges are fine. Generally better than most alternatives in a busy terminal, the food is decent, and the bar is reliably stocked. They’re not the transcendent experience the travel internet makes them out to be, especially at peak hours when they’re crowded. But they are consistently better than sitting at a gate, and on the days when they’re quiet they’re genuinely pleasant.

What I will say is that they occasionally do something fun that elevates the experience. Right now, with the World Cup in full swing, several Centurion Lounges have set up dedicated martini stations — a small touch that makes a long layover feel like less of an ordeal. It’s the kind of detail that reminds you someone is paying attention.

Priority Pass and partner lounge access. The Platinum card’s lounge access extends well beyond Centurion. Priority Pass membership opens hundreds of lounges globally — on international itineraries this is particularly valuable.

Travel credits and hotel benefits. Fine Hotels and Resorts program, airline fee credits, hotel status matches — worth reading in full if you haven’t.

The additional cardholder economics are simple: my partner pays the primary fee, I pay a meaningfully lower additional cardholder fee. We both get lounge access. We both get the travel benefits. If you have a partner or spouse who travels — have the conversation.

We’ll get into a lot more detail on lounges in a future issue.

The Stack In Summary

Four cards. Each with a specific job. For me:

• Chase Marriott Bonvoy — hotel status, points accumulation, the long game of loyalty

• Chase Aeroplan — Air Canada boarding, Star Alliance points, NEXUS reimbursement

• Bank of America Preferred Rewards Cash Back — overflow spend, actual money back, no management required

• Amex Platinum — lounge access, travel benefits, the texture of the road

This may look different for you. Build your own stack to reflect your banking relationships and travel patterns — matching mine may not make sense for your scenario.

The road is going to cost you money regardless. The question is whether that spend is building something or just disappearing.

Build something.

Do This Before Your Next Trip

Look at your last three months of travel spend. Add up every dollar that went on a card that wasn’t earning you something meaningful.

That number is your starting point.

Next week: Bogotá. The food, the running, the people, the emeralds, and the unexpected. Tuesday.

— JE

50 Weeks publishes every Tuesday. Forward this to someone who is still putting everything on a single airline card and wondering why their points never add up

Sleep Debt?

Writing this on the flight home from Bogotá, Colombia. Up at 3:00am to catch an early flight. Writing about sleep debt. Ohh the irony. More on Bogotá in a future issue — it deserves its own.

This issue started with my partner.

A toddler, she reminded me, already knows everything we spend years trying to relearn.

Three things. That’s all a human being needs to function. Sleep. Nutrition. Love. The entire list. Everything else — is built on top of those three things. The foundational “infrastructure”. Remove any one of them long enough and the house begins to crumble.

If you allow it - the road is very good at chipping away at those three things. And one could probably argue that sleep debt is the worst of the three. But sleeping better is only part of the answer. The debts that accumulate fastest — the love debt, the friendship debt, the presence debt — don’t show up on a fitness tracker. They show up in the people around you. And they might matter more than the sleep.

The home week is where you pay them back. But only if you treat it like infrastructure rather than a pause between the real thing.

The Three Debts That Actually Matter

I will be specific as I always try to be.

Sleep debt is real and measurable. The research is unambiguous — sustained sleep deprivation affects cognitive performance, emotional regulation, decision making, and physical recovery. I have an Oura ring and it mocks me constantly about my sleep debt. Most executives who travel heavily are running a chronic deficit they’ve learned to normalize. They call it being busy. Their bodies call it something else.

Love debt is the one that accumulates the fastest and gets noticed the latest. It’s not dramatic. It’s the gradual erosion of presence. The dinners where you’re physically there and mentally in the inbox. The weekends where you’re home but not really home. The conversations that happen in the margins of everything else. I may or may not ever admit this played a part in the failure of my first marriage (see Issue #004).

Friendship debt is the quietest of the three. The friends who stopped texting or calling because you were always traveling or working. (Shout out to my buddy from years back, Steve, who never stopped!) The relationships that required maintenance you kept deferring. The connections that were load-bearing in your life before the road took over and that you haven’t thought about in six months.

All three compound. All three are repayable. But you have to be intentional about it.

How You Actually Pay It Back

This is the part most wellness content skips because it requires specificity rather than inspiration.

For love debt the answer is protected time that belongs entirely to the relationship. Not grand gestures — those are guilt responses, not investments. What works is the ordinary and the consistent. For me specifically, four hours on a golf course with each other, talking, catching up and being fully present without the constant interruption of phones, texts and emails. The long walk with no destination and just being together.

A senior executive I know takes dance lessons on Friday nights with his spouse during home weeks — not because either of them necessarily wanted to learn to dance, but because it created an hour of holding each other, to be close, to show affection in the middle of an otherwise relentless schedule. The form doesn’t matter. The protected time does.

For friendship debt the answer is simpler than people make it: reach out to one person you’ve been meaning to reach out to. Not a group text. A direct message or a call to one specific person. The road gives you something useful here — a “what’s up checking on you” text takes 20 seconds to send when you are waiting on the tarmac.

For sleep debt — keep reading. There’s a practical recommendation at the end of this issue.

This Isn’t Just for Road Warriors

You don’t have to be on a plane every week to run these debts. You can accumulate all three sitting at a desk in the same city, in the same house, while being mentally elsewhere.

The question is the same regardless of how many miles you log: are you making intentional deposits into the relationships and experiences that actually sustain you? Or are you running a deficit and calling it busy?

The debt compounds either way. The only variable is whether you’re paying attention.

Now. About That Sleep Debt.

I promised you a practical recommendation and I want to be upfront about something before I make it: this is not a sponsorship. Nobody is paying me to say this. It is a product I discovered, pay for myself, and have been using long enough to have an opinion worth sharing.

The product is CBDfx — specifically their CBD and melatonin sleep gummies.

I know. I was skeptical too. I am not a wellness influencer and this is not that kind of newsletter. But here is what happened.

I was running a significant sleep deficit after a particularly brutal stretch of travel and admittedly after a fun long golf weekend with my closest pal — he tossed back a few CBDfx gummies, after a late night of dining and boozing. He woke up bright eyed and bushy tailed. I woke up and popped 4 Advil. That evening I tried CBDfx with exactly zero expectation. It really did work for me.

The difference was notable enough that I kept using it. The specific thing that sold me: no grogginess. Most sleep aids — melatonin included at higher doses — leave you foggy the next morning in a way that is genuinely counterproductive. CBDfx doesn’t do that. You sleep. You wake up. You function.

I track my sleep with an Oura — which if you travel heavily and haven’t looked into is worth its own issue — and the difference in my sleep quality scores since adding CBDfx to my routine has been measurable. Not marginal. Measurable. Sleep scores in the high 80s and 90s.

It’s not a miracle. The debt still accumulates. But this is the most effective tool I’ve found for paying it back efficiently on the nights when sleep is the one thing I can actually control.

It would be nice to be sponsored - but I am not ! Not affiliated. Just what works for me.

Do This Before Your Next Trip

Identify which of the three debts has accumulated the most. Sleep, love, or friendship.

Make one specific deposit this week. Not a resolution. Not a plan. One actual thing.

Then carry that credit onto your next flight.

Next week: The credit card stack I actually travel on and some funny recent lounge stories - not terribly interesting for everyone but I’ve been promising this one for five issues. It’s finally happening. Tuesday.

— JE

50 Weeks publishes every Tuesday. If this one resonated — forward it to someone running a deficit they haven’t named yet.

Walk Good.

Writing this on return from starting the week in Toronto and ending in Kingston. But it’s Jamaica that’s on my mind. Specifically two words a colleague said to me as we parted ways this week. I hadn’t heard them before. I haven’t stopped thinking about them since.

Walk Good.

In Jamaican Patois — the creole language born from the island’s colonial history, its African roots, and its joyful reinvention of English — walk good is how you say goodbye.

But it means considerably more than that.

It means go safely. Go with intention. Go as your best self. The kind of hospitable blessing that most languages don’t have a direct equivalent for — the gracious bid that the person leaving will move through the world well. Not just arrive safely, but travel with grace. With purpose.

A colleague shared it with me as we parted ways in Kingston, and given my ear is not quite yet caught on to the nuances of Patois, I asked him politely to repeat. Casually, warmly, the way you’d say it to someone you genuinely wished well.

I’ve been thinking about it ever since.

Walk good is not just a farewell. It is, accidentally, the most precise description I have ever encountered of what this newsletter is actually trying to help people do.

We talk a lot in these pages about travel infrastructure. The running. The gym membership. The NEXUS program. The systems that make a relentless schedule survivable. But all of that infrastructure exists in service of one thing: the ability to move through the world well. To show up at the destination — the airport, the hotel, the boardroom, the front door of your own home — as a functioning, present, energized human being.

Walk good.

Ya Mon.

What Walk Good Means - 50 Weeks

That phrase has been quietly describing this 50 Weeks newsletter since Issue #001. Here is what I mean.

• Build the infrastructure. The card stack. The gym membership. NEXUS. The house car account. The systems that make the road survivable are worth the effort to build before you need them.

• Protect something that belongs entirely to you. A marathon. A golf game. A run at 5am. Reading. Listening to soundtracks for movies for inspiration. Guitar. Whatever it is — it is not optional. It is load-bearing.

• The airport is an office. Treat it like one. Where you park, how you board, which terminal you choose — these are decisions, not accidents. Make them deliberately.

• The home weeks are as important as the road weeks. You cannot walk good on a depleted account. The deposits you make when you’re home are what fuel you when you’re not.

• The best travel hack is also the oldest one. Be kind. Be present. Be the guest worth remembering. None of the infrastructure matters if you show up depleted, distracted, and running on empty.

I didn’t expect to find the thesis of this newsletter in a Kingston farewell. But the road has a way of teaching you things when you’re paying attention.

Next week: Sleep debt. You think you know what it is. You don’t. Not all of it. Tuesday.

— JE

50 Weeks publishes every Tuesday. If this one hit close to home — forward it to someone who needs to read it. Road warrior or not.

The Decision I Made at Mile Four

Writing this from my home office in New York before the next 4 week travel stretch. Commuting downtown NYC the last couple of mornings, I’ve watched runners moving up and down the West Side Highway in the early dark. I’ve been one of them. There is something about the Battery Park waterfront at 6am that makes the rest of the day feel very manageable. This issue is about that.

There is a version of the road warrior lifestyle that looks impressive from the outside and slowly hollows you out from the inside.

The minibar that starts to feel like a reasonable decision at 11pm. The workout that keeps getting pushed to tomorrow. The goals that existed before the travel schedule took over and quietly never came back.

I’ve lived that version. Most heavy travelers have.

This issue is about the alternative. Not the Instagram version of wellness — the green juice and the meditation app. The real version. The one that actually works when you’re exhausted and the last thing you want to do is lace up.

Before I Lose Half of You!

This is not a running newsletter. And this is not a pitch for marathon training.

It’s about this: the road warrior lifestyle will consume every hour you give it. It has an infinite appetite. If you don’t protect time for something outside of it — something that exercises your mind and body in a completely different register — it will take everything and give you back a version of yourself that is less sharp, less present, and less effective in the very meetings and boardrooms you sacrificed to be in.

It doesn’t have to be running. It can be music. Photography. Yoga. 10,000 Steps. Learning a language. It can be anything that requires you to show up as a human being rather than a professional.

The only requirement is that you protect it. That you treat it with the same seriousness you treat a board meeting or a call with your boss. That when someone tries to schedule over it, you have a reason to say no.

Build it into the infrastructure. Because if it isn’t infrastructure, it’s just a good intention — and the road has a long history of consuming those.

The Running and the Thinking

Here is the most personal thing I will write in this newsletter.

Every significant decision I have ever made in my life — I mean the real ones, the ones that changed the actual shape of my life — was made while running.

Buying and moving homes. The clarity that comes at mile four of a run, when the analytical brain finally stops arguing with itself, has saved me from bad decisions and pointed me toward good ones more times than I can count.

Career changes and job moves. Some of the most consequential professional decisions of my life were not made in boardrooms. They were made on running paths, often alone, often early, when the only input was my own instincts with nowhere left to hide.

Major organizational decisions. Some of the biggest calls I’ve made as a leader — restructuring teams, making difficult talent decisions, knowing when to push and when to step back — came into focus on a run. Not in a meeting room with a deck in front of me. Alone, moving, thinking.

The right hire. I’ve made some of the best talent decisions of my career by letting a run do what a reference check never can — gut check a decision I’d already made intellectually but hadn’t yet made honestly.

My divorce.

One of the hardest things I have navigated as a human being. Running didn’t make it easier. But it gave me a place to process it honestly — without an audience, without performance, without the need to have the right answer before I was ready. The miles held a lot of grief that had nowhere else to go.

I don’t know the neuroscience of why running unlocks something that a desk or a meeting room cannot. What I know is that for me — and for a lot of the road warriors I know who run — the miles are where the real thinking happens.

If you have a decision you’ve been circling. A conversation you’ve been avoiding. A question you haven’t been able to answer because there’s always something else in the way — go for a run. Not to solve it. Just to give it some space.

You might be surprised what comes up by mile three.

The Six Majors

For me, the thing I chose to protect was running. And right before COVID I set out to run all six World Marathon Majors. Tokyo. Boston. London. Berlin. Chicago. New York. I’ve done all six now. It is one of the things I am most proud of — not because of the times, not because of the medals, but because of what it took to complete them while living the life this newsletter is about. Fifty weeks a year on the road. Early alarms in cities I sometimes couldn’t name without checking my phone. It fueled something in me that I didn’t know was running low until I started filling it back up.

Not because I’m fast. Not because I had a sponsor or a coach or a perfect training plan. Because I needed something outside of work that had a scoreboard. Something that didn’t care about my title or my calendar or how many cities I’d been in that week. Something that would be there at 5am whether I felt like showing up or not.

Training for a marathon as a road warrior is not complicated. It is just inconvenient — which is different. Mornings work. Early evenings before team outings work. Most cities have running paths that are genuinely beautiful pre-dawn when nobody else is on them. And if you can find a running club or a colleague (or a super inspiring boss - shout out to TK) who runs in the cities you visit regularly, even better. The accountability of a running partner in a city that isn’t yours is surprisingly powerful.

The logistics are simpler than people think. Running shoes, a pair of shorts, and thirty to sixty minutes. That’s the entire barrier to entry. You are never too busy for that. You are sometimes too willing to convince yourself that you are — which is a different problem entirely.

The Infrastructure of a Life

We talk a lot in this newsletter about travel infrastructure. The card stack. The gym membership. The trusted traveler programs. The systems that make a relentless travel schedule survivable.

But there is a deeper infrastructure underneath all of that. The one that determines whether you show up to all of those airports and hotels and meetings as the best version of yourself or a depleted approximation of one.

For me, running is load-bearing in that infrastructure. Remove it and things start to fall.

Find your version. Build it in. Protect it like a meeting you cannot move.

The road will take everything you give it. Make sure you’re giving it the right things.

A Question for the Road Warriors Reading This

I’ve told you what keeps me going. Now I want to hear from you.

What do you do to keep your energy levels high on the road? Not the obvious stuff — the sleep hygiene tips and the hydration reminders. The real thing. The one that actually works for you when the travel schedule is relentless and the tank is running low.

Reply and tell me. The best answers will shape a future issue — and I know this community has some genuinely good ones.

Do This Before Your Next Trip

Identify one thing — one goal, one hobby, one practice — that has nothing to do with work and that you have been letting the travel schedule crowd out. Put it on your calendar for your next trip. Not as a hope. As a commitment.

Then show up for it the way you show up for everything else.

Next week: The things you see when you travel this much. Most of it blurs. Some of it doesn't. Three moments from the road that I haven't been able to shake. Tuesday.

— JE

50 Weeks publishes every Tuesday. If this one resonated — forward it to someone on the road who needs to read it.

The Moves Most Road Warriors Never Make — But Should

Somewhere between my second hotel this week and my sixth airport since early May, I realized I've become the person who has opinions about parking garages. This is apparently who I am now. You're welcome.

This week is about two things that sound small but quietly separate the road warriors who thrive from the ones who just survive.

One is a government program almost everyone gets wrong. The other is a membership almost everyone dismisses as a luxury.

Both have changed how I travel. Let’s get into it.

NEXUS: You Probably Want It — But Not For the Reason You Think

Everyone talks about NEXUS like it’s a border crossing superpower. Dedicated lanes, no lineups, breezing through immigration while everyone else shuffles forward in a miserable single-file parade.

The reality? It helps. But on a busy day at Pearson or one of the other Canadian airports, you might shave three minutes. Maybe five. It is not the game changer the travel influencers make it out to be.

Here’s what it actually is: a travel infrastructure decision that pays for itself before you even use it.

What NEXUS Actually Covers — And It’s More Than You Think

Most people think NEXUS is one program. It’s actually three in one:

Global Entry privileges in the US. When you land from an international flight into a US airport, you use the Global Entry kiosks. No separate Global Entry application required.

CANPASS privileges in Canada. The Canadian equivalent for arriving into Canadian airports. One card, both directions, both countries covered.

CATSA Plus security lanes at major Canadian airports. This is where NEXUS quietly saves more consistent time than immigration ever will. Faster security, shoes stay on, laptop stays in the bag. If you move through Pearson, Calgary, or Vancouver regularly this is a genuine daily quality of life improvement.

TSA PreCheck on US flights. Your NEXUS number functions as your Known Traveler Number. Enter it when booking any US flight and you’re in the PreCheck lane automatically. If you don’t have standalone PreCheck, NEXUS covers it.

RFID land border crossing. If you ever drive between Canada and the US, the card works at dedicated RFID lanes at land crossings. Faster than a passport, no comparison.

One card. Five programs. And here’s the part that stops most people cold: it costs $120 USD for five years. That’s $24 a year. Still remarkably underpriced for what it covers — and if you’re already carrying the Chase Aeroplan card we talked about last week, the $120 fee is fully reimbursed as a statement credit every four years. Effectively free. The Amex Platinum covers it too. If you have either card, there is genuinely no reason not to have NEXUS.

Got kids? Children under 18 are admitted to the program free of charge when a parent or legal guardian is a member. If you travel with family across the border at any frequency, this alone is worth the application.

The Global Entry Extension Trick

Here’s the insider piece most people miss entirely.

If your Global Entry is expiring and you hold NEXUS, it automatically extends your Global Entry for five more years. No reapplication. No new interview. No fee. It just happens.

For anyone who crosses the border regularly this is significant. Global Entry renewal has become increasingly slow and annoying. NEXUS sidesteps the entire process.

The Walk-In Secret at Toronto Pearson

Now for the part nobody tells you.

The conventional wisdom says to apply online, wait for an interview slot — which can take months — and potentially travel to some far-flung border crossing because that’s the first available date. I’ve heard of people driving to Buffalo for this. Respect the commitment. There’s a better way.

Walk in at Toronto Pearson. Departures level, Terminal 1.

Officially, they don’t do walk-ins. Unofficially, show up early morning or mid-afternoon when things are quiet and they will generally take you. It doesn’t work every single time — nothing here is guaranteed — but I and people I know have done it successfully. Be polite, be prepared with your documents, and be patient. The worst they say is come back.

One important prerequisite: you need to have an interview already scheduled in the system — even if it’s months away at another location. The walk-in essentially moves that appointment up. Don’t show up cold without one.

Important: the Pearson walk-in covers the Canadian side of your NEXUS interview. You still need to complete the US Customs and Border Protection interview separately — but you can handle that through pre-clearance right at Pearson before boarding any US-bound flight. No separate trip. No Buffalo.

The whole process is far more approachable than the official portal makes it appear. Don’t let the wait times discourage you from just showing up.

Have a NEXUS or Global Entry story — good or bad? Reply and tell me. Collecting them for a future issue.

Enough about borders. Let’s talk about what you do with yourself once you’re through them.

Why I Joined Equinox and Never Looked Back

Let me tell you about 4:15am in a hotel I won’t name.

The fire alarm went off. Not a gentle chime. The full thing. Lights. Horn. The kind of alarm that doesn’t give your brain a chance to negotiate. One second asleep, next second standing in a hallway in a t-shirt trying to remember which floor I was on.

Full evacuation. Robes, confusion, someone’s roller bag, a couple who looked like they were reconsidering every life choice that led them to this parking lot at this hour. We stood outside in the dark while the building got cleared. By the time I was back in my room it was past 5am and sleep — real sleep — was simply gone.

I lay there for about four minutes doing the math. Then I got up, laced up, and went to the gym.

By 7am I had a full workout in, showered, had coffee, and was sitting at breakfast genuinely ready for the day. Not surviving it. Ready for it. Three more hours of staring at the ceiling would have produced the opposite. The fire alarm didn’t ruin that day. It accidentally made it one of the better ones.

That is not a coincidence. That is a system.

Why Equinox Specifically

There are cheaper gym memberships. I know. But the Equinox all-access membership works across every location in every city they operate — and in the cities I travel most, they are everywhere. New York, Toronto, Miami, Dallas, South Florida, Westchester, Greenwich. You walk in, you work out, you shower in a facility that is genuinely excellent, and you leave feeling like a functioning human being.

The shower alone is worth more than you think when you’ve been in transit for six hours.

A few things I’ve learned:

Yes, it’s obvious. Most people still don’t do it: skip the hotel gym when you can. Most hotel gyms are three treadmills and a cable machine in a room that smells like it’s been sealed since 2009. An Equinox nearby is almost always a better experience.

Hit the gym before team dinners and group outings, not after. Happy hour is a trap — two drinks, heavy apps, and you wake up feeling worse than the day before. Forty-five minutes before a team dinner and you show up sharper, more present, and you’ll actually remember the conversation.

The corporate discount is real. Many large employers have negotiated Equinox rates meaningfully below the published price. Ask your HR or benefits team before you pay full price. If you want specifics on how to find or negotiate one — DM me. Happy to help.

Morning workouts are non-negotiable for me on the road. Not because I’m super disciplined. Because I’ve learned what happens when I skip them. The road is relentless. The gym is the one hour of the day that belongs entirely to you. (Except when you run into friends out of nowhere who look like their twin brothers randomly on a Monday morning in NY! - shout out DH !!)

Curious what cities I’ve found the best Equinox locations in? Reply and I’ll send you my shortlist.

The Pattern Underneath Both of These

NEXUS and Equinox seem like unrelated tips. But they’re actually the same idea: the road warriors who travel well are the ones who build systems in advance rather than reacting to whatever the day throws at them.

A fire alarm at 4:15am doesn’t have to ruin your day. That only happens when the infrastructure is already in place.

Build the infrastructure.

Do This Before Your Next Trip

Go to the NEXUS portal right now and check your expiry date. If you don’t have it yet — start the application today. If you’re expiring within 18 months — start the renewal process now. And if you’re in Toronto anytime soon, you already know where to go. If you want an Equinox referral with a decent corp rate you know how to reach me!

Next week: Training for 6 World Major Marathons as a road warrior.

— JE

50 Weeks publishes every Tuesday. If this helped you, forward it to one person who crosses the border regularly. They’ll thank you.

Ground Truth: Why I Stopped Taking Ubers to the Airport and Never Looked Back

There is a particular kind of misery that frequent travelers don’t talk about enough.

It’s not the middle seat. It’s not the delayed flight. It’s the Sunday evening Uber surge — the driver who can’t find departures, the driver who just finished a Turkish kebab and has made peace with the fact that you will smell it for the next 47 minutes, or the one that knows better than the GPS. And then you give him four stars because you feel bad and swear you’ll never do it again.

You do it again.

After one too many of those, I rebuilt my entire ground travel approach. What follows is what actually works — and what I wish someone had told me three years and approximately 200 bad Ubers ago.

Park Your Own Car at LaGuardia. I’m Serious.

I know. Bear with me.

Terminal B has a dedicated parking garage connected directly to the terminal via a short covered walkway. No shuttle bus. No waiting in the rain. No driver doing three slow loops around arrivals because he can’t figure out which lane is his.

Here’s the math most people never run: a car service from Westchester to LGA and back costs $180–$250 on a normal day. More with surge. The Terminal B garage runs $35–40 per day — and cheaper if you book online 24 hours in advance. On a two-day trip you’re already ahead. On a full week trip it’s not even close.

But the real value isn’t the money. It’s the control. Your car. Your music. Your timeline. No negotiating with an ETA that keeps moving. No explaining to someone why you need to be at departures, not arrivals.

My CFO would probably thank me if I told him. I haven’t told him. (Some advantages are worth keeping quiet.)

One important caveat: avoid JFK right now if you can. The ongoing terminal renovations have turned that airport into a genuine ordeal — Uber or not. I’d give it another four years before it’s functional again. LGA and EWR and even HPN are your friends in the interim.

Curious what my full ground travel setup looks like in cities where I can’t drive? Drop a reply — if enough people ask I’ll do a full breakdown.

When You Can’t Drive — Do This Instead

Sometimes you’re in a different city, on a longer trip, or the parking math just doesn’t work. In those cases, the mistake most road warriors make is defaulting to Uber out of habit.

A few things that work considerably better:

Build a local car service account in every city you visit regularly. Not an app. An actual account with an actual operator you’ve spoken to. Call them. Give them your preferences. They remember you. The drivers are consistent, the cars are clean, and there’s no surge pricing at 5am when you desperately need to be somewhere.

The hotel house car is one of the most underused perks in travel. Most luxury properties have a house car or a preferred car service relationship. If you’re a known guest, the front desk will arrange it without you asking twice. It can be complimentary within a certain radius — nobody advertises this, so you have to ask. But ask before you assume, because the alternative can be a $500 ride to the airport in a very nice Mercedes that nobody warned you about.

Confirm your exit the night before, not the morning of. It sounds obvious. Almost nobody does it consistently. (FWIW - I ALWAYS take UP Express to Pearson when in Toronto, I don’t bother with Ubers or the traffic... super consistent and you literally never have to step foot outside via the Path, even in the super frigid Toronto tundra winters)

How to Board Air Canada Like You Paid for the Front of the Plane

This one took me longer to figure out than it should have — and it costs almost nothing.

Air Canada boards in zones, and Zone 2 is where you want to be. You board immediately after business class and top-tier status holders. Bins still have space. The aisle isn’t a contact sport yet. You pick your preferred seat the day before without paying for it, and the gate agents won’t make you gate-check when you’re in this zone.

Quick sidebar: building status on Air Canada has gotten genuinely harder since they moved to SQDs. The short-haul Toronto and New York commutes barely register. Long-haul business class used to be the fast track — those days feel further away now. So you need other tactics.

(Side note: I once had a boss — fifteen-plus years ago — who would publicly call out anyone on the team who checked a bag. At town halls. By last name. “Check A Bag — [insert name here].” Dramatic? Yes. Effective? Absolutely. I have not checked a bag since. You’re welcome.)

The simplest way to land Zone 2 boarding without elite status: the Chase Aeroplan card.

Preferred boarding on Air Canada is a standard card benefit. Not a status challenge. Not something you earn over time. It’s just there, from day one. Add in Aeroplan points that transfer across the Star Alliance network and it’s one of the better travel cards for anyone who moves through Canadian airports with any regularity. If you’re Canadian, I believe TD Bank has a comparable product — worth looking into.

Next month I’m doing a full breakdown of the card stack I actually travel on. If you want to be notified when that drops, make sure you’re subscribed.

The Best Travel Hack Is Also the Oldest One

I want to close this week with something that has nothing to do with apps, cards, or parking garages.

This past winter I spent a lot of time at one particular property in West Palm Beach. (DM me if you want the name — happy to share directly.) Over the course of several stays, I got to know Phil — the Director of Food and Beverage. Not by engineering it. Not by mentioning my status or my travel frequency. Just by showing up, being genuinely warm, and treating him like the talented professional he clearly was.

Honestly? I think what sealed it was my daughter. She was kind and curious and lit up every breakfast, and Phil noticed. He started stopping by our table every time we sat down — not as a courtesy, as a genuine connection. When she left her Apple Watch at the pool one weekend, Phil spent thirty minutes personally tracking it down.

By our second visit of the season, he handed me his business card.

That card has been worth more than any loyalty program I’ve ever enrolled in. A text gets answered. Rates that don’t exist online get found. Access that isn’t publicly available quietly becomes available. Not because of status — though carrying Marriott Ambassador certainly doesn’t hurt — and not because of spend. Because we were kind, consistent, and treated a talented person with the respect his role deserved.

Every serious road warrior I know has a version of this story. A sommelier who holds the last table. A concierge who finds the reservation that doesn’t exist. A front desk manager who upgrades you before you’ve even asked — because they remember your name without looking at the screen.

You cannot manufacture these relationships. But you can absolutely create the conditions for them. Slow down occasionally. Be present. Treat the people running these properties as the professionals they are. Let your kids be kind.

The world runs on relationships. The airport, the hotel, the restaurant lounge at 6am on a Tuesday. All of it.

Be the guest worth remembering.

Next week: Is NEXUS actually worth it — or just another travel flex? I’ll give you the honest answer, including what most people get wrong about how to use it and a trick to get Canadian border appointments scheduled immediately !

— JE

50 Weeks publishes every Tuesday. If this resonated, forward it to one person who lives in airports. And if you have a Phil in your life — reply and tell me about them.

I was in a Centurion Lounge earlier today — LGA, which tells you everything you need to know about my life — when I overheard someone explaining to their travel companion which credit card to use at the bar.

They were wrong. Confidently, completely wrong.

That moment is why I’m writing this.

Most travel content is produced by people who took one great trip, figured out how to get a business class upgrade, and decided they were experts. They optimize for the vacation. The aspirational getaway. The once-a-year honeymoon redemption.

I optimize for survival.

I’ve been on a plane every single week for over 2 years, and before that, I traveled for 18 years at least once or twice a quarter Internationally. Not as a travel blogger. As an executive running real work across time zones, with back-to-back cities, Sunday evening departures, boardroom commitments the morning after a red-eye. The airport isn’t a gateway to adventure for me — it’s my office, my dining room, and occasionally my gym.

That changes what matters.

What this newsletter is actually about

50 Weeks is written for people who live this life — or want to understand it. Senior executives, road warriors, and anyone who has ever calculated whether a connection through Charlotte or Newark or even Westchester county airport is worth the risk.

Every week I’ll cover one or more of the following:

• Points as a financial instrument — not hobby collecting, serious optimization

• Lounge and hotel intelligence — reviewed with real frequency, not a one-time visit

• The executive travel stack — tools, tactics, and what your company should be negotiating on your behalf

• Airport and routing intelligence — the stuff that only comes from repetition

• The lifestyle layer — staying sharp, healthy, and occasionally finding a good golf course worth rerouting a trip for

• Guaranteed healthy Sleep aids that actually work and are all natural.

• And other random stuff. How to get Corp discounts at hotels when that rate is no longer available. How to get upgrades through tricks and tips. Etc. sometimes it works sometimes it doesn’t.

But generally there is always a way. That’s my motto

No affiliate bait disguised as advice. No “top 10 packing tips.” Just what actually works, from someone who has no choice but to get it right.

A few things about me

I’m a senior executive at a large financial institution. I travel for work, not for content. This newsletter is a side project born out of equal parts boredom in airport terminals and genuine frustration with how badly the existing travel media serves people like us.

I’m based between New York and Toronto, Canada and in the winter Florida where I sneak away for weekends to avoid the cold, which means I have opinions about both Air Canada’s Maple Leaf Lounges, Centurions, American’s Admiral and the freebie Premier Plaza and of course the occasional drive from West Palm to PBI on a Sunday night.

I’ll leave it at that for now.

What’s coming in the next few issues:

• The credit card stack I actually use — and why most executives are leaving serious money on the table

• Terminal 4 vs Terminal 8 at JFK — a real comparison for people who actually have to choose

• How to think about points as a balance sheet item, not a reward

If any of this resonates, subscribe. Forward it to one person who lives in airports. That’s all I need to get started.

See you next week — probably from a lounge.

— J

50 Weeks publishes every week. Free to start. Paid tier coming soon for deeper dives