[Seven days to launch] I’m starting to feel the pressure. Which feels perfectly normal for this time of year.

It’s the Wednesday before Thanksgiving and a week before I leave on this trip. Truthfully, I feel more stress about the turkey and the pies than I do about the trip, but that is the way I always feel on the Wednesday before Thanksgiving.

I’ve taken some steps to lessen my stress this Thanksgiving. Instead of pulling an all-nighter and making (the traditional) “One Pie Per Person,” desert buffet, I’m only making one pie, one pumpkin cheesecake (with a gingersnap crust) and I have purchased one of my brother-in-law’s excellent pecan pies. And I’m not going nuts with the turkey either. I’m preparing the Julia Child deconstructed turkey recipe, brined in apple cider.

I still feel a little under the gun because of the trip. here is a list of the things I need to get done before I blast off.

• Write to some clients reminding them about my trip and the time zone differences.
• Call my banks and credit card companies and ask them to not shut off my funds if they see a charge in Bolivia or Thailand.
• Covid and flu vaccines.
• Basement clean-up. + Spider eradication + Spray foam insulation (ew…)
• Yard clean-up.
• Enroll in health insurance for 2026.
• Update the Home Users Manual for my wife (I’ll write a post explaining this soon).
• Make copies of critical documents to have as a backup.
• Download a few hours of TV shows and movies.
• Random paperwork.
• Work up a mock-up for a new podcast that focuses on my trip (more later).
• Set-up a YouTube channel for the trip.

But before all that, it’s pie, turkey and family. 🙂

Let’s go.

[Eight days to go] I’m traveling with three pieces of Apple hardware. It might seem like overkill, but there’s some sound reasoning in my choices.

Being a writer means I kind of need a dedicated laptop with me. It’s hard to write posts like this without one. Yes, I could have chosen an iPad with a Magic Keyboard, but that ends up being around the same weight and bulk as my MacBook Air. I also manage a half dozen websites, execute design, write strategy documents and proposals, so I feel better having a machine that can access multiple email accounts and serve as a clearing house for client work.

I chose the iPad Mini because of its weight and size. I purposefully keep email and social media away from the iPad Mini, so it can have plenty of storage space and serve as a dedicated tablet for travel documents, maps, lists, and entertainment. It fits nicely in my sling bag, which means it can go with me when I explore a city, or be close at hand when I want to access episodes of The Diplomat on a long flight. The Apple Pencil Pro is a nifty tool as well. It allows me to take a giant whiteboard with me everywhere I go by using Apple Freeform. And it allows me to eliminate the need for a paper notebook.

If I could jettison the iPhone, I would. But I do need it to make actual phone calls. Plus, it’s an excellent way to capture video/images on the cheap. I have a couple of dedicated lenses (telephoto and anamorphic wide-angle) by Moment that mount into a special Moment case, allowing me to capture some excellent images. I do have social media on my phone — I find it hard to delete those apps, as much as I want to.

Other stuff. I’m bringing along a couple of wired and wireless earbuds from Apple, as well as a bunch of cords and chargers that all fit into a reusable silicone bag.

Weight matters. This setup weighs nearly five pounds. Which is a lot to carry around the world. That represents 16.6% of my total gear and clothing by weight. If I find I’m not using my laptop that much, I will likely ship it home and save myself 2.7 pounds. (But I don’t see that happening). I’m kind of hoping my 12 Pro Max iPhone shatters while I’m traveling so I can buy a lighter, faster version, but until that happens, my inner cheapskate forces me to put up with its weight because it works like a champ. And the iPad Mini? It’s perfect the way it is. It’s saving me the weight of three or four paper notebooks, and it does so much more than paper, so it has earned its place in my sling bag.

Let’s go.

[Nine days to departure] I had a bit of a scare this weekend when I noticed a sudden increase in floaters in my right eye. This can be a sign that something is wrong after having cataract surgery. But thankfully, my eye doctor, Michael Ruby, was able to see me this morning and put my fears to rest. Everything looks fine in both eyes. The retina looks good. All is well.

I was getting really nervous that I would need some kind of additional eye surgery before leaving on this trip. Which would really mess up my plans, and the plans of my daughter, Sunny who is coming with me to São Paulo. Fortunately, all is well. False alarm. Let’s go.

[14 days to launch] I’m feeling decidedly whelmed. Not overwhelmed. And certainly not underwhelmed. But decidedly whelmed — appropriately struck by the gravity of what will begin in two weeks. Here’s the countdown. (If you’re reading this days or weeks after it’s writing, I apologize for the confusion.)

Let’s revisit the checklist to see where we are at:

To-Do:

• Make changes to cell phone plan
• Activate the phone eSIM.
• Notify banks and credit card companies that I will be traveling.
• Acquire NBA league pass for Boston Celtics. Or maybe not. 
• Make a copy of critical documents. Passport bar code, drivers license, Immunizations, Travel Receipts.
• Get flu and covid vaccine (call doctor to get it set up).
• Basement project
• Bedroom project
• Prep for not being here: Fill up propane tanks, finish home users manual, A few hours cleaning up around the home’s exterior.
• Let’s Go.

Ongoing

• Continue to pitch clients for digital nomad work. 
• End subscriptions to services I will not use while traveling. Netflix? Prime? Apple TV+?
• Begin the process of getting the necessary visas for Brazil, Bolivia, Ecuador, Mexico, as needed.
• Download guides for destinations. Kindle App?

As you can see, the items on the to-do list are dwindling. The bedroom project is just about complete except for a quick vacuuming. The basement project will be done by tomorrow, end of day. The outdoor clean-up is pretty simple. Everything else will take an hour or less.

Let’s go.

[15 days to departure] I’m listening to a podcast of an interview with a sleep expert about the importance of sleep. And I may be in big trouble.

One of the negative side effects of modern travel is that it messes with the human sleep cycle. In four different ways. First it interrupts the timing of our circadian rhythms by rapidly relocating our bodies and dropping us into a location where the sun does not set at the same time it did in the previous location. Second, the overall quality of sleep when a person moves from hotel to airline seat to hostel to hammock to futon drops considerably. How can it not? Third, travel often messes with the regularity of sleep in a big way. And fourth, the quantity of sleep we can get can be adversely effected, night to night.

While I’m South America, this may not be a huge problem. It’s very close to my native time zone. It starts with a 15-hour flight to Brazil, but during the day. After landing, I’ll jump into bed in my São Paulo accommodation when it’s dark and then I’ll try very hard to get 6-8 uninterrupted hours of sleep. Later that month, I have a few overnight bus and plane rides. And I’ll be in one place, for the most part, for six to ten days at a time. So the quality, regularity, timing and quantity of sleep will remain pretty much the same.

But when I fly to Japan, I will leave the west coast of North America which is 11 hours behind Japan and lose a footrace with the sun, which will lap the plane as it races around the globe. And as we cross the international date line I will lose a day (not that big of a deal. I think my iPhone’s clock can handle that). I will try very hard to get eight hours of sleep on the plane but will likely end up being awake for somewhere around six or seven hours, landing in Tokyo feeling like I need to go to sleep, but it will be 6:30 in the morning. I might need a couple of days to recover from that flight. Or a nice, long soak in an onsen.

When I’m at home, I usually don’t have any problems getting to sleep and staying there. I pride myself on being able to get to sleep when I need to and then get at least seven hours, but I’m wondering if taking this trip will wreak havoc on my sleep habits. I hope not.

All this thought of sleep is making me sleepy. Let me pick this up in the morning.

Let’s go. To sleep.

[16 days to go] I am using Apple productivity tools — Reminders, Notes, Numbers, and Calendar to keep track of hundreds of trip details. With stunningly good results.

It began when I started to budget my trip using a spreadsheet template that I downloaded from a couple of popular, and wonderful, but now sidelined, YouTubers. This tool was a complete and total game changer and I have updated my budget using the template they created maybe a dozen times, including last night at 1AM when I couldn’t sleep (see previous post). And because I use Apple hardware (MacBook Air, iPhone, iPad), I did it all in Numbers, which is Apple’s version of Excel.

Almost simultaneously, I was making lists of things I needed to do before my trip, usually writing them in my paper notebook, on multiple pages, but then the list got so long and complicated, I needed to digitize it. I had known Reminders was on my phone but I did not know a lot about it, so I watched a video on how to get the most out of it.

And then my brain exploded.

The Apple Reminders of today is nothing like the weak Apple Reminders of 12 years ago. As I started making lists and creating various categories (business, personal, trip-related, scheduled, and more), I was really able to get my head around trip planning.

Once I had a good spreadsheet, and a punch list of to-do items, I needed to start grabbing the numbers and tasks and make them real by spending some time and money by booking flights, researching sites, and securing accommodations. Which, of course, resulted in an email in-box full of mis-matched reservation confirmations, tickets, tour itineraries and more going to a couple different email addresses. To pull those all together, I started to use Apple Notes, which allowed me to create a trip document with videos, links, maps and attached emails/plane tickets and more. All of the components in the Apple note are stored on iCloud — another Apple product I could not live without. I created the trip plan on my laptop that contains all of the important documents, maps, links, budget spreadsheets and important numbers (like passport, known traveler numbers and frequent flyer account numbers) and it synchs with my phone and my iPad. I color code things red if they are TBD, Green for flights and blue for things I want to remember, so I don’t forget anything.

And then, since all of these programs essentially talk to one another, when an event becomes scheduled, it suddenly pops up in my calendar automatically. (This saved me when I noticed on my calendar that I had booked a flight I needed but in the wrong month!)

This means I have a list view, a spreadsheet view, a 360-view, and a calendar view of my entire trip, that are all connected in one Apple Note. If I make changes on one device, it is reflected on my other two devices (when they connect to wifi).

Better still, I am able to share this Apple Note document with family so they can have the same info I have and they can also add info to the file that I can see and use.

Having all of these tools to organize a thousand different details and keep them all at my fingertips is pretty much amazing. Next I’m going to see if I can also integrate Google My Maps or custom Apple Maps for personalized itinerary maps. (editorial note: After a little fiddling, it appears Apple Maps still has a ways to go to eclipse Google Maps. Oh, well.)

[16 Days until departure] A weird thing is happening. I’m feeling several emotions at once about this trip. Anxiety. Excitement. Dread. Confusion. Elation. Fear.

I’ve done a lot of planning around this trip, as you know if you’ve read a few posts. But I’m not completely sure if all of the plans will come to fruition. The first two months have been booked, aside from accommodations in Japan (and flights for Barrie to join me). And these are some of the most intense, expensive and varied legs of the trip.

It’s a little overwhelming and as a result, my body is feeling like it wants to stay in one place. Inertia is the desired state. It’s that time of year on Nantucket when we light a fire in the wood stove, make a pot of coffee and stay in. And I’m about to go on the move for a year, give or take a couple of months. It just feels off.

Brazil, Bolivia, Colombia, Galapagos, Mexico, Japan, Hong Kong. Seven countries in two months. And six of those seven countries represent half of the places I will see for ten days or less. Plus, I do plan to move around a good deal in Japan to experience some city life and some rural life. That’s a lot of hopping around squished into 16% of the year.

By the time I get to the Philippines in February, I will be ready to stay in one place for a while. Then I’ll get a month in Vietnam. And then a month in Thailand. That’s three countries in three months. Indonesia in May will be a few hops as I explore the archipelago.

After that, I’m willing to bet that I will have a good sense of whether I’m better suited to slow travel or sped-up travel. And I can adjust accordingly.

I’m glad I wrote this today. I’m feeling a little better about the launch as a result. I can handle December and January knowing that February is coming.

Let’s go.

[19 days to departure] I was talking to a friend about this trip and completely out of the blue, they blurted, “You’re not dying are you?”

Well, I’m not.

And I am.

I haven’t been diagnosed with anything. I’m in pretty good shape. I feel good. Some days, great. But at the same time, I am on the part of the ride that slopes downward. We are all dying in a way. The day we come into being we begin to move in the direction of not being. Some of us get a long stretch to get there and some have a short trip.

The whole point of me taking this trip is precisely because I’m not dying. I’m living. And I want to live as much as I can while I can still enjoy it. I can’t think of anything more depressing than waiting until I have some terrible disease to pack a bag and see the planet.

What I tell people is that I wanted to take this trip while I can still get up off the couch.

As Andy Dufresne in one of my favorite movies says, I choose to get busy living.

[20 days to go] I’ve tried to work out all of the times I will be available for calls and connections while I’m awake. It looks like I’ll be getting up for some early morning calls (5AM in Bangkok is currently 5PM on the East Coast). And some late-ish afternoons as well (4PM in Cairo is 9AM EST).

As one can imagine, time differences of 7-14 hours means that when folks on the East Coast are asleep, I’ll be mostly awake and vice versa. But there are times when calls are pretty easy. For example, I just had a call with a couple of folks from Japan who needed a house sitter (it did not work out, but they were lovely) and we chatted at 7PM on the East coast while they were having their coffee 14 hours in the future at 9AM in Fukuoka. I created the chart above to help family and friends (and clients) navigate the multiple time differences.

[24 days to launch] I am ten days post cataract surgery, and the results have been excellent.

Surgery is never risk-free, but my cataract surgery went off without a problem. It’s the most-performed surgical procedure in the world, after all. If you’re squeamish about these kinds of things (like my friend Tom is) just stop reading now. Mission accomplished.

But if you are curious about it, here’s how my surgery went.

First I got a referral from my eye doctor on Nantucket. I went to see the surgeon for a consult and I was impressed by the organization. I was probably one of 100 patients that were moving in and out of the offices and exam rooms of the Ophthalmic Consultants of Boston (OCB) offices on the Cape. There was a line out the door! I was one of maybe three patients in the waiting room who was under 70 years old — my doctor noted that I was on the young side for this kind of procedure. They measured my eyes, did some tests and put those drops in my eye to dilate them. I met with the Surgeon, Dr. O’Connor and he could not have been nicer.

Originally, I was told that I could only get one eye done — the left eye. The right eye would require a contact lens until its cataract had progressed to the point of needing surgery. But, as it turns out, the test they did indicated that surgery in both eyes was needed. A good thing to get out of the way in the same (relative) timeframe.

I had a choice between standard lenses to correct my nearsightedness (but not my astigmatism, so post surgery I would still need to wear glasses), or a “toric” lens that corrects both my nearsightedness and my astigmatism, so I could be glasses-free, except for the drugstore readers I need for close-up work like writing this post.

I opted for the toric lenses, even through it cost me around 12% of my trip budget. It’s worth it to me to be able to walk, swim and drive without glasses. (And as we have discussed, I have ways to make up that trip budget deficit.)

I let the doctor and his team know I needed to do the surgery before December 3rd and we scheduled my time in the OR at the OCB center in Plymouth. It’s kind of a pain to live on an island and have this procedure done. But still worth it.

The morning of the surgery, I drove to the OCB surgical center from the hotel across the street, and checked in. I was one of maybe six people in the waiting room. My wife/nurse was there, too. They don’t like you to drive after surgery, so Barrie was there to take me back to the hotel room after the procedure.

Eventually they called my name and took me into the prep area. There was a good amount of waiting around, eye drops and questions from the nurses and the nurse anesthetist. They put a plastic shield over the eye they were not going to operate on. Dr. O’Connor came in and put a blue dot on my forehead above the eye he was going to operate on. They checked my vitals. The nurse anesthetist put an IV port on the back of my hand. (This was the most painful part of the whole procedure) Dr. O’Connor came into the prep area and marked my eyeball with a little pen (my eye had been numbed by then) to orient the lens implant during surgery.

When it was my turn, we went into the OR, they tipped me back in my chair and put a pillow around my head, then they started the IV. I’m not sure I felt the anesthesia during the procedure, which took about 8-9 minutes, but I did feel relaxed and unconcerned by what was happening. A drape was put over my face and all I could see was the light shining down in the OR. Dr. O’Connor made a small incision, broke up the cataract with an ultrasound probe, gently vacuumed out the lens cavity and positioned the new toric lens. Done.

After 20 minutes back in the prep area, I was given a bottle of water (they have other snacks, but I was fasting), escorted out, and brought to my car where Barrie was there to drive us back to the hotel. There was some discomfort, but not much — like an eyelash stuck in my eye. After some rest, we were able to go for a walk, do some shopping and eat at the Olive Garden (we’re family).

The next day I had a follow-up visit and things looked good. My vision was still a little blurry, but better than it had been. I drove back to the boat and had a second follow up ten days later in Plymouth. All good.

Three weeks later, I went through it all again on my right eye with equally good results. I have a follow up this week and 20 more days of drops in my right eye.

I am so glad I will be able to see clearly on this trip! Can you imagine what a nightmare it would have been to be in a country where I don’t speak the language and need to get a new pair of glasses made?

If you require this kind of procedure, don’t hesitate. I’m very happy with the results.

Let’s go!