How can one man circle the planet without packing for every possible climate? Hell, it’s not easy. But I think I’ve figured it out.

How was I able to plan this crazy trip where I won’t need four winter layers, without spending half the time in airports and without spending twice the cash I have on hand? I broke it down and then put it back together again.

I started by running an excel spreadsheet with a somewhat liberal budget. And the result was a trip that was easily $5,000 over my budget (well, actually, under, but it ate into my $5K emergency fund, so let’s call it over).

At that point, I looked at the most expensive destinations (Australia topped the list at $250 a day). And made a mental note that I could skip those until the next trip if I had to.

Next, I built a table with a list that included all of the places I would like to visit. I ran the list of destinations, in a rough east-to-west order and then added months along the top. Then I color-coded each location based on high season, low season and shoulder seasons using AI to scrape information from a bunch of different web sites quickly. That looked like this. Note the big red blob in the middle which represents SE Asia in the hot, sticky, wet monsoon season. Avoid.

This allowed me to see the best times to visit each location.

After that, I was determined to stay in the green areas and avoid the red areas. For example, no one wants to be in Indonesia when the monsoon season overlaps with burning season (when farmers clear their land by setting it on fire). Not unless they like to be soaking wet while hacking up a lung…

When I had this set up, I was able to create a rough itinerary and then build a map using Google My Maps (very handy) to check my routes and make sure that I wasn’t singlehandedly burning enough jet fuel to set all of the farms in Indonesia on fire in October. I quickly realized that some places on the itinerary were really far apart and I was able to refine my itinerary to something that looked like the map above. I also realized that there were some destinations I had to eliminate from my trip entirely. Like India (India is freaking hot, man), South Africa (freaking far, man), and Australia (freaking far, freaking hot and freaking expensive, man).

Here’s what it looked like on the table.

I’m hitting both Bali and Albania in the shoulder season to save a little money and avoid the crowds. Everywhere else (give or take a city or two) I’ll be there at the perfect time to enjoy some warm weather. I may pack a light, down, packable, puffer jacket, but it will be used, mostly, as a pillow, I’m hoping.

Finally, I reloaded all of my destinations into my handy budgeting spreadsheet and I was able to account for every twist and turn, every used guitar purchase, every plate of curry, down to the last dollar. Literally — there is $1 left in my travel account when I return, two days before Christmas of 2026.

And here’s a little secret. I overestimated the cost of accommodations in order to assure that I can find places within my budget. But there are always ways to save on places to stay. Hostels are everywhere and there are plenty of short-term rental opportunities that provide discounts for stays longer than two weeks. This gives me flexibility.

Oh, and here’s another little secret. My current budget does not take into account that I’m ultimately going to save several thousand dollars using points and miles from credit card purchases. These points/miles can either stretch my budget or upgrade my accommodations and flights. That 21-hour flight from Sri Lanka to Portugal? It could easily be in first class…

I’m 98% confident that this will be my itinerary in 2026, with a one- or two-day adjustment here or there for flexibility. Let’s go!

My worldview is quickly becoming a worldview in a literal sense.

Lately, I have viewed everything that happens — in the news, in my community, and in my life — in the context of my upcoming trip around the world. And this week, with the ridiculous, infuriating disaster in the Oval Office, I have to wonder how I will be received, as an American, in other countries. I’m not ashamed to be an American but I’m certainly not proud either.

That Lee Greenwood song rubs me the wrong way.

How can you be proud of a country that doesn’t lead on important issues like climate change, human rights, or individual freedoms? How can you be proud of a country that can’t deliver the basics like healthcare, clean water, nutrition, education, and safety to all of its people? The only categories we lead in are gun violence, incarceration rates, political lobbying spending, and type one diabetes.

Freedom is a myth in this country for a lot of people. And a lot of them believe that myth with their whole being.

It sounds like I hate America. I don’t. I’m disappointed that we are not living up to the standards set by the people of previous generations. The self-sacrifice. The ingenuity. The social contract we have with one another.

That said, I want to be clear about one thing. I’m not taking this trip because I want to get away from the US. I’m taking it to experience other societies and cultures and see what I might be able to bring back to my life here.

My philosophy is that flag-waving is overrated. I would rather identify as a citizen of the world than the US. After all, we are all in this together.

I can’t change my nationality. And I’m not going to sew a Canadian flag on my backpack (Although I have only deep respect and admiration for our neighbors). I’m just going to have to meet people overseas on their level and be as candid and forthcoming as possible about my country. We are not perfect. Far from it. I wish it was different. Lots of us do.

I’m also determined to not be the “ugly American” who views every other culture as inferior. I’m taking this trip, after all, to learn and connect with all kinds of people.

A lot of people around the world hate Americans. I hope to change some minds.

There are ten more months from today before I hit the road, and I plan to purchase a few things to make the trip better in some way. Here’s a rundown of what is still on my list or has recently been purchased.

Travel Insurance — I’ve written about this a couple of months back. And I’m still trying to decide between Safety Wing and Global Assist. If anyone has experience with travel insurance for folks over 60, I’d love to hear it. Cost: $2,800.00, give or take.

A bigger passport — interestingly, one of my most significant unanswered questions is, will I have enough pages in my passport? Some experts (Like Brian Kelly, founder of The Points Guy and author of “How to Win at Travel”) say to get the biggest passport with 50+ pages, and some say, there’s no need. If you look at the itinerary I posted yesterday, it looks like I plan to cross 26 borders, and my passport has 26 pages, which feels like cutting it close to me. But the rules on how I can get a larger passport book when I already have a perfectly good passport are hard to follow. This requires more research. Stay tuned. Cost: $130

Passport wallet — I’m not sure if I will be getting a passport wallet or not. I have a nifty mini sling bag with room for a phone and cards and it’s RFID capable and it can fit a passport. But it’s a little thick. And I’d rather not hang something like that from my body in the streets of Bangkok. Plus passports take a beating. A quick check of Amazon.com shows that I can pay as much as $99 for a Belroy passport wallet (I have a Belroy Card Pocket wallet already and I love it, so I trust the brand. But $99?) or I could spend as little as $29 for a leather passport holder with room for cards and cash that basically has the same features. There’s even a similar wallet for $9. I may have to cheap out on this one. Cost: $9.

Tracker cards — I just bought two Huthur Tag tracker cards to test out in my sling bag and my luggage. And if they hold up during my next trip, I’ll get one or two more for my (potential) passport wallet and my regular wallet. These cards are less expensive than Apple Airtags ($19.99 versus $25), they work the same way, they are rechargeable, and they are thinner, so they can be slipped into more places in my luggage. The only downside to these that I can see is that they recharge wirelessly and right now I don’t have a MagSafe wireless charger, so I will need to add that to the shopping list. Cost: $19.99 + $10 for a charger and cable.

S-carabiner — I have a really heavy lockable carabiner (see below) but it would be nice to have a simple, lightweight, titanium carabiner to hang hats and water bottles from my sling. These s-carabiners from Nite Ize come highly recommended. And a three-pack is $12. Hard to say no.

Lock cable — I’m not sure I need this extra weight in my bag, but I may be sorry one day if I don’t have a way to secure my valuables. I have the Matador beta lock. The cable adds some versatility. And it’s just $10.

New Phone — I have the Apple 12 Pro Max, which is four years old. The newer iPhones have improvements to the camera which I will put to good use. But, the truth is, my current phone is fine. Will I buy a new phone? I probably will. But only after the new iPhones come out, so I can buy last year’s model at a discount. Cost estimate: $700.00.

DJI Osmo Pocket 3 — This little handheld video camera continues to get rave reviews. Do I need one? No. Do I want one? Yes. Will I buy one? That depends. First, it depends upon the video capabilities of the iPhone 16. So I will have to wait until after October to make that determination. Second, it depends on whether I can find a used Pocket 3 for sale somewhere. And third, it depends upon if I can find room for this thing in my luggage. I probably can. Cost estimate: $475, used.

Collapsable kettle — this is another one of those items I really want, but might not be able to bring. Mostly because of space considerations. If I bring my Aeropress coffee maker, which is amazing, compact, and easy to use, I’ll want a kettle. But It still takes up space. I’m on the fence on this one and likely will make a game-time decision when I do my final packing test run-through. Cost: $39

Epica travel adapter — Got to have one. So I’ll be getting one. Cost: $23, or $49 for all the bells and whistles.

Buff — A buff is useful for warmth as a scarf, as an eye mask, as a hat, as a face mask. Cost $32

Earplugs — My son gave me some earplugs for Christmas but they were too small for my massive ears, so I will be buying a pair of high-tech earplugs soon. These Loop Quiet 2 plugs come with a range of tip sizes.

Toothpaste tablets — With the TSA limit on liquids and gels, going solid on a few things makes sense. Saves weight. Makes security easier. I already use bar soap and shampoo bars, but I’ve wanted to try toothpaste tablets, which are not actually a paste, but hell, what are you going to call them? I’m currently testing these Duo ToothTabs™ (This is my trademark, I’m starting a new trend) out. They are a little gritty and they come in a glass bottle. But they do the job. Bonus: you can buy them with caffeine which you can absorb while you brush in the morning. Not recommended before bed. Cost: 2 months: $40.

Medicine organizer — It pays to travel with a mini-pharmacy. For $5 I bought this medicine organizer on Amazon. A lot cheaper than the ones being advertised on social media. And they come with stickers so you can label your OTC meds and other stuff. I can fit my toothpaste tablets for day and night on one side. Meds like ibuprofen, pepto and immodium on the other. Cost $5.

Flashlight — most people would say that a phone has a flashlight already, so why would I need a separate flashlight? The reason is that a phone’s output is 5 lumens and a good flashlight can put out 8,000 lumens or more. A separate flashlight that can clip on the brim of a hat so it can be used hands-free is very useful. And one that can put out a sudden blast of light can blind a mugger giving you enough time to run away. Also, if you lose your phone in the dark, it’s nice to have a flashlight to help you find it. I’m looking at a few different flashlight manufacturers and will likely write about this later. Cost: Varies.

Amphibian shorts (2-3?) — I own shorts. I own bathing suits. But I might want a pair of shorts or two that can double as a bathing suit. My plan is to spend a lot of time in swimmable waters next year, so this will likely be a good investment. Note to self, a non-leather belt might be a good thing to look into as well. Cost $32-$49.

Travel pants — I’m only bringing one pair of long pants on this journey. Okay, maybe two. But they need to be super comfortable, have a little stretch, are durable, and can work in a couple of different scenarios (on a plane, roving the streets of Tokyo, visiting a Buddhist temple in Thailand, going out to dinner with friends). Cost: Varies

Packable puffer jacket. I hate to buy more winter clothes but the ones I have on hand are just too bulky to bring on a year-long trip. I need a puffer jacket that can roll up and stow in one of its pockets. Maybe serve as a pillow on an airplane. The idea is, with a warm underlayer, like a hoodie, and a waterproof outer layer, like my Patagonia rain jacket, a packable puffer jacket like this one from Quince will allow me to brave cold days and nights. At least until I can get to Southeast Asia where it’s hot. Cost: $80-$250.

As you can tell from some of my previous posts, I love planning this trip. Making lists. Executing budgets. Researching tours and side trips.

And right now, I have an itinerary (and a detailed budget — see below) that checks a few critical boxes.

• Box one: It circles the globe in one year.
• Box two: It allows me to be in warm places (> 60° F, 16° C) for most (not all) of the trip, so I can get away with a minimum of cold-weather clothing.
• Box three: It keeps me under a reasonable dollar amount with a little cash ($5,000) and points held in reserve for “emergencies.”
• Box four: It takes me to a few places I have always wanted to visit like Japan, Australia, SE Asia, Bhutan, Egypt, and Morocco.

Will my trip follow this plan to the letter? Probably not. No, scratch that. Definitely not. There’s no way it can.

Case in point: I was looking at a 9-day group tour in South Africa in November of 2026 that involves five days on safari. It’s on my itinerary now, but it’s so far in the future and close to the end of my trip that a lot can happen to make it hard for me to do that expedition. I could run out of money. I could fall in love with Vietnam and have trouble leaving. I could get sick. I could hear about a cool boat trip to Fiji. I could be captured by a rogue band of Norwegian tourists and be forced to play my guitar for them for a month. I could miss my flight to South Africa.

In fact, so many things could happen, that the likelihood of me going on that tour is probably around 10-15%. And that probability may rise the closer we get to November 2026. Then again, it may fall.

It’s in these situations that I fall back on a quote I have always loved from Dwight Eisenhower: “Plans are useless. Planning is indispensable.” Ike was talking about war, but this is true in non-battle scenarios. Planning means you’ve thought about all of the things that will, could, or might not even happen. As well as a few things that definitely will not happen, but you plan for them anyway.

Also, whenever I think of Ike’s quote, another quote from Mike Tyson comes to mind: “Everyone has a plan until they get punched in the face.” Mike was also talking about war, albeit a shorter one. Mike and Ike knew that having a plan is not as critical as knowing when that plan becomes obsolete — usually when the first thing goes wrong.

For me, making plans is an oddly comforting and enriching experience. It gives me a reason to get smarter on the subject of travel. It also allows me to see the future and work out the numerous ways I can take this trip. That’s why I have created what I call “wildcard weeks” in this itinerary. And they become more useful the further I go into the trip.

A wildcard week (or month) is a time to reset. At that point in the trip, I can make plans to stay where I am or go somewhere else and I have budgeted the costs for travel and accommodations for the wildcard. In some instances, if I feel like saving some money and not going on the wildcard trip I can keep my powder dry and remain where I am, or change the destination to someplace cheaper. Notice that on my itinerary, the last 30 days is a wildcard. My goal is to enter that last 30 days with around $3,500.00 and a good idea of how I want to spend my final month circling the globe.

Sometimes the best plan is to work in a way to change the plan in the middle of the plan.

Anyway, here’s my itinerary as of February 25, 2025. Let’s go!

December 26, 2025: Boston
December 29: LAX
December 31: Honolulu
January 3, 2026: Sydney Australia Brisbane, Australia
January 18: Bali, Jakarta Sumatra Indonesia
January 28: Singapore
February 1: Manila, Boracay (or some other quiet island) the Philippines
March 1: Tokyo, Osaka, Kobe, Hiroshima, Etc.
March 29: Wildcard: Okinawa, Hong Kong, Taipei, S. Korea?
April 5: Hanoi, Danang, Nha Trang, HCMC Vietnam
May 1 Phnom Penh, Siem Reap Cambodia
May 13 Bangkok, Phuket ( and other islands/cities)
June 9: Bhutan 6-day tour
June 15 Kolkata, India
June 16: Sri Lanka
July 14: Wildcard India Tour Mumbai, New Delhi, Goa?
July 19: Istanbul, Turkey
August 1: Bucharest Romania
August 11: Budapest, Hungary
August 18: Prague, Czechia
August 26: Wildcard (Europe)
September 1: Albania
September 27: Wildcard
October 1: Egypt
October 8: Tangier, Marrakech, Sahara, Morocco
November 1, Portugal
November 11: South Africa, SA Safari Tour
November 27 Wildcard to someplace warm/relaxing for 30 days?
December 20-ish Home

UPDATE, March 13: I have refined this itinerary and have removed a few destinations to streamline my trip and not spend so much time in transit. Revised itinerary:

December 27, 2025: Boston, LA, Honolulu
January: Philippines
February: Vietnam
March: Thailand
April: HongKong, Japan
May: Indonesia, Singapore, Bhutan
June, Sri Lanka
July, August, Sept and part of October: Loop through Europe
October/November: Morocco, Egypt
December: Wildcard Location

Every year, I don’t create New Year’s resolutions. I pick a theme. And I have that theme stamped on a silver washer that becomes a simple bracelet that I only take off when the year ends. 

It’s something of a guiding sentiment for the year. In the words of Dr. Jason Fox, whose books and writings have inspired me a great deal, it’s a fuzzy beacon that lights my way for twelve months. I’ve been doing this for a decade now. Here are the themes I have adopted for the past ten years. 

• 2016 Rebel Scum — An homage to Star Wars. The rebel scum were the good guys, out-gunned by the Empire, winning against the odds.
• 2017 Catalyst — this was a year I needed to help others change. 
• 2018 Astronaut — Astronauts are the future explorers. The bravest among us. 
• 2019 Invent Water — Shorthand for, “Jump off the diving board and invent water on the way down.” A year when I took a big leap.
• 2020 Chef — The chef is the creative and spiritual leader of the organization. 
• 2021 Resistance — physical and mental resistance were a big thing for me at this time. 
• 2022 Differenter — This year I needed to break out of the mold.
• 2023 Sponge — My spirit animal. I wanted to remind myself to soak everything up. 
• 2024 Tick, Tick, Tick. — A subtle reminder that the time we have on this earth is not infinite. 

So why, this year, am I a “machine?” 

Machines are purpose-built. They do things with precision and repeatability. When finely tuned, they take in inputs and create outputs. Emotions are not critical to machines. Machines are dependable. They get stuff done. 

And this year, as I plan my trip and manage the thousands of details of that journey along with the necessities of home and work, I kind of need to be a machine. I need to get stuff done.

Next year, when I am on my trip, I can be more of a free spirit. I can let the winds blow me around the earth. I can follow my gut and be creative and artistic. I can break a few rules. 

But for now, I am a machine. Precise. Productive. Dependable. 

I just did a quick budget rundown of costs for my trip, double-checking with online sources (namely budgetyourtrip.com), and here’s a basic exploration of the least expensive and most expensive places I plan to visit. I have a target budget of $110 per day. Some of my destinations are well under that amount and some are way over. 

As a rule, the more civilized a place is (Singapore, Greece, Australia, Japan) the more expensive it will be. And the more under-developed a country is, the less expensive it is — with one exception. See below. 

You might think I’m planning to spend more time in the cheaper places and less time in the wildly expensive places. And while this is essentially true, there are some exceptions. 

Top five most expensive places I plan to visit. 

1. Greece $230 per day. (One week or less) Yikes. The most I will spend in Greece will be seven days, and I may escape to neighboring Albania sooner than expected if I’m able to see what I want to see in Athens. I have heard there are some lesser-known and less-traveled islands where I might be able to live more inexpensively.  
2. Australia $200 per day. (Two to three weeks) I have some friends in Sydney and Brisbane, otherwise, I might skip the three weeks in Australia or reduce the number of days here. That is unless I can find some super cheat code for reducing the cost of Australia during the high season.
3. Singapore $172 per day. (One week or less) This may be a shorter visit than the week I have planned, although I hear it is a beautiful place to be. 
4. Portugal $170 per day. (One week or less) This is another place I have friends and I’ve always wanted to visit, so I’m willing to put up with the up-charge. Unless my friends decide I have to sleep on their couch. If so, dinner is on me!
5. Japan $150 per day. (One month) Unlike the four expensive destinations mentioned above, I plan to spend a full month in Japan. It’s one of the countries I must experience. Still, I sense that it will be possible for me to live below the $110/ day margin on most days. I don’t drink and I’m not planning to buy many souvenirs. If I can find accommodations for around $50 it may be easier to achieve. I may end up breaking my stay in Japan into three locations, beginning with Tokyo. 

Top five least expensive places I plan to visit. 

1. Egypt $55 per day. (One week or less) This surprised me. I expected Egypt to be much more expensive. I may end up spending more time here. Although once I’ve done a food tour, seen the Egyptian museum, and visited the pyramids, my reason for being in Egypt may have become exhausted.
2. The Philippines. $70 per day. (One month) Of the 28 days I have planned in the Philippines, four or five days will be in the capital City of Manila, and the rest of the time I plan to check out one or two islands. I will likely up-spend for accommodations and still stay well under my daily target budget. 
3. Sri Lanka $70 per day (One month) Few places on my itinerary excite me like Sri Lanka. The first thing I plan to do when I land is rent a tuk-tuk and explore. 
4. Indonesia $70 per day. (2-3 weeks) This destination may end up costing slightly more because I may meet my wife in Bali and I may also take a group coffee and tea tour while in Indonesia.
5. Cambodia $75 per day. (2-3 weeks) The more I learn about Cambodia, the more I want to be there. This may end up being a longer stay if I can find the right accommodations and vibe.

The other nine destinations not listed average $102 per day with Turkey on the high side at $140/day and Vietnam on the low side at $80/day.

How does all of this break down? Overall, I plan to spend 54% of my trip, or 197+ days in seven locations for one month each at an average cost of $98 per day. I also plan to spend 17% of my trip, or 63 days, in three locations (three weeks each) for $131 per day. Plus there are nine destinations representing another 17% of my time that I plan to visit for one week, or 63 days total at $136 per day. This leaves 43 wildcard days (12%) where I will either be in transit or will seek to extend my stay in one place or another. If I can keep these 50 wildcard days to under $80 per day, I will stay well under my budget. Even with $5,000.00 in a “safety” fund. 

Can you tell I enjoy planning this stuff?

Sometimes you just need to wait a little while — or thirty years — for your dreams to catch up to you.

As a creator, the movie, Pulp Fiction has inspired me in a bunch of ways. In the way it tells a story out of order. In the way it makes evil characters the hero. In the way minor characters are celebrated — every part played in that film is critical to the narrative. In the way people couldn’t stop talking about what might have been in the briefcase that Jules and Vincent were delivering to Marcellus Wallace. In the way it seemed to instantly become a part of our collective consciousness with certain lines becoming part of the social lexicon.

And there was one such line that helped to inspire my trip around the world, in a small way. When Jules and Vincent were eating breakfast in the diner, looking like a couple of dorks in their borrowed t-shirts, and Jules announces that he has decided to give up “the life.” And after he gets the briefcase to Marcellus, he plans to just “walk the earth like Caine in Kung Fu.”

When I saw that movie for the first time (and I’ve seen it a bunch of times since then), that line struck me like a thunderbolt.

“Yeah. Walk the earth. Like Caine. That sounds amazing. Wandering from place to place, meeting new people, and getting into adventures. that’s what I want…,” I remember thinking to myself.

[An aside: Also, let it be known that Kung Fu was my favorite TV shows when I was a kid. I have a feeling that the same can be said for Pulp Fiction’s Director, Quentin Tarantino. Not only did he reference Kung Fu in this script, he later cast David Carradine to play Bill in the Kill Bill movies.]

While I was energized by the idea of walking the earth back then, I also remember thinking, “That’ll never happen.”

Pulp Fiction came out in October of 1994. By then my life was heading in a rather set direction — away from walking the earth and toward something more grounded. I was a new father, soon to be a father of two. I had moved to Nantucket and we were starting to talk about buying a home here. I was working hard to provide for my family and serve the needs of a handful of great clients. Walking the earth was about as elusive and unlikely as knowing the contents of Marcellus Wallace’s briefcase.

That was 30 years ago and things have changed and now I can actually think about walking the earth. I’m actually doing it.

According to Jules, he was going to walk the earth until “God puts me where he wants me to be.” My plan is a little different. I plan to come home after a year so I can walk the earth again at a later time. And unlike David Carradine’s character from the TV show, I’m going to avoid getting into a kung fu battle everywhere I go. Art does not always need to imitate life, after all.

Okay, so here’s a little side project I’m working on and I would love to know if readers feel this is something that could gain some support. I originally created this for myself but as I continued to work on this idea, I began to see some limited commercial value for travelers.

I’ve spent the last week creating illustrations of everyday objects. The goal: to create a travel journal that is around 250 pages long with the first 8-10 pages containing images like what you see here. Images that a traveler can use to communicate with people who do not speak their native language. Let’s say you want to buy some eggs or garlic. You point. You share. And you are understood. This method is much faster than firing up Google Translate and works if you are in a spot where Internet is not working.

There are also a few pages with the phonetic spelling of five key phrases: “Hello, Excuse me, Please, Where is___? and Thank You.”

I’ve done a rough layout of this project already. There are 10 image categories:

• Food
• Animals
• Places
• Transport
• Weather
• Medical Emergencies
• Help
• Common Objects
• Articles of Clothing
• Activities

Plus, it’s a travel journal. So travelers can take notes or keep a running narrative of their experiences in this little A5-sized booklet. Ultimately, these kinds of journals become something that travelers refer back to over and over. Personally, I fill up these kinds of journals often. I can’t live without them.

The idea is to maybe sell these on Kickstarter before I leave for my trip and hopefully, this project will create a small amount of cash flow. I’m also considering a limited printing of t-shirts or posters of some of the more iconic images. What do people think? Let me know in the comments.

Also, if anyone knows of a good printer who can create Moleskine®-like A5 journals, I’d love a link.

I’ve really had some fun with this. I estimate it will take me 8-9 weeks to get the next draft ready for printing. Stay tuned.

Sure, there are a lot of twenty-something folks out there calling themselves digital nomads these days. But how many of them have 30 years of experience doing it?

My digital nomad schooling began when I moved to Nantucket back in the mid-90s. The internet was somewhat new and we all accessed the online worlds of AOL and CompuServe and ftp on a dial-up modem. I remember working on a project with my friend Lee Busch and he told me about the World Wide Web and internet browsers like Mosaic and Netscape — a whole new world opened up to me. (That was when he helped me buy the domain I recently sold to pay for my trip!)

I had one of the first Mac laptops, a grey Powerbook 145 (I think it’s still in my basement in a box somewhere), with its funky little trackball, monochrome screen, and rotating feet. Living on an island, I had no choice but to work wherever I was. There was no office to commute to unless I got hired to write headlines by some ad agency in Boston or suburban Hartford. I worked in my home, or at the local internet cafe, or at a coffee shop just off of cobblestoned Main Street.

The work I do is conducive to solo activities and remote teams. Back at the beginning of my career, I spent most of my time working on advertising ideas. Headlines. Concepts. Visual imagery. These days, it’s a mix. Some writing. Some coding. Some design. Some podcasting. Some name generation. Some strategic research and thinking.

A lot of what I do involves digital technology — laptops, phones, iPads, cameras, microphones — but it doesn’t have to. I can get a lot done with a pen and a notebook. I can work online or off. And over the years I’ve compiled quite a list of locations where I have gotten billable work done. These include:

Airplane — From a tiny 9-seat Cessna to a big commercial aircraft, I’ve worked in them all. I estimate that I have taken 1700+ commercial flights over my career.
Train — The rhythm of train travel is strangely conducive to ideation. I also worked on TV, radio, and billboard ideas to launch a new train line a few years back.
Car — Either driving or as a passenger, I’ve worked up some good ideas on the road.
Boat — Living on, and commuting to and from, an island, I’ve had plenty of practice working on the water. Even once on a scallop boat.
Bus — I’ve written on a bus and I’ve spent a few days shooting TV commercials on a moving bus. There’s a treat for you.

Beach — Client meetings and work sessions.
Coffee shop — Like everyone else.
Bed — many times. It’s the most comfortable spot.
Hammock — I’ve worked in outdoor hammocks and I’ve even slung up a hammock inside my studio a few times.
Bathtub — We built a great outdoor shower with a stand-alone tub that is a spectacular place for generating ideas.

Hospital room — I recall writing headlines for a coffee company at a family member’s bedside years ago.
Restaurant — keep the coffee coming.
Park bench — Ah, fresh air
Hotel room — When I was traveling each week to various freelance locations, I stayed in literally hundreds of hotel rooms. (The wifi is never as good as at home.)

Public libraries — Shhh…
Parking lot — I can recall in the early days of wifi, sometimes it was hard to find a signal and I ended up discovering random connections to the internet from parking spaces at odd hours in order to send and receive assignments.
Picnic table — more fresh air.
Conference room — some of my best work has been done in empty conference rooms. They tend to be a great place to stick a freelancer who needs to get down to the task at hand.
Kitchens — I’m in one as I write this.

I’ve also worked with Clients and partners in a bunch of different time zones. I’ve worked with folks in Thailand, Australia, the UK, Hawaii and the Middle East. It makes very little difference. Once, I even worked on two projects simultaneously, one with a client in California and another with a client in Norway. Those were some long days. But the work got done!

So to all of my clients and prospective clients who are wondering how I’m going to get their work done when I’m circling the globe: it’s just business as usual.

I knew my grandparents had traveled overseas after the war. But really, I had no idea how much. Until about a decade ago.

When I cleaned out my father’s lake house after his death, preparing to sell it, I discovered a few things that I could not throw away. One was an O.D. canvas bag issued to my father by the Army Air Corps in the 40s and a suitcase that my grandfather used to refer to as his “grip.”

“Where is my grip?” he would say in his 90s as if he was fixing to fly off to someplace exotic, even though he was suffering from cognitive decline for the last five or six years of his life.

Inside the grip of the late Arnie Malcolm Sanders was a strong musty smell and a few clues about the grandfather I barely knew. I have to admit that, as a child, I was a bit afraid of my father’s father. My grandmother was very nice to me and all of my siblings. We knew her as “Nunu.” But my grandfather, as I remember him, was a joyless, stern, gruff man. He had a voice like a saxophone. And did not suffer the frivolity or antics of his grandchildren. My father was the youngest of six children, so by the time my siblings and I came along, the novelty and excitement of grandchildren may have worn off for Arnie.

Here are some things I have learned about him since I inherited the grip.

He was born and grew up in Marshall Wisconsin where he was, for a time, a member of the 1909 Marshall City Basketball Team, and was also the postmaster working in the post office that was on the first floor of the AE Sanders Building, which also housed the general store my great grandfather built and ran until he retired and sold the business. Arnie got married to a nice girl from Waterloo Wisconsin and started a family around 1915. He was well-known as a good singer and would often be called upon to perform at public meetings and events in his small town. The depression was a difficult time for his family and he worked as a traveling salesman for a food company. The family moved to Iowa for a short period of time (my father was born there) and then back to Wisconsin. WWII was a difficult time for the family with the loss of their oldest son in 1944. From what I can tell, most or all of the five remaining children who didn’t have children of their own by then enlisted and served.

Arnie retired in the late 50s. And he and Velma spent a lot of their time traveling the world. I knew that they had been overseas from a photo of them on the backs of camels in front of the Pyramids at Giza. But I had no idea how extensively they traveled until I found their passports. The passports I found were from 1963 and 1970. There must have been one from 1956 or 57, but it was not among the documents in the grip. The passport book from 1970 was unsigned and unused. My grandmother passed away five years later. But the one from 1963 was well used and based on what I can read from the smudged and faded stamps in it, they traveled to many of the places I hope to go on this trip. Japan. New Zealand. Singapore. Hong Kong. India. Ceylon, which is now known as Sri Lanka.

Fun fact: my grandmother collected small elephant figurines. She had hundreds of them (I think one of my cousins inherited them). And I have to imagine that many of them were acquired on these trips.

My own father and mother did not have the opportunity to see the world when my dad retired. By then, my mother was ill and in decline. We made one trip to Europe when I was a teen and a few vacations to the Netherlands Antilles and Florida. But nothing terribly exotic.

I wish my grandparents were alive to answer questions about their travels. Maybe some of my cousins will know more.