Reess Kennedy

Ideas, sharings, projections

Category: Travel

The Science (vs. Art) of Travel

I see the highlights from the travels of others and think, “that looks awesome.” Then I go off on my own travels and realize, indeed, traveling to new lands is awesome. But it’s also hard.

Generalizing this: Travel is hard because you have to make many decisions about your experience in a land you’ve never been before. Making the wrong decisions while traveling is bad news. Because you’re in a strange place these decisions can be more expensive to correct than they otherwise would be. Like most things in life I’ve realized that the act of traveling well is a balance between science and art.

When traveling there is the logical use of tools to plan a trip and then the intuitive art of “going by feel.” You must remain open to this intuitive side in full recognition that you’re visiting a new place and all your logical planning may break down when you’re actually in the thick of it.

With all this said: below is my first stab at a running list–which I’ll update over time–of “science-based” and “art-based” tips to maximize value and minimize inefficiency while traveling.

Notes on format: These are structured as positive directives in the form of “do this” instead of “do not do this.” Trying to determine and write out what you should do instead of what you shouldn’t do is more useful.

Art: mix in local blogs from travelers not on and deciding when these recommendations overrule TripAdvisor

Science: Use an atm to get money instead of money exchange for lower fees.

Science: Tell your bank in advance you’re going away.

Science: Research ahead of time convenient locations using Google Maps, identifying historical sites and looking up the location of the nicest hotels and then back out for other available hotel options in price range

Science: Still consider using a lonely planet guidebook. Human curation from a few people, some with much deeper area knowledge, can really help augment or simplify the mess that endless user reviews on TripAdvisor can become. And books don’t run out of batteries. 

Art: know when to email friends for recomendations

Science: Use filters to get a quick lay of the land and idea of top spots.

Art: Serendipitous running.

Art: Know when to strike up a conversation and when not to.

Art: Know when to live in the moment and when to take a pic for family and friends.

Science: Don’t eat spicy food if you’re not used to eating spicy food. I know you’re on vacation and want to be adventurous but

Science: Pack light and breathable clothes you can wash.

Art: Know when to breath.

Art: know when to just be quiet and alone.

Art: Know when to make friends. Share their knowledge.

Art: Know people and salesmanship when on a trip — when to trust a tourism operation and when not to.

Thoughts on working smarter (vs. harder)

I think about how I can work smarter every day.

Only working harder just doesn’t work. It doesn’t actually help you reach your goals faster. When I have children this will have to be one of the key discussions we have. I’ll say, “Son (or daughter), look at that man doing job x over there. He’s working very hard at that job. He can work even harder but it won’t get him very much more in return. Yes, he’s better off working hard than he is loafing off and we certainly need someone doing that job but his life options are limited in that role. Adding more force will do very little to change his quality of life. My point: There is a very low ceiling to how far you can go exclusively with hard work.”

Then I’d say that the greatest value comes not from the application of more force but from the very focused, strategic execution of smarter actions. If you wish for a bigger life — and to have a great positive impact on the world — you have to consider how you can scale your value. Entrepreneurs and Silicon Valley people talk about “scaling” ad nausiem, I know, but it’s a pretty good word. And the simplest way I can think of what I mean when I think of the aim of “working smarter” is to work in such a way that I can scale the value I add to the world.

The most successful people in the world are experts at scaling value. Every self-made wealthy person has, at one point, taken one idea, then made millions of copies of it and sold it to everyone. Entrepreneurs do it with technology, they do it franchising, they do it with creating funds and then “funds of funds” and writers do it with writing publicly accessible blog posts like this or with the publication of books and, of course, entertainers do it with the global distribution of their songs and films.

Scaling value requires the creation of efficient systems that work. In a complicated world where we want to sell our wares to millions of people we need to have great systems in place and the people with most abundance are people who are “systems thinkers.” Creating these systems isn’t easy. You do have to work really, really hard to figure out the right process but it’s the only way you’ll be able to create something that’s bigger than you are. It’s the only way to escape the very low limits of the “man doing job x over there.”

Footnote 1: Hacking the current system is just as important as creating new systems  

Chris Sacca can be, apparently, be a little arrogant and his response to a question in a recent Tim Ferriss interview is no different. Chris says: “… in my case I was always just smart as hell. I went to college for math starting in seventh grade … and I have always known that if there is a system somewhere I’ll figure it out. I’ll hack it.”

I liked this. If you’ve spent time as a computer programmer you do start to think more about how things interact and how you can hack existing systems. From this it seems important to note that when thinking about how to work smarter one should be just as thoughtful about how to hack existing systems as to how to create new systems. 

Interestingly, Chris goes on to talk about the myopia he thinks is prevalent in Silicon Valley given the number of people who, he thinks, don’t experience the same anxieties and hear the same “voices in their heads” that others do. It starts here around 29 minutes.

Footnote 2: Not everything must scale and sometimes too much scale can be harmful

I’m in Hong Kong right now. There are so many people here and there are so many people working hard at their respective street-side shops each day. These people do add value to the world and I don’t think everyone can be a systems thinker and “franchise their enterprise.” In-fact, I really love small, locally-owned businesses and really think many of these business owners do okay for themselves and love what they do and that’s amazing! This post, like anything I write, is a brain dumping. It is, however, also a true reflection of my consumption with thinking about how to create systems.  And I related to the fears Chris expresses at the link below about how, in effect, systems can become so freaking big and efficient and powerful that they create a potentially unhealthy imbalance in the world. You could argue that some of the large tech firms out there have reached this level of “potentially problematic scale.” But maybe this is another post!










2015 retrospective

I’m better positioning myself for 2016 by taking a moment to take stock of 2015.

Overall, there are always highs and lows. I wrote out a monthly list of personal and professional accomplishments and failures but it’s too long (and the failed efforts started to piss me off) so I just extracted the good stuff and, in aggregate, it made me happy and even more excited about all there is to do and achieve over the next twelve months so this is some of the happy stuff I will include below, categorized by subject:

Best Purchases of 2015

Kindle PaperwhiteI love this thing. I wrote a post about why. I recently added the “Send to Kindle” extension which allows me to send long blog posts to my Kindle for superior reading and storage. I continue to love the highlighting and “Vocab Builder” functionality.

Rebel Desk: I did a lot of research on adjustable sit-stand desks and ended up going with a Rebel. It was something like $800 when I bought it and now it’s $599 with free shipping, which is still a little spendy but still way less than many of the electric ones and, overall, a great value. I really prefer the crank adjustment that comes with it. The really expensive sit-stands are electric but I don’t need anymore electronic stuff to plug in and the crank is smooth and easy on my Rebel. I actually can’t imagine a sturdier desk at full height and I don’t regret getting the glass top despite the need to clean it often. The glass makes it look cool and makes it seem like it’s taking up less space in my small Manhattan apartment.

Sistem 51 Watch: I wasn’t always a watch man but I am starting to feel naked without one on my wrist. My Mom got me the cream-colored Sistem 51 for my birthday in August and I absolutely love it. It’s fun, in a very antique way, to be able to listen to the natural click of a watch that doesn’t use any battery power. It’s just masterfully engineered. I don’t profess to understand everything about how they pulled it all off, I just like it — something about it being hermetically sealed and protected from any contaminants. I’ve found that as long as I am wearing it, it keeps pretty good time too.

Toshiba VHS to DVD Recorder: I helped convert a bunch of family movies to DVD to preserve them digitally and help clear up some space and this machine is easy to use and did the trick.

Personal Notes and App Improvements: 

I wrote a post on all the apps and tech stuff I use to organize my life earlier this year.

I end up writing down a lot of thoughts each day while I am on the go using the standard iOS notes app and for a long time I felt guilty about using this app, thinking that one of the two million other “to do” apps were likely better. I tried Asana for a bit since I use it for other stuff and even a few others but the truth is, after a bunch of trial, Apple’s Notes app just opens faster than all the rest of them and speed is the most critical feature in an app for spontaneous notes. I thought the fact that the notes app doesn’t have a great API or export feature would be a deal breaker but I found some code that will export the notes with a timestamp to Evernote. I wrote about it here. Problem solved, I’m content and I’ve stopped wasting time thinking about what else is out there.


I didn’t stray too far from the shire.

VT / Ski: Got in a nice weekend at Stowe with a fun group and enjoyed another day trip to Hunter with Manhattan’s Paragon ski club that busses NYers from Union Square up to Hunter. It’s a good deal.

Maine: I went to Maine in May to a “camp” I’ve been visiting since I was little. May is still really cold in Maine. It was only three weeks after the last ice thawed off the lake but we had a great time climbing Bald Mountain, cooking some delicious steak in tinfoil on the Weber, going for the 10 mile run into town, putzing around on the little Rangeley boat a bit with the same engine my Grandfather put in it decades ago and spotting a big old mouse on the drive up.

Hamptons: Fun weekend away. Beautiful place. I was actually annoyed how much I liked it. I’ve held that the Hamptons must be unnecessary for me given my parent’s live in a coastal Connecticut town only an hour outside Manhattan but unfortunately the Hampton’s really delivers with its wine vineyards, beautiful farms with roaming horses, art scene and great beach access to Atlantic waves — far more exciting than the Long Island Sound surf I am accustomed to. So damn you Hamptons for actually being nice and no longer allowing me to dismiss you.

Massachusetts: Another wedding weekend that rocked in Willamstown. Willams College has one of the nicest Track and Field facilities I’ve seen — and this was a small DIII school. I stopped in Lenox on my way back to visit my Grandfather’s grave site — which, apparently, was never finalized so I was walking around the cemetery confused for a long time.

NJ: Got away for a bachelor weekend in Atlantic City. The gambling part of the city seems to be falling apart with a few casinos eerily abandoned. Outside this area, however, the Jersey Shore seems alive and well with many families on vacation. We got a cool Airbnb pad and I am just loving the options that Airbnb opens up.

New York: Doug’s wedding weekend in upstate NY was a blast. Growing up in CT I didn’t get to the Hudson River Valley much but it’s beautifully verdant and it was a great getaway. I had been madly working on a speech for the rehearsal dinner I wasn’t sure would “hit” so I was happy when it seemed it went well. Doug and Marisa really worked their tales off planning and everything came together perfectly.

Detroit and Ann Arbor: Went to visit Al with the guys. He’s all grown up with a real house and kids and everything. It’s pretty awesome and Ann Arbor is a nice town. I ended up scoring $150 when we went to a Detroit Casino for a bit. This was especially fun because I am such a poker novice and only went along to play because I was following the guys. The old men at the table started to be suspicious of me when I began winning pots. Some thought I might be a “professional flopper” who feigns to be a novice to gain competitive advantage.

PA: A couple great trips to NE PA with my little lady.

Other events and fun stuff: 

Gay Pride Parade: This really may be the best day of the year in New York City. This year’s historic ruling on same sex marriage made it very special.

Clapton at MSG: They said this would be Clapton’s last time playing at MSG or in the United States so I had to get tickets for my Dad for his 69th birthday. It turns out paying a couple hundred bucks for seats to Clapton at MSG will still get you super nose bleed seats, but it was still fun.

Brian Regan at Radio City: I love this guy. I don’t think this performance was his best but it was cool that it was streamed live on Comedy Central as we were watching. This was a first for the network. And Radio City is really cool.

Broke 30 for five miles: This really isn’t impressive but I am not running as much as I used to so sub six minute pace is okay on an upper-medium effort. This gave me enough motivation to daydream about what I could do on Thanksgiving Day 2016! My best time is about three minutes faster on the course which I believe I ran when I was 17. Next year I’ll be twice that old and I still feel very strong so this gives me more motivation to stay fit and see what I can do next year.


Okay, I have to conclude this post because it’s starting to get annoyingly long and too self-centric. It seems like I am just writing down everything I did this year and I don’t think this is useful anymore. My aim is only to share stuff that’s important to me if I think it might also be useful to others.

Still, I think writing down all one’s highlights from the previous year at the dawn of a new one is, generally, a good activity — whether you share it or not. It’s easy for me to always feel “I should have done more” but when I look back I feel less anxiety about what I might have left undone and more gratitude about what I was able to do and, more importantly, after organizing my past year on paper a bit I feel more excited about the present and the year to come.

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