A Career Break as a Tax Planning Strategy

It’s been a few months since the last time I posted, so I apologize if you noticed.  My travels over the last four months across the U.S. and the Caribbean have been a lot of fun, but they just didn’t seem as blog-worthy as South America and Africa.  Here are some pics anyway.

Going forward I will be focusing most of my writing on topics related to investing as I transition from world-traveler back to investment manager.  What follows was originally posted at my new company’s blog at www.emeraldspark.com/blog/:

Please note that I am not qualified to give tax advice and none of the information below should be used without the guidance of a professional tax adviser who is familiar with all the relevant facts.

It’s time for the often fruitless social convention of making New Year resolutions. Twelve months ago mine was to have the year of my life. I’m happy to report I actually stuck to this one. After years of dreaming, I had finally built up the resolve to take a career break and travel the world.

It wasn’t an easy decision to temporarily part ways with what had so far been a successful decade-long career as an investment manager. If you go back even further, I had consistently maintained some form of steady employment since I was 15 years old, so the idea of not having an income was initially quite terrifying. What if I hadn’t saved enough? What if I wasn’t able to find comparable employment when I got back? But as I stood perched on the rooftop of the Windsor Excelsior Hotel in Rio de Janeiro overlooking some two million revelers at the largest New Year’s Eve Celebration in the world, I knew I would not regret it. Continue reading


Closing Out Cape Town

My last month in Cape Town was a quiet one.  I lived in a peaceful cottage in the Greenpoint neighborhood and spent most of my time simply relaxing or working on my book.  When I did go outside it was usually for a run along the Seapoint promenade or for a solo hike up Lion’s Head or Table Mountain.  I did make a few friends and we were able to share in some quintessential Capetonian activities such as a full-moon party atop Lion’s Head and a day trip out to the Cape Point.  I think it’s best told through photographs.

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World Travel Packing List

One of the biggest questions I had before I left, and one I often get from other people now, is what do I pack?  After deciding where to go, deciding what to bring with you is the most important thing to figure out.  And if you’re traveling for an extended period of time to places where you can’t likely buy something if you forget it, it’s something you don’t want to get wrong.  It’s all about striking the balance between packing light, but not finding yourself in the middle of Africa without something you need.  It’s been eight months now since I quit my job to devote my time, energy, and resources to the noble cause of traveling the world for fun, and I think I have the packing list down.

There are certainly going to be a few things off my list that you can’t live without, but here’s what I consider essential:

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The Garden Route

Kat came back from the oyster festival in Knysna in pretty rough shape.  She had been yacking on the car ride back and her whole body was shaking.  She didn’t know what it was.  I did.  It’s called a hangover, and it’s what us older people get when you go on a massive booze fest and it is only amplified when you don’t get any sleep.  She’s all grown up now!  Unfortunately she was in no condition to manage much of anything so she asked me to come to the airport with her.  It was probably a good thing I did as there was a problem with her ticket that required a little bit of higher brain function and a lot of patience to sort out.  All was taken care of in the end, though.  I didn’t mind helping out either, especially since it meant I could meet my pal, Tim, at the airport.

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Welcome to the Mother City

56 days of overlanding through Africa ended in the cosmopolitan city of Cape Town.  The first couple days there we spent most of our time simply enjoying the amenities of modern civilization.  Hot showers, cinemas, McDonald’s, things like that.  The girls headed out for a spa day, while we guys set out on the usually difficult task of finding decent haircuts in Africa.  There were seven of us, so it wasn’t possible for us to all get a chair in one place.  Instead we ended up in three different places ranging from Scar, the best salon in Cape Town as we were later told, all the way down to a one-eyed barber down on Long Street.  Unfortunately I found myself at the latter.  So while Taylor, Drew, and Odin was enjoying a quality haircut, shampoo and scalp massage, Shannan, Frenchie, Thor, and myself were getting mauled by a half-blind geriatric.  And worst of all we didn’t spend that much less than they did.

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When somebody asked how Swakopmund was spelled Frenchie turned to the map next to him and said “S-W-A-K-zero… aw fuck!”  He was nominated for the Numpty on account of it but lost out to Bianca who earlier had forgot how to count to nine.  Seven truck days separated Maun in Botswana from our next outpost of civilization, which would be the aforementioned German seaside town in Namibia.

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