Recap: 5 Months on the Road

Next week, Automattic (the company I work for) is having a company wide meet-up in Whistler, and all new hires have to give a four minute flash talk (apparently, it used to be required for everyone). So, with that, I’ve decided to give mine on living in one carry-on bag, and therefore have been thinking about my nomadic journey the last five months.

This blog post captures my thoughts, and therefore, read at your own will. It’s bound to be annoying, head-too-deep-in-belly-button, millennial and first-world. In fact, I’m positive it’s all those things, so feel free to stop reading… right… now. Or proceed if you like that kind of stuff 😉

The Backstory

I moved back to the US from Singapore at the beginning of 2016, and despite significant efforts to acclimate (talking tech, talking trump, talking local-sourced produce), to enjoy the local goods (esalen, silent zen retreats, weekend trips along the california coast, cheese, wine, classpass), to make a home (my apartment looked like west elm and the 60s had a baby, or maybe that’s just how west elm is these days), I didn’t like San Francisco. I fell in love with the city in 2008 during a fellowship at, then again in 2010 after joining Google (a reprieve from living in Boston and working in private equity), but in 2016, it wasn’t clicking.

Last September, I took a 2.5 week solo trip to Peru – hiked Machu Picchu and the rainbow mountain, slept on an island in the middle of Lake Titicaca, ate lots of ceviche – and while I was there, I met a fellow traveller who was once in tech and had been traveling around Latin America in a van the last five years. We talked about books, about travel, about California. It wasn’t unusual – traveller banter – but it highlighted the box I’d put myself in. A few weeks later, he sent me a cartoon that translated to “I’m sorry I was always afraid and didn’t enjoy my life” and asked a few thought-inducing questions (e.g., would you stay in an unhappy relationship in fear of being alone? if you tried something different for 6 months, a year, and didn’t like it, how hard would it be to go back?)

The email came at the same time I was bedridden back in San Francisco with Dengue Fever (side note: my manager told everyone I had jungle fever… yep, that’s different). And, strangely enough, I was relieved to be home and not at work. That’s when I decided I needed a change. I reapplied to Automattic, interviewed and now nearly a year later, I’m typing this from a coffee shop in Mexico City.

The Philosophy

On that same Peru trip, I read lots of books: The Conquest of Happiness, The Course of Love, The Girls, Sapiens, part of On Beauty and don’t judge, Crazy Rich Asians. Sapiens was the most eye opening, The Girls had the best prose, and The Course of Love left me nodding in agreement.

Here’s what stuck from Sapiens:

  • Humans are bound by beliefs. What societal beliefs am I bound by?
    • Yet the only place where such universal principles exist is in the fertile imagination of Sapiens, and in the myths they invent and tell one another. These principles have no objective validity.

    • This is why cynics don’t build empires and why an imagined order can be maintained only if large segments of the population – and in particular large segments of the elite and the security forces – truly believe in it.

    • The modern economic system would not have lasted a single day if the majority of investors and bankers failed to believe in capitalism.

    • First, you never admit that the order is imagined. You always insist that the order sustaining society is an objective reality created by the great gods or by the laws of nature.

    • You also educate people thoroughly. From the moment they are born, you constantly remind them of the principles of the imagined order, which are incorporated into anything and everything.

    • If I alone were to stop believing in the dollar, in human rights, or in the United States, it wouldn’t much matter.

  • Humans weren’t always “settled.” What if I’m not meant for domestic life?
    • This completely changed their way of life. We did not domesticate wheat. It domesticated us. The word ‘domesticate’ comes from the Latin domus, which means ‘house’. Who’s the one living in a house? Not the wheat. It’s the Sapiens.

  • Humans don’t value their time. What if I treated time as more valuable than money?
    • The pursuit of an easier life resulted in much hardship, and not for the last time. It happens to us today. How many young college graduates have taken demanding jobs in high-powered firms, vowing that they will work hard to earn money that will enable them to retire and pursue their real interests when they are thirty-five? But by the time they reach that age, they have large mortgages, children to school, houses in the suburbs that necessitate at least two cars per family, and a sense that life is not worth living without really good wine and expensive holidays abroad. What are they supposed to do, go back to digging up roots? No, they double their efforts and keep slaving away.

    • We have invented countless time-saving devices that are supposed to make life more relaxed – washing machines, vacuum cleaners, dishwashers, telephones, mobile phones, computers, email. Previously it took a lot of work to write a letter, address and stamp an envelope, and take it to the mailbox. It took days or weeks, maybe even months, to get a reply. Nowadays I can dash off an email, send it halfway around the globe, and (if my addressee is online) receive a reply a minute later. I’ve saved all that trouble and time, but do I live a more relaxed life? Sadly not. […] Today I receive dozens of emails each day, all from people who expect a prompt reply. We thought we were saving time; instead we revved up the treadmill of life to ten times its former speed and made our days more anxious and agitated.

    • The story of the luxury trap carries with it an important lesson. Humanity’s search for an easier life released immense forces of change that transformed the world in ways nobody envisioned or wanted.

So pair Sapiens with a lot of Seneca (“It is not that we have a short time to live, but that we waste a lot of it”) and Alan Watts, I soon I was off on a different trajectory: nomad life. I wanted to mix travel with work, save money and have more time for writing, walking, daydreaming and reading.

The Practicalities

This is my second nomadic stint, albeit, more full in than last time. Here’s some practical tips for those considering the same journey.

  1. Sell Everything – You’ll be tempted to put your stuff in storage, but don’t do it. It’s so freeing to get rid of it all.
  2. Get a Remote Job – [Insert plug for my company, Automattic]
  3. Buy Some Gear – Some people love “the gear.” That’s not me, but I’ve found these thing useful:
    1. Pack-it Cubes: Saves space in your bag
    2. Hanging Toiletries Bag: Keeps you organized
    3. Rick Steve’s Carry-on Backpack: Super easy to lug around
    4. Roost Laptop Stand and Portable Mouse / Keyboard: Keeps back pains at bay
  4. Pack in Monochromatic Colors – Easier to mix and match (see my closet in Malaga, Spain)
  5. Be Comfortable Wearing the Same Thing Over (and Over) Again – That green jacket. That maxi dress. That lavender lace dress. That green dress. That panama hat. That beige scarf. For all the options I have in location, I lack in wardrobe
  6. Pack in Layers – I’ve been to Berlin (sub 0°C) and also Greece (42°C) with the same bag. It’s all about the layers
  7. Get Ready for Questions – I never realized how often people ask “where do you live?” And, I also didn’t realize the answer “nowhere” can get awkward quick. Some people are fascinated, others bemused, some narrow in on whether I’m dating or when I’ll settle down. I need a better quip and have been known to feign monk via a series of koan-like riddles (e.g., I live nowhere and everywhere. I own nothing and everything)
  8. #KonMari – I’ve already thrown away three dresses, a pair of shoes and workout clothes. And returned a camera
  9. Get a Hobby – When traveling alone, you’re alone… a lot (duh). Make sure you have activities to keep you engaged. I write, read, walk and take photos
  10. Schedule Time with Friends and Family – I try to meet-up with someone every 4 weeks – whether that’s a work trip, a personal trip or a family trip. I think that’s why I haven’t been plagued by loneliness
  11. Book long-term rentals – I’ve been staying in 1-bedroom Airbnbs and check about the wifi connection and discounts before booking
  12. Have patience – Aer Lingus lost my bag (which they forced me to check) for three days with the dress I was suppose to wear for a friend’s wedding. Despite being very easy going (to a fault), I’ve had two bad Airbnb experiences (this is now bookmarked). The water went out in Tbilisi. The heated water went out in Mexico City. It’s not going to be perfect.

The Takeaway

This lifestyle isn’t for everyone. In fact, a study by the University of Virginia found that a quarter of women and two-thirds of men would rather subject themselves to electric shock rather than be alone with their thoughts (#).

If you love the idea of home, if hygge is your jam, then maybe this lifestyle isn’t for you. Experiences are on trend (#), but that doesn’t mean it’s for everyone. In short, you do you.

As for me, I’m heavily skewed towards “N,” in Myers Briggs land (#):

“Individuals with the Intuitive trait prefer to rely on their imagination, ideas and possibilities. They dream, fantasize and question why things happen the way they do, always feeling slightly detached from the actual, concrete world. One could even say that these individuals never actually feel as if they truly belong to this world. They may observe other people and events, but their mind remains directed both inwards and somewhere beyond – always questioning, wondering and making connections. When all is said and done, Intuitive types believe in novelty, in the open mind, and in never-ending improvement.”

And also an ENFP (borderline E/I):

“The ENFP personality is a true free spirit. […] When it comes to new ideas, ENFPs aren’t interested in brooding – they want to go out and experience things, and don’t hesitate to step out of their comfort zones to do so. ENFPs are imaginative and open-minded, seeing all things as part of a big, mysterious puzzle called life. […] It’s a big world out there – perhaps even a little too big. ENFPs are fascinated by new ideas, both in terms of developments in fields they are already familiar with, and when new subjects come along.”

Five months in, and nomadic life still feels right. If you’re interested in a similar journey, let’s talk 🙂

2 thoughts on “Recap: 5 Months on the Road

  1. Do you know who else doesn’t like answers like ‘nowhere’? Homeland Security. For example, “What’s the country of your permanent residence?” 😐 I came over to say hi because I met Tess at WCUS, and she mentioned you’re nomadic. I’m going on 2.5 years now.

    Liked by 1 person

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