The different ways of traveling

Written on 27th April, 2014
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One of the incredible side-effects of doing retreats 3 times a year with my startup is that I get the opportunity to travel and experience completely different cultures.

On top of spending a week and a half with the rest of the Buffer team on retreats, in the last two occasions I have made a decision to stay or continue traveling in the same area beyond the end of the retreat.

For our latest retreat at the start of the month, 16 of us were together in Cape Town and I have stayed here 2 weeks so far beyond the retreat. I’m not sure yet whether I will continue to stay longer, or whether I will return to San Francisco. This uncertainty in itself is an example of a new way of traveling which I’ve been experimenting with.

How I’ve adjusted my traveling in the last few years

I’ve been very lucky to be born in a time where there is such a thing as work that doesn’t depend on where you are. We’ve set up Buffer as a completely distributed team (now 20 people across 18 cities in 5 continents), and I’ve had the opportunity to travel a lot already during the Buffer journey.

Leo and I started Buffer in the UK, and after 8 months we moved to San Francisco. We spent 6 months in San Francisco, then 6 months in Hong Kong, and then 3 months in Tel Aviv. After that I lived in San Francisco again for the last year and a half, with a little traveling at time.

The result, for me, of traveling to so many different places is that I started to carry much less with me to each subsequent place. I realized that you really don’t need much to travel, or even to live. In fact, you don’t need much in life at all. I’ve become a big fan of one bag living.

In addition, these experiences were the first time I’d experienced “living” in a place rather than “visiting” a place. Being able to stay 3 months or 6 months meant that I could make new friends, discover the culture in a deeper way and experience working and living there. It relieved a lot of the pressure of “seeing all the sights” in a short space of time, and even on shorter trips now I don’t try to cram too much in.

Traveling around Asia

Our second Buffer retreat was in Thailand in December last year. 10 of us stayed in Bangkok for a few days and then in 2 villas in Pattaya for a week where we worked together and went on a boat trip to a nearby island.

After the retreat, I decided to experiment with traveling by myself, something which I hadn’t properly done before. It was an incredible experience, so freeing for everything to be in your control. Even just the fact that it’s down to only you to get around is interesting, you have to be the one to ask directions or make the effort to meet others, rather than relying on a friend (which I sometimes do).

When we do a retreat, it’s quite a busy time and we fit a lot into the week, not to mention the natural excitement and pressure of meeting people, sometimes for the first time. After Thailand, I decided to travel to Singapore for 6 days, then Taipei for 4 days and then make my way to Japan for Christmas to see my brother, his wife and my little nephew.

It was a great experience to see all these different places in the space of a few weeks. At the same time, I didn’t manage to feel a part of any of these places, I didn’t get past experiencing things on the surface.

Staying in Cape Town

My recent experience in Cape Town is in contrast somewhat to that of traveling around Asia. Rather than visiting other countries in Africa (which would be a lot of fun) I decided to simply stay in the retreat location of Cape Town for a few extra weeks. After the week of retreat, I found an AirBnB place and I could start to build my early morning routine go to the gym again. I found a few coffee shops and a co-working space, and I got to know some people. I did a speaking event and met the startup community here.

With each day that passed, I felt like I got some extra insights into how things work here. I met locals and learned some of the Afrikaans words and some of the differences in how they speak English, too. I quickly stopped feeling like a tourist, although I have been on Safari, hiked to the Lion’s Head and had a kitesurfing lesson. During the week I’ve worked just like I would anywhere else.

I’ve become much more spontaneous with my plans and let things flow based on who I meet and how I feel. I have accommodation for only a couple more days here in Cape Town, so this afternoon I’ll start looking on AirBnB again for the next part of the city to experience.

In the future, I think I’ll take every opportunity to stay a few weeks or even a few months in a place, rather than trying to visit as many places as possible. I’ve found it much more fulfilling to become part of a place rather than simply seeing a place, even if it I’m only temporarily part of it.

Photo credit: Dimitry B