The different ways of traveling

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

Want to help your hometown? Pack up and leave


I’ve done a lot of traveling throughout my journey with Buffer. I started in the UK, and since then I’ve lived in Hong Kong and Tel Aviv as well as San Francisco where I’ve now settled for the longer term.

When I was in my hometown of Sheffield in the UK, I became quite involved in the (then tiny) startup scene, and even ran a meetup for startups. The choice to move to a different city was quite a big one, and later the choice to leave the UK completely was a step even further.

I often hear the argument that people should stay in their hometown to help the startup ecosystem. I believe that paradoxically, the best way to grow the ecosystem in your hometown might be to leave it.

I think there’s this myth that the best way to help your hometown is to stick around. I also think there is a misconception that the way to help is to focus on the community, more than on yourself.

Focusing inwards, in order to be able to help others

One of the key things I’ve learned is that you can help a community far more by focusing inwards, on yourself, than you can by spending a lot of time working on the community itself.

"The greatest gift you can give to somebody is your own personal development. I used to say ‘If you take care of me, I will take care of you.’ Now I say, ‘I will take care of me for you if you will take care of you for me.’" - Jim Rohn

Indeed, in a recent post on the gender bias in the tech and startup world, Melissa Miranda concluded:

"The best way to have more women at the top is to climb up there myself."

Kate Kendall, a great friend and a founder I am inspired by and respect a lot similarly mentioned in a recent post:

"I cannot continue to provide for others if I don’t get my own company’s foundation firmly planted. I look forward to giving more again soon. Once I first learn how to ask."

These are some very wise words. The message is clear. Many who have taken considerable steps along their journey are realizing that their best way to help is to focus inwards on themselves, in order to become more and have more to offer. This is certainly the approach I am aiming for, too.

Refreshing your environment and your circle

One of the toughest things to accept as an ambitious entrepreneur is that you are affected by your environment and the circle of friends you have. We have far less willpower and self-control than we like to admit to ourselves.

Seneca wrote in a letter somewhere between 63 and 65 AD that even the most accomplished men are affected by the “crowd” they choose to be amongst:

"Even Socrates, Cato, and Laelius might have been shaken in their moral strength by a crowd that was unlike them; so true it is that none of us, no matter how much he cultivates his abilities, can withstand the shock of faults that approach, as it were, with so great a retinue."

If Socrates himself would be affected by a crowd who did not push him and encourage him, how can we hope to even achieve a sliver of the success he had unless we decide carefully who and what we choose as our environment? Seneca advised in this same letter:

"Ponder for a long time whether you shall admit a given person to your friendship"

I got lucky myself. Something drew me to Birmingham in the UK, from my hometown of Sheffield. Then, after Buffer reached ramen profitability Leo and I had a craving, a calling to visit San Francisco. After arriving and spending 6 months in Silicon Valley, lack of visas forced us to travel the world and live in places such as Hong Kong and Tel Aviv.

It was through this journey I learned the power of a fresh environment and starting new friendships. With each new place, I had a more specific criteria for who I would let into my true circle of friends. Today, I have much freedom and I am surrounded by people who never judge and always encourage. The difference this makes is something I can’t put into words. Leaving your hometown is the best way to deliberately sever those ties and step into the unknown and the chance of great possibilities.

Finding somewhere to thrive

With an inward focus and a desire to shape your environment in a very deliberate way, I think that if you choose to try and do these things in your hometown, you are very much at a disadvantage.

There is no way I would have been able to develop as much as a person if I had not jumped on a plane to a place where I knew nobody. I love my friends and I love my family, but the truth is that stepping away has helped me tremendously to become a better version of myself, and paradoxically to allow me to help them even more, too.

There’s probably a place in the world that is better for your business than where you are right now. For AirBnB, it was New York:

While at incubator Y Combinator, Paul Graham looked at their plans for Airbnb and asked them the simple question, “Where is your market?” The founders said that New York seemed promising. To which Paul, gesturing wildly with his hands, said, “Your users are in New York and you’re here in Mountain View.” The founders were dumbfounded, saying they were in Mountain View for Y Combinator. Paul repeated himself. “Your users are in New York and you’re here in Mountain View.” After a pause, he added, “What are you still doing here?”

For us, it is San Francisco. We’re a distributed team, but many of the conversations we need to have with startups we partner with and the social networks we are providing a service on top of, happen much more easily when we’re in the same location as the majority of them and can grab coffee face-to-face. I’ve come to agree with what Brad Lindenberg said in a blog post recently:

"I am convinced now that in order to be a player, you need to have a presence where your target market is because if you do, things can happen really quickly."

A lot has happened in my hometown of Sheffield since I left. There is even a startup accelerator there now. If I hadn’t left, I’d not be on a level where I would comfortably and excitedly be a mentor for the accelerator. Would you be able to help more if you let go of your roots and focused on yourself?

Photo credit: Christine Vaufrey