Meet Simon, the traveller behind 366 Pictures

4 minute read

We love a good story. And they say a picture is worth a thousand words. Sound like a bit of cliché? Well it is. Stick with us.

TransferWise user Simon first came to our attention because of the mischievous references he used when making payments. Unfortunately that got him flagged by our anti-fraud team - but we quickly established that it was all a joke - no harm done.

We got chatting with Simon and found out that he runs a pretty cool project, 366 Pictures. 366 Pictures was originally started in 2012 (the last leap year), when Simon embarked on an epic mission to take a photo a day and tell a story. Every day. For a year. (That’s where the 366 comes from).

The mission was accomplished - and some beautiful stories emerged alongside equally stunning photography.

In 2016 (another leap year), Simon was back on the road with camera in hand searching for more.

We loved the project, so we had a chat about how it all began.

How 366 Pictures start?

I started the project back in 2012 because I knew I had a pretty intense year or travel ahead of me.

I didn’t want to lose all those memories in a mass of pictures that I would rarely look back on, so I thought giving myself the task of picking a picture from each day, and telling the story of that picture, would capture the year really well. And it really did!


Why did you decide to repeat the project?

People had been asking me for a while whether I’d do it again in 2016. In all honesty, I wasn’t sure if I had the energy, but, on New Years Eve 2015 (after a few beers) I was persuaded. Of course, second time round I knew what a mammoth undertaking that would be, but I also knew the rewards.

What was the biggest challenge?

The biggest challenge is getting out there every single day to find a photograph worth publishing.

Rainy days always present a challenge - I don’t like the rain. Often it’s the days when you least expect to find a great picture that you find the real gems. In many ways that's the great thing about the project, being forced to really engage with every single day and moment of your life: looking at everything, being hyper aware of your surroundings and the world around you.

Have you found you see the world differently since you started 366 Pictures?


Throughout the project I see things that I imagine most people overlook or don’t notice. I’m always looking for a great image and story to tell. Some days the picture will be average, but the tale behind it will be great, other days I’ll love a simple picture that might have very little story behind it.

Which is your favourite picture?

In 2012 it was a picture of three monks walking along a street in Thailand.

I had actually gone somewhere to take pictures of a sunflower field, but as I got back on my motorbike in front of a temple, I saw three monks with umrellas walking. I could see the shot that they were walking into, and with seconds to get the picture, I took the camera from my pocket and without even looking at the screen, I pointed it and took the picture through heavy traffic.

It was a lucky shot

3 monks

In 2016 I found myself in the back streets of Jaipur, India, looking for the source of some pretty loud Indian music that sounded like a lot of fun. I stumbled upon a wedding and was quickly ushered onto the stage to dance with family members who were celebrating in dance.

It was such a fun moment, the picture isn’t amazing, but the moment will stay with me forever.


How did you find out about TransferWise?

I’ve been travelling the world for many years, with a bank account in the UK. One day I was checking my expenses and saw a massive charge. I thought I’d been the victim of a crime.

Little did I know this was just the charge the bank was imposing on me for using my card abroad. Not cool.

Now I use TransferWise to move my money around the world to various accounts I have, or direct to friends I am visiting so they can give me the cash when I arrive. I honestly consider Transferwise an essential for anyone who travels and needs to move money around.

The app makes the whole process simple and fast. I wouldn’t be without it.

You can check out the full 366 pictures project on Simon's website.

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