How having the courage to head out alone can pay dividends.

Curiously, I’ve often found I meet more people when I travel alone than I do when accompanied by others.

A few years ago I headed off on my own to the Maltese island of Gozo for a few days of ‘chillaxing’ with a book by the pool.

I’d been aware of a group of British painters who were staying in the same hotel, as it was hard to ignore their easels propped up all around the grounds each day.

That evening in the bar I got chatting with the group’s teacher, an older white-haired gentleman called Ley Kenyon. He was coping well with students who’d arrived for his course with a wide range of abilities.

The more we talked, the more I learnt about him. He wasn’t only an accomplished painter, but also a diver who’d worked with Jacques Cousteau and taught the Duke of Edinburgh to dive.

But there was more. Ley was a Prisoner of War in Stalag Luft III at the time of the Great Escape in March 1944 and – he explained – had been asked by the British commanding officer to make a visual record of the digging of the tunnels. So he’d gone underground himself to draw.

‘Where are your drawings now?’ I asked, sure they’d be safely locked up in a museum somewhere.

‘Oh, they’re upstairs.’

What? Yes that’s right, they were in Ley’s suitcase, in plastic sleeves, and a couple of minutes later they were down in the bar where I inspected them incredulously.


Extraordinary pieces of history, right there in my hands.

I honestly believe we wouldn’t have ended up chatting if I’d not been on my own, and it’s an powerful reminder that it’s often possible to forge human connections in the least expected circumstances. Human connections are so important when it comes to our wellbeing, but connections are much less likely to happen if you don’t step outside your front door.

So, perhaps, rather than bemoaning the fact that you’ve got nobody with whom to go somewhere, head out on your own, tread boldly and keep an open mind.

You never know who you’ll end up talking to.

6 thoughts on “How having the courage to head out alone can pay dividends.

  1. Circumstances have forced me to go it alone – I started with visits to familiar places but now I am spreading my wings ! It can be exhilarating and I have met some lovely people.

  2. Amazing John. I’d certainly like to enjoy more interactions like that. I do sometimes tend to clam up though when I’m on my own so I’ll take your suggestions to heart!

  3. What a wonderful experience, Jon, to meet and talk to someone with such an amazing story to tell. I would want to see all his pictures too!

    Stepping outside the front door, to many, is stepping out of their comfort zone, let alone actually being the first person to speak to someone you don’t know. I am really pleased I don’t ‘suffer’ with that problem. I walk every day with Dog and every day I say hello or good morning to everyone I can. I’m not trying to be a nuisance! I just think it’s polite to acknowledge people you come across…don’t suppose I’d do it if I was just walking through the streets if a big city….but even in our small city/town, I smile at people I walk toward.
    A smile costs nothing, it’s free after all!

  4. I meet people all the time when I travel alone!

    One of my favorite experiences was meeting an old guy on a train who told me a funny story I never knew growing up, about a failed attempt at putting an early-stage wind turbine, named The Whooshie by the locals, on the side of a mountain just a couple of miles from my house. Turns out the turbine messed up everyone’s cable TV so it had to come down. (This was the 70’s so wind farms and cable TV were in their infancies.) I work in the utility-scale wind industry, so hearing about the Whooshie was hilarious. Train cafĂ© cars and dining cars are some of the BEST places to meet people.

    I’ve taken as many solo trips as I have with family or friends. On those trips alone where I’ve met interesting people it probably helped that I’m Southern, since we are sort of trained from birth to be friendly to everyone. However, that can be a problem on ones first time in certain cities. I’ve learned over the years to adapt and I can “read” people who would be interesting to talk to much better now than in my twenties.

    I love to travel alone, but I have to admit, I start getting lonely about 7-10 days in, even with all the interesting people on the train or in the restaurants or the hotel breakfast bars. I think everyone has that point where they’re ready for home.

  5. You are so right! Because my husband is now in a nursing home, I spend a great deal of time there. I have reconnected with an old friend and made many new ones among both the caretakers and the residents. There are new friends waiting just beyond the front door if one has the courage to open it and step outside. Thanks for the reminder.

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