058 • The biggest mistake I made when I started travelling

Jul 14, 2024

I’d never travelled outside my own country before last month. Three weeks in Portugal and Italy later, there’s one clear thing…

Travel solo if you want but don’t be solo. Do things with people - it makes everything so much better.

This was something I was slow to figure out. I thought that just because I make most of my work efforts by myself, I could enjoy the sights and experiences in a foreign country the same way.

But I was completely wrong. Entirely without exception, my favourite experiences from the trip involved one or more other person.

What’s also interesting was that there was little correlation between the assumed significance of the moment and how much fulfilment I gained from it.

I’d take having dinner or drinks in a back street with a couple of people I’d recently met over standing in front of the Colosseum alone.

But why was this the case??

My best guess is that we innately want to share experiences with people.

The positive feedback loop of seeing that someone is feeling the same awe and joy at an experience is absent when by yourself - you could be standing in front of some of the most important cultural artefacts and feel dissatisfied.

So that’s my lesson for this week. Almost everything, especially new experiences, is better when someone shares it with you.

Have a great week!

-- Theo

P.S. I'll share some specific stories from this experience in the corresponding video issue I release for this newsletter next week...