It’s About The People You’ll Overhear

Next week, Wheel & Anchor will be stepping back out into the world, as our first trip in two years introduces participants to the wonders of Madeira. It’s also special in another way: the very first LiveAways program, with all the benefits I talked about here, letting you stay a little longer, get a little deeper, really drink in the place … and spend hours overhearing the conversations of strangers.

Ponta de Sao Lourenco, Madeira
Ponta de Sao Lourenco, Madeira

Maybe that sounds slightly creepy. Eavesdropping has a dodgy reputation: take Gandalf hauling Samwise Gamgee up by his ear after discovering him listening in on the wizard’s conversation with Frodo, in Lord of the Rings. The message there is clear: overhear the wrong people and you could end up being marched into Mordor. That’s you properly warned.

But stealthily listening to conversations around you is actually terrific fun and one of the great joys of travel – if it’s done the right way, of course. 

I’m talking about the public exchanges, the ones outside bars and coffee shops, the unguarded amiable banter that never says anything truly confidential because it’s just the wrong time & place for that. The safe chats that meanders their ways around nothing much at all.

Have you missed that, during these pandemic years? 

When was the last time you sat at a table in the sunshine, within earshot of strangers (little knowing this would be the last time you did it for a while)? Can you remember anything specific about it?

On that day, I guarantee the joyful phenomenon known as serendipity struck you. It strikes all the time around bars: all those strangers with their alien ways and unknown inner worlds, gently sozzling or hypercaffeinating themselves to deal with (or prepare for) a long day. All those overlapping universes of experience and knowledge! It’s so easy to see and hear and learn something new.

Madeira Wine
Madeira Wine

There you were, sipping your drink, and you overheard an unsolicited snippet of entertaining conversation…

“…so he says to me, ‘how do you like your tea: strong, weak or just right?’ What does that even MEAN, John?”

“Yeah but, you know why paper-cuts hurt so much, right? Right? Because it’s so fascinating, listen to this…”

“Yes yes yes, I know it’s my own fault, stop telling me that. I should have stopped at the first cocktail. Yes I KNOW, darling. I’m looking for sympathy, not for advice.” 

“They’re leather though. It’s unethical. I can’t buy brand new leather boots! It’s against my principles. I mean, I have some already, but I want to keep them for special occasions.”

…and without meaning to, you listen in for a minute or so, and learn something about what it’s like to be another person.

Or you stop at a park bench to munch a sandwich, and a person having the same idea sits down at the other end, and if you’re both feeling extremely brave, you stumble into pleasant but super-awkward small-talk. (This is a British perspective. Your mileage may vary considerably.)

Lake Cascade in Madeira Park
Lake Cascade in Madeira Park

However it strikes, you know how it feels: that thrill of excitement at the pleasant surprise of it, a meeting between you and something or someone unexpected in a way that leaves both sides of the equation a little enriched and wholly delighted in a way it’s hard to describe. 

(And maybe, just maybe, that most precious of things: an introduction to something you never knew you didn’t know.)

But it’s a weird word for a slippery concept. Where’s it from?

It’s a late January day in 1754, and Horace Walpole, writer and 4th Earl of Orford (not Oxford – that’s not a typo), is scratching out a letter to his friend Horace Mann.

It’s one of those “things are tolerable, old boy, if tedious and rather wearying” letters that English people have excelled at for hundreds of years, so let’s skip to the interesting part:

“…this discovery, indeed, is almost of that kind which I call Serendipity, a very expressive word, which, as I have nothing better to tell you, I shall endeavor to explain to you: you will understand it better by the derivation than the definition.

I once read a silly fairy tale, called “The Three Princes of Serendip [a former name for Ceylon, now Sri Lanka]”: as their Highnesses travelled, they were always making discoveries, by accidents and sagacity, of things which they were not in quest of: for instance, on the them discovered that a mule blinds of the right eye had travelled the same road lately, because the grass was eaten only on the left side, where it was worse than on the right – now do you understand Serendipity?

One of the most remarkable instances of this accidental sagacity, (for you must observe that no discovery of a thing you are looking for comes under this description) was of my Lord Shaftsbury, who, happening to dine at Lord Chancellor Clarendon’s, found out the marriage of the Duke of York and Mrs. Hyde, by the respect with which her mother treated her at table…”

Perhaps because of the sheer dullness of the example Walpole chooses to illustrate his theme, the term serendipity would take at least a century more to catch on (the first recorded use of serendipitous is from 1943).

But now? Now it’s firmly in the public domain – and good job too, because we’ve never needed it this badly.

When you’re travelling, serendipity is inescapable because everything is just so foreign and new. Accidental discoveries are easy when everything you meet is a relentless parade of novelty. That’s one of the great gifts of exploring the world.

Sunset over Funchal Madeira
Sunset over Funchal Madeira

A far harder challenge is finding serendipity everywhere, including at home. For this reason, it’s been hard to come by these last few years – with a subsequent dire effect on our moods. 

However you find it, serendipity is good for you. For a start, it feels nice, making you feel alive and connected and part of something bigger and more meaningful. It puts a spring in your step – and without it, life seems monotonous, drab and depressingly boring.  

And secondly, it’s a human need, something that bolsters good mental health. Without it, we’re more likely to develop anxiety, crushing loneliness and other truly miserable mental states. The less curious we feel about the potential serendipitous adventures we could be having, the more that anhedonia can take hold, the inability to feel interest & pleasure in your surroundings that’s strongly associated with depression. 

Now the tide is turning, taking us back out into the wider world to meet those strangers we’ve been keeping our distance from for good, sensible reasons – and we’re about to rediscover just how good serendipity feels. 

As Gordon said last week, it’s all about the connections … and a great way to ease back into that kind of reconnecting is to sit somewhere with a coffee or glass of wine and see who & what you can overhear. We absolutely can’t wait to start doing that again.

Wheel & Anchor’s LiveAways programs are running through 2022 and 2023. Check the Tours page for details.  

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