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I’m supposed to be in Italy right now.

My partner and I had a 10-day trip to Puglia booked. A “proper holiday”, the kind you feel smug telling people about, especially when they reply with, “Oh, lovely!” 

But then our dog, Dolly, got sick. As the departure date approached, it wasn’t hard to make the decision not to go; I couldn't imagine being away during that time. We managed to cancel the hotels and get our money back. A few days later, however, Dolly died.

As the flights were still booked, we did contemplate going after all. A lot of people told me that it “might be nice to get away”. But I didn’t see it that way. 

Going away wasn’t going to solve my problems. A holiday wasn’t going to cure my grief, I’d just be sad in a beautiful setting because those kinds of feelings follow you wherever you go.

So we stayed at home. And I tried to find ways to cultivate the kind of refreshment a holiday might usually give you.

Today in the newsletter, I’m thinking about holidays. Why we love them, the myths we hold about them and a counter-intuitive way to enjoy our time off more.

Recently, my friend texted me to ask me where she could go for a restful holiday.

She wasn’t coming to me because I’m full of travel recs (more on how I don’t identify as a “travel lover” another time), but because she was too overwhelmed to figure out where to go. 

I understood the assignment. She was caught in the nasty trap of desperately needing a holiday, but being too burned out to do the necessary research to book said holiday. I sent her a link to a cute B&B in Somerset.

I knew what to send her because I knew how she was feeling. The way I go about booking holidays is realising, usually too late, that I need a break. But before I can do anything about that, I’ll first spiral about the practicalities – and additional expense – of taking time out as a freelancer.

So I knew that what my friend was really saying to me in her request for a holiday rec was that she desperately needed rest. Like her, I too conflate holidaying with resting. My ideal vacation involves doing very little. I like going to a cosy hotel in the winter or a lazy pool spot in the summer. I want to eat tasty food, have at least one nap a day, walk a bit and read.

While it doesn’t sound like much, I do seem to expend a lot of effort in the pursuit of doing nothing. I’ll pour all that’s left of my energy into trying to plan a trip that’s optimised for laziness.

When I think about my holidays, I most look forward to the time away as a chance to relax. But why do I think I need to go away to get some rest?

In the run-up to a holiday, I work myself up trying to get everything ready so that I end up more stressed and in more “need” of the time off. 

That myth of a restful vacation becomes something of a self-fulfilling prophecy. I’ll tell myself that I need to get away in order to relax, but then I’ll get more stressed as I prepare for the trip. I’ll cram too much into the days beforehand, from finishing up work tasks to finding time for a pedicure. By the day before departure, I’m a wreck. And yet, rather than question this approach, I’ll see it as evidence of how much I needed that holiday in the first place.

But do I actually need a holiday or do I just need more breaks in my regular life? Would I be so desperate for a holiday if I had a little more breathing room in my day-to-day?

We have this misguided belief that taking a holiday will refresh us and amp us up for work. I can say that I’ve never come back from a holiday feeling like that. Even long ones. Instead, I feel something closer to this:

The myth of the restful vacation is fuelled by our cultural impulse to commodify leisure time.

We prize productivity so highly, that holidays become our reward for working hard the rest of the year. We literally “earn” our time off. You need to be working at a company for X amount of time before you accrue your days off. Often, a perk of staying loyal to a company is that you get more days off for your service.

The harder we work, the fancier the holiday we expect. We justify it with “I work hard, I deserve it.” As icky as I find that concept, I’ve fallen prey to it myself. I just did with the Italy holiday – I booked us bougie hotels, justifying the expense because we haven’t had a “proper” holiday since before the pandemic. What do we even mean when we say proper holiday? Usually, it’s just an excuse to spend more money. 

We think that travel is aspirational, something we should strive towards because visiting new places and experiencing new cultures will better us. As we tick covetous destinations off the bucket list, travel itself becomes an achievement. And yet, we rarely seem to bring that betterment back to our regular lives, let alone to our own local communities. As Agnes Callard wrote in the New Yorker: “Travel turns us into the worst version of ourselves while convincing us that we’re at our best. Call this the traveller’s delusion.”

Despite what you might think right now, I’m not trying to say we shouldn’t go on holiday. Quite the contrary!

I want to be able to enjoy my time off even more. I want to feel as relaxed as I aspire to feel abroad all the damn time. I want to do less not just when I’m away, but also at home. 

So maybe we need to take a good look at why we feel the need to take a vacation in the first place. What does the holiday-mode version of ourselves do that our real life doesn’t? Put simply: how we can reduce stress in our everyday lives so that we can enjoy our vacations even more. 

Someone who did make it to Italy this summer is the online creator Caroline Winkler. I think she might have even been in Puglia; she made a cute travel vlog about it. 

In it, she talked about how we can’t wait for the nice trip to choose how to live our lives and that instead we can “live as we vacation”. We can “distil the joy of travel into something [we] can access every day”. 

For me, right now, the joy of travel is space. Space to rest, space to grieve and space to heal. 

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