It was mid-June, and I had a mountain of work assignments to complete before my much-anticipated sojourn to the Balkans. I may be preparing for a long vacation, but my work life wasn’t taking any breaks. I had to power through and meet all those deadlines. On top of that, I had an entire holiday to plan, one that’s taking place in a continent I was completely foreign to. I didn’t know then, but it turned out to be a much larger hill to climb than my career commitments.

Before writing each article, I’d usually have a clear outline of what I wanted to say. I’d have a clear direction and whatever research I did was for a specific purpose and outcome. Planning a vacation, on the other hand, isn’t the most straightforward affair. How was I supposed to know which restaurants offered the best local cuisine with an idyllic ambience, which hotels were the most strategically situated with all the amenities we would need, which attractions we couldn’t miss, and which ones were too predictable and dull? And what about all those hidden gems, best-kept secrets and one-of-a-kind experiences that aren’t as publicised on Lonely Planet and TripAdvisor?

I was scrambling. In utter chaos mentally, struggling to juggle my work responsibilities and the burden of planning the perfect vacation. It wasn’t long before I abandoned all hope of looking my best, as the stress of it all caused more zits to appear on my face.

Travel is meant to be an escape, a time where you could get away from reality, sip on endless glasses of sangria, and take a breather, both literal and spiritual. I hear friends waxing lyrical about the ecstasy of jetting off, and above all, the anticipation, the waiting and the planning of the trip. It’s better than the trip itself. They would say. The excitement you feel peaks here. Sometimes, the actual experience isn’t as thrilling as the days leading up to it.

Yet, it felt more like extra work, extra research. There was a lot more organising to do than I’d expected, as if I were heading a tour agency all by myself, putting itineraries together with no room for error or missing details. Coupled with the unknowns and uncertainties of a foreign city, it takes that much more effort to feel safe enough to have fun on the trip.

It means that I had to eliminate as many question marks as possible. I needed to know how to get from place to place, what time the shops closed, what I should avoid, what customs I should follow. All this prep work triples when there’s a language barrier too. The longer the trip, the longer the planning. And did I mention this wasn’t a solo trip?

Even if you’ve figured out the practical issues of the vacation, there’s still the question of fun. What can you do to maximise the fun for a group of diverse individuals with diverse tastes? The last thing you’d want is to spend a month in the city of art and culture, only to miss out on its most iconic museum. It’s like going to Naples without trying the pizzas, or heading to Niagara and skipping the falls—except it might not be as obvious as this.

Perhaps your research had failed to tell you about that underground espionage-themed speakeasy, which you’d unwittingly been walking past every day. Realising it only on the flight back home makes you feel like you could’ve done better, like the holiday automatically became less remarkable in hindsight because of this missed opportunity.

Of course, it’s not as simple as that. Let’s say I did discover this hidden hotspot and brought my posse there. There’s always that off chance that someone in the group isn’t into secret speakeasies or drinking alcohol, period. You can’t have anyone in the group not enjoying themselves, can you?

The stress of travel, thus, comes also from the evils of managing people. What everyone wants often clashes with each other. You’ve got homebodies bumping heads with the thrill-seekers, and independent voyagers getting annoyed with those “too scared to be alone” group tour junkies.

It all boils down to the expectation of a perfect trip, one that would cure all pains and promise unforgettable memories. Because we expect bliss and adventure on a bed of roses, as if life becomes absolutely problem-free when we travel, we pressure ourselves into pulling off the impossible. We buy into the illusion of blue skies and rustic caverns, when the truth is, the grass looks more yellow than green, and the romantic alleys are really just part of someone else’s daily commute.