There Are Two Kinds of Travellers: Those Who Love to Plan, and Those Who Don’t
Top image credit: Unsplash, Marvin Meyer

To adapt the immortal words of Britney Spears: there are two types of people in the world / the travellers who plan, and the ones that don’t. 

And these two types of people are so fundamentally different they might as well be someone who does CrossFit and the rest of us normal people. 

Unfortunately, Priscilla Lum and Tan Wee Kiat, 32 and 30 respectively, got married before they discovered that their better half was the antithesis of their innate travelling type. Prior to getting hitched, the furthest they had travelled together was a staycation on Sentosa; their trip went without a hitch because, well, for most Singaporeans, Sentosa is probably more accessible and requires less planning to get to than somewhere like Bukit Gombak. 

But disaster struck when they started planning for their honeymoon to France. 

Or, as Priscilla clarifies, “His ‘plan’ was to not plan anything at all!”  

An accusation to which Wee Kiat immediately retorted: “Isn’t the point of a holiday being free and doing anything you want?” 

Wee Kiat then showed me an Excel document of Priscilla’s meticulously planned schedule, of which I will adapt an essentially accurate version because I was not allowed to take a photograph of it (“Paiseh lah”): 

7 AM: Wake up!!!
7.15 AM: Finish brushing teeth, washing face, showering.
7.30 AM: Apply cosmetics, moisturizers etc.
8 AM: Set out for breakfast at the Les Halles market. Buy the tarte ratatouille.
9:47 AM: Catch the 9:47 AM train to Versailles.
. . . 

You get the idea. 

And you haven’t even seen the planning for the plan, which involved carving out specific dates and times to sit down and have a discussion on the most comfortable flights to take, the most Instagrammable hotels, the best season to visit … or the multi-page packing list that was so specific it stated the number of tissue packets and hangers to bring.

“This is worse than my BMT. My sergeant was nowhere as anal as her,” Wee Kiat complained.

Said tarte ratatouille that must be finished within 30 mins. Credit: Priscilla and Wee Kiat
Extreme as it sounds, when Priscilla explained her thought process, I could see the rationale behind it. 

“It’s all about maximizing happiness, isn’t it? Because it’s our honeymoon and I’m travelling with the person I love, I want everything to be perfect. It’s the only honeymoon we will take.” 

 For people like Priscilla, a trip abroad is a capstone event in their life against which everything else will be measured and compared. It serves as a highlight, a mental refuge to which they can retreat when work gets dreary. When relationships get strained, it even reminds them of happy times spent with their partners and thereafter renews their sense of commitment to the relationship. 

Such an elevated perception of overseas trips thus necessitates perfection and everything being planned down to the last detail.

In fact, Priscilla admits that she sometimes wonders if she finds the planning more pleasurable than the trip itself. It has something to do with the idealised images that all her research and planning generate, which, in a virtuous (or vicious, depending on where you come from) cycle, make her return to her planning with even greater enthusiasm. 

It may seem excessive and unhealthy, potentially leading to Paris syndrome (in which people manifest anxious and depressive symptoms when they find out the real Paris is nowhere near their mental image of Paris). But, if we’re honest with ourselves, such obsessive trip planners are whom we rely on when things go wrong. 

Struck with a sudden bout of diarrhoea and there’s no toilet paper in the nearest public toilet? Thank the heavens someone like Priscilla thought to bring along tissue packets—and hand sanitiser. 

Lost, hungry, cold, bemoaning endlessly the futility of life in a rural town where the next bus to the city 50 KM away comes in 1.5 hours? Well, maybe you should have listened to your Priscilla-type friend and finished breakfast at 9.30 AM instead of 9.55 AM because you wanted to take the perfect Instagram shot of your wobbly soufflé pancake. 

And what’s wrong with wanting to ensure everything is in place for an overseas trip? When we track our daily expenses or obsess over every small step on our career trajectory, we are deemed prudent and well prepared, so why the double standards? 

“Because it affects others. It has negative externalities,” grumbles Wee Kiat.

For some travellers, planning and packing are part of the pleasure. Credit: Unsplash, Arnel Hasanovic
Let’s look at this same portrait from another angle. 

Wee Kiat is the archetypal spontaneous trip-goer. His idea of a fun trip is to show up at the airport at 9 PM after work on a Friday, with nothing in his haversack (except some pairs of clean underwear, his passport, and a good wad of Singapore dollars), and buy a ticket for the next flight to a nearby Southeast Asian country.  

His lack of packing has never bothered him. Wee Kiat reasons: “We live in a globalised economy, right? There are pharmacies, Uniqlos everywhere. I can buy anything I need wherever I am. So why bring along my whole room?” 

As for the fact that he never knows what he’s going to do when he touches down on foreign soil, he explains, “To me, the joy of travelling is getting lost and wandering around the streets, talking to the locals. Not visiting cafes just because it’s on a listicle. I want to be a traveller. Not a tourist. And you don’t need an itinerary for that.”

That’s how he spent his early 20s—spontaneously boarding a flight to Da Nang and visiting its beaches one weekend, and a flight to Jakarta and eating “the best street food [he’s] had in his life” the next—because he wanted to “destress from [his] intense uni course”.  

In that phrase “destress from [his] intense uni course”, we discern Wee Kiat’s approach to travel. It is, basically, the antithesis of Priscilla’s view of travel as a milestone event of life—for Wee Kiat and people like him, travel is a break from life in which you get to escape expectations and responsibilities. 

That’s why excessive planning—or any planning at all—grates on Wee Kiat’s nerves. When he plans for something, he sees it as work or intellectual labour, which is precisely what he wants to avoid in the first place.

Thus: the fundamentally irreconcilable difference between Priscilla’s and Wee Kiat’s travel philosophies. The former is contingent on travel being a concrete destination, one in which you have to plan for or you’d end up getting lost. The latter sees travel as the journey of getting lost, in which any act of planning is an unwelcome waypoint.

Other travellers would rather lose themselves in a back alley like this than visit tourist attractions. Credit: Priscilla and Wee Kiat
So how does the couple—still happily married, I should add—resolve this impasse?  

Well, they didn’t really. Priscilla still indulges in her love for planning (she has a separate planner and notebook for each trip she takes), but doesn’t force Wee Kiat to participate in the process—the only things he has to agree on preemptively are the dates. It is only on the day of the flight itself when Wee Kiat finds out where they are headed to, thus preserving the spontaneity he loves.

What about the rigid regimentation of the daily schedule? 

It’s this aspect that Priscilla compromises on. She now schedules in “getting lost/wandering time” for Wee Kiat, which can span anything from a few hours per day to an entire day. While Wee Kiat would love to get lost in a foreign city with Priscilla, and Priscilla to enjoy all her soufflé pancakes with Wee Kiat, both recognise that, for a marriage to work, the individuals in the marriage have to first feel fulfilled.

But it doesn’t mean both types of travellers can’t travel happily together. Credit: Priscilla and Wee Kiat
When I bring up, the online duty-free store of Changi Airport, as a potential solution to the couple’s deadlock, Wee Kiat immediately cringes. To him, duty-free shopping is just another form of planning to him that is disguised as planning. 

But when I point out that with iShopChangi, he can even turn up at Changi Airport empty-handed, his eyes light up. I explain that he can shop last-minute on the website and collect all his travel essentials, like a bag, water bottle, and SIM card right at the departure terminal right before flying.

“I’ve always wanted to be one of those bad-ass people who don’t even bring a bag to the airport,” he gushes.

“And I always forget to bring a water bottle on my spontaneous trips.” Wee Kiat says guiltily. “I know, I waste a lot of plastic when I go overseas.”

On the other hand, I need to do no convincing for Priscilla to come on board with the idea. iShopChangi’s upcoming iShopTheWorld online festival will feature not only their usual duty-free products, but also aggregate exclusive flight, accommodation, insurance and other travel deals on their site, which makes planning for your next trip even easier. 

“It’s kind of like a Pinterest of all my favourite things,” Priscilla says. “Now I can even incorporate airport duty-free shopping as part of my planning.”

And by logging in to iShopTheWorld’s page daily as part of the campaign’s daily challenge, Priscilla will earn points that go towards her chances of winning $1000 in travel vouchers. It’s exactly the sort of clockwork, repetitive act that gives Priscilla a pleasurable tingle. In addition, if she spends S$100 on iShopChangi in September, she will stand a chance to win a free round-the-world holiday for herself and Wee Kiat (worth up to $20,000). 

“Maybe you can tell Wee Kiat that,” she laughs mischievously.  

This post is brought to you by iShopChangi. From 2 to 30 Sep, iShopChangi will be running the iShopTheWorld online travel festival. It will feature site-wide discounts for your favourite duty-free products, deals with travel partners like Agoda, Changi Recommends and Klook, and fun daily activities in which participants stand a chance to win $1000 in travel vouchers or even a round-the-world holiday for two. 

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