I turned forty in a Dublin pub I never planned to visit, holding a Guinness I’d been thinking about for months. Before I travel, I love the planning phase. I almost like the planning as much as the trip itself. But this pub had never once turned up in my weeks of research.
I started my planning months before this trip. General must-see first, then deeper into food, history, and art. Dublin is a city known for storytelling, so I read the authors who’d come out of it. I told myself I’d stay away from the generic “perfect itinerary” posts and the identical top ten lists.
Two things mattered to me on this trip. I wanted to drink a Guinness in Dublin on my birthday. I wanted to feel the essence of a city that legendarily knows how to tell a story. Everything else was just details to fill in around those two things.
The Parts I Never Planned
Some things are famous because they are just that good. I booked the Guinness Storehouse and the Jameson Distillery. Both were excellent experiences and exactly what a well-planned trip should include.
But the Guinness I actually remember came from a pub recommended by a clerk in a whisky shop. Recommended the way you’d mention something to a friend and not a tourist. It turned out to be the exact right place to turn forty.
A few days later, the same thing happened again. I didn’t want to see the Cliffs of Moher in a packed tour bus on a fixed schedule, the way many people see them. So we hired a local driver for the day. We got there early, and the fog rolled in cold, so the visit itself was short. We skipped the main places where the big groups were headed. On the way back, the driver took us to a chocolate factory that felt like it was in the middle of nowhere. It was perfect.
Neither place existed in any of my research or planning. Both are part of that trip I want to go back to.
Satisficing
In 1955, the economist Herbert Simon coined “satisficing”, a combination of satisfy and suffice, to describe choosing an option that’s good enough instead of holding out for the theoretical best. He later won a Nobel Prize in Economics for the idea behind it: no one can process every variable in a real decision well enough to find a true optimum. We’re all working from an incomplete map. The only real choice is when to stop reading it.
Decades later, psychologist Barry Schwartz split decision-makers into two camps built on Simon’s idea. Maximizers keep comparing until they’ve considered everything available. Satisficers stop once something clears the bar they set. Across his research, maximizers were more likely to regret their choices and less satisfied with them, even when nothing was wrong. You can think of it like a search tax: the cost of continuing to look, charged even if the extra looking turns up nothing.
My Dublin research wasn’t wasted. But the part of the trip I remember most was the unplanned moments: the stranger’s tip and a driver’s detour.
What the Culture of More Gets Wrong
We’re taught that thoroughness is care. If you don’t consider every option, you didn’t do the work. But there’s a point where more research stops protecting an experience and starts drowning it.
Scarcity says leave nothing to chance, cover every angle, and you’ll have earned the best possible version. Sufficiency says decide what you actually came for, then leave enough space around it so that someone else’s favorite pub has a chance to find you.
A Small Practice
Before your next trip, purchase, or major decision, write down the one or two things you most want out of it. Then give your research a fixed window. One evening, one weekend, whatever’s honest for what’s at stake. When the window closes, stop looking, even knowing there’s more out there. Leave the rest of the space open on purpose.
The space is where the magic shows up.
See you next week.
P.S. I’d love to hear about the unplanned stop that you remember most from a trip.