Don’t Let the Perfect Be the Enemy of the Good
Why “good enough” is usually the best travel decision you’ll make
Over the past few weeks, I’ve been writing a lot about risk. Not eliminating it, because as we’ve discovered that’s not possible, but understanding it, managing it, and deciding which risks are actually worth taking. This week is simpler. It’s about something an old coworker used to say all the time: “Don’t let the perfect be the enemy of the good.” At the time, I’ll admit, I got tired of hearing it. But like a lot of simple ideas, it sticks…because it shows up everywhere once you start paying attention.
For me, travel is one of the clearest places it shows up.
We tend to overthink our trips before they even begin. The itinerary becomes something to optimize rather than something to experience. More cities, more countries, more “must-sees,” all packed into a fixed amount of time. On paper, it feels efficient. In practice, it often just means moving faster than the experience can keep up. A good itinerary leaves room. The “perfect” almost never does.
The same instinct shows up in how we get there. We wait for the ideal routing, the perfect departure time, the exact aircraft, the connection we like instead of the one we don’t. None of that is unreasonable on its own, but taken together it creates friction. There is almost always something slightly off. The perfect flight rarely exists. A good one gets you where you need to go at a price you can stomach, which is the whole point.
Accommodation follows the same pattern. Every hotel is a tradeoff between price, location, and comfort. You can optimize for one, maybe two, but rarely all three. And yet it’s easy to spend hours trying to find the option that somehow does. Eventually you book something that’s good enough, and once you arrive, it usually is. Not perfect, but entirely sufficient and pleasant for what you actually need it to do.
All of this builds toward a bigger realization: the “perfect trip” itself is mostly a myth. You can plan structure: where you go, how you get there, where you stay, but you cannot plan the parts that actually make a trip memorable. Those tend to be the unplanned moments: a conversation with a local, a detour where you got lost, something that happens because the plan wasn’t airtight. The same way life at home isn’t defined by perfectly executed days, travel isn’t either.
That’s why the idea of not letting perfect get in the way matters more than it seems. Waiting for ideal conditions like more time, better timing, a cleaner plan, often just delays the experience or might even prevent it from happening altogether. A good trip taken now is almost always better than a perfect trip that never happens. And once you’re on the road, holding too tightly to perfection can make the experience more rigid than it needs to be.
None of this means planning doesn’t matter. It does. But there’s a difference between planning to enable a trip and planning to control it. The former gets you moving. The latter often keeps you stuck.
The Bottom Line
There is no perfect itinerary, no perfect flight, no perfect hotel, and no perfectly executed trip. There is only the one you take. And more often than not, it’s the imperfections…the small deviations from the plan…that end up defining it.
Over to You
What’s a trip you almost didn’t take because it wasn’t “perfect”? And aren’t you glad you went anyway? What made it memorable?