How Knowing Your Personality Type Can Help You Plan a Better Trip, According to an Expert

Happiness expert Gretchen Rubin offers tips for maximizing fun and minimizing tension based on the four tendencies outlined in her quiz.

If there's one occasion that should be all about happiness, it's definitely vacation. Traveling brings untold joy, but depending on the vibe of your companions, it can also bring tension, indecision, drama, and stress. Fortunately, there's a five-time NYT bestselling author and happiness expert to the rescue. Gretchen Rubin, co-host of the Happier podcast and founder of The Happiness Project, is well-versed in finding harmony with people whose tendencies are different from ours in all situations, including when it comes to planning and taking a trip.

Blue journal with paper airplanes on the cover
Courtesy of The Happiness Project

The first step is her Four Tendencies quiz, which reveals your personality type based on responses to inner and outer expectations. The options include Rebel, Questioner, Obliger, and Upholder. To help decipher how these relate to traveling, we turned to Rubin, who believes your tendency influences the kind of vacation you find relaxing and fun.

"For a Rebel, Rome might be this beautiful place to wander around," she says. "Someone else might feel like there are a million things to do in Rome and they're going to do every single one." There's no wrong way, Rubin emphasizes, adding, "Sometimes, having the vocabulary to understand the different perspectives helps you talk through how to get that perfect situation."

View of journal documenting trip to Tokyo
Courtesy of The Happiness Project


"To a Rebel, it's very unappealing to feel locked into a schedule," Rubin says, adding that the type has a tendency to upset others who spend a lot of time making plans and itineraries that their friend or loved one now wants to throw out the window. One approach: "Say, 'Hey, we're in Paris, and it could be really cool to check out the flea markets. I heard about this great cheese tour, or there's this gorgeous museum — what do you feel like doing?' You need to give them the feeling of choice, and not lock them in." That said, Rebels make awesome travel companions for that very freewheeling approach and spontaneity, "which can lead to fun, unexpected moments."


"Questioners love information, so they're probably the ones doing all the deep research: What's the best hotel? How do we get the best deal? What can't we miss?" The problem they may face, Rubin says, is analysis paralysis. Too much information makes decision-making hard for a Questioner who researches endlessly. Ideally, they're paired with a different type who can help reach a resolution. Rubin, who's married to one, says, "It makes him happy to know why we're doing each activity, so letting him plan it helps us both enjoy the trip more." When on the road, Questioners should remember it's OK to do things even if the "why" is unclear. "Sometimes, you don't know what you're getting yourself into," says Rubin. "And that's part of the fun."


"The thing about an Obliger is they're not always good about saying what they want to do if people around them are saying, 'I'm going to do this,'" says Rubin, adding that Obligers struggle with speaking up and being heard. An exercise to combat this is to have all parties write down three things they really want to do in their destination and compare notes, making sure something from every wish list is incorporated into the itinerary "This is a way for everyone to feel respected without anybody feeling like the trip is fun for others and not themselves," she says. Obligers are usually game to join activities and go along with the plan, if it's important to their friends or family. But even if they typically struggle with boundaries, Rubin advises, "Remember, this is a vacation and they should be able to do things that are fun for them, too."


Rubin, an Upholder, admits that this type "can be rigid." She notes, "We have a vision of what's supposed to happen and we can get disoriented if someone changes plans." That goes for unexpected weather or a last-minute cancellation. This type can also get caught up on executing a plan — which can be appreciated by those who put in effort to create the itinerary — and sometimes lose track of the exciting discovery part. Where possible, build in extra time to absorb slight itinerary shifts. "And be in a place with a lot of freedom and open time," says Rubin. Conflict is more likely to arise on trips where everyone is wrangled into the same activities. "Upholders should also remember that travel is not about marching through a to-do list; it's about settling in and experiencing it."

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