Plan the Feeling First: Ramit Sethi's Framework for Unforgettable Trips

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Overview

Ramit Sethi opens with a claim about their own vacations: by the time they're actually traveling, they aren't thinking about money at all. They say they will never sit in a resort restaurant wondering whether they can afford the shrimp cocktail, because those decisions were made long before. Over trips from Kyoto to Morocco to Italy, Sethi has developed a planning framework they describe as personal and intentional, and they argue it applies to a weekend getaway as much as to a $25,000 dream vacation. Their central point is that great trips don't come from spending the most. They come from knowing what you want and what you don't, spending extravagantly on the first, and cutting the second even when other people think you should see it.

23 min read

Why Most People Plan Vacations Backwards

According to Sethi, most people start in the wrong place. They pick a destination that has no real connection to them, then go to a travel site and start pricing things. Sethi compares this to opening the kitchen cupboard, finding almonds, coleslaw, slightly rotten lettuce, jelly beans, and pickles, and announcing that you're going to make a magical meal. People start with logistics, such as whether Delta or United is cheaper, instead of asking what they want to experience or feel. In Sethi's telling, that is how you end up working through random checklists and complaining at Disneyland about how expensive and hot it is.

Sethi says the first question should be what kind of experience you want. Sometimes that's complete relaxation: a resort, time by the pool, eating, and not much else. Sometimes it's adventure, like the medina in Morocco or gorilla trekking and safari in Rwanda. Sometimes it's family, such as spending hours every day with relatives in their home in New Delhi. Any of these can be magical, but you have to choose.

Sethi argues that choosing a destination at random has a hidden cost. If you get off the plane and ask ChatGPT what to do, and you only get ten days or two weeks off a year, you haven't just lost the $4,000 the trip cost. You've also lost the time and the chance to create memories. Sethi adds that people deserve at least one moment of awe every quarter. It could be as extravagant as a sundowner at sunset on a Kenyan safari, or as close to home as watching the sunset at the park while your kids play soccer.

Lower the Stakes, Raise the Magic

Sethi points to a familiar scene: parents at Disneyland who are irrationally angry at a young child's tantrum because "we spent all this money and time to come here." Sethi calls this understandable. Trips cost a lot of money and time, so people pile all their expectations onto a single moment and get frustrated when it isn't perfect.

Sethi proposes changing two things at once. First, lower the stakes. Not everything has to go perfectly, things will go wrong, and you can laugh about it. Second, when things do go right, they should be magical. That means refusing to spend time on things you don't care about, such as a museum everyone says you must visit, and going deep on the things you love, even to a degree other people find strange.

As an example, Sethi describes commissioning a bespoke tour in Japan from a local guide based in Kyoto, built around their specific interests. The guide recommended visiting a temple so Sethi would understand some of the aesthetics involved. Sethi said they would go if she truly believed it was necessary, but that they weren't interested in temples at that point. They didn't go. Sethi's summary: "your money is good money," and you get to decide what you see.

Planning 12 to 18 Months Ahead

Sethi says they and their wife never land somewhere and then start searching online for things to do. They usually plan trips 12 to 18 months in advance. Every December they hold what Sethi calls a "rich life review." They decide how many trips they'd like to take, whom they'd like to bring, and what kinds of places they want to go. They check whether the numbers make it possible, but they always start with the vision ("what if," "wouldn't it be cool if") and work out logistics afterward.

Sethi estimates that planning a major trip, such as two to four weeks in Japan, takes them two to three months at an unhurried pace. They say a lot of pre-work is already done: a document of friends and family they'd like to invite, a list of hotels they want to stay at, and a bookmark folder for nearly every country they want to visit. Sethi says it wouldn't matter if planning took a year, because they enjoy the process.

Sethi applies the same thinking to transit, which many people dislike: rushing to the airport, hauling bags and car seats, long security lines, uncomfortable seats. If that part matters to you, you might book a car service, pay for expedited security, check bags despite the common advice not to, or upgrade your seat because your guilt-free spending allows it and you want to arrive rested. Or you might deliberately buy cheaper seats so you can stay an extra day. Sethi says both choices are valid. What matters is that the trade-offs are explicit, agreed on if you're traveling together, and owned, because nobody is forcing you to take the trip.

Escaping "Default Vacation Mode"

Sethi repeats that the first question is never "How much will this cost?" but "What do we want this trip to feel like?" A very cheap trip can be adventurous, and a very expensive one can be purely relaxing. In Sethi's view, cost and experience are only slightly correlated.

Sethi compares the common alternative to what happens when the financial industry asks people about their "financial goals." Ordinary people suddenly start speaking in stilted jargon about retiring diligently and saving four to five percent, which Sethi says isn't how anyone actually thinks. On vacation, people similarly turn into a "default vacation person" who feels obliged to see every museum and sight. If you haven't been to a museum in your hometown in seven years, Sethi asks, why would you care about one abroad? It's fine to say you aren't interested.

Sethi traces this to a broader pattern. When they ask people "What is your rich life?", many can't answer, because most of us move through life as consumers who mimic others: the same clothes, cars, and activities. Rare vacations then default to the same template. Sethi frames travel as a chance to learn who you are, citing the saying "We are never as American as when we are abroad." Travel exposes what you enjoy, what you expect, and what you'd never noticed, and Sethi urges people to do that reflection before the trip. They add that if you have a little money to hire an expert for two hours, that person will gladly share their life's work with you.

"Must Be Nice": Intentionality at Any Budget

Sethi acknowledges that some viewers dismiss their travel videos as unrelatable because of the difference in income. Sethi thinks this misses the point. The hotels may differ, but the lesson is about intentionality, which you can apply with half or a tenth of the money.

Their example: when Sethi and their wife wanted quality time with some couples they know, they sent an email saying where they were going, that spending time together mattered to them, and exactly what they had in mind: one big dinner together, one excursion, and plenty of time on their own. They shared the hotel so the others could decide whether they liked it and could afford it, and they gave the dates. Sethi notes this works just as well with a hostel as with a luxury hotel. The point of money, they say, isn't to throw it around on everything but to spend extravagantly on what you deeply love.

Case Study: Gorillas in Rwanda

Sethi walks through how one trip came together. After several relaxing trips, including a Thai beach and a Mexican resort, Sethi and their wife asked how they wanted to feel the next year and realized they wanted adventure. They were healthy and fit, and they knew there might be places they wouldn't be able to visit someday.

They then asked each other what "adventurous" meant, since it could just as easily mean three weeks of cooking or ceramics classes in the Japanese mountains. Sethi wanted something tactile and physical, and their wife agreed. While looking through their list of countries, she suggested seeing the gorillas in Rwanda, and Sethi immediately knew that was it. From there the details followed: how long people typically stay, and since Rwanda is a long trip from the US, what else they might want to experience in the region.

Sethi describes being about six feet from the gorillas. Babies ran around pulling hair, adolescents postured to look big and strong, and the huge silverbacks mostly dozed with their eyes closed, occasionally opening one eye to quiet rambunctious youngsters with a grunt that made everyone understand who was in charge. Sethi says they felt connected to nature and grateful, because they had talked about and planned this for years. Walking through a tea plantation and then lush jungle, Sethi remembers thinking that this was exactly what they wanted to feel: wet grass, sweat, moving their bodies. At that moment, they say, money was the last thing on their mind.

Bookmarks, AI, and the "Barbell"

Sethi says they enjoy each trip three times: once while planning, which they compare to bringing a piece of art to life; once while traveling, living what they've planned for months or years; and once afterward, when they post photos and videos and relive the trip through other people's reactions.

Sethi never plans from a blank page. If you were told you'd be in Bulgaria in six months, you'd probably have no idea what to do. So whenever Sethi reads something interesting in their daily reading, whether it's about Amsterdam, Mexico City, or New Delhi, they bookmark it. When a trip comes up, they have hundreds of saved restaurants and experiences to choose from, filtered by the vision for that trip.

For people without such a list, Sethi ran a test. They gave ChatGPT a description of themselves and their wife, including their ages, interests like design, and what they do and don't care about, and asked for a five-day New York City itinerary. Because Sethi knows New York well, they could judge the result. They rated it about 80% good and a great starting point, with a few solid restaurants and decent hotels. Where it fell short, in Sethi's view, was that it didn't suggest anything that would be memorable for years.

That's what Sethi looks for. They describe their approach as a "barbell": skip the fine-but-generic middle and look for the extremes. That might be someone cooking in a back alley or a very high-end restaurant, or something personally relevant, like a textile shop whose owner will show them behind the scenes how the textiles are sourced. It could be cheap or expensive, near or far, as long as it will be remembered.

Invisible Scripts and the Dream Phase

Sethi asks viewers to examine their "invisible scripts," deeply held beliefs about travel that shape how they plan. Examples include: we don't have enough time; it'll be too expensive; we'll need a vacation from the vacation; other people get to take trips like that but we can't because we have three kids; I'm easygoing and just like to wander; I only want to go where the locals go.

Sethi notes that when they see people booking ten hours a day minute by minute, they usually sense scarcity behind it, a belief that "this is the only time we'll be here, so we have to see everything." Changing that script to "we'll have an incredible trip, and if we love it we can always come back" would, Sethi argues, transform the itinerary and how the trip feels.

Sethi also argues that the planning phase is the time to dream, not to shut ideas down as too expensive or unrealistic. Ask "What if it were even more magical?" or "What would you do if we could do anything?" Sethi says some people avoid these conversations for fear of disappointing themselves or a partner if they can't deliver. Sethi sees it the other way: dreaming together has connective power. You don't have to do everything you brainstorm. You decide together what fits your vision, budget, and time.

The Overscheduled Itinerary: A Story Against Themselves

Sethi admits to having overscheduled trips. Early in their relationship, their wife planned their itineraries. In Bangkok, after a full day out, they had planned to nap before a nighttime food tour, but things ran late. They changed clothes and went straight out. Sethi remembers being extremely irritable, sweating, and not enjoying some of the best food in the world, even though the guide was perfectly nice. Sethi says the problem wasn't the guide or the city. It was them.

Their wife took the feedback. On the next trip, she asked Sethi to plan one day, Thursday. When Thursday arrived and Sethi explained the plan, she just looked at them. Sethi had packed the day from morning to night exactly as she had done in Bangkok. Sethi says they realized in that moment, "Oh my God, it's me." Sethi's lesson is that planners, from the comfort of home, keep adding things that sound cool, like at a buffet where everything seems free. They end up picking from a checklist instead of designing an experience.

The episode led to a conversation about their travel style and a new rule: one major activity per day, such as a food tour or a sight. Now their rule is one major activity every two days. Sethi notes this works because they tend to take longer trips. For a four-day trip to the other side of the world, they doubt one activity every two days would be enough.

Sethi says some of their best travel memories came from unscheduled time. They don't fear being unproductive while traveling. They compare it to watching hours of TV at home without guilt, or to a lion resting in the sun that will be ready when it's time to act. On a seven-day trip, you might schedule two late-start mornings so everyone can do their own thing. Traveling with parents, you might reserve an afternoon block each day for them to nap before dinner.

What's Worth Spending On

Sethi recalls a college trip to Las Vegas with friends: cheap Southwest flights for about $59, then an airport shuttle that dropped everyone off at their resorts. Sethi's group was last, and the driver announced over the mic, "And now for our high rollers at Circus Circus." Sethi says the roast was deserved, since it was the worst hotel in Vegas, and they knew it well because their parents used to take them there as kids, give them $20 for the kids' games, and see them six hours later. Still, the friends had an amazing trip and still joke about the driver. Fancier casinos with better food didn't matter because they were there to hang out together. Sethi's takeaway is that more money doesn't create memories. Feelings, connection with the people you're with, and the stories you create do.

Sethi and their wife now spend much more, but they've learned what they don't care about. Fancy restaurants aren't important to them when traveling, so their evenings are mostly free of reservations. They will, however, spend heavily on private experiences tied to their interests. On one tour of a home designed by an architect, they spent over an hour in a single small room, asking the architect about lighting choices, how afternoon light compares to evening light, wall textures, and how he designs his own home with kids who make messes. Sethi acknowledges this might seem boring to others, and says that's the point: "Your rich life should confuse other people," because true luxury is getting exactly what you want.

Morocco is Sethi's example of deliberately skipping the standard experience. Visitors typically go see rugs, but Sethi doesn't like Moroccan rug design and prefers Persian and Indian designs, so they declined repeated offers to visit rug stores. Instead, they went deeper elsewhere. At a textile shop, they chose thread colors, watched weavers at the loom, and had a coat made, which they say feels meaningful to wear because they saw how it was made. At a beautiful hotel, they took the general manager for a walk and asked how the property was created and staffed, and how it delivered in Morocco the same service the brand delivers in India. Sethi admits this sounds "freakishly weird," but says it's what they love.

Saving Without Guilt

Sethi's saving method is straightforward. If a trip a year away will cost about $12,000, they divide by 12 and automatically move $1,000 a month into a dedicated, named travel account, such as "Japan 2027" or "Family Italy Trip." By departure, the trip is already paid for. Sethi says they intentionally oversave so they never wonder on vacation whether they can afford gelato.

To estimate cost, Sethi says you can reach a number that's about 85% accurate in roughly ten minutes by focusing on the main cost drivers. For most people those are flights and accommodation, plus some daily spending on food and excursions. Over time, Sethi and their wife have developed daily spending benchmarks. Sethi cites luxury travel advisors, who they say typically quote about $1,000 to $2,000 per person per day, up from around $1,000 before COVID because hotel rates have risen sharply. Sethi stresses that this is a luxury figure and most people spend nowhere near it, but knowing your own number lets you estimate a trip by counting days.

Sethi then criticizes a pattern they often see: people spend carelessly all year on things they barely care about, then become hyper-frugal on the vacation they've been talking about for months, agonizing over a Dole Whip at Disney. Sethi asks why someone would spend mindlessly for most of the year and then turn into a grumpy guy at the one thing they claimed to value. If travel is one of your "money dials," Sethi argues, your spending should reflect that. Plan and oversave so you feel ease and abundance while there. The underlying principle, according to Sethi, is using systems (automatic saving, automatic investing, and carefully managed fixed costs) so that spending on a dinner while traveling carries no guilt. Sethi recommends their conscious spending plan as a way to know your numbers.

Designing a Trip for Someone Else: The Mexico Example

Sethi recounts advice they gave a student in their money coaching program who was taking family to Mexico and wanted to make it special. Sethi's answer was to be thoughtful, and that the trip starts the moment the parents leave their house.

Sethi walked through a scenario. A black car picks the parents up, maybe the first time they've ridden in one. At the airport, someone helps with bags and the unfamiliar steps of international travel, which Sethi estimates costs $100 to $150. In Mexico, someone holding a sign with their names meets them and takes them to an SUV stocked with cold water, beer, and cold towels, and a uniformed driver tells them the resort is 25 minutes away. At the resort, staff take their bags. Sethi advises reminding the parents beforehand to let them. The front desk greets them by name with a welcome drink and hands them a handwritten note from their child: Mom has a spa appointment waiting, and Dad will be escorted to the pool to join everyone.

Over the following days, Sethi suggests leisurely breakfasts, a hands-on cooking class, and a professional photographer, since the whole family is rarely together. At dinner, Sethi suggests bringing old photos of each person and asking them to tell stories, like what people wore in the '70s. Sethi says this is worth more than any bigger hotel room, because the money wasn't just thrown at the problem. It was spent thoughtfully.

Ask for What You Want

Sethi emphasizes that you can ask for what you want respectfully, and that it's fine when the answer is no. At the hotels they stay at, they send a pre-arrival letter, which Sethi says hotels appreciate because it helps them serve guests. For example, since they aren't into wine, which hotels often leave as a welcome gift, they ask for berries or local fruit instead. Sometimes it isn't available, and that's fine.

The principle, as Sethi puts it: if you don't shape the experience yourself, you'll usually get a mediocre version of what everyone else gets, because travel businesses cater to the average traveler. On a private food tour that normally ran about four hours, Sethi and a friend asked in advance whether it could be two and a half. The guide said of course. Otherwise, Sethi says, they would have sat through four hours, politely enduring "another thing."

The Ranthambore Dinner: "This Is the Whole Point of Money"

Sethi closes with one of their favorite memories. Because relationships are one of their core values, Sethi and their wife invited Sethi's mother and aunt, who are sisters, on a trip to Ranthambore, a tiger safari destination in India. Although both were born and raised in India, neither had been there. The adventure started on the overnight train from New Delhi. Sethi had booked first class, picturing something like Delta, and found an Indian sleeper car instead. Still, the sheets were clean, and in the morning uniformed porters took their bags and drove them in SUVs to the Oberoi, which Sethi calls their favorite hotel brand, especially in India. There was a greeting ceremony, the mother and aunt were told not to worry about bags, and spa appointments were waiting. The next day's safari was bumpy and adventurous, though they didn't see any tigers.

One night, Sethi took the chef aside and asked to create a special dinner for their wife, mother, and aunt, based on where each grew up and their favorite dishes. The chef loved the idea, sat down with Sethi, and asked about each person, such as whether their wife's favorite was paneer. Sethi told the family only to be ready around 6:30. Since they were in the middle of nowhere, clearly staying on the property, a golf cart drove them around a corner to hundreds of candles and Rajasthani music, with the chefs waiting and a personalized menu at the table. Sethi says they could hear the surprise in all three voices, and that the moment they'll never forget is their aunt asking, "Why did you do this for us?" Sethi recalls thinking that this is the whole point of money: creating experiences that let people know they are valued and loved. In Sethi's words, if you can create one unforgettable meal, you can create one unforgettable trip, and from there an unforgettable life.

Sethi ends with a question for viewers: not luxury or business class, but what one specific, meaningful thing would make your next trip unforgettable? A cooking class with your kids, a month in Tokyo, or taking your parents somewhere they never imagined and making it easy for them.