The Vacation Paradox
When the pressure to maximize every moment of a vacation can overshadow the enjoyment of the trip itself, driven by high expectations, extensive planning, and social media comparison
Before we begin, a little made up definition and concept, by yours truly:
Vacation Paradox (noun):
The conflicting experience where the excitement and anticipation of planning a vacation is coupled with stress and anxiety over making it perfect, often leading to feelings of overwhelm. This phenomenon is further intensified by the pressure to maximize every moment of the trip, driven by high expectations, extensive planning, and comparisons to idealized travel experiences seen on social media, which can overshadow the enjoyment of the vacation itself.
As someone who loves to travel, I often find myself overwhelmed by the intricacies of planning the perfect vacation. Whether it’s for myself or for clients, the immense pressure to make every moment count is ever-present. Knowing that vacations are precious opportunities to relax and explore, I feel an acute sense of responsibility to ensure that no second is wasted. The research, time, and energy required to plan a vacation that comes close to perfect can be daunting!
When Things Go Wrong Despite Careful Planning
A recent trip to Ibiza with my husband Mark is a perfect example of how even the best-laid plans with good intentions can go awry. With my schedule packed with client itineraries, Mark kindly took the reins on planning our vacation. He did extensive (good) research and booked activities we both thought we’d enjoy. However, once we arrived, we found ourselves canceling plans and opting for spontaneous activities instead.
We realized that we hadn't been entirely honest with ourselves about what we wanted from the vacation. We booked day parties and late-night events back to back that we couldn't handle staying up for, chose a “nicer” wellness hotel farther from literally everything, and underestimated the inconvenience of extra travel time driving around the island. I unexpectedly cut my foot on the second day, making dancing and walking for longer stretches of time nearly impossible.
Despite these missteps, we had some amazing days of exploration and fun by being willing to pull the emergency brakes and switch things up when needed. We canceled lunch plans and rode electric bikes giggling around the island of Formentera, which we absolutely fell in love with. We opted not to go clubbing at Pacha from 12am to 6am, because we were fucking tired and wanted room service and TV and injury rehabilitation instead.
We realized the trip was so hard for us, because we could see the potential of a perfect trip in Ibiza, and that in itself was infuriating and frustrating. A trip slightly less than perfect left us feeling like we were in the vacation uncanny valley, and we felt a sense of unease and extreme disappointment.
I am a huge believer that mistakes happen for a reason, and every accidental misstep is a learning for future trips and plans. This trip led to us having a huge conversation about prioritizing what we actually need on vacation, over what we think we want. Because of this, we spontaneously decided to cancel existing plans later this year just so we can return to Ibiza and Formentera and do things right, on our terms, with our good friends, when we have more energy and the right conditions to party.
Professional Insights on Vacation Planning
When we set realistic goals and expectations for trips, they tend to go much smoother. The pressure to see and do everything can be overwhelming, but when we plan a balanced vacation with our needs in mind, it always turns out better. This lesson has been reinforced time and time again, both in my personal experiences and in my professional life as a travel advisor.
In my experience planning vacations for clients, I always start by asking about their travel goals — whether they want to prioritize health and wellness, relaxation, culinary experiences, art, or a blend of these. A common challenge clients face is choice paralysis: not knowing which location to choose, then feeling stuck on where to stay and what to do. I advise them to make an informed decision on location quickly, as the longer they wait, the more time-sensitive and expensive the planning becomes. The first decision is always the hardest, and once you choose a direction, the other roadblocks begin to disappear.
When it comes to expectation setting, expecting at least one thing to go wrong on every trip can help in appreciating the moments when everything goes right.
The Influence of Social Media
Social media can significantly impact travel expectations. I recently had dinner with a friend who had been to Croatia. From her social media posts, the trip looked perfect — relaxed and meticulously planned. However, she revealed that the trip was far from perfect, filled with rain, insane friend group drama, and mishaps left and right. This was a good reminder that social media often showcases only the best moments. I am guilty of this on social media too, and strive to be more honest about my travel experiences through this newsletter, which I consider my honesty zone and realistic travel journal. I bet most of my social media followers saw my Spain post and thought that the trip was incredible and incident free!
Personally, I experience vacation FOMO due to social media all the time. Seeing people I don’t even know traveling to locations on my dream list used to get to me. Now, I try to feel compersion for those who can travel and explore, viewing it as a gift. So many people don’t have the ability to travel, either because they cannot afford to or aren’t able bodied, so I’ve tried to reframe my FOMO into a feeling of happiness and gratitude that other humans can experience something so special and life changing.
The Emotional Impact of Planning
The pressure of planning the perfect vacation affects me more when I am planning for my clients than for myself. Mishaps can happen, but they often feel like life-or-death situations because it’s my job and a direct reflection of my capabilities. In the end, everyone is always happy and appreciative, and the good reviews for my services bring a sense of overwhelming relief. But even when things are out of my control, like flight delays or rental car mishaps, I always feel an overwhelming sense of liability.
To balance the excitement and stress, I reframe planning as something I get to do rather than something I have to do. I am grateful that my passion is also my full-time job. It’s not brain surgery or major government policy decisions, so it’s not really life or death; I’m creating fantastic experiences for others to enjoy and reflect on fondly for years to come! I get to give my clients a well-deserved vacation from the tedium of planning!
Practical Tips for Vacation Planning
Here are my strategies for prioritizing and simplifying vacation planning:
Capacity and Bandwidth
Be honest with yourself on how much bandwidth you have to plan your trip. Planning a trip can be very overwhelming and can be a lot of work, which is why I personally find it easier to offload all of the emotional labor onto a travel advisor, especially for BIG trips, like a honeymoon, where you’re already tapped out from planning a wedding. I plan 99% of my own trips, but I delegated our honeymoon planning to another travel advisor, so I wouldn’t get sucked into the vortex of making sure everything was perfect. When I considered planning this myself, everything felt so high stakes!
If you don’t have the means to hire a travel advisor, break planning and research up into manageable blocks and tackle it a chunk at a time: Start with goal setting, then move to location ideation, flights, then hotel research and booking, followed by activities. Choose a destination that excites you, but be realistic about travel time and logistics.
Communication
If you’re traveling with others, communicate with your travel buddies about expectations and travel planning roles, and document these responsibilities to ensure everyone is on the same page. Have these conversations early on and don’t leave task delegation to the last minute. Keep plans in a shared spreadsheet or note, so they’re easy for everyone to access and reference.
Save Locations
Use tools like Google Maps to save dream locations for future trips, even if you don’t have immediate plans to visit. That way, when the time comes, you have at least a few places in mind to check out.
Itinerary Planning
Create a detailed plan for only half of your day. Leave the other half open for free exploration or relaxation. Don’t plan more than one big adventure or activity per day! You don’t want to exhaust yourself and take the fun out of your vacation.
Reservations
Make dinner reservations and activity reservations, especially during high season when they are necessary, but keep breakfast and lunch casual and flexible so the schedule isn’t too rigid.
Spontaneity
Be okay with scrapping a plan if it doesn’t feel right!
Budgeting
When it comes to budgeting, be honest with yourself about what you can afford and leave some wiggle room for unexpected expenses and mishaps. Things happen, even when you think they won’t, whether it’s flight delays and lost luggage or rental car mishaps and accidents (which leads to another point: always make sure your credit card covers rental car insurance, and if it doesn’t, buy the damn insurance, trust me).
Personal Travel Philosophy
My approach to vacation planning has evolved over the years. I used to be a travel maximalist, trying to do everything possible, even if it meant cramming a zillion things into a three day weekend, because I was scared that I might not return to whatever place I was in and thought — what if I didn’t get to experience every single nook and cranny of it?
Now, I focus more on what I actually want from a vacation and what would make it successful for me. If I don’t get to do everything I want, I can return at a later time down the road and do everything else. I’ve reframed every first trip to a new destination as a scouting trip.
The vacation paradox — the stress of planning and then enjoying the perfect getaway — is a common experience. By setting realistic goals and expectations, embracing spontaneity, and focusing on what truly matters, it’s possible to navigate this paradox and find joy in both the planning and the journey.
Here's to loving, living, and finding peace in every travel moment, and laughing at mishaps along the way. Things will go wrong. Embrace the uncertainty and move forward.
P.S. — This is going to be my last post for awhile, as I am officially headed to South Afica, Zimbabwe, and Mozambique for my honeymoon on Friday. I’ll be out of office and away from the computer until August 7, so this means I’ll be taking a little break from publishing here. When I get back, expect in depth posts on Cape Town, our safari experiences, Victoria Falls, and a dreamy beach in Mozambique…
Chat soon!
Comparison is the thief of joy. There is a general lost sense of adventure in travel, it seems to be more about status and ticking off the list… which in someways is good for the rest of us 😉