Reclaiming Spontaneity in the Age of Overplanning
2025-10-28 · 19 min
Rigid, detailed planning is often driven by intolerance of uncertainty, a documented psychological pattern where over-preparing is used to manage discomfort with the unknown. Rather than reducing anxiety, this approach can intensify it, since every unplanned or unchecked detail starts to feel like evidence the trip is being done "wrong."
In This Episode
Kiara opens up about her own struggle with overplanning and how learning to leave room for spontaneity changed her travel completely. She walks through a trip to Belgrade where nearly every planned excursion got cancelled by weather, only for a group of hostel expats to show her a version of the city no itinerary could have produced, then a construction-rerouted trip across Romania to visit a former student built entirely on the advice "just show up." She unpacks why influencer checklists and "must-see" lists generate more FOMO than they prevent, the psychology of intolerance of uncertainty behind compulsive planning, and gives concrete, practical ways to build small pockets of spontaneity into an otherwise structured trip.
Chapters
- 0:00 — Opening questions: when did you last travel without an itinerary?
- 0:36 — Today's topic: spontaneity and finding balance
- 1:11 — The Belgrade story: cancelled excursions become the trip
- 2:04 — The travel-influencer checklist era and manufactured FOMO
- 4:16 — What overplanning gives you, and what it quietly costs
- 4:52 — What travelers lose when they stop leaving room for surprise
- 7:09 — The joy of letting go
- 7:35 — The Iași-to-Oradea trip: "just show up"
- 9:50 — The emotional shift of releasing control
- 10:44 — The power of saying yes: wineries, workshops, strangers in Moldova
- 11:22 — Budapest in reverse: when someone else's lack of a plan becomes the plan
- 12:35 — Practical ways to build spontaneity into a planned trip
- 14:17 — Advice for the fully unplanned traveler
- 14:32 — Tuning into your senses as a grounding technique
- 16:28 — Closing reflection: how will you put the guidebook down?
Travel isn't a checklist. It's a conversation. The more space we leave for surprise, the more we discover what travel is actually about. Connection, not control.
It's time to realize that the best part of your travel may not be the one that's in your Google Doc.
Structure may give you direction, but spontaneity is what's going to give you your stories.
Once I found that I was creating space in my itineraries for that spontaneity... that led to other adventures and side quests that actually became more memorable and more influential in my time in the destination than those that were previously planned.
Read the full transcript
[0:00] When was the last time that you took a trip without an itinerary? What made you realize that your travel might have been too planned out? Did you ever have one of the highlights of your trips be something from an unplanned moment? We're going to dive all of this into more. On this episode of Put the Guidebook Down, I'm going to go into a topic which is one that took me a long time to overcome and one that I'm still not super okay with. And that's okay. Travel is a learning process and it's an ongoing journey. Welcome back to another episode with me, Kiara, the creator of Kultura Travel as your host.
Today's episode is going to be all about spontaneity and how to find balance for planned adventures and spontaneity within your trip. In last episode, we talked a little bit more on a more difficult subject about this idea of travel fatigue, burnout, how to recognize it and how to get out of it. Now, today's episode is one of the ways that we suggested as a method to reclaim your energy when it comes to travel and to avoid the burnout.
As I mentioned, this is something that I have struggled with as someone who likes to plan everything out to a T. It's really the spontaneity that helps us go deeper into our travels and to create those memories that are the most impactful on your experience. For me and my travel journey, this took a while to get to this point of understanding. It wasn't until probably in my second year in Moldova when I was on a side quest to Belgrade in Serbia, when almost all of my excursions and trips beyond the capital got cancelled due to bad weather and the holiday season. It was at this point that I met a group of amazing people in my hostel who had been living in the capital for several months now, who took me under their wing and showed me a different side of Belgrade that I wouldn't have experienced or seen had it not been for my planned trip falling through.
So it's time to realize that the best part of your travel may not be the one that's in your Google Doc. It may be the one that goes beyond the ChatGPT-generated itinerary and off the beaten path. Let's put the guidebook down and get into it.
So in today's society, there's this whole travel influencer era and movement, where you have a bunch of travel bloggers, influencers, and content creators essentially creating the quote-unquote perfect guides for you to go on a three-day, five-day, seven-day adventure. The list goes on. And if you follow it to a T, you are ensured to have a great, memorable adventure. The way this content is also being phrased is to generate this FOMO that comes with it, because maybe you're not getting the number one Instagram spot, so therefore you're not going to have the best photo. You're not going to have the most Instagrammable moment that gets you thousands of likes, tens of thousands of views, and gets you recruited to be an ambassador for a travel company.
What I like to ask is, has these lists really changed the way that we approach travel today? Is it for the better, or is there some learning that needs to be done? In my opinion, it's a combination of both. This wide variety of content that's being generated now and curated to be available to you is helping us find other ways to travel to a country maybe we haven't known or previously heard of. It's nice to have those checklists to make sure that you are hitting some well-known spots, or maybe UNESCO heritage sites. However, it's creating this pressure for us, maybe that we feel or don't feel, and it's just kept internally, that if we don't hit these spots that are being put onto those lists on social media, then we really didn't visit a country that we said we did, and that's completely false. Therefore these lists are creating a misdirection when it comes to travel, and keeping people maybe away from experimenting with a new travel journey or going off the beaten path. It's killing the presence when it comes to travel, and the serendipity that comes when you go off on your own and maybe go against the social norms.
Now, as I mentioned, this overplanning can be really good because it helps you have structure to your itinerary, make sure you're hitting enough spots that you feel you have successfully and sufficiently traveled to your destination. However, it's limiting your connections with the locals, limiting your connection to the place you're visiting. It's starting to maybe decrease the amount of curiosity that you may have for a destination, because you're so focused on hitting the checklist. This is where I want to draw attention to today, and it's one that I also will leave you to think about: what are travelers losing when they stop planning space for surprise? They're losing the ability to form those connections with locals, to go deeper into the place they're visiting, maybe to have a unique experience that pushes them outside their comfort zone or challenges their thought processes that they had before they came to their destination. For some people, that's a little uncomfortable. That's okay. Part of travel is learning how to step outside your comfort zone or to find your limits.
Some people may try to avoid this uncomfortability by planning an action-packed itinerary with things to do from wake-up to bedtime. However, I have to ask, is this more stressful to you than being excited for your destination and your trip? Because for me, I previously was one that would plan everything in their itinerary down to the T to make sure that I was hitting everything that the travel influencers in the industry was telling me that I had to hit in order to be successfully traveling to my destination. And this created more stress, because I had this feeling of FOMO looming over me, saying I'm forgetting something, I'm not hitting that destination, like for example that temple, or hitting that five-star restaurant. Therefore I'm not traveling correctly according to society's standards.
Therefore, once I found that I was creating space in my itineraries for that spontaneity, or the time to have conversations with people in my hostels or the locals I meet along the way, that led to other adventures and side quests that actually became more memorable and more influential in my time in the destination than those that were previously planned. Why? Because the ones that were more spontaneous had me in a more real, authentic setting, whereas the originally planned destinations, the only goal was to take photos. So when I had the spontaneous adventures, those were built upon real connections, relationships, and real experiences. Today's day, we spend hours searching for the hidden gem. The truth is, if everyone's posting about it, it's not really hidden anymore. So it's time to put those guides down, put the influencer-recommended checklist down, and venture into a different path.
Let's go now into the joy of letting go when it comes to your travel planning. I feel like I've talked about this a lot already, and it's something that I will continue talking about just because Moldova was such an eye-opening experience for me on many different facets and levels. With it, this is the one where I was forced to do slow travel and to go more into spontaneity rather than planned travel, because I had a lot of time there. Also because I was becoming more comfortable with being in the unknown.
During one of my trips into Romania, I decided to challenge myself to go from just where I normally go, in Iași, Romania, all the way across the country to a city called Oradea. And it's on the complete opposite side of Romania. So in order for me to get there from my host city, I had to take three trains. And it would normally be three trains, but because of construction, it changed my pathway. So I actually took a bus, a train into a train station, and changed to a bus that took me through the mountains and villages to get to Oradea. Now, this whole trip was actually not planned. This was one of my first few adventures where I was challenging myself to go without any plans. And the reason for my travel was actually to see one of my friends and former students who had now switched to Oradea to study at university.
So I had sent her some ideas of things I found in local guides, or maybe some influencers who had travelled through the area, though there's not many, so it was really local influencers, and I was going off the recommendations, some she was familiar with, some she wasn't. She told me not to worry, just to show up. Now, it's very hard for me to just let go like that. I have to tell you, it was one of the most chill and fun adventures I've been on. And it's not just because, for one, I wasn't being the guide and focused on hitting everything in the itinerary, that I got to see my friend — it was also because along the way I ran into other people who happened to have crossed paths with me previously on one of my other journeys. I got to go meet up with their families. I then got to go meet up with my friend's friends, and they took me to a clothing market. Everything else was just so new and not what I had planned. It was just like a nice surprise, it was getting new gifts along the way, new experiences. It was just something that, this feeling, I didn't want to stop from ending, because I knew that with this choice of spontaneity, I was having a completely different experience — one that is more locally focused, one where I was able to focus on building relations and connections with the people that I was meeting along the way. Truly, those are the connections that I still have to this day. This is something that I could not have gotten if I just did my original planned itinerary. Anastasia, thank you so much for that — I'm looking forward to our next adventure whenever it is in the future.
Getting back to the conversation, as I mentioned, there was kind of this emotional shift that happened when I stopped controlling every outcome or every task or destination I was hitting. It became more lighthearted and more focused on just being in the present moment instead of thinking about what's next. For me, as I started this episode, this whole idea was something that was very uncomfortable for me to overcome, since I was one that liked to control every aspect of my travel itinerary. This fear of not hitting everything that I was told I had to do is one that's had the most memorable outcomes in my life. It is now one that I look forward to whenever I do all my other itinerary planning — I always leave gaps in space for the spontaneity.
Now, going back to Moldova, the power of saying yes when you agree to moments or experiences that weren't on your map or itinerary — this is incredibly powerful. Now, you always want to use your intuition and safety with it. Just having that open-mindedness leads you to new experiences and to new people, new opportunities. This is one where I'll give another example beyond just Moldova, because in Moldova I just kept saying yes to these random adventures that I felt safe going on. I would end up at a new winery. I would end up at a local's house. I would end up in some sewing workshop. It was just all these other things that led to a whole holistic experience in the country.
Another one I'll give is when I was a tourist in another country — I visited Budapest, which if you haven't visited, I highly recommend. One of these experiences actually was reversed a little bit. So I had a planned itinerary. I had met people in my hostel who just really showed up with no plans, and to me this is still to this day really crazy — I respect a lot of people who can do that, or they show up to the hostels with no other trips booked, or their return train back. I wish I could do it, I'm just not there yet in my travel journey. I met these people, and I ended up sharing my plans with them, and they end up just saying yes to everything — they joined me on my entire journey through Hungary and Budapest. Now I have met great friends that I'm still in contact with to this day, and actually one of them came to visit me in Moldova during my second year and filmed a documentary with me — you'll actually be a guest on my podcast later. It's a testament to just saying yes and going with the flow and just going open-minded into your travel. Very powerful. You never really know what you're going to get.
Let's talk about this in the practical sense. How would you build spontaneity into your travel? Because maybe you're not completely like someone who I've mentioned previously that just shows up to a destination with no plans. Maybe you're someone who is like me previously, where you have everything planned down to a T. Now you're just looking for a happy medium. My best advice is, if you're on the extreme of having everything planned, to start with leaving gaps in your itinerary for that spontaneity — whether this is just a couple hours in a day, maybe it's one entire day dedicated to just going with the flow and wandering around whichever feels right for you at this time and whatever you're most comfortable with. Give that spontaneity a chance. Create the space for it to happen. You have to do your part by going out and just seeing what's happening in the community — talk to people, look on Facebook events for what's going on, look at the local tourism board page to see if there's any local festivals. It's then on to you to go with what you want to do in that spontaneity.
If you're on the extreme end of no plans, showing up to a destination, honestly, power to you — I don't know if I have any advice for you to become more spontaneous. I guess my best advice would be just to talk with more locals, to give some more structure to your spontaneity, and maybe to look at Facebook events to see what's going on in the local community so you can plan around that event. Just, more power to you, honestly, you're doing a great job already. Maybe we'll do another episode then about how to give structure to your itinerary if it's needed. But at this point, you're already super spontaneous, so that's really good.
Another one of my tips is really to turn into your senses, to ground yourself and find yourself tuning into the present moment. What does this mean, what does this look like? Ask people what's to do that's not on Google Maps, especially if you're going to some countries that aren't very up to date on their Google Maps listings, such as Moldova or Central Asia — you will have to ask people for directions, so why not ask them what to do. The second one is to tune into your senses — so what do you smell? Do you smell good food? Follow that direction. If you're hearing loud music, maybe follow that direction — maybe you're going to end up at a concert or a festival. Look at what's happening around you in your environment rather than looking for that set schedule. And the last one, as I will keep saying in this episode and all the other episodes, is to learn a few words in the local language, and use those in conversations with the locals. By using the local language, you are expressing your interest in the culture and people of the place you're visiting, and therefore they're more open to having conversations with you, especially if you're going to ask for recommendations — they'll be like, oh my gosh, they actually really care about who I am and my culture, I want to help them get the real experience. Boom, side quest initiated. Structure may give you direction, but spontaneity is what's going to give you your stories.
This spontaneity addition to your travel itinerary is kind of a mindset shift, one that's going to take time to adjust to, especially if you're just one that needs to open up to more balance between having the plan structure and giving spontaneity a chance. You learn how to deal with that FOMO and to go against the checklists. This spontaneity, I promise, is going to be worth it in the end, because it's going to help you reconnect with your curiosity, your presence, and humanity in general, because this leads to cultural travel experiences and really authentic ones, because you're engaging with your local surroundings and environments and people. And especially if you do the grounding technique of tuning into your senses to help show you what other opportunities are available for you in your travel, it's going to lead to a good story.
So if I could give you one question to reflect on from this episode, it's: how will you put the guidebook down? Literally, this is the name of our podcast. I want you to reflect on how you're going to put the guidebook down. What feeling comes with that? Is that feeling one that you're okay with? Is there discomfort there? How do you overcome that discomfort? Just reflect on that point of putting the guidebook down and what that looks like to you. Remember that travel isn't a checklist. It's a conversation. The more space we leave for surprise, the more we discover what travel is actually about. Connection, not control.
I want to thank you for tuning in to this week's episode. I hope you learned a little bit about what spontaneous travel can be, whether it's full spontaneity or just some partialness — maybe how you can implement that spontaneity into travel and why it really matters to you. It'll help overcome your travel burnout. Most importantly, it's going to give you that authentic travel experience with some of the best memories that come from your trip, because you're focused on going deeper, not just taking the surface-level photos of the destination to say you've been there.
Thank you for tuning in. We have a lot of exciting things going on at Kultura Travel — we're starting to put out customized itineraries, we're building officially the first phase of the app. Please continue to follow, engage with our content. I would love to know if you've ever ditched a plan or your travel itinerary — what was the story that came out of that? I love our spontaneous travel stories, please share them with me, either on Instagram at Kultura.Travel or directly into our Substack or email. Thank you so much. Be sure to tune in to next week's episode — we're going to have another special guest. November is just going to be a whirlwind of different voices, perspectives, and stories coming on from people I've newly met, also some of my closest friends and colleagues I've met along my travel journey. Stay tuned. Thank you, everyone.
Frequently Asked Questions
Why does trying to plan every detail of a trip often create more anxiety than it prevents?
Rigid, detailed planning is often driven by intolerance of uncertainty, a documented psychological pattern where over-preparing is used to manage discomfort with the unknown. Rather than reducing anxiety, this approach can intensify it, since every unplanned or unchecked detail starts to feel like evidence the trip is being done "wrong."
What is intolerance of uncertainty?
Intolerance of uncertainty is a psychological construct describing a tendency to find unpredictable or unknown situations distressing, often leading to excessive planning, worry, or avoidance as a way of managing that discomfort, even though these strategies tend to maintain anxiety rather than resolve it.
How can travelers build more spontaneity into a trip without abandoning structure entirely?
Leaving a few open hours or one unscheduled day within an otherwise planned itinerary, asking locals for recommendations instead of relying only on apps, and following sensory cues like smell or sound can create space for spontaneous experiences without requiring a fully unplanned trip.
Do unplanned travel experiences actually create better memories than planned ones?
Many travelers report that unplanned or spontaneous moments, like unexpected friendships or detours, become the most memorable and meaningful parts of a trip, often because they involve genuine connection with locals or fellow travelers rather than scripted sightseeing.
Why do travel influencer checklists and "must-see" lists sometimes make trips more stressful?
Influencer-driven checklists can create pressure to hit specific locations or experiences to feel like a trip was done "correctly," which can generate fear of missing out and reduce the sense of curiosity and presence that leads to deeper cultural engagement.