Adventure is a State of Mind
Have you heard of “the messy middle?” It’s the phase of every project that falls between the fun and exciting beginning and the sweet satisfaction of successfully reaching your goal. It’s a term often thrown around in business contexts. It’s also frequently discussed in the context of creativity by the likes of Brené Brown, and it’s the title of a book by Scott Belsky.
The messy middle is the phase that is often the most challenging and filled with anxiety and self-doubt. In the messy middle, there are plenty of challenges and frustrations but minimal excitement and rewards.
The messy middle can also impact travelers, both during travel planning and during the adventure itself.
The Messy Middle and Travel Planning
Here’s the scenario – you and your favorite travel companions have an inspired idea for a travel adventure. Maybe it’s to visit Japan during the cherry blossom season (Sakura). Maybe it’s to travel to Iceland for the Northern Lights. Maybe it’s a trip to Italy to visit four different wine regions and sample your favorite wines at their source. Whatever the plan, you’re all so excited you can hardly sit still! Everyone gets out their phones and computers. Instagram and Google Maps are consulted. Everyone checks their calendars and, miraculously, you all have the same days available! Maybe, if the price is right, you can even book the airline tickets. And a discussion begins as to what kind of housing you want and who will be in charge of making reservations.
Although it’s not impossible to plan the entire trip in one marathon planning session, it’s highly unlikely. So there will still be lots of research and decisions to be made and credit cards to be entered before the process is done.
And that takes us to the messy middle of travel planning.
It is at this point that planning can become a bit of a slog. I love planning trips, but there is often a point at which reality sets in and the planning isn’t as much fun. It may be the realization there isn’t an easy way to get between two towns we want to visit. Or I look at the available hotels or home stays and worry that my travel companions won’t like them or will find them boring. Or sometimes the plans we made in that first, thrilling wave of planning start to fall apart – we realize there’s a local music festival going on during the time we want to visit, and all of the hotels are already booked. Or (and this has happened multiple times), the airline changes our flight arrangements so that we are arriving at a significantly different time… or even at a different location!

As changes are made, the plan may begin to look different from your original vision. The compromises can feel like defeats if the plan drifts too far from the original, or maybe you start to lose sight of the original inspiration. For example, the difficulty in finding transportation to the vineyards results in only visiting one wine area in Italy when visiting vineyards was the original theme of the entire trip.
This is the point at which even the most seasoned, independent traveler can feel overwhelmed and frustrated. If no money has been committed yet, there’s even a risk that the trip might get cancelled as the excitement wears off and the planners decide it’s not worth the work.
The Messy Middle and the Journey Itself
Even if the planning doesn’t experience any hiccups (unlikely, but possible), travel itself has a sort of messy middle. Social media and television travel shows make travel look consistently beautiful and exciting, but anyone who has taken more than one trip away from his or her hometown knows that travel can be difficult.
At times it can be frustrating. Or dirty. Or exhausting. Or boring.
Yes, travel is all about the journey, but sometimes the journey between two places is not the highlight of your adventure. And it’s not going to be something you take photos of… unless you’re wanting to share the pain with family and friends. It’s dusty roads and sticky train seats. It’s weather that is unpredictable and delays that outlast your drinks and snacks. It’s addresses that seem to hide from you and long blister-creating hikes.
The good news is that some of those difficulties become funny stories we share when we return home. And none of the difficulties last forever. But if we focus too much on the pain of the messy middle, it can diminish our enjoyment of the overall travel adventure
The good news is there are ways to manage the messy middle so it’s not quite so painful.

Accept the Messy Middle is Normal
First of all, accept that this is a normal part of travel. Actually, this is a normal part of life. If you always expect everything to go perfectly to plan, you’re going to experience a lot of frustration and disappointment. Whether you’re traveling the world or staying at home, life happens. And sometimes it isn’t what we hoped it would be.
When I was working as a psychologist, I sometimes worked with children on the Autism Spectrum who struggled whenever their lives were not following the schedule they expected. One of the strategies we used was to have unexpected things included as part of the schedule. For example, their parents could remind them that after school, they would come home, change their clothes, have a snack, and do something unexpected. With this expectation in place, the parents could plan a positive surprise for their child, but it also gave them a little buffer for things that might need to occur but weren’t planned, such as stopping by the grocery store for milk and bananas on the way home.
When we expect the messy middle, it doesn’t stress us out as much. Instead of being upset that no one can agree on a hotel and deciding to cancel the entire trip, you recognize what is happening and can take a step back to regroup, assess the group’s goals and needs, and problem-solve to find a solution.
When you’re stuck on a train that smells funny and is too loud to allow sleep, you can accept that this is part of the process of getting to the beautiful seaside and instead focus on how you’re going to tell the story to your friends.

Don’t Give Up
If you’re stuck on a smelly train, you’re not likely to get off mid-journey. If you’re planning a trip with friends, however, and the planning is becoming frustrating, it may be tempting to give up and decide the trip isn’t worth the effort.
Don’t give up!
That temptation to throw in the towel is a sign that you need to take a step back and assess what’s going on. Are there problems with the plan? Are there group dynamics that need to be addressed? Or is it just the messy middle?
Any large endeavor requires endurance, and it’s during the messy middle when that is most obvious. With little reward for your efforts, it’s easy to think the work isn’t worth it.
That’s when it’s important to focus on why you’re doing what you’re doing. Take a break from the planning and watch a movie set in the country you are planning to visit. Or go out for a meal at a restaurant specializing in that country’s cuisine. Most of us are capable of doing great things if we’re motivated. Sometimes we just need a reminder of why we’re doing what we’re doing.
Avoid Procrastination
Honestly, I’m not judging the procrastinators of the world. I’m one of you! It’s too easy to put off difficult things. But, procrastination also has a price.
First of all, there’s the mental toll. When you put off doing something you need to do that isn’t that fun, such as making hotel reservations, there is a feeling that you’re escaping something difficult. Unfortunately, you don’t truly escape it, and the awareness that you still need to do it sits in your brain taking up space and energy.
A bigger cost to procrastination, however, is missed opportunities. There is an anonymous quote you’ll find on inspirational plaques and websites – “The cost of procrastination is the life you could have lived.” This applies to travel planning as well to life.
I’ve learned this lesson the hard way. There have been times when, due to the struggles of trying to find the perfect place to stay (it doesn’t exist, by the way), I’ve put off reserving a hotel or house. You know what happens then. When I finally make myself sit down and make the commitment with my credit card, those great (but not perfect) locations are gone. So, by putting off the difficulty of the decision, we end up with fewer and less desirable choices.
To get through the hardest journey we need take only one step at a time, but we must keep on stepping.
Chinese Proverb
Keep Moving Forward
When you’re in the messy middle of your travel adventure, usually your only option is to move forward. It’s obvious that to get to where you want to go, you need to keep moving (literally) rather than staying somewhere you don’t want to be.
During planning, it might not be as obvious, but the same principle applies. If you’re feeling the drag of the messy middle, the way to get out of it is to do something. Make the next decision.
If it’s hard to feel you’re making progress, create a checklist of the tasks that are left so you can see your progress.
If you’re overwhelmed by how many tasks there are left to do, just pick one. Pick a hotel in one of the towns you plan to visit. It doesn’t matter if you reserve the towns in the order you’ll be staying there. Or buy your train ticket or reserve your rental car, even if you don’t have your hotel reservations yet. Seriously. If the planning is at a point that you’re not clear what to do next, that indicates that it really doesn’t matter which thing you choose.
And once you get some momentum, it often becomes easier to keep going.

Don’t Compare Yourself
This is related to accepting that the messy middle is normal. It’s rare that people share the messy middle, so when you’re looking at your friends’ Facebook and Instagram photos, you’re only seeing them posed in front of the ocean sunset with their beautiful hair and darling clothes on the evening they went out for a delicious seafood dinner.
You’re not seeing them hot and sweaty lugging their bags off of the smelly train.
Similarly, people rarely share their experiences of the messy middle when sharing their travel planning.
I’m as guilty of this as anyone. When I shared how to choose where you want to stay, I made it sound like a logical, step-by-step process. And while there is some logic to the process, I didn’t share the descriptions of me sitting on the couch with a pile of notes and travel books wanting to cancel the trip because I don’t know which neighborhood in London would best fit our needs. I also didn’t share how I had difficulty falling asleep because I was worrying our family would be disappointed with the house we rented in Greece.
Editor’s Note: The house Sandi picked in Greece was absolutely fabulous, and she needn’t have lost any sleep over it!
Remember that not seeing the messy middle on social media or hearing about it from your friends doesn’t mean they haven’t experienced it when planning their trips.

Ask for Help
I’m not good at asking for help, but when I feel stuck, that’s often a sign that I really need to be asking for assistance. Sometimes it’s because of a clear problem – for example, asking for directions during your travels – and sometimes it’s because you can’t see your way out of the messy middle.
When you’re not sure what you need, just letting others know you need some sort of help may be enough. For example, if you’re overwhelmed by the planning, ask one of your travel companions to take on some tasks. Or, maybe what you need is just for them to talk through the tasks with you and help problem-solve.
When I was stressing over choosing a house to rent for the family in Greece, I talked with some of our family members about priorities – How close did they want to be to the beach? To restaurants? To public transportation? Just having those brief discussions gave me a fresh perspective to look at the choices and finally make a decision.
The Value of the Messy Middle
The messy middle isn’t the most enjoyable part of travel and travel planning, but it is a necessary part. The mess is where the magic happens! Without the messy middle, dreams never become reality.
Has the friction of the messy middle stopped you from turning your dream of travel into reality? How can you change your approach to the messy middle to stick with it and create your own travel adventure?
