What’s Your Travel Challenge?

Why aren’t you traveling? What’s stopping you from booking the trip of your dreams?

The most common question readers ask me is how they can travel more. I reply that the answer depends entirely on why they’re not traveling more right now. But unless we take a minute to take stock of where we are right now, and examine the forces in our lives that are preventing us from traveling, we’ll encounter the same obstacles over and over again.

So let’s examine why you’re putting off traveling right now. You can answer these questions in your own head, on paper or with friends. Or reach out to me in the comments, via email or direct message or share your thoughts on any of my social media platforms if you’d like to discuss your challenges with our awesome community of travelers. If you choose to answer me directly or address the group, your answers will help me refine tools to specifically address your travel obstacles in the future.

So let’s figure out what’s holding you back so you can make this your best travel year ever.


Art in Grand Forks, North Dakota

Are you broke? I get it. I know what it’s like to look at those airfares and want to cry because they seem like they’re so far out of your reach. I know what it’s like to have pennies, not dollars left at the end of the week and I know the panic that comes when there’s absolutely nothing left to stretch.

I’ve traveled as a completely broke student, an almost broke college graduate and a basically broke minimum wage worker, so I know from experience that it can be done. The new share economy means that there are more discounted lodging options than ever before and with  little planning, you can score discounted fares, tickets, activities and more. Plus, you can always volunteer your skills or swap your own resources! If we need to talk more about how to save money for and during trips, just let me know.

Do you lack focus? I feel you. I want to go everywhere, all the time, right now. That enthusiasm is great, but it can sometimes leave us feeling restless and overwhelmed. This fear of missing out is it’s own kind of burden. All those “Places I Want To Go” Pinterest boards and overflowing “Someday Travel” files on our desks (and in our brains) just remind us of how much we want to do.

If focus is your challenge, we can work on that. Let’s help you decide your priorities, focus your energies and make those dream trips happen.

The riverwalk in Milwaukee, Wisconsin

Are you short on time? I’ve been there. I know what it’s like to be so busy at work that you just can’t get away, so those unused vacations days pile up as your stress level increases. I know what it’s like to have a child permanently in your arms, where even a shower or a nap or two minutes to use the bathroom alone all seem like impossible luxuries, instead of, you know, just taking care of your own basic needs.

But take it from someone who’s done it, it is possible to carve out time to travel, even with an impossible schedule and/or small kids at home.  If tips and tricks to carve out free time to travel are on your wish list, tell me so I can help you out.

Are you uninspired? Maybe you’ve conquered your bucket list and you’re wondering, “What’s next?” Or maybe you kinda wanna do a couple things, but nothing sparks your interest.

Resting and nesting is totally okay. We all need it from time to time. But if it’s gone on too long, you want to shake it up, or you’re worried you’re in a rut, let me know and we’ll get your imagination going with some fresh inspiration and new challenges.

Do you have health challenges? This is a tough one. I’ve been blessed with good health overall (knock on wood), but all it took was one severely sprained ankle in Amsterdam and traveling with my grandmother, who has limited mobility, to understand that traveling with health issues requires creativity, focus and a sense of humor.

Happily, there are lots of incredible trailblazers out there who know the challenges you’re facing and they’re revolutionizing the travel industry. And many destinations all over the world are making their cities and attractions more accessible than ever. These travelers and tourism professionals can offer incredibly helpful and specific guidance to help you plan your trip. Let me know if you need me to introduce you.

Georges Seurat’s “A Sunday Afternoon on the Island of La Grande Jatte” at The Art Institute of Chicago.

Are you waiting for everything to be perfect? Sometimes we put off a trip to a destination because we want to wait until we have enough time, money or energy to do it the “right” way. (Bucket list destinations and trips that celebrate a milestone are especially prone to this pressure.)

But you know what? There is no right way. And there’s no way to see everything. Even people that live next to glorious parks and in amazing cities and right next door to the wonders of the world report that they’re still exploring them and learning new things after years of visiting. So if you need help releasing your ideas of travel perfection (Lord knows I do!), drop me a line. Let’s work on it together.

Does planning make you feel overwhelmed? This happens to me sometimes too. Sometimes too much choice is a paralyzing thing and we just want a way to cut through all the flight trackers and fare sales and travel alerts and hotel deals and just wake up and go. I get emails and DMs all the time from readers who really want to go somewhere, but they literally cannot figure out the first step to make it happen. It happens much more often than you’d think.

If this is you, you’re not alone. Let me know if you need help cutting through the noise and making confident decisions. There are tools, strategies and communities that can help.

Is your travel style different from those you love? I hear you. It can be a bummer to crave a urban getaway when the family just wants to do the usual theme park tour again this summer or to inwardly cringe when your friends have a list of trails to hike when you really just want to swim in the ocean. And if your group has a luxury resort budget and you’re on a backpacker budget, that’s a challenge too.

But there are lots of destinations that work for multiple generational travel and offer activities for a range of budgets and travel preferences. The real challenge is finding a way to discuss and plan all this ahead of time, so that everybody can have the trip they want. Let me know if you need strategies to help ease your way.

Leuchtenburg Castle in Germany

Does travel make you anxious? This issue is common too. I love traveling, but some people in my family don’t. They have worked to develop routines and systems that make them feel calm, happy and safe and they worry that traveling will disrupt them. And readers and friends often refer people in their own lives to me that need a little help taking a few steps out of their comfort zones.

If this is your, please know that you can ease into new situations instead of jumping and that you can honor and recreate the situations that bring you comfort on the road. There are lots of people who share your anxiety and they’re conquering their fears right now. Let me know if you want me to help you do the same.

All of these fears, challenges and concerns are valid. Your own particular travel challenge is specific to you and your situation, but it’s not unique. If you want to overcome your own travel obstacles, you can.

I know this because I’ve done it myself. In fact, I’m still doing it. And I’ve seen other people do the same. So if you want to join us, now is the time to act. All you have to do is speak up.

You just have to take that first step. Tell me about your travel obstacles in comments below or send me an email or a direct message on social media if you’d rather not make them public. (I will never, ever share anything you tell me unless you say it’s okay.)

Let’s make this the year that you take steps overcome your travel obstacles. Let’s make this the year that you  have the adventure (or retreat or service project or family vacation) that you’ve been dreaming of. Just let me know how I can help.

What about you?
What’s your biggest travel obstacles?
How have you been working through your obstacles?
What can I do to help you reach your travel goals?
Do you want to travel close to home or far away and why?
How can this site help you overcome your travel challenges?
What do you wish you’d known when you started conquering your travel obstacles?
How do you want other travelers to help and support you in these goals?

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Prairie Style File is curated by Alicia Underlee Nelson. All rights reserved.

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