At least once a day someone says to us, “WOW! You’ve been traveling full time for seven years? That’s SO COOL.”

And it is. Cool. It’s exactly what we want in this life, for now. Not forever. It’s been a great way to spend the better part of our kids’ formative years together.

We’re not living this way by accident. We chose it on purpose, and for us, it’s perfect. That does not; however, mean that it’s all wine and roses, beach photos, and perpetual vacation. In fact, it looks a whole lot like real life, only unfolding in more places and languages than usual.

If you’re considering taking off on an open ended journey, it’s quite likely that you’re looking at your big dream through rose colored glasses. It’s quite natural, really.

It’s easy to see the flaws in the place we are standing and feel the current miseries acutely. It’s harder to see what will become sand in your shoe once you begin wandering. I would never try to dissuade someone from their dream. And I will happily assure you that open ended travel is well within the reach of virtually every person who has that great wish in his heart. It’s only a matter of logistics once the decision has been made. However, in the interests of full disclosure, I would like to point out 10 ways that open ended travel is the furthest thing from sexy.

Yes, it’s true that seven years into the project we are making more money than we did when we quit real jobs, and we’re working about half the time. That sounds great, doesn’t it?

It is great.

However, what’s contained in the spaces between words in that sentence should not be over looked, and that’s a stock market crash, high level desperation, and a good three years of seriously unsteady financial and career footing while we figured shit out. We couldn’t see where we are now from where we were standing then, and frankly, it was very scary.

If you’re changing careers and hoping to reinvent yourself as a freelancer or entrepreneur on the road, know that it’s a heck of a lot of work, the paycheck isn’t always steady, and you can plan to have several years of roller coaster action. Maybe it will be less stressful for you. I hope it is. Nonetheless, don’t make this leap just expecting a magic parachute to open and everything to go smoothly. Expect to work. Without the rose colored glasses.

I wept on the beach on Canadian Thanksgiving in Penang, Malaysia, with a phone to my ear. I wanted with my whole heart to be home with my extended family on the day they spread the ashes of my only uncle over the lake I was born on. Instead, I had tears running down my face at a dinner party with 8 other traveling families who well understood my conflicted heart. Skype calls on Christmas morning from Guatemala, or Borneo, or Africa, just aren’t quite the same as being able to hug grandparents for real.

Even if you think you’re so ready to be gone that even the holidays can’t get you down, think again. It might not be the holidays for you, but there will be times of profound homesickness and profound loneliness if you travel long enough. Sometimes it’s people you’re lonely for. Other times it’s places, or seasons, or memories. It might be something as simple as a lack of a favorite food that tips you over the edge.

While there are a great number of people who think the idea of an open ended adventure as a lifestyle is kick ass cool, there are an equal number who think it’s utter madness. Some of those people are currently your friends. Be prepared for pushback from them. Be prepared for some of them to let you walk away, without making the effort to keep holding the other end of the rope on your relationship.

There will be people who think you’re mad for quitting your job, selling your house, taking your kids out of school, or any number of other conventional rules that you break by taking the leap. For some people it will be enough of an issue that it ends your friendship. Be ready for that. Weigh it into the cost of your decision.

My son just informed us, in the last five minutes, that he is having rather severe right quadrant abdominal pain. The first thing that leapt to mind is his appendix. Mine burst when I was about his age. My brain then started spinning with the possibility of a late night boat ride of an hour or more to the town across the lake with the private hospital and ultrasound machine, the horrible tuk tuk ride that will ensue and what a drag it will be if it IS his appendix in backwater Guatemala. It’s probably not his appendix. He’s taking a walk to see if he can stretch his muscles out and an ibuprofen to see if it’s something minor that will go away. This is the same kid who did spend an overnight in a hospital in Thailand trying not to die, and got stitches in New Zealand, and weathered a concussion and x-rays in the same summer on a pass through the USA, where we did NOT have insurance at the time.

It’s not that healthcare is inadequate in the rest of the world. Actually, with a few notable exceptions, we’ve found it excellent in most places we’ve needed it. (Pro tip: Private hospitals) It’s that the whole process is just scarier when you’re out of your comfort zone, as you almost always are on the road. Making yourself understood in a country where you don’t speak the same language as the doctor. Dealing with prescriptions for meds that aren’t used where you come from. Worrying about insurance and reimbursement when you’re responsible for all of that yourself. It’s a lot. It’s scary sometimes. The moments when we have been at a hospital with an injured kid, or up in the middle of the night somewhere off the beaten track wondering if we should brave the completely unknown to find medical help have been some of the worst moments of our journey.

That’s a reality.

If you have five hundred outfits in your giant walk in closet and a shoe rack that stretches the length of a ten foot wall in two layers, and you’re attached to that, you might want to reconsider the idea of open-ended long term travel. For real.

Truth in advertising: I have one pair of shoes. One. We have three outfits a piece most of the time. If we’re in one place for a while, a couple more might accumulate, but when we move on, the clothes do not. I am still wearing, several times a week, two athletic tank tops and two hiking skirts that I bought in Australia in August of 2013. I hiked 800 km in those babies last summer. They are still in my pack. I only buy clothes I really love because I know that we’re going to be seeing each other often.

And also, expect to hand wash your unmentionables in hotel sinks and hang them to dry across all continents. If you’re crazy enough to travel with a tribe the size of mine, then multiply all of that inconvenience times six. Don’t say I didn’t warn you.

Once upon a time I had a Chevy Suburban. I also had a lovely Toyota mini-van (which never attended a soccer game, so technically I could not be called a soccer mom, in spite of the mode of transportation!) Oh, and we had a motorcycle; that was sexier. We sold it to buy touring bicycles. The pedal kind. Definitively not sexy.

Now, we walk. A lot. Everywhere, in fact. It is not uncommon for me to walk miles in a day, just going about the business of living. I know in Portland that’s considered progressive, forward thinking, “green,” and trendy. Whatever. I’m not making a political or social statement, it’s just how I need to get groceries and to my once a week massage.

I take chicken buses and dream of the wide seats in my truck, which is stored in a barn in Indiana at the moment. I carry groceries for a family of six on my back, every single day. It looks great on a postcard. It sounds so cool on paper. In practice, it’s often difficult and inconvenient. Especially during monsoon.

Thanks to books like The Four Hour Work Week, people have this idea that being a digital nomad is this glitzy life of tango dancing and poolside computer work while sipping a Mai Tai. There are moments of those things, but they are like shooting stars: rare and fleeting.

The reality of juggling a real career (the kind that makes actual money, like, adult money, kid raising money, investing for retirement money) while traveling full time is somewhat different.

Expect to work in cafes that are loud. Expect not to have an ergonomically correct chair, ever. Expect to be up at two in the morning because it’s noon in the time zone that your meetings are scheduled. Expect to work from your bedroom, from the floor, from the roof of the van you’re driving across the continent because the only way to get adequate cell signal to connect is to get on the roof of the fucking van. True story.

If you’re taking off on this open ended adventure with a significant other, you’re going to find that traveling together while balancing work and long term life on the road changes (and sometimes tests) the dynamics of your relationship. You might find that you have to work a little harder on some aspects of your relationship than you did at home. For me, this means an exercise in developing patience and extending grace most days, as home, office, and school inhabit the same space as playground, backpack, and love life. It also means curating alone time, which is harder to come by sometimes.

Not only will you find it necessary to be more mindful of tending the relationships you take with you, you’ll find that the relationships you leave behind but want to continue take more effort than they did before. Water cooler and elevator conversations won’t happen naturally. Weekly coffee dates with friends are abandoned and relatives will sometimes feel like you’ve dropped off of the face of the earth. From their perspective, you kind of have. Try to remember to see things from their perspective as well as your own. Here’s a reality: You’re the one that chose to take off and leave, that puts the ball solidly in your court when it comes to reaching out and maintaining the relationships that matter. Do you have a plan for that? You might want to make one.

It might sound weird to you when I say that I really don’t remember the last time we were on vacation. Aren’t we constantly on vacation as we bop around the globe and live in fantastic places? In a word: NO. We are not on vacation. The longer we travel and the more we integrate our work into our life in a way that balances well for us, the less we tend to take vacations, actually. On the one hand, perhaps that’s because we don’t need them as much. We love our lives. We are living our dream for the moment, so escape seems unnecessary. On the other hand, we have to intentionally structure time to step away from work and to find a place, or an activity that is actually restful from our routine as a family. That’s more of a challenge than it seems like it would be.

Vacation is not an exotic destination or an exciting adventure: that’s Tuesday afternoon. Vacation is often far more soporific. When friends ask what “vacation” means to me, I laughingly tell them that “vacation” is defined as not having to do laundry or cook for our tribe of six. It’s also defined as the ability to put down all online work and not worry about deadlines. It’s not unusual for us to have one or the other of those things, but very rarely do we have both.

If you are suffering under the illusion that open-ended travel will somehow free you from everything that is hard about life and all of a sudden the stars will align, things will magically come together, and you’ll have everything you dream of on a silver platter, let me relieve you of that.

Open-ended, long term travel is wonderful, it’s an adventure, it’s an exciting way to live life, it’s the opposite of tedium, to be sure. It is many things, but it is NOT easier than your stationary life now, I promise you that.

The very thing that makes open-ended travel appealing to people: the adventure, the variety, the freedom, the excitement of new experiences, these are the same things that make it hard, and then harder. You’ll have bad days, weeks, and months on the road. You’ll battle the same sadnesses, the same difficulties, the same character flaws, the same relationship struggles, the same financial trials. It will all go with you. What you won’t have is the indulgence of your comfort food, your grandma’s quilt to curl up under, your 120 channels of cable tv to escape into, or even the luxury of being able to whine in your own language about it.

The “adventure” you crave while you’re sitting at home dreaming can be translated to “struggle” once you are on the road. In retrospect, it is often far more romantic than it is in the moment. You will hit the wall. You will wonder what you were thinking. You will wish, sometimes, to go home and curl up under something comfy. Don’t delude yourself into thinking the grass is always greener on the other side of the fence.

Perhaps it seems like this whole post is negative, and you’re feeling like I’m trying to talk you out of your dream. Nothing could be further from the truth. Long term, open-ended travel has been everything I hoped it would be and more. It’s been the best choice we ever made for our family. It’s taken us to places, literally and figuratively, that I never would have predicted we would go. I’m so thankful for that.

Not all of those places, however, were places we expected or places that we wanted to go. There are positives – many, many of them. I write about those positives often. There are; however, some negatives. If not negatives, then, “realities.”

Too many of the people out there living, and promoting, this lifestyle gloss over those. That’s not right, and it’s not fair. Every week someone sends me an email to the effect of, “This is so much harder than I thought it was going to be… what am I doing wrong?”

The answer, with a chuckle, is, “You’re right, it is hard. Life, no matter which path you choose, is hard. Long term travel isn’t some magical fix for the mundane. It’s actually more work than staying home. You’re not doing anything wrong, you just need to adjust your expectations to something a little more realistic.”

So, there you go, this week’s dose of realistic expectations, coming to you from the idyllic Lago de Atitlan, Guatemala. You’re welcome.

Read more about the realities – both the good and the bad – of open-ended, long term travel:

Photo credits: Berkomaster