What No One Tells You About Living and Working on the Road

September 6, 2016

What No One Tells You About Living and Working on the Road

Because of the work I do for Rockstar Finance, I skim hundreds of blog posts and news articles each week, and there are a handful of themes I see over and over again. Paying off debt, embracing minimalism, building wealth and retiring early are among the top five. But the topic of “quitting your job to travel the world and do what you love” is, without a doubt, at the top of that list.

The success stories sound dreamy. People write about how they live on as little as $1,000/month in various countries, with accompanying pictures of laptops on beaches and books in hammocks. Instagram feeds are filled with ocean views, mountain tops and cold drinks dripping with condensation during afternoon siestas. And the captions that go along with them express nothing but joy and gratitude. It seems like a fantasy come true. However, like so much of the curated content we are exposed to, it’s not the reality for the many of those who are trying to live and work on the road.

The reality looks a little more like this: driving for 8+ hours then barely being able to keep your eyes open long enough to check your email (let alone respond to any). Waking up in a motel the next morning and realizing the wi-fi doesn’t work. Having to shower in the dingy motel bathroom then rushing to Starbucks at 7am, so you can try to get some work done before you hit the road again. And not seeing anything in the city you just slept in, except for the inside of that motel, Starbucks and maybe a grocery store (if you’re low on snacks and want to pick up a prepackaged salad or sandwich).

Driving days are definitely the worst. While you’re on the road, your only concerns are making sure you have enough gas, food, water and podcasts/music to get you through the day. And when you finally arrive at your next destination, all you can think about is relaxing and sleeping. Work doesn’t even cross your mind, unless you’re behind or have missed any deadlines, in which case it fills you with anxiety – but not enough anxiety that you’re willing to stay up all night to get it done. You need to be rested for long driving days, and you know that your sleep (and sanity) is more important.

After a few long driving days in a row, the overwhelming sense of how much work you have to do takes over, and you know it’s time to finally sit down and get things done. Of course, by then, you’ve arrived in a new place where you want to explore and spend time with friends. And wasn’t that the point of this whole thing? To drive around and see people? So then the next struggle begins: trying to balance spending time outside exploring with spending time inside working. (I would also like to point out that pictures of laptops on patios are ridiculous. Working outside in the sun is crazy. You and your laptop will battle over who is going to overheat first, and either way you will eventually both lose.)

Finally, you reach your breaking point and have to accept that you might only see half of what you wanted to in your new city. Whether you like it or not, you need to spend a full day (or even two) in front of your computer. But how can you write about anything other than this amazing adventure you’re on? You want to keep track of all the places you’ve seen, experiences you’ve had and lessons you’ve learned. You do not want to write about the best credit cards or anything else that is so far removed from what you’re living in this exact moment in time.

Your first two articles for a new client are due soon, so you decide to tackle them both in one sitting. When you’re done, you log into the content management system they use (also new to you) to upload them, and discover a requirement for both articles that you never knew about: quotes from interviews. Now you’re frantically emailing your contacts, trying to get two interviews done in the next 24 hours. It’s never going to happen, so now you have to tell your brand new client that you’re going to miss the deadlines on your very first assignments. Who told you working on the road was dreamy? They lied.

The requirement of these interviews mean you’ve crossed nothing off your to-do list, and instead have only added to it. The anxiety deepens, as you worry clients will drop you, or this grand adventure will ruin your reputation as a freelancer. You begin to realize you’re never going to see that park or climb that mountain or eat at that restaurant. And oh my gosh, it’s cute that you thought you were actually going to be able to read any books on this trip. Don’t tell anyone you packed eight, because they will laugh at you for only finishing half of one in the first three weeks.

Now, it’s not all bad. The landscape of each state is burned in your memory, as are the miraculous thunder and lightning storms you’ve driven into. Being alone with your thoughts helps you stockpile ideas for your book. The days and evenings you spend with friends you haven’t seen in months or even years (or ever, aside from online!) are worth all the trouble. And getting to see cities through their eyes is priceless. But every time you get back to their house/your motel, the nagging feeling that you need to open your laptop and work sinks in. This is not a vacation. You have chosen to work.

And therein lies the distinction. I’m not complaining about the struggles I’ve faced while trying to work on this road trip. I’m not particularly sad or stressed about these experiences, either. I chose to work. I could’ve chosen not to, but I thought I could handle it so I said yes. I made that choice and I take all the responsibility for what it has come with. But if I’m being honest, I wish I had said no. I wish I had chosen not to work on the road – because it’s not easy or particularly fun to have to pull yourself away from the adventure aspect of it, in order to get things done.

Am I grateful I even have the opportunity to do both? Sure. I couldn’t have gone on this road trip at all, if I still had a full-time job. But working for yourself is still a job – and trying to work on the road is even harder than working at home. It’s not all rainbows, sunshine, beaches and hammocks. It’s coffee shops with uncomfortable chairs and spotty wi-fi. It’s higher risks of miscommunication with clients and the potential to miss deadlines as a result. It’s a complete lack of routine, which isn’t always great for productivity. And it’s less time that can be spent exploring the place you travelled to.

So the next time you read a story written by someone who claims to love every minute of living and working on the road, try to take it with a grain of salt. Understand there are still long hours, tiring days, sacrifices and mistakes to be made. Through heavily-edited content, we’re made to believe otherwise, but I can promise you it doesn’t always feel like you’re “living the dream”.

Like any story on the internet, this is mine and it’s personal – so it’s not the reality for everyone who attempts to do what I am doing. But I refuse to add to the long list of stories that make it sound like living and working on the road is oh so amazing. I won’t paint you a pretty picture and say it’s easy or even particularly fun. And I won’t say that I always walk around radiating my pure joy and gratitude for having this opportunity. Instead, I will say that this experience has been both challenging and rewarding, and I know I will learn and grow from it all.

And the next time I do something like this, I won’t be bringing any work with me.


  • Reply Andrew September 6, 2016 at 5:04 am

    There is definitely something appealing about travel and working, until you have to do it. Thanks for the shot of realism. I used to think I wanted travel in my job until I had to do it for a month straight, there is only so many hotel rooms and dine out meals you can have before you realize that the dream in your mind is not the reality. That said travel without work is more enjoyable for sure. Hope the rest of your trip goes smoothly.

    • Reply Cait Flanders September 6, 2016 at 3:10 pm

      Oh yea, I can’t even imagine having to travel for my job… I don’t know how people do it!

  • Reply Physician on FIRE September 6, 2016 at 5:11 am

    I prefer the Facebook’d version of life much better than this veritable dose of reality. You know, the “Everything is Awesome” version where it’s all smiles and you hang out all day with cool people, like Batman. Wait, you haven’t seen the Lego Movie? You should.

    I did a lot of road tripping this summer. Six 20-hour round trips and a 34-hour round trip. I would not have been able to keep up with the blog without a decent laptop, scheduleed “downtime”, and an occasional public library. I was fortunate to be traveling with my family most of the time, so my wife could spell me from driving. I have done 17 hours straight myself several times, and that makes for a long, tiresome day.

    I hope your clients were undersanding; I’m sure they are, or will be if they read this post.

    -Physician on FIRE

    • Reply Cait Flanders September 6, 2016 at 3:19 pm

      Haha, I’m sorry for disappointing you. Going forward, I will go back to curating a more fabulous version of life :P

      • Reply Physician on FIRE September 14, 2016 at 11:44 am

        That’s more like it! You can’t call yourself C$ and not live fabulously 24/7.


  • Reply Rob September 6, 2016 at 5:16 am

    See, when tackling any new activity / challenge / adventure, etc. you’re bound to encounter good things along with the bad. It’s a learning experience. It’s rare when everything goes 100% peachy keen the first time around and no surprises (good or bad) occur. So, with that said, you carry on, don’t get discouraged, learn from your experiences, draw up plans to compensate (including more “contingency fudge factors”) and so adapt the next time round and enjoy yourself as best you can, all the while making plans on how you will tackle this adventure when you do it again next year. And you will of course do some more of this travelling (along with perhaps some, if not less working) again next year, won’t you Cait? :-)

    Just remember, it’s like riding a bike – at first you fall off at times but eventually you get the hang of things and how to better “peddle” each day and then you find that it’s smooth riding after that. Like they say, if at first you don’t succeed, then try try again. Right? Hang in there and take it one day at a time.

    • Reply Cait Flanders September 6, 2016 at 3:20 pm

      I will definitely do more travelling like this, but truly don’t want to work on the road. I don’t mind writing and maintaining the blog (that’s not work), but I’ll be telling clients I’m on vacation next time!

      • Reply Vicki@Make Smarter Decisions September 9, 2016 at 6:55 pm

        I wondered about the blog and whether that was part of the “work” you were talking about. (I didn’t think so but glad you clarified here). We will be getting ready to do some serious road trips (for a month or more at a time) next fall and I was considering trying to keep an on-line adjunct faculty job. You answered so many of the questions I had floating around in my head. We are here (son’s a senior in high school) – and if I work this year, I can give up that gig and not worry about it as we travel (or ever really!) Great things to think about.

  • Reply Matt @ Optimize Your Life September 6, 2016 at 5:22 am

    “I would also like to point out that pictures of laptops on patios are ridiculous. Working outside in the sun is crazy. You and your laptop will battle over who is going to overheat first, and either way you will eventually both lose.” I think this every time I see a picture of a laptop in the sun. I have tried it before. It is miserable.

    I think the lack of routine would be the biggest hindrance to me working on the road. I need a routine to be productive and to stay ahead of everything.

    It sounds like it is definitely an experience you are learning from, so that is a great thing to have if only for the personal growth it creates.

    • Reply Cait Flanders September 6, 2016 at 3:22 pm

      It’s definitely a learning experience, and one I’m glad to be going through! And of course, we always wish we’d done things differently in hindsight, right? So it’s all good. But next time, no work :P

  • Reply Maria September 6, 2016 at 5:23 am

    it took me years, literally years, to realize that taking work with me on holidays is ruining my holidays and not improving the quality of work. I am an academic, so I have lengthy periods when I am free not to go to the office, so I travel quite a bit (I know it’s a luxury, but it doesn’t mean it’s always easy to navigate). So my system lately is to decide that i work X number of hours a day in the morning, first thing after I get up (if I stay in one place for, say, 2 weeks), or to schedule working days on longer trips when I move from one place to another.

    • Reply Cait Flanders September 6, 2016 at 3:26 pm

      That’s smart, Maria! And I’ve done that in Colorado: woken up early and gotten work done before really starting the day, and it’s helped a lot. But I’d rather be sleeping :P

  • Reply Casey Elliott September 6, 2016 at 5:53 am

    Maybe you need to slow down- spend more time in one place, stop driving 8 hours a day. You dont have a time limit!! there is no rush!!

    • Reply Cait Flanders September 6, 2016 at 3:28 pm

      I don’t drive 8 hours every day – I just said driving days are the worst (usually have 1-2/week). And I do have a time limit. There have been certain places I need to be by certain times for various commitments, and I need to be home sometime in the first week of October.

  • Reply Roberta September 6, 2016 at 6:13 am

    Cait, you’ll find a way of handling it all, because you’ve accomplished so much over the past couple of years! Got to say that I couldn’t see myself able to handle all the workload while travelling and travelling. However, it’s good to hear that you do take some time out to recharge with friends (old and new) while you’re on your journey.
    Keep on driving safely, sleeping soundly, and lots of blogging!

    • Reply Cait Flanders September 6, 2016 at 3:28 pm

      Thanks, Roberta! <3

  • Reply TJ September 6, 2016 at 8:36 am

    “And the next time I do something like this, I won’t be bringing any work with me.”

    This is a very interesting observation. When I made my Facebook announcement about going on an “indefinite road trip”, there was never any plans for it to simultaneously be some sort of hopeful profitable venture.

    I really do have to ask myself if the “moneymaking ideas” I’ve had are because while I knew that this was something that I wanted to write about, was I also extremely uncomfortable with the narrative being “dude who saved up a lot of money and has the privilege of not bringing additional cash during the trip….”.

    That being said, I definitely do have a chip on my shoulder to prove to myself that I am a smart enough and hardworking enough to support myself on the road.

    But what if I fall on my ass in the process? It’s a very real possibility. I mean, trying to build your own business when you have no stable home life and have already shut off your primary income stream probably isn’t the smartest way to go about it.

    So I need to be sure not to let any potential business failures (or successes!) distract me from the original reason for the road trip. To rediscover my passions. To try out new potential cities to live in. To enjoy happy moments with old friends and new ones. To try all of the regional foods.

    Thank you for writing this. It’s important to hear about for anyone who is thinking of taking that leap, certainly someone who has already decided that he is going to actually do it, but who has no idea about the realities of the life that is ahead of him.

    • Reply Cait Flanders September 6, 2016 at 3:33 pm

      I think the best advice I can give you is to be flexible. Every day is a little different, and you have to be willing to change your plans, try new things and just go with the flow. That will apply to all different kinds of circumstances, from what you do for fun to how much/what you decide to do for work. No matter what, you’ll make some mistakes and learn from it all. I’m excited for you!

  • Reply Kate @ Cashville Skyline September 6, 2016 at 8:36 am

    Working from the road is tough! I don’t miss those days of struggling to find decent wifi, something to eat, and sneaking naps wherever I could. Those long stretches of nothing between cities can be brutal. See you soon, friend.

    • Reply Cait Flanders September 6, 2016 at 3:33 pm


  • Reply Chris @ MindfulExplorer September 6, 2016 at 8:38 am

    Thanks for sharing this personal reflection Cait
    I would think the biggest struggle you are having is timeline, do you feel that you have to keep to the schedule? Could you slow down in each community and drive shorter distances? I believe you stated you have a specific timeline and this itself may be the biggest hurdle you are battling.

    As for routine, this is huge and for me would be the hardest part. Creativity flows easily from that same chair by that same window in the same house at the same time a lot more easily than your current situation.

    I know we can’t help with your assignments or do the driving for you, but know we are here to support your experience on living a new way.

    • Reply Cait Flanders September 6, 2016 at 3:35 pm

      You are the best, friend! And you are certainly right that the first few weeks were probably tougher because of the great distances I drove. I’m NOT driving as much in the final 4-5 weeks, hanging out in Colorado, Arizona, California and Oregon for at least a week each. So I’m hoping that will help. But I’m also hoping to finish all my work in Arizona, so I can enjoy my time on the coast :)

  • Reply David Cain September 6, 2016 at 8:48 am

    Hey Cait! This has been my experience too. Traveling is something we associate with free time and relaxation, but when it comes down to it, it really takes a lot of time just to get around and get your bearings, and the travel itself can be stressful. Those images of laptops in hammocks were a big inspiration to me when I decided to pursue the entrepreneur life, but it’s kind of a joke now. I work, and I travel, but I was never able to do both at the same time.

    • Reply Cait Flanders September 6, 2016 at 3:36 pm

      Somehow I’m not surprised we’ve had similar experiences, friend. Can’t wait to talk about it all + more in two weeks!

  • Reply Michelle September 6, 2016 at 8:50 am

    I really do love traveling and working full-time, but I do enjoy it much more now that we live in an RV and we can bring our home everywhere with us. It was definitely a lot more tough when we were just traveling in our Jeep and doing everything as we went.

    We do have limits to traveling days now that we live in an RV, and you may want to try that as well in the future. We never try to go more than 250 miles in a day, which is around a 6 or 7 hour day with dogs, stops, and breaks in an RV. We also only move around once or twice a month, so that helps as well.

    I agree about working outside with a laptop! I have only done it in comfortable weather. I see pictures of people doing it in 90 degree and up heat and I’m wondering how that’s even comfortable, haha!

    Not bringing work with you is important too. I always try to work ahead (right now I’m 1.5 months ahead with content) and it really helps to manage a much better work life balance.

    • Reply Cait Flanders September 6, 2016 at 3:40 pm

      1.5 months!? Holy smokes. See, I think the difference there is you’re probably talking about working on your own blog versus doing client work. It’s impossible to be that far ahead with client work, when writing assignments hit your inbox just a few weeks before they are due. Anyway, I definitely plan on staying in places a lot longer for the duration of my trip! But I’m also hoping to get my work done in Arizona, so I can relax for the final 3+ weeks. :)

      • Reply Michelle September 6, 2016 at 4:11 pm

        Exactly. I don’t do freelance work anymore, so that really helps me out.

  • Reply Julie@ChooseBetterLife September 6, 2016 at 9:04 am

    So true, Cait. There are recruiters for locums positions from Montana to New Zealand, but the inside of an ED looks pretty much the same everywhere. So I’ll work at home and then go on a real vacation, thankyouverymuch.
    …but it can’t be a two-month vacation, so every now and then I’m tempted to live and work abroad. Thanks for the reminder that it is a choice, and we can’t always choose to have everything all at once.

    • Reply Cait Flanders September 6, 2016 at 3:42 pm

      See, I think if I was living in ONE city for two months, this would be a lot easier. All the travelling around is what makes it more difficult to manage any amount of work. I still dream of going to the UK for a few months, and I would work from there… but I’d like to stay in one place for a few weeks at a time, so I could settle in and really experience “life” there.

  • Reply Maureen September 6, 2016 at 9:17 am

    One of the sites I really like is the Professional Hobo who does work on the road. However she talks about slow travel where you spend time in each place you visit so you have time to take it all in. While you have planned a trip to travel quite a bit in a short time, it is not slow and not allowing you the time to see all you wish to. This may be why your experience is not what you had hoped.

    • Reply Cait Flanders September 6, 2016 at 3:43 pm

      It’s true to some degree but I knew what I was getting into. And I could’ve enjoyed it a lot more if I didn’t have to work. I should’ve just taken a two-month vacation.

  • Reply Susanne September 6, 2016 at 9:24 am

    Thank you Cait! Finally, a realistic version of life on the road. We live in the PNW, about 6 hours south of you in Oregon. When our last child left for college we bought a tiny, two room vaca home in Baja. It’s nestled in a green cardone cactus forest, and from upstairs you can soak in the deep blue Sea of Cortez and a rugged mountain range that the sun sets on each night. Sounds amazing, right? It is. And it is not. It take 4 days of 10-13 hours of driving to get to. The house was partially unfinished so our last two trips have been all about driving 30 minutes to the nearest Home Depot for building supplies, not to mention the days and days of working on the house. Time on the water? Almost zilch. Expense? Ay yi yi. I also feel guilt for being there, away from our children, extended family, and real life. Shocking first world problems for sure. The house is 99% complete now and we hope to sip alcohol, windsurf, and generally relax from here forward. The guilt of being there without my family? Not sure as a mama I will ever fully overcome that. I am convinced our little sugar shack vaca home will always be part love, part work, and always real life. Would we do it all over again? Yes. Why? The temporary break from work (the kind that pays the bills) is wonderful. Walks through the cardon forests, swimming in the salty sea, sunsets from our rooftop with margarita in a plastic cup in hand is pure pleasure, and we’d be crazy to give in to the difficult part and miss out on the sublime. Once again, thank you for the very real reality check. Happy travels and may your next trip be work free!

    • Reply Cait Flanders September 6, 2016 at 3:51 pm

      Oh my gosh, Susanne, thank you so much for sharing details about your vacation home + life here. It sounds like getting the home ready for future vacations wasn’t exactly fun… actually, it sounds like work. But now you get the payoff: real vacations. Enjoy, enjoy, enjoy! :)

  • Reply Ms. Montana September 6, 2016 at 10:17 am

    I was so glad I didn’t have paying work that had to be done during our 6 week trip this summer. I thought I planned really slow travel, but I should have taken twice as long in each place. Next time I would plan for “work days”. It was too hard to squeeze writing around the driving, adventures, visiting people and just trying to make life work (showers, laundry, cooking.) I think if you did another trip, you would find your pace.

    • Reply Cait Flanders September 6, 2016 at 3:51 pm

      And I will definitely do another trip! But I really, really, really don’t want to work during it. I would rather work my butt off for weeks leading up to my departure date, so I could relax and enjoy every minute of my time away from home.

  • Reply Penny @ She Picks Up Pennies September 6, 2016 at 10:21 am

    I love the honesty of all of your posts. Following you on Twitter has been wonderful. I can’t imagine juggling all that you are, but I also appreciate so much that you carved out time to let us all benefit from your experiences. I did just a teeny bit of work in Vegas and again in Costa Rica. It was kind of fun compared to regular work, but it wasn’t what I would have preferred to be doing while traveling!

    • Reply Cait Flanders September 6, 2016 at 3:53 pm

      I remember feeling that way when I was working remotely for my last company and travelled to San Francisco, NYC and the Dominican Republic. I worked part-time while there and I always regretted not taking the time off instead.

  • Reply Millennial Moola September 6, 2016 at 10:28 am

    Been in the “Wifi doesnt work” situation many times. Surprisingly, the most frustrating place that happened was in Switzerland. Perhaps because they’re paranoid about internet security, you must verify your signin to networks with a Swiss phone number, which is pretty hard if you aren’t Swiss. Thank goodness my buddy had a normal connection with a password and I could use his phone to login,

    • Reply Cait Flanders September 6, 2016 at 3:53 pm

      Oh wow, that’s intense! I found NYC wasn’t very wi-fi friendly either (which surprised me). Lots of coffee shops will only give you 1 hour of wi-fi (or none at all).

    • Reply Swissrose September 10, 2016 at 1:11 am

      Yes, I live there.
      As a Swiss I find this is a problem all over Europe – except in McDonald’s in France, which I rely on every summer when I get to spen 5-8 weeks in Brittany… so very much a first world problem ;o

  • Reply Justin September 6, 2016 at 10:45 am

    Travel can be stressful enough without cramming in a full time job on top of it all!

    We do long term (3-8 week) travel every summer when the kids are out of school and I’m the main travel coordinator (bus schedules, flights, hotel reservations, figuring out what we’re going to see each day, etc). Rarely do I find time to focus on writing anything worth publishing. More likely I want to watch some Netflix, surf the web, or play some games (or nap!). No way would I want to be stuck writing when I want to relax or hit the road for the next destination.

    The only way it would work for me is if I dialed the travel schedule way down. As in very slow travel. A week or two in one spot before moving on. That’s what we tend to do anyway, and there are certainly times in those longer stays where I would be able to handle some writing assignments.

    • Reply Cait Flanders September 6, 2016 at 3:55 pm

      Yes, and that’s how the latter half of my trip will look: spending at least a week in a few places. But now I want to get all my work done before, so I can REALLY enjoy my time in those cities, haha. Thanks for sharing your experience, Justin!

  • Reply Tony W September 6, 2016 at 11:43 am

    Sounds like work. I experienced much of that in my cubicle. LOL

    • Reply Cait Flanders September 6, 2016 at 3:55 pm

      Ha, you know it, Tony!

  • Reply Sarah Noelle @ The Yachtless September 6, 2016 at 11:46 am

    Hooray for debunking heavily curated, idealized Internet myths! :)

    I find combining work and travel to be challenging too. Usually I end up just not doing any of the work at all and then having to deal with the consequences when I get back. :/

    Also, I’m seriously impressed you even finished part of one book!

    • Reply Cait Flanders September 6, 2016 at 3:56 pm

      I was riddled with guilt while reading it… but wanted to finish it! I haven’t started a new one since :(

  • Reply Kevin Holesh September 6, 2016 at 12:24 pm

    Love your honesty, Cait. Life on the road definitely can be stressful. When we tell a lot of people about our road trips, they are disappointed when we tell them we still work fulltime while we’re traveling. They picture 4 months of exploring the beautiful southwest United States during the winter and hiking every trail along the way. Reality is, we spend most of our time on the boring stuff: laptops, cooking, and running errands. We just do it with a view.

    For us, the best thing we did was slow down. We knew we wanted to live this lifestyle for at least a few years, so there was no hurry. We spent a minimum of 10 days in each place, which equals about 7 work days, one errand day, and two days to explore. Even that feels like we’re moving too fast and we’re constantly leaving things in the rear view mirror because we didn’t have the time to see everything.

    And I completely agree. Driving days are the worst. No matter how long or short the drive, it eats up a day of mental energy.

    • Reply Cait Flanders September 6, 2016 at 4:07 pm

      Oh my gosh, thank YOU for being real about the fact that even 10 days isn’t long enough to see everything you want to see! THIS IS SO REAL. I’m spending 10 days in Denver + Boulder, and know I’ll never get to do/see it all. But it’s definitely felt better to slow down and spend more time here, so I’ll try to keep this pace for the final 4-5 weeks of my trip.

  • Reply Maggie September 6, 2016 at 1:11 pm

    Thanks for being brave enough to say it, and with humour! I have always looked at photos of laptops and pools and wondered about the logistics – how does the laptop not overheat and die? Where is it plugged in? But most importantly, how does one develop enough willpower to sit on a gorgeous beach and work? I’m happy to keep my work and my vacation quite separate, even if it means that I’m not a digital nomad.

    • Reply Cait Flanders September 6, 2016 at 4:08 pm

      Haha, I could NEVER work poolside. Sunshine/pools are meant for swimming + reading books only.

  • Reply J. Money September 6, 2016 at 1:52 pm


    My favorite thing about you, Cait. Not afraid to tell it how it is.

    Cannot WAIT to see you later this month! Let’s *not* do work together when we hang, okay? ;)

    • Reply Cait Flanders September 6, 2016 at 4:08 pm

      DEAL!!!!!! Can’t wait to see you, friend! xoxo

  • Reply Amanda | musicalpoem September 6, 2016 at 2:28 pm

    When I went to Hawaii, I agreed to work half days when I was there (I didn’t have enough leave to take a “full” vacation and I had to be in HI for my brother’s graduation). I am SUPER grateful my employer was so flexible and accommodating with my schedule, but man. It sucked getting up at 7am to work when on vacation… especially if I had been out late the night before!

    • Reply Cait Flanders September 6, 2016 at 4:10 pm

      A good reminder for me, as I want to go to Hawaii in the next couple of years. I won’t work for a single second!

  • Reply Natasha Ready September 6, 2016 at 4:37 pm

    So so so true!! I went on an epic adventure with my brother (who subbed in for a friend who bailed) during my second year of my BAPC program at Royal Roads. Brutal idea. I remember sitting in our hostel in Bali working on an essay while my brother went out with all the new people we had met at our hostel. But it was my choice to travel while I was in school. Now that I’m done, I definitely prefer to keep work and travel separate when I can. It’s easier to enjoy yourself on a fun adventure when you don’t have deadlines looming in the back of your mind. :) Big lesson learned for me. (I’m also the type that piles too much on my plate when I don’t necessarily need to. I’m working on that.)

  • Reply NZ Muse September 6, 2016 at 9:24 pm

    Travellers need weekends too = seriously! Those travel days (whether driving, train, bus, etc) reeeeally take it out of you.

    I remember spending a full day each in places like Santorini, Naples, holed up working. It’s a privilege but it’s still work.

  • Reply Linda Sand September 7, 2016 at 8:54 am

    Technomadia.com talks about this on their blog as well. I remember them saying taking computers to the beach means getting sand in places you don’t want it.

  • Reply Our Next Life September 7, 2016 at 12:51 pm

    Oh I totally fell victim to that Instagram fantasy, too! When we moved to the mountains, I had this vision that I’d go work out on the deck with my coffee every morning and take fabulous snaps of it all. Hahahahahaah. Uh, yeah, didn’t happen. Or happened once, for like five minutes, at which point I realized all those photos are a lie. :-) And even though I’m not technically a digital nomad, I travel so much for work that it often feels like I am, and all of this is so true. Some of it gets easier if someone else is footing the bills for hotels with reliable internet (it gets better with each passing year), and airport wifi is generally decent these days (finally), but I can only imagine that a road trip nomad could have a much tougher time trying to make work doable on the road. Sending good vibes for the rest of your trip!

  • Reply Revanche @ A Gai Shan Life September 7, 2016 at 1:18 pm

    I learned the same in the past several years. You can do a lot more when you’re not tethered to an office but you have to DO A LOT MORE. So I’ve taken 6x more “vacation time” than ever, and traveled further than ever (Europe, Hawaii, domestically!) but I’ve worked almost every trip. That was my choice but now I’m making the choice to actually take more of those days off. In order for that to happen, I have to make more changes but at least I’m halfway to the perfect set-up and not starting from scratch :)

  • Reply Heather September 7, 2016 at 2:22 pm

    I wonder what the key to simple living on the road is. Whether it’s really defined by working or not working. Is it possible to apply a simple living perspective, whilst tackling the unpredictable nature of being on the road? I don’t know Cait, but I’m sure by the end of it, you will have come up with some good answers!

  • Reply giulia September 8, 2016 at 4:01 am

    Everytime I saw a pic of people that works under the sun I think about the fact my mobile became hot after 30 minutes of texting, working 8 hours under sun could kill my devices, but is true when you work for yourself is not always easy find good balance but seems you’ve did a great work!!! I like to read your posts!!!

  • Reply Carrie Smith September 8, 2016 at 9:18 am

    Ahh Cait, this post makes me so sad. :( It honestly just sounds like you need more road trips to practice working/living on the road. This is your first road trip while being self-employed, yes? It took me several attempts to go on 2-3 week road trips and balance my work stuff succesffully. IT JUST TAKES TIME! I promise.

    Also, it sounds like you need better systems in place (ahem, Asana!) and maybe even a VA to help while you’re on “vacay”. This helped me A TON and now I don’t stress when I need to go out of town at a moment’s notice. I have a really good system and I love workcations now. :) Please don’t give up!

  • Reply JH September 8, 2016 at 7:45 pm

    I find that both the work and the relaxing/exploring suffer because my mind is not fully present on what I’m doing at that moment. At least part of me is feeling like I’d rather be (or should be) doing something else so I’m not doing anything very effectively. Is that your experience too? I’m trying to get better about not feeling guilty or disappointed about what I’m NOT doing at any given moment so I can give my all to the activity of the moment, but that’s so much easier said than done! Loved the perspective in your post. Sounds like you’re having an amazing adventure!

  • Reply Finance Solver September 8, 2016 at 7:51 pm

    Every time I read about a successful blogger who’ve been able to quit their job to go out on the road, I get a little jealous but I don’t always consider the downsides to being out on the road. Great post on detailing both the positives and the negatives as the negatives often get overlooked when someone out there is doing something interesting.

    I can’t imagine working when I’m out on the road. I wouldn’t be able to enjoy the scenery because of the way I function. I try not to multitask and that resulted in me unable to focus on multiple things at once. It sounds like you’re making it work though and keep up the great work! :)

  • Reply Jen @ Saving with Spunk September 9, 2016 at 12:28 pm

    I’ve done cross country driving and it is not glamorous, especially in a car. Driving is exhausting! Safe travels to FinCon, and hopefully your drive back will allow for more funtivities. :)

  • Reply Harmony@CreatingMyKaleidoscope September 9, 2016 at 1:21 pm

    The grass is always greener, right? We have a plan to go on a long road trip once we reach financial semi-independence. I will likely have to do some work from the road, but will keep your story in mind. I will try to make it flexible work that can be done when the conditions are right. Also, Mr. Smith will likely be driving a lot of the time, so I will hopefully find a way to do something productive while he’s driving. By that point there may be more options when it comes to portable WiFi.

    I feel your pain on the books. I brought a whole bunch with me on our recent vacation, with three kids. Yep, I only got a couple chapters into ONE of them. Unless, of course, if we’re counting Dr. Seuss, Paw Patrol, and books about dinosaurs. I was able to do some crochet though :)

  • Reply Tiffany @ HappyThankfulHopeful September 11, 2016 at 8:18 pm

    I love the honesty in this post! I’m re-thinking my career and considering starting my own consulting business. I’m one of those that loves the idea of flex time but in reality I need separation between work and home/relaxation.

    Filing this nugget of reality away for the future consulting business.

    Thank for keepin’ it real, yo. ;)

  • Reply Ten Factorial Rocks (TFR) September 14, 2016 at 4:13 am

    Interesting points, Cait. I think FB and Instagram have caused as much misery as happiness, mainly because the people who see the happy pictures don’t realize it is the BEST moments people put on social media, not the unhappy and longish boring parts that fill the space between the best moments. I think there was a study done that said modern social media causes stress and unhappiness due to this belief others have a happier life than you – at least that’s what their shared pictures tell you.

    I travel quite a bit for my job, and while it get tiring, it is the stress of completing your work before you catch your return flight that makes it worse. Over time, you discover neat little tricks to handle this so work travel becomes second nature to you. Consulting has other stressors that a full time job doesn’t have, and while it gives flexibility, you also should deal with wild swings in income. Everything has its pros and cons. Enjoyed your good post!

  • Reply Nick True September 14, 2016 at 7:08 am

    YESSS. This is so good. I travel all the time right now for my job (currently typing this from a hotel in CA – I live in TN).

    Travel is tough. You think you’re going to be way more productive than you are, and it just doesn’t happen that way.

    Thanks for the brake check Cait!

  • Reply Fritz @ TheRetirementManifesto September 14, 2016 at 7:48 am

    Cait – thanks for the reminder that when I FIRE in < 2 years, I'm not ever going to be obligated to work again. If I CHOOSE to write, I'll write. Freedom is valuable, and your article reiterates it's importance. BTW, congrats of the Rockstar Finance highlight today!!

  • Reply Mrs. Picky Pincher September 14, 2016 at 8:55 am

    In many ways I think it’s more difficult when you work for yourself. There’s a constant nagging pressure to get things done; it’s a pressure you put on yourself and it’s so difficult to relax. I don’t know if I could handle a gig plus a road trip! I do think it’s important to stay busy, but not to the point where it interferes with enjoying the trip. :)

    • Reply Aryana September 14, 2016 at 3:19 pm

      Yeah, I agree with this. I was a freelancer in the past and it was HARD – often because I didn’t know if I was working too much or too little. Relaxing was tough.

  • Reply Derek October 11, 2016 at 12:12 pm

    I feel you.

    When we traveled full time for 7 months I was shocked by how much time was taken up by, uh TRAVELING!

    Suddenly 30% of your life is just preparing to travel, traveling, or un-winding from traveling. We saw and did some amazing things but it wasn’t like we were just hanging out and rock climbing 18 hours a day.

    All that traveling and living on the road was incredible, amazing, life changing.


    I’ve never been so far out of my comfort zone. In fact, I had almost no comfort zone for weeks at a time. It was hard, but I learned a lot and grew a lot during those 7 months.

    I’d do it all again, but GOOD LORD IT WAS HARD!


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