Why I’m Scared to Live Alone on the Road (But Am Doing It Anyway)

August 15, 2016

Why I'm Scared to Live Alone on the Road (But Am Doing It Anyway)

As I’m writing this, I’m sitting in a Starbucks in Victoria, hiding in a corner with my headphones on and crossing off the final items on my work to-do list. My car is half-packed for the Great American Road Trip, missing only my day pack and pillow (a luxury I can bring, because I packed light and there’s lots of room in my car). And by the time you’re reading this, I’ll be on my way.

It’s hard to believe that an idea I’ve had for years is finally happening. For as long as I’ve been writing this blog, I’ve dreamt of travelling around and connecting with more of my online friends in real life. So you would think that I might feel nothing except joy and excitement. But the truth is, I’ve spent the past week riding an emotional roller coaster.

First, I was stressed about trying to get all my work done. Somehow, I accomplished more in the past seven days than I did some months this year, which proves how much I can do when I set my mind to it. But then the “see you later’s” started. And then our sweet dog, Molly (12), was showing symptoms that needed to be addressed by a vet – and from there, my thoughts began to spin out.

What if something happened to her when I was gone? What if something happened to any of my family or friends? How would I ever forgive myself if I wasn’t here? How would I even deal with that when I was alone on the road, where it could take me days or even a week to get home? The worst what-if situations kept popping into my head, likely heightened by how stressed I was about work and the fact that I wasn’t sleeping well. But they were bad enough that I almost delayed the trip.

I almost texted friends to say I’d have to come a little later – or skip their states altogether. I wrote the sentences and almost hit send – but something made me pause. Positive feedback from the vet helped, as did reassurance from family that everything would be fine. But I also knew the voice in my head was fear, and that I couldn’t let it stop me from going on this trip.

I wish I could say I am one of those people who gets on a plane or goes on a trip and simply exudes their sense of adventure. You know: the ones who seem to have no fear and can ride the waves as they come. True nomads, in every sense. But I would be lying, if I said that. To be brutally honest and real, I have to tell you that I’m a little scared to leave home for two months.

When I was considering delaying my departure date, I hit pause on those text messages to friends and asked myself what I was afraid of. The answer had nothing to do with the road trip itself. If my car breaks down, I’ll pay to fix it. If I feel scared to camp somewhere, I’ll pay for a motel. Those are the only things that could really go wrong and, fortunately, money could fix them. So, I’m not scared of that.

Instead, I’m scared to leave my family and friends (and dogs) for two months – and as I dug deeper into that, I realized it’s probably because of how much I’ve come to rely on them, this past year. I’ve explained before that I moved back to Victoria to help my family. But I also don’t think I could’ve gotten through the last year if I hadn’t been surrounded by the people I love. All the laughs, walks, hikes, adventure days… and constant kisses from the dogs. I’ve needed it, to stay sane and happy.

So, in this world of inspirational posts and motivational quotes, I’m going to tell you the truth, which is that I cried a lot this week. I cried at home, in the car and at the animal hospital. I even cried at my favourite breakfast spot (thankfully, they know me and didn’t mind). I’m sad to leave. I’m sad I won’t be able to see the people (and pets) I love for a while. I know this road trip is going to be full of challenges and personal growth. And I’m scared to go through some of it without loved ones at arm’s reach.

But I’m more scared of missing out on everything the next two months could hold for me on this road trip. And even though I can’t say for sure that I’ll get in the car and exude a sense of adventure, at first, I have a feeling most of my concerns will float away when the ferry leaves the shore.

I shared these feelings with my friend Katie, who has done a lot of long-term solo travel, and she said something I’ll never forget:

You could read that and think it only relates to making decisions that will help you stay safe. Personally, I’ve learned the importance of trusting your gut so many times that I know I will always take the measures needed to feel secure. But her words remind me of the reason I want to stay safe, in the first place, and that’s because I have an amazing life to come home to later.

For as excited as I am to explore for the next two months, I know I will be equally excited to cross the border and take the ferry home in October. I can’t wait to hike in Montana, hangout with new friends in Minnesota, spend quality time with old friends in Colorado, and camp all along the California coast. I’m going to enjoy every minute of it. But on that last day, you’d better believe I’ll be smiling on my drive home, as I think about seeing the dogs and sleeping in my own bed again.

PS – I can’t say for sure how much I’ll blog about the trip itself, but you can follow along on Instagram. Keep in mind, the pics I share will be of places I’ve already seen and left behind (a safety tip I read on many solo female travel blogs).


  • Reply Kate @ Cashville Skyline August 15, 2016 at 4:34 am

    You’re going to have the most amazing time, Cait. Fear is completely normal. But once you’re out there, I’m sure you’re going to love it. Be safe! I’ll look forward to seeing you in San Diego!

    • Reply Cait Flanders August 21, 2016 at 8:01 pm

      Can’t wait to see you too, friend!

  • Reply Dayle August 15, 2016 at 5:07 am

    Have the best time!!! It’s going to be awesome :D
    Happy trails!! xo

    • Reply Cait Flanders August 21, 2016 at 8:01 pm

      Thanks, Dayle! xoxo

  • Reply Our Next Life August 15, 2016 at 5:33 am

    I couldn’t agree more with that quote! I think a little fear is good in all things — it means you’re challenging yourself and growing, too. But I get it, especially leaving your dog! Wishing you an amazing trip full of adventure, as well as a sweet return home in a few months. :-)

    • Reply Cait Flanders August 21, 2016 at 8:03 pm

      Thanks, friend! And thank you again for the beautiful guest post. I’m so grateful you were willing to share it with my readers. <3

  • Reply L August 15, 2016 at 5:40 am

    Hi Cait,

    I hope you have an amazing trip, I have no doubt it will be amazing and you will learn so much about yourself. I hope you do some recaps about what you saw and what you learned about yourself. I always love reading about people that are brave enough to go on an adventure:)

    Good luck, enjoy and be safe!


    • Reply Cait Flanders August 21, 2016 at 8:04 pm

      I’m mostly sharing pics on Instagram and Facebook, for now! I don’t want this blog to become 100% travel/road-trip-related, but will share a bit here and there. You can find new pics on Instagram daily, though! :)

  • Reply Rob August 15, 2016 at 5:54 am

    Hi Cait,
    Time to think upbeat positive happy thoughts about your upcoming trip and stop needless worrying. Your family, friends (and dog) that you are leaving behind (for 2 months, which really isn’t that long a time) will do just fine. They all (including the dog) don’t all depend on just you being around, ya know! :-) I’m sure that your parents, your siblings and your friends will all pick up the slack and look after each other just fine during your absence. Change (like going on a new road adventure) can appear daunting at first – just thinking about all the unknowns and “what could go wrongs” ahead. Once you get started though you see how exciting and how quickly time will pass. So as we like to say to each other, take a deep breath, relax, and don’t sweat the small stuff. You’re going to have a blast, my friend. Trust me.

    • Reply Cait Flanders August 21, 2016 at 8:05 pm

      You’re so right – as always – my friend! I can’t believe the first week has already come and gone. Where did the time go!? I already wish it would slow down! Not thinking about “home” at all yet. Just enjoying my time in various cities, and getting excited to keep seeing friends along the way :)

  • Reply Matt @ Optimize Your Life August 15, 2016 at 6:13 am

    Best of luck, and have an amazing time!

    • Reply Cait Flanders August 21, 2016 at 8:05 pm

      Thanks, Matt!

  • Reply TJ August 15, 2016 at 8:29 am

    That’s so smart about putting photos up after the fact – and I think that would be a good tip for anyone who is going it alone. You can never be too careful.

    Wishing you the very best on your road trip.

    • Reply Cait Flanders August 21, 2016 at 8:05 pm

      Thanks so much, TJ!

  • Reply Penny @ She Picks Up Pennies August 15, 2016 at 8:32 am

    I love the idea of analyzing our fears. They keep us safe, but they’re also worth pushing up against. I am so excited for you on your adventure, and I cannot wait to follow along.

    • Reply Cait Flanders August 21, 2016 at 8:06 pm

      Yes, it wasn’t easy to accept that fear was (almost) holding me back… but I’m glad I pushed through it! The first week has been amazing, so far. :)

  • Reply Julie August 15, 2016 at 8:39 am

    Have an awesome trip!! I definitely understand your feelings about your pup. I was a crying wreck leaving my dog last summer for just a two week trip! I have more separation anxiety than my dog does. It can be hard, but the adventure is worth it and just think of those excited dog kisses when you get back home.

    • Reply Cait Flanders August 21, 2016 at 8:07 pm

      Yes, why is it so hard to leave them behind, hey!? Our wonderful friends get lots of love from the people we leave them with. But I think it was a reminder of how special the love they give US is, and I’ll miss that for the next couple of months :)

  • Reply Michelle August 15, 2016 at 9:41 am

    I really hope that we are able to run into each other! I’ll be in Moab until September 11th, then we’ll be spending time in Bryce and Zion for the week after that until we get to San Diego :)

    • Reply Cait Flanders August 21, 2016 at 8:08 pm

      I think I can hit Moab before the 11th! Will keep you posted, but I bet we’ll meet up there :)

  • Reply Carolyn B August 15, 2016 at 10:25 am

    Your friend is a genius; I love her quote.
    In 20 years you will look back and be so happy with and proud of yourself for this adventure. I say that with 50 yr old eyes that would love to travel back in time and live life more daring than I have.
    Yes, please write your blogs even if you can’t post them on the website or Facebook until later. I can’t wait to hear about your adventures.

    • Reply Cait Flanders August 21, 2016 at 8:09 pm

      I’m already so happy with the decision, Carolyn, and it’s only been one week! Very happy I didn’t change any of my plans :)

  • Reply Ms. Montana August 15, 2016 at 11:26 am

    Ah, have fun! It was so difficult and stressful for us to leave on our 6 week trip this summer also. But in the end it was just incredible! And I am so happy for your that Montana made your list. There is no place we love more. If you happen to head through the Flathead Valley and want to get some amazing ice cream, it will be my treat. =)

    • Reply Cait Flanders August 21, 2016 at 8:10 pm

      So sorry I missed you, but I have a feeling I’ll be back in Montana again sooner than later! Will definitely take you up on that ice cream one day :)

  • Reply Barb August 15, 2016 at 11:30 am

    Many, many years ago I started off on a cross country adventure on my own (age 34) and I was terrified. I even stopped about two hours after leaving home to call my on again, off again boyfriend to describe a noise my car was making. I told him I’d changed my mind and was turning around to return home with my clearly unreliable car…blah, blah, blah. He told me that was nonsense and that my car was fine and that I was just scared and that I should continue on. He was right and I reluctantly kept going.

    The thing is, I met the man I would marry while on that trip. I shudder to think of how close I came to not meeting him and having a life with him. Today we have been married almost thirty years and I look at the grandchildren I wouldn’t have if I not faced my fears and I am SO grateful for the push to travel alone.

    Yes, it is scary and a bit of caution is a good thing. Caution helped me realize when two unsavory men were too interested in me and I revised my plan on where to stay that night based on the bad feeling I got from them. But days later I met my future hubby and trusted my instincts by letting him get to know me and we married the following year.

    So go Cait on your trip (as you plan to do) because who knows what adventures await you… Take care and have fun!

    • Reply Cait Flanders August 21, 2016 at 8:13 pm

      Wowww, Barb, thank you so much for sharing that incredible story with me! I can already tell that I’ll build stronger relationships with friends and people I meet on this trip, which I’m so grateful for. Your story is an excellent reminder to trust your gut in all situations, especially with people. :)

  • Reply Cathleen August 15, 2016 at 11:41 am

    Old Danish proverb: “Away is good but home is best.” You are already showing us your gratitude for your life and all you are thankful for–and thanks for sharing that. I can’t wait for your trip! Have an excellent adventure.

    • Reply Cait Flanders August 21, 2016 at 8:13 pm

      Thank you so much, Cathleen! <3

  • Reply Michelle Hargrave August 15, 2016 at 11:50 am

    I had a similar experience a few years ago, with a great opportunity to travel to places I’d always wanted to see. For awhile I was wishing I could cancel it and stay home but didn’t know what I would tell people! Now that trip is one of my best memories. I hope you have a wonderful visit to Minnesota – fall is a perfect time to come here.

    • Reply Cait Flanders August 21, 2016 at 8:14 pm

      Oh my gosh, Minnesota has been my favourite state, so far! It helps that I’m spending it with good friends who are amazing hosts. But it’s so green, the temperature is perfect, the food is unreal… I’m so happy to be here. :)

  • Reply Leigh August 15, 2016 at 12:54 pm

    Good point on the photos! I always post them later because I feel like taking photos is enough of a distraction from the moment that I don’t want to also spend the time posting them…and that way, I can also pick my favs! :) Can’t wait to follow along with your trip on Instagram!

    • Reply Cait Flanders August 21, 2016 at 8:16 pm

      Oh yea, that’s also true, Leigh! One of the best parts of being on the road, so far, has been that I’m not looking at my phone all day. I don’t have time! Except to check Google Maps occasionally, haha.

  • Reply Alyssa @ GenerationYRA August 15, 2016 at 12:59 pm

    Cait – I am SO incredibly excited for you, and also happy to hear that fear didn’t prevent you from embarking on this solo road trip. It is challenging, but how wonderful to know that you find love, comfort and adventure whether traveling or at home with loved ones. It often seems that people are constantly trying to get away, but you find solace in both places. I cannot wait to hear about what you discover on your journey and hope to see you in Oregon!! :)

    • Reply Cait Flanders August 21, 2016 at 8:30 pm

      I think the only way to appreciate travel for all it can be is to also have an appreciation for why home is important too. So while I’m going to enjoy this for the next six weeks, it’ll also feel good to go home for other reasons. The point is never to run away, but to experience something new for a while. You will DEFINITELY see me in Oregon, where we can talk more about this. :)

  • Reply Tracie August 15, 2016 at 1:12 pm

    Those people who act like they’re not afraid are faking it! I went to Iceland by myself last May and postponed it for a day because I had too much anxiety. My anxiety brought me to tears and it was not even my first time traveling alone! It turned out to be one of the most incredible experience of my life, and Iceland is one of my top favorite countries now! I plan to go back in November to see the northern lights.

    Everyone on Facebook saw the happy pictures. My mother only got a text with me saying what time my flight got in and where I saw staying. No one knows I cried the day prior and changed my departure date. Enjoy this time! You will make memories that you tell people about for the rest of your life!

    • Reply Cait Flanders August 21, 2016 at 8:31 pm

      Thank you so much for sharing your similar experiences, Tracie! I appreciate it more than you know. I swear, all the anxiety and fear DID go away the day I left… but those few days before we awful! So glad I didn’t give in to it. <3

  • Reply Kelly August 15, 2016 at 1:56 pm

    I envy you.. You are about to do something I personally don’t think I could ever do. I don’t like being by myself…heck I am VERY directionally challenged anyway & on purpose don’t spread my wings very much because I get lost easily .. I took a chance & went with my daughter choir trip to New York & even though we were in a group it was very nerve wrecking.. Plus my daughter convinced me to go out on our own at one point & we got lost… It WAS SCARY.. & I had a meltdown..needless to say not my crowning mom moment. But we survived & one day I’ll laugh about it… Maybe 🙃

    • Reply Cait Flanders August 21, 2016 at 8:33 pm

      You’ll definitely laugh about it one day, Kelly! My friend David once told me that it’s important to get lost sometimes, because it means you’ll see something else. :)

  • Reply Linda Sand August 15, 2016 at 2:18 pm

    I have another young, Canadian, blog friend* traveling solo right now–in Bulgaria where she doesn’t speak the language! If she can do that, you can do this! Just keep reminding yourself that you CAN do this!


    • Reply Cait Flanders August 21, 2016 at 8:34 pm

      Oh that’s so cool, Linda! Checking her blog out now :)

  • Reply Peggy August 15, 2016 at 3:30 pm

    Remember. You can always fly home. And back to get your car. We’re never too far from home when we’re never too far from an airport.

    • Reply Cait Flanders August 21, 2016 at 8:34 pm

      You’re right about that, Peggy! Thanks for the reminder :)

  • Reply Bette August 15, 2016 at 3:40 pm

    Cait! My mantra is, “Feel the fear, but do it anyway.” I’ve been telling myself this for more than 50 years (I’m a fearful being, LOL) and as I look back, all my great adventures required me to repeat this mantra to myself over and over again. Good luck and keep moving forward!

    • Reply Cait Flanders August 21, 2016 at 8:34 pm

      I will happily adopt your mantra, Bette! Thanks for sharing it with me :)

  • Reply Katherine Blaney August 15, 2016 at 3:56 pm

    This sounds like an incredible trip! Good on your for facing the fear! You are going to have an awesome time and learn so much along the way. Enjoy! I know what it’s like to leave my dog behind even for a few days – that’s the tough part but the lovely bit is how excited they are to see you when you get back! (Friends and Family too but they don’t show it quite the same… haha)

    • Reply Cait Flanders August 21, 2016 at 8:35 pm

      Haha, I know, I can already hear the little crying noises one dog will make when I get there. :)

  • Reply Claudia @ Two Cup House August 15, 2016 at 4:12 pm

    Have a fantastic trip! Looking forward to meeting you at FinCon! 😀

    • Reply Cait Flanders August 21, 2016 at 8:35 pm

      Thanks, Claudia! See you sooooon!

  • Reply Josie August 15, 2016 at 7:53 pm

    For what it’s worth, I cried all the way to the airport with my mom consoling me before the greatest adventure of my life. 3 months solo (with some group tour travel) in Africa. You’ll have an amazing adventure. Sometimes you just need to cry first. As a side note, as a mother now myself, I suspect your parents are waaaay more scared for you to go off on your own than you are to go and leave your family. However, as good parents, they will probably hide most of their fear :) By the way, I am enjoying the new travel slant to your blog lately! Safe travels.

    • Reply Cait Flanders August 21, 2016 at 8:41 pm

      Oh my gosh, thank you for sharing that with me, Josie! I don’t want to say I’m glad to know other people cry before going on solo trips (that sounds weird) but it’s good to know I wasn’t alone. And my family hasn’t expressed any fears, but you’re right, they probably have lots! I check in daily :)

  • Reply giulia August 16, 2016 at 1:20 am

    Your firend Katie is right, if you are a little bit scared means that you aren’t going to do something stupid/dangerous…but hei is absolutelly normal have this feeling about family, dog, friends and home but I’m sure you’ll manage every feeling good!!!:D

    • Reply Cait Flanders August 21, 2016 at 8:42 pm

      Thanks, Giulia! So far, so good :)

  • Reply Alyson August 16, 2016 at 3:28 am

    Hey Cait,
    I have felt the same thing twice in the past couple of years – fear of leaving. Before I went travelling for four months, and before I moved from Canada to Australia. In both instances, I thought about everything I would miss (weddings, birthdays, family parties, etc.) and about what I would do if someone gets really sick or passes away (my grandparents are very old). Travelling for four months wasn’t as scary, as I knew that I could always pay for an early flight home if need be (luckily nothing happened and I loved my four months travelling – but you’re right, I was VERY happy to come home). When I was offered a job in Australia, I almost didn’t accept the job because of my grandparents (i.e., what if I never see them again?) and I had been asked to be in two weddings this year which I knew I wouldn’t be able to come back for. Ultimately, what tipped the bucket for me was my grandparents – they were SO excited for me, and even before I had accepted the job they were introducing me as their granddaughter who was moving to Australia to teach at a university. They are so proud of me, and that helped make my decision easier. While the goodbyes were hard, and being so far during difficult times is not ideal, it was the right decision – for my career aspirations, and most importantly, for me.

    • Reply Cait Flanders August 21, 2016 at 8:43 pm

      You’re so right, Alyson. Reading through your comment also made me think: we worry about what we’ll miss when we leave home… but what about the things we’d miss by not going on these trips!? So glad to hear everything worked out when you made the right decision for you. <3

  • Reply Susan August 16, 2016 at 6:44 am

    Good luck! I hope you enjoy every minute of your trip, and yes, coming home too! :)

    • Reply Cait Flanders August 21, 2016 at 8:44 pm

      Thanks, Susan!

  • Reply David Cain August 16, 2016 at 8:14 am

    So glad you didn’t dial the trip back. I can’t wait to hear about your travels. I was so nervous when I was about to leave on my big backpacking trip. All I could think about was things going wrong. When I said goodbye to my family at the airport, my sister hugged me and said “You’re going to have so much FUN!” I remember being kind of surprised at the idea that it might actually be great — it had been so long since I had felt anything but worry towards it.

    Anyway, obviously it’s going to be super awesome. See you in San Diego!

    • Reply Cait Flanders August 21, 2016 at 8:48 pm

      Oh friend, I’m so glad you shared that you have also experienced some of this before travelling by yourself. It helps to know I’m not alone – and that it’s just another part of the human experience. I also appreciate you keeping me company when I was waiting out the storm in South Dakota. We’ll have so much to talk about in San Diego! :)

  • Reply Chris @ MindfulExplorer August 16, 2016 at 1:48 pm

    Thanks for sharing some powerful personal emotions Cait. You’ve got this though and will have an amazing time. Furthermore you have a diverse and wide spread following ( aka safety net) to call on if you need anything along the way. Now go have fun !

    • Reply Cait Flanders August 21, 2016 at 8:49 pm

      Having tons of fun so far, friend! We’ll have lots to discuss when I get back in October :)

  • Reply Vicki@Make Smarter Decisions August 17, 2016 at 4:04 am

    There’s no place like home! But your adventure awaits and I love how you have taken the time to not just embrace what lies ahead, but consider what you’ll leave behind. Such a wonderful piece. Safe travels and looking forward to hearing about your exciting and maybe not so exciting times on the road!

    • Reply Cait Flanders August 21, 2016 at 8:55 pm

      Thanks, Vicki! For as difficult as that week was, emotionally, I am oddly grateful I experienced it… because it reminded me of all I have in my life. <3

  • Reply Julie@ChooseBetterLife August 20, 2016 at 9:47 pm

    Can’t wait to see you in September and hear about your travels so far. Your feelings are completely… normal… and human. Each long trip starts with fear mixed with excitement. The middle has growth and confidence. And the sweetest words you’ll ever hear are from your own customs agents saying, “Welcome home” at the end, right before you hug your family. It’s a wonderful circle- enjoy!

    • Reply Cait Flanders August 21, 2016 at 8:56 pm

      Thanks, Julie! Can’t wait to discuss this more in person soon :)

  • Reply Jennifer August 21, 2016 at 2:49 am

    Hi Cait!! I’m so excited that you’re finally taking this leap! As someone who has done a lot of solo travel, I can tell you the simultaneous feeling of excitement and nauseous is normal – and part of the fun! I won’t lie, you’ll probably have tears somewhere along the road, but you’ll also create wonderful memories that you can’t even imagine now. Be safe and I can’t wait to hear all about it (and follow you on Insta!) xo

    • Reply Cait Flanders August 21, 2016 at 8:57 pm

      I fully expect there to be tears, at some point on this trip… but I also know I can get through it, and it’ll only be temporary. Appreciate your support, hun!

  • Reply Ava Meena August 22, 2016 at 3:21 am

    Everything that you’re afraid of is completely understandable. When my husband and I agreed to move to Germany for a year we had many of the same fears, missing life events or having a death in the family. We are unable to travel back and forth to home freely because of our pet bird (very difficult to cross borders with him). But, like you, we agreed that what we would see and learn would be worth it and that it would be too sad to miss out on these things because of fear. Wishing you all the best for your trip.

  • Reply Scott August 22, 2016 at 5:21 pm

    Happy travels to our fellow Canadian – enjoy the many glorious sites our neighbours to the South have to offer. Remember how hard you work to have the freedom to have an adventure like this – you owe it to yourself to have an amazing time. Your family will be safe, your dogs will be well and you’ll have nothing but smiling faces to greet you when you get back.

  • Reply Linda @ Brooklyn Bread August 23, 2016 at 10:01 am

    This was lovely. I think if you are never doing anything that makes you scared, you’re not living life. It’s the things that give you butterflies that you will always remember and that will really shape your life.

  • Reply Heater Bridges September 1, 2016 at 8:11 am

    So happy to have stumbled apon you. My husband and I are on a new journey empty nesting. Learning to simplify our life and enjoying the journey along the way. Some how we got lost. Enjoy your travels!! Much love from Texas.

  • Reply ZJ Thorne September 11, 2016 at 9:57 am

    Everything about this rings true. And I’m glad you are posting places after you’ve left them.

    Anything could happen at anytime and paralysis can set in. But if our fear always dominates our actions, we won’t get the grand adventures we desire.

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