How To Wander



Dear explorers,

If you’re like most—if not all—of the human beings that I know, you have some fears and worries about the future when traveling solo. If you’re femme-identifying, you may even feel some pressure to harbor greater fears than you initially came up with yourself.

I’ve put together five of the most important tips when traveling solo—the ones that you never find on online checklists or other blogposts.

Trust me, I didn’t just pull these out of thin air. Last summer I took the 2nd “big” trip of my life: bicycling and finding my way across the U.S. from Virginia to Hawaii, solo, with almost no money and no real plan. I’ve played the part and learned the lessons the hard way so that I can share them with you.

  1. Know yourself.

Know yourself… What? Isn’t that why we travel? We want to get to know ourselves better? Figure out the meaning of life? The Fountain of youth.. all that cliché stuff?

I don’t mean knowing your life’s purpose, knowing if you want 2.5 kids, or knowing your greatest desires. I don’t even mean that you should know what you want to eat for lunch tomorrow.

What I mean is quite simple: identify your strengths, weaknesses, excitements, and fears. These four things will really come out of the woodwork along the way and mold your travel story.


Let me explain how these four things will guide you:

Strengths– These will carry you through the rough or difficult times. You’ll better be able to predict when you can carry yourself. You’ll know the parts of you that you’ll most likely be able to depend on. Keeping them in mind will offer you confidence, helping you feel calm and secure as you travel, no matter what’s going on around you.

Weaknesses- These are what to look out for. If you know what you struggle with, you are better able to decide how to avoid it or if you want to face it head on. Either way, it gives you more control.

Excitements– These things give you butterflies when thinking about your travel; they give you something to look forward to. When you have a list or idea of “excitements” then you can use them as fuel from your past (looking back at things that inspired and allowed you to feel more whole) to push you forward. When they happen, you may find the feeling of accomplishment that encourages you to keep wandering.

Fears– These things are very different from your weaknesses. Many of us have fears that we have never experienced before. Therefore, we do not know if they’re weaknesses. Fears are usually born by the unknown, or a trauma that you carry with you. If you can take a look at these beforehand you can use different tools to work with them when you come to a bump on the trail.

How do you figure these out? Simply sit down with a pen and paper and create four separate lists. Speak with honesty. These lists are for you. They will be your personally-tailored guides as you travel!

2. Practice

What will you do if you’re challenged? If your weaknesses are creeping through? How will you work with them? What will happen if your fears are dancing in front of you?

These questions are not to make you panic or imagine the worst. They’re here to encourage you to set out a time and space to run through these situations in your mind. Feel through them.


For example, one of my weaknesses is a lack of sense of direction. Last summer I set off following only paper maps.  I knew that this may be a challenge for me. And oh, it was.

I got lost countless times and panicked each time until I realized that I had already gone through this situation in my mind. I knew that I needed to stop, breathe, and look around. I needed to consult other maps. If that didn’t set me in the right direction, I would ask for help. If there were no people, (and at times that was the case) then I would take out my phone or emergency device and call someone who could help. Although I already had this plan organized in my head, it can be challenging to stay level in the heat of the moment.

One day I got so far lost that I ended up calling the police. They came, found me, and left me on the highway where I could continue. Yes, I was embarrassed, but I pushed through a scary situation and was able to ride on.

You can also do different things physically to prepare. They seem like common sense, but be sure to make the time for them before you go!

For example: Are you afraid to camp alone in the dark? Camp in your back yard for practice. Have a fear of swimming in large bodies of water? Take swimming lessons. You get the idea.

Most importantly, get into the situations in your mind before you physically get there. Practice, feel, and logically think through them. The feeling of preparation- mental and emotional-  is one of the most valuable things to take with you when you travel.


  1. Use your intuition.

You may hear this a lot from parents, grandparents, and those who have given up on trying to stop you from traveling. You may roll your eyes or even consider using this advice. Either way, please take this tip seriously and practice it every step of your journey.

Wander, Hawaii


Have you ever been in a situation that could have turned dangerous but you listened to that “little voice” to find your way to safety?

Have you ever just had a feeling and thankfully followed it?

These are examples of using your intuition. Your intuition is like a built-in, invisible compass. The great thing is that you can access it or hear it any time that you are willing to listen.

Sometimes we don’t avoid dangerous situations, or feel surprised to find ourselves in them. But we always have the choice to listen to our inner guidance and act accordingly.

For example: When I was in California, I decided to couch surf like I had done a handful of times before. I always cashed out with good experiences. One time, I chose a place to stay that sent some little flashing lights off in my head. I ignored them. I wanted to stay at that place because I would have my own space and it was close to some forest that I wanted to lose myself in.

As soon as I got there, I felt uncomfortable. It wasn’t just because I was staying in a house with a few men (as I had done before with no problems) but that there was a strange feeling inside me that felt wrong. I ignored it and talked to the host more.  I was trying to convince myself that it was an okay place.

Later that evening, I ran into some people that I knew and they asked me about where I was staying. I hesitated and told them that I felt very unsure of my situation. They quickly offered another place to stay with someone that they knew and trusted. It seemed like a lot of work at the time because I had to go back to gather all my items, pack up my bike, and explain to the host why I was leaving. I didn’t want to say out loud that it felt unsafe and uncomfortable to stay there. But it felt right to leave.

We drove straight back to the house, I packed my things quickly and left with the other host. The next morning, I realized that I had left my water bottle (important on a bike trip) in the first house. As I rode back over to get it, my insides begged me not to go back in. I could see people inside the house through the windows and it didn’t look like a situation I wanted to get back into. I turned around and left it. My safety was more important than any physical thing—than any comfort. When I sat and looked back on the experience later, I had the feeling that I had saved myself from a very scary situation.

Listen to your insides. They know what they’re talking about.

I’ll keep the last two tips short and two the point.


  1. Allow for change in your plans.

    One of the biggest plans I have ever made was to bike the TransAmerica Trail –straight through–no questions asked. I wanted to see every inch of it. I wanted accomplish something and learn along the way. Most importantly, I wanted to be able to say that I did it.The opportunity quickly arose to get off the trail and wander with other people to other places. At first I was resistant (yes, that good old ego) but then I decided that enjoying myself and having these fulfilling experiences would help me feel more whole. And that is exactly what they did.

Now I get to reminisce about a handful of times that I let myself create. Now I can say that I’ve been to a stranger’s wedding in Virginia, that I’ve cycled through the Redwoods of California and gone cliff jumping in Hawaii. These beautiful moments wouldn’t be in my memory if I didn’t choose to venture off the set trail.


Your fears, weaknesses, excitements, and strengths change as you travel. Your intuition may guide you away from the first copy of your plans. That’s okay. Do what feels right. Allow for changes in your plans. They may turn out three times as better than anything that you could have planned!


  1. Accept help.

This is something that I’ve had a good deal of trouble with but have thankfully learned to do.

One day while I was traveling, I found myself on the coast of California. (On the side of the road, to be exact) I didn’t know anyone; I was cold, money-less and tired. Nothing was going right. I couldn’t figure out how to fix my bike and I knew I wouldn’t make it to my destination before it got dark. When I finally got into town, I felt like I couldn’t support myself anymore. I wanted to go home. I realized that I had to do something… but I felt like I had no options. So, I lost it. I had a mental breakdown on the sidewalk.

That sidewalk happened to be in font of a house, and that house happened to have two wonderful owners. They came home just in time to offer me the support that I needed. They gave me a warm meal, a place to sleep and parental-love. It was the security that I needed. I ended up staying with them for over a week, and I still consider them my second-parents!

If I hadn’t have let them help me, who knows what I have done. My point is: sometimes you feel like you can’t do anything for yourself. This is false. You can let someone help you. That’s the biggest help that you can give yourself at times. The only way that you can have everything that you need is to accept that others may need to pass some of that good help to you along the way. Accept it with honesty and grace.

Good-will alone is something that you can cash in and travel the world with—but that’s another story.


Happy Exploring!




With love,



(A big thank-you to Helen Otto and Michael Amani for all of your wonderful ideas and edits that you’ve contributed to this post!)


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  • Laurel Smith
    April 28, 2017

    This is si exciting! I admire you so much!! I cannot express how much admiration, respect, and love I have for you. You are a true gem and I hope to see you again, soon, in your future travels. You’re an inspiration to me and many others, I’m sure.
    Your words were so wonderful to read. I will go back to them again and again for inspiration. They’re not only travel guidelines but LIFE guidelines! Seriously 🙂 You’re wise beyond your years and I feel fortunate that we crossed paths. Safe travels ❤

    • Calen
      May 1, 2017

      Ahh! What a compliment. Thank you, so much, for sharing that! <3

      I truly hope that you know how much you contributed to making my travels special and full. It honestly was such a blessing to get to connect with you, and I am so happy that social media allows us to continue to keep up with you. I also feel so much love that I get to continue to be able to connect with you! You know that if, no– when, I am in your area again I will for sure be looking to see you!!

      Thank you for using your time to read my words for all of the support. <3

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