A Solo Road Trip: Why I Spent 4 Months Driving Around the US Alone

Going on a solo road trip is on my Mighty Life List. I’ve never driven cross country before – not alone, with friends nor on a family trip. Even though I lived in California for five years.

To be honest, I really don’t like to drive. Yes, I’m fully aware that this probably (definitely) has everything to do with why I haven’t gone on a solo road trip yet. Being behind the wheel just stresses me out. Especially when I’m in unfamiliar cities and towns.

This is the exact reason why I want to go on a cross-country road trip by myself, though. I want to face the fear and prove to myself that I can do more than I (allow myself to) believe I can.

So, earlier this year, I had planned to drive from Massachusetts to Florida for the winter. My car, on the other hand, had plans to fall apart (and need one repair after the next) just one week before my planned departure. I took this as a sign that it just wasn’t my year to become a snowbird and I shelved the plan for a later date.

Update: I finally went on that road trip to Florida!

Then I noticed when an old colleague and friend of mine was on a road trip of her own. I lived vicariously through her Instagram photos and updates, taking note of her winding path across the US and any tips she shared. I remember thinking, “Wow. What an amazing time she must be having.”

Months later, I reached out to her, curious if she’d be willing to share the story of her solo road trip here on She Goes With Purpose. To my great appreciation, she said yes!

I’m excited to get started, so I’ll let Jen introduce you to her epic 4-month long solo road trip.

Why I Spent Four Months Driving Around the Country

Hi! My name is Jen and I recently completed a four-month solo road trip across, around, and all over the US. I hit 46 out of the lower 48 states. I dipped my toes in the Atlantic, Pacific, Great Lakes, and the Rio Grande; stood on mountain peaks and smelled the sagebrush in the desert. Along the way I laughed, I cried, I swore, and I felt like I was really living.

In some ways, this trip was just a whim, more of a “why not?” than anything else, but in other ways, it’s the exact opposite.

The idea of a road trip had been lurking in the back of my mind for a long time, and finally, it felt like I might as well do it now while I can. There were also many reasons why I felt like this trip was the exact right thing for me to do at this particular moment in my life. I found myself in kind of a perfect storm of conditions lining up to create this adventure.

First, the timing was right

Logistically speaking, the timing was perfect for me to explore.

I lived with my mom in order to save money and figure out what to do next. So, I didn’t have to worry about rent or where to store all my stuff.

Also, I was unattached and figured it made sense to do something a little crazy like this before I get all “settled down.” Not that being married and/or having children means you can’t go on epic adventures!

Lastly, I had a job I didn’t care about and could easily leave. Partly, I believe, because I knew something major was brewing in my life.

It might be my “Last Hurrah”

Recently, I reached a point where I wanted more stability in my life. Since graduating from college, I have had some really wonderful jobs. I have no regrets and I’m insanely grateful for all the opportunities I had. None of my jobs lasted longer than a year, though. This is by design, which allowed me to get a feel for many different fields.

Lately, though, I’ve found myself ready to settle into something more long-term. I’m not necessarily ready for a lifetime career, but I would like something I can really dive into and evolve with. I want to spend a few years really getting to know… something.

Before I get all settled into a stable job (maybe with some benefits? I hear they’re pretty great), I wanted to do something I wouldn’t be able to do once I entered a more structured life. Like, you know, a four-month solo road trip.

Inspiration

This brings me to another crucial reason for my trip. I’ve hoped to establish a more stable career. I’ve just had no idea what kind of career I wanted to pursue.

My problem isn’t so much that there’s nothing I want to do with my life, it’s that I want to do everything. I’ve had so many moments where I pictured myself in one career and thought “yep, I could do that.” Then I’d come up with some other idea and the exact same thing would happen.

As I started to settle into the idea of a solo road trip, I knew that having so much unstructured time would allow me to really get to know myself, to explore my likes and dislikes. I wanted to find out what really inspires me, and what I’m truly passionate about. Ideally, I hoped to figure out what it might be that I could spend the majority of my time working on.

I was hoping that by experiencing so many new situations, something would finally stick.

Spoiler alert: I was struck by all kinds of inspiration on this trip, and actually have made some major career decisions because of it.

Exploration

Alright, let’s take a little break from all the deep, introspective reasons and go really concrete for a minute.

I’m lucky enough to have a decent amount of travel experience under my belt. I went to some great schools that sent me everywhere from the American Southwest to a semester in Vienna. I am immensely grateful for these opportunities, and it has slowly but surely seeped into my personal life as well.

When I finally started traveling alone or with friends, instead of just on school field trips, I became unstoppable. I love to travel. It’s not constant: I don’t think I’ll ever be suited for a fully nomadic lifestyle. I am usually thinking about where else I want to go and when I can make it happen, though.

When thinking about all the amazing places that exist in the world, I felt like I hadn’t seen very much close to home. Most of my travel so far had been in Europe, which was wonderful, but I was curious about the country I happened to be born in.

I’ve lived in New England my whole life and firmly consider myself to be a New Englander. I have no desire to relocate and this trip only confirmed that. I still felt like I couldn’t really be sure until I had actually seen some other options.

This is a huge country, with so much diversity inside its borders: geographically, culturally, and culinarily. I wanted to experience it all for myself. So, a cross-country solo road trip seemed to be the answer.

Connection

At this point, I have friends scattered all over the country. (all over the world, actually, but there’s still a concentration of them here.) I decided it was about time to see some of them again, and this trip would be a perfect opportunity.

So before I started, I spread the word about my trip and asked people to get in touch if they wanted a visit. I was actually amazed by the response I got, and a big part of my trip ended up being visits to people from all different phases of my life.

This was super fun because along with getting to see some really cool people, I also got to have them show me the really cool places they live. There’s nothing like having a local guide to get a true feel for a new place.

I was also able to strengthen friendships that had been slightly neglected and to see people in a whole new context, which was a lot of fun.

Freedom | Having my own wheels and agenda.

One reason why I was waiting tables while still living at home is that I had needed some time to recharge. The last job I had right before moving home was truly amazing. I learned so much from it but in a lot of ways it was hard for me. The job required me to give a lot of myself and, although I gained a lot from it, I found myself in need of a little selfishness before jumping into something else.

While treading water for a little while, my metaphorical batteries recharged. After a few months of that life, something changed and I needed to get out. I needed to be free and most importantly I needed to do something that was all about me. Spending some time cruising around alone seemed like the perfect answer. The whole time I was on the road I’d be able to do whatever I wanted, whenever I wanted.

The freedom of living in my car, as opposed to pretty much any other form of travel, was exactly what I needed. I wanted to be able to do whatever I felt like doing, and not have to worry about buying tickets, schedules, or waiting around for my transportation. I certainly didn’t feel like worrying about what a travel companion might want to do.

This seems like a good time to add that it never even occurred to me that this would be anything other than a solo trip. I needed to do this, and I needed to do it alone. I haven’t regretted it for a moment.

Sometimes I did wonder what I got myself into. In the end, everything about the trip was exactly what I needed.

These are the major reasons I ended up on this adventure.

Honestly, though, there are several more. I never had one single overarching goal. There were so many things that I hoped to accomplish or gain, and I kept coming up with new ones along the way.

I’m still trying to process the trip, which I don’t think I’ll ever be done doing.

That’s part of the beauty of it, though.