6 Pieces of Life Advice from a Freelance Writer Who Ditched the Office for Van Life

Celena Carr-Thomas is a freelance writer and designer who’s spent the last two and a half years traveling the country on an endless road trip with her husband/business partner. In that time she’s visited 30 states, 10 national parks, hiked hundreds of trails, and launched a freelance business. This is the story of how she got here, and her advice for anyone interested in van life, being a digital nomad, or just starting a freelance career.

Why I walked away from my corporate career to travel and freelance

Back in 2015, my life was a lot different than it is today.

On paper it was great. I owned a home in a nice neighborhood. I had a great partner I was about to marry and a solid group of friends. I’d worked my way up the corporate ladder at a job with a good salary, stability, and benefits.

But I was burnt out and miserable most of the time, and then ashamed the rest of the time for not appreciating all this privilege and good fortune.

At work, I liked what I did and I adored my team, but the conservative company culture was a struggle for me. Remote work was unheard of, and there was a huge emphasis on meetings and getting buy in from 10-50+ people on every decision. As someone who appreciates decisiveness and autonomy, it just wasn’t a good fit. 

After spending most of my 10 years at the company trying to change the culture, it finally dawned on me that maybe I was the one who needed to change jobs and find something that suited me better. (It sounds so obvious now, but it was hard to recognize when I was in the middle of it!)

At the same time, my hometown of Portland, Oregon was changing a lot. It turns out that being the darling of the New York Times dining section for 5+ years and having a comedy show built around your hip and quirky vibe leads to a lot of growth — and traffic. By the time we got married in 2015, my husband and I were spending more time trying to escape the city than enjoying it.

So it wasn’t a huge surprise when three days into our honeymoon I announced that I didn’t want to go back to my job, and we also decided we wanted an exit plan from Portland. It took another 9 months for me to hand in my notice and start my freelance career, and a little over a year for us to sell our house and part ways with all of our stuff so we could do the van life thing.

Setting Up a Freelance Business on the Road — Pros, Cons, and Things I Wish I’d Known

My husband had been a freelance designer off and on between full-time design jobs for more than 10 years, so I had the benefit of starting out with someone who knew the ropes. But I still had to learn a lot of those freelance and small business lessons on my own, and land new clients, while also learning how to make full-time travel work.

After two and a half years of life as digital nomads I don’t have it all figured out, but I’ve learned a ton and these are the best tips I have for anyone considering starting out as a freelancer or a digital nomad.

1. If you want to travel and work, slow travel is best.

Our first year out, we covered the country coast to coast, moving at least once a week (usually more), while juggling pitching new clients, getting our work done, and learning how to run a business and live together 24/7 in less than 150 square feet.

We saw some seriously beautiful, bucket-list worthy spots and managed not to go broke that first year, but we also missed out on a lot of places because we didn’t leave enough time for both work and exploring. Sometimes it also felt like the only things we did were driving, working, and chores.

Our current routine is much slower and we find 2 weeks to a month (or more) works much better. It lets us take care of business but leaves enough room to get a feel for a place and have fun, too.

2. It’s okay to take a pay cut to freelance — but be sure you can embrace budgeting

A lot of people like to claim that freelancers make more than salaried employees. But it’s important to understand that they’re talking about hourly rates. Most freelancers don’t get in 40 billable hours a week for 52 weeks a year, so comparing hourly rates of freelancers vs. employees is like comparing apples and grapefruits.

I’d love to tell you that I’m matching my old corporate, managerial salary dollar for dollar, but that wouldn’t be true or realistic. Finding clients and building a business takes time, and especially if you’ve been in your career for awhile, you probably won’t make as much freelancing as you did in your 9-5 job when you’re starting out. Plus you can wave bye-bye to benefits like company-paid health insurance, and 401K matching.

But, as long as you have a plan, some savings, and are willing to embrace a new budget, that’s okay. If it’s something you really want to pursue and your worst case scenario is going back to a full-time job (i.e. your current scenario), then you have absolutely nothing to lose. 

3. Working for yourself is both way harder, and way more rewarding

Being my own boss is pretty much the best thing ever… most of the time. I get to decide when and where to work, which projects to take on, and I’ve found that freelancing really suits my personality. But running my own business means I’m not only the boss and the employee, I’m also the accountant, the collections person, the account manager, the semi-competent IT person, the janitor, and everything else. Some people get to a point where they outsource these tasks, but in the beginning you’re probably not going to want to spend money on them, so make sure you’re okay taking on all of those roles.

4. Most decisions (except maybe face tattoos) are temporary

We’re not spontaneous and adventurous people by nature in spite of the carefree image our lifestyle projects. I’m the kind of person who starts my taxes in January and my husband researches toothbrushes the way most people would a new car. But we have a great friend and fellow traveler who always reminds us that deciding we want to do something now doesn’t mean we’re deciding to do it forever.

While we currently have no plans to return to full-time office (or remote) jobs, that doesn’t mean we never will. We have no idea what the future holds, and I’m no longer scared about that. A lot of my initial fears about freelancing involved statements that started with “What if…” What if I fail? What if we don’t make any money? What if I can’t do this? What if I don’t like it?

Spending a ton of time anticipating negative outcomes is a really bad use of your time. Take that energy and use it to make a concrete plan to help you succeed instead. How will you find your first client? What’s a personal project you can work on to show off your skills if you have a lull in work? 

5. Starting a freelance business is more about relationships than being “the best”

It’s true that it’s very helpful to have a well defined skillset and some relevant experience to start a freelance business, but there are millions of freelancers out there, so it’s pretty impossible to be the best in any given field.

You shouldn’t let that stop you from trying out freelancing if it’s something you feel passionate about pursuing. Building a client list and getting repeat work isn’t easy, but it usually comes down to delivering your best effort, meeting deadlines, and being nice to people.

As someone who used to hire freelancers I can tell you that I’d rather work with someone with a slightly less talented or experienced any day if they were easier to work with than the superstar. That doesn’t mean you can be lazy when it comes to your craft, but it does mean you can stop driving yourself nuts by comparing yourself to every amazing writer on LinkedIn, or designer and photographer on Instagram.  

6. Don’t believe the internet, especially Instagram

I know that when I use the phrases “van life” or “digital nomads” and people imagine our lives, they picture us in some perfect climate doing a couple hours of work, then knocking off to hang on the beach with our 20-something digital nomad pals who somehow make six-figure salaries and have perfect abs, and then we all go do yoga around the campfire.

Our lives are nothing like that. We’re not in our 20’s. Our only 6-packs are in the fridge. We work. A lot. I have a second unpaid job as a travel planner. Things break. All the time. Cell phone coverage maps lie. Especially when we’re on deadline. We’re often the only people under 65 and not retired in a given location because most people who do this are retired. There have been weeks when we haven’t been able to shower. And no matter what the internet tells you, a baby wipe is not the same as a shower.

I could go on, but my point is that along with all the beautiful scenery, sunsets, and freedom, van life and digital nomad life are still real life. If you go into it expecting it to be like the (often staged) glimpses you see on Instagram, you’re going to be super disappointed. 

On the other hand, if you’re ready for a messy, unpredictable, and occasionally/frequently frustrating adventure, then you’re ready to start your freelance career, take on van life, and become a digital nomad. The reality won’t look like anything like an Instagram post, but it’ll still probably be the best thing you’ve ever done. And if it’s not, you’ll do something else!

Looking for more nomadic inspiration? Check out our post on 10 Inspiring Digital Nomads You Can Actually Aspire to Be.