Hipcamp Journal

How I Escaped the Cubicle...

...to become a travelling Freelance Artist


Cover Image: Sketching on top of Rattlesnake Ledge in a Kelty lawn chair in North Bend, Washington.

It all started with a dream. A vision of what my life would look like if I spent each day doing things I loved and living with passion. I wanted to be outside, to explore new places and use my creativity to make things that deeply mattered to me.

Straight out of college, I started working in the college industry as a Graphic Designer who designed merchandise for hundreds of universities across the country. After three months of working there, I was promoted and began overseeing large projects as well as travelled to the industry trade show. I was 22, excelling at work and doing everything that I thought I was “supposed to do,” but somehow still finding myself unsatisfied at the end of each day. I was grateful for the opportunity to work in that position, but I slowly saw my passion for life dwindle away as I spent week after week stuck in an office cubicle with my fingers glued to a computer keyboard.

I had been freelancing as an Artist and Designer on the side for many years, which allowed me to get my hands on a vast range of creative work. I said “yes” to anything that came my way and took on projects that ranged from huge 20 ft mural paintings on walls, feature and cover illustrations for magazines, custom artwork for album covers, commissioned oil paintings for proposals and home decor, and several logo designs and brand identity systems for start up companies. I always loved freelancing because it gave me a change of pace from my routine schedule in the office. I would often head to work from 9 am to 5 pm at my desk job and then drive home and work on an oil painting for my freelance business from 7 pm to 11 pm, sometimes later, and then wake up the next day to do it all over again. I became exhausted after juggling both jobs for 10 months and was anxious to get out of the office and explore the world. I was hungry for inspiration and wanted to bring back my passion for life. So after much research and planning, I took the plunge..and called it quits with the cubicle to pursue my dreams and travel the world.


grand canyon digital illustration.jpg

My digital drawing of a sunrise in the Grand Canyon created in Adobe Illustrator.


That was about five months ago. Since that time, I’ve travelled to British Columbia, Alberta, Washington, Montana, Colorado, Utah, Texas, Minnesota and Idaho. I’ve had the chance to work remotely and spend time exploring mountains, trails, lakes, wildlife, forests and so much more. While on the road, I illustrated and designed an adult coloring book and a series of women’s tank tops for Parks Project (a merchandiser for the National Parks Services). Most recently, I spent two weeks traveling with the adventure filmmakers The Outbound Life and helped shoot an adventure film for the Resorts of the Canadian Rockies. During this time, I’ve also become sponsored as an artist by one of the largest art suppliers in the country. I’m currently in the process of starting up a series of watercolor painting workshops where I will teach others how to paint in nature.


driving through Yoho National park.jpg

Taking a break from driving to soak up the beauty of Banff National Park in Alberta, CA.


But aside from just creating art and travelling, I also want to inspire other people to find what they’re truly passionate about and pursue their dreams. I’ve been on this journey of creating a life I used to dream about and I want so badly for others to do the same. We’re in such a unique time right now where the internet and social media make it more manageable than ever to create a career that is flexible and allows you to work from wherever (i.e. #vanlife). Whether you want to be an entrepreneur, a digital nomad, an adventure photographer or a freelance writer there are several ways to get into this “work from anywhere” lifestyle.

Before you call it quits with your cubicle, there are several things you should do to prepare for this next phase of life. It takes a lot of self-motivation, grit and putting yourself out there to be successful, but I believe it’s absolutely worth it. I’ve outlined three practical steps to help you before going off on your own in your career.


Screen Shot 2016-08-16 at 10.22.36 PM.png

The original drawing of the Red Fox that’s part of my tribal animal series for the coloring book “Awesome Animals of the National Parks.”


1. Grow Your Network

Before you go off on your own, it’s important to have a network of people that you can reach out to and ask for advice. Be intentional about meeting people that have years of experience doing the things that you want to do. Cast a wide net to gain as much wisdom and perspective as possible. This is your time to act like a sponge and soak up as much information as possible from those around you!

Bonus tip: I can’t stress enough how important it is to build relationships in person whenever you can. Emails are good, and phone calls are better but having a conversation with someone face to face is invaluable. I’ve invested a lot of time and money into attending industry related events in my city and around the country to meet with people face to face. Creating your network takes a lot of effort, time, boldness and intentionality but it’s always worth it.

13217311_1719821601630973_5340392829866724187_o.jpg

This photo was taken after I had just finished spending hours painting Mt. Hood at Trillium Lake, Oregon for a DJI video last fall.


2. Stay Organized & Plan Ahead

The second step on my list is focused on organization skills. In order to stay organized, I have a couple of calendars, several phones apps, a set of alerts and reminders, and a running planner where I write down goals for the week. All of these things help me stay on task. I also have a little Field Notes journal that I use to write down everything I do each day at work. This might sound tedious, but it helps me gauge my productivity as well as motivate me to stay on top of projects and upcoming deadlines. Getting a good organization system set up before you start your business will help you stay professional and self-motivated.

In addition to staying organized, I also am intentional about planning ahead and keeping my business in motion. To do this, I have running lists of ideas about people to reach out to, events to attend, things to draw, etc. It’s great because if I have an idea that pops up in my head but don’t have time for it at the moment, I can add it to my list and come back to it later. This helps me when I have a bit of creative block and need something to propel me forward so that I never have a shortage of ideas or work.


Screen Shot 2016-08-08 at 2.16.49 PM.png

A digital drawing of an Oru Kayak in a dreamy, fall landscape. I created this in Adobe Illustrator.


3. Develop an Online Presence

This last step is very important since we live in a time where technology is so abundant and most social media platforms are free. Each online platform serves a different purpose and it’s important to be intentional about what you want to convey for each one. I have a professional website that shows a selection of my work as well as some past clients and contact information. I also have an Instagram portfolio that shows the latest works I’ve been up to, including in-progress sketches. My Instagram is a lot more interactive and shows more personality in comparison to my website. I also have a Facebook page where I will occasionally post a series of photos or exciting news to engage with my Facebook community. Lastly, I use LinkedIn to connect with business professionals and occasionally post about about big news or projects I’ve completed.

My advice with having an online presence is to pick one social platform to really kill it at, and then have a few others as well that serve specific purposes. We have to be online curators of our work and carefully craft our message to the world online.


emerald lake.png

A watercolor illustration of one of my favorite spots in Rocky Mountain National Park, CO.


Cannon-Beach-Oil-Painting-resize.jpg

Racing against the sunset to finish this oil painting of Haystack Rock at Cannon Beach, OR for a DJI Video.


Trillium Lake.pngScoping out Mt. Hood before flying the Inspire 1 drone and capturing an aerial photo of the mountain to paint from on site for the DJI video “Drone Art.”


How I Escaped My Cubical and Became Traveling Artist

Lisa is a freelance artist and designed based out of Chicago. When she's not working on her art or traveling to the mountains, she can typically be found eating sushi with friends, training for a half-marathon or longboarding with her dog, Wrigley. Follower her work on Instagram or website.


Hipcamp black tent
previous entry
How to Celebrate Labor Day with Hipcamp
next entry
Happy Glamping at New Mendocino Campground