Meet Jessica Stiles | Freelance Editorial Project Manager

We had the good fortune of connecting with Jessica Stiles and we’ve shared our conversation below.

Hi Jessica, have you ever found yourself in a spot where you had to decide whether to give up or keep going? How did you make the choice?
I think about this all of the time. My husband, Greg, and I have overcome a lot of obstacles together and it is very difficult for us to ‘give up.’ When things get challenging, sometimes I worry that challenges we perceive as a minor hurdle is actually a huge red flag to stop and reconsider. When this happens, it is important to refocus on our long-term goals and determine if overcoming the challenge is going to get us closer to the future we envision. But it’s not always a simple ‘yes’ or ‘no.’ There is also value in understanding the journey we are taking. Sometimes the most direct route, although a conduit to reaching our goals, excludes rich context and lessons learned. This is wisdom that is earned, not taught. Years of failing forward and being willing to try new things, despite the risk of it not working out, is what gives us confidence going into the next challenge.

We quit our corporate jobs in 2018, and since then have been traveling full-time. Initially, we weren’t working, but eventually we spent everything we saved for the adventure and decided we wanted to extend it by finding work that was compatible with road life. I am a freelance editorial manager and project manager, offering editorial organization, planning and editing services as well as traditional project management services. Greg is somewhat of a ‘Jack of all Trades’ and has fluctuated between working in a ski shop, doing construction, and working with outdoor and travel brands to build ambassador partnerships and affiliate programs. All the while, we both work on creating our Drifter Journey brand that has inspired many like-minded people to cut ties from the status quo and start persuing their dreams.

Self-employment is not for the faint of heart and we’ve considered giving up and go back to punching a time clock many times. However, the freedom to manage our own time and to be our own boss is such a rewarding feeling that we have yet to throw in the towel on our business ventures. For us, making the decision to keep going or give up always comes down to making the comparison between working for ourselves or working for someone else.

Alright, so for those in our community who might not be familiar with your business, can you tell us more?
Greg and I are a full-service team. With his background in Sales and Account Management and mine being Project Management, Editorial Managment and Strategic Planning, we handle a wide range of tasks for our partners. Content creation is a large aspect of our day-to-day work, including video production for product reviews and our own YouTube channel. Greg maintains excellent communication with our partners and we pride ourselves on exceeding expectations. In tandem, I create project schedules and manage teams to provide seamless execution of the project goals. This includes managing a timeline, budget, and contingency plans as well as monitoring KPIs to determine the project’s success. These projects cover a variety of fields and I can plan and facilitate anything from an editorial calendar to a product launch.

Our abilities were hard-earned and we are continually learning. Our corporate jobs gave us the business savvy necessary for such an endeavor, but we have gained wisdom working on our own as well. Tailoring our services to each client is a point of pride for us. We have enough experience with big and small companies, alike, that we can do so.

We never would have gotten to this point had we not taken the risk to quit stable jobs and go for it. There have been many scary moments along the way, where we felt like we weren’t sure about what to do next. But we continue to learn and grow from experience, from mentors, and from our own will to just figure it out.

Who else deserves some credit and recognition?
We started traveling full-time way before it became socially accepted and ‘cool.’ Our parents weren’t thrilled about us quitting our jobs, selling our home and effectively becoming vagabonds. Mentors at work expressed concern about us exiting the workforce at an age where we were coming into our ‘peak earning potential.’ We faced challenges like sourcing healthcare and income while traveling that most people working regular jobs don’t. One person who facilitated our final escape from our corporate jobs was our financial planner. Most people would assume a financial planner would discourage this life change. However, we reviewed our plan with ours and wanted to make sure we had our financial future secure before taking the plunge. Since graduating college, we paid off student loads, avoided additional debt, and managed to save our nest egg for retirement. We wanted our financial planner to validate our estimates for what our savings would accrue and if it would be enough to live off once we hit retirement age. After going through our spreadsheet and talking about 10, 20 and 30-year averages, he confirmed that we had estimated correctly. Assuming the market sustained the long-term returns we have seen over the past few decades, our retirement plan was solid. We got to talking about the plan to travel and how our parents were less than approving. I’ll never forget the next thing he said to us. He said, “You guys are smart and capable people. If you end up not liking the van thing, you can find another job and you’ll be fine.” It was something we both know about ourselves, but it was the exact thing we needed to hear from someone we looked up to. The smallest sliver of encouragement was all we needed to feel a thousand times more comfortable about the decision we were making.

Website: https://www.drifterjourney.com

Instagram: https://www.instagram.com/drifter.journey

Linkedin: https://www.linkedin.com/jessicastiles

Youtube: https://www.youtube.com/drifterjourney

Image Credits
Images provided by Jess Stiles, Drifter Journey Inc