We caught up with the brilliant and insightful Jillian & Jeremy Hinskton a few weeks ago and have shared our conversation below.
Jillian & Jeremy, thanks for taking the time to share your stories with us today One of the toughest things about progressing in a creative career or as an entrepreneur is that there are almost always unexpected problems that come up – problems that you often can’t read about in advance, can’t prepare for, etc. Have you had such and experience and if so, can you tell us the story of one of those unexpected problems you’ve encountered?
There are three unexpected problems which occurred within our first year of business which have paved the path we are on today. We realize this is a lot to unpack, so feel free to only pick one that best fits your audience. ;-)
1. Becoming travel YouTubers three weeks before the world shut down (COVID) with no advance notice and no backup plan.
–1a. Context: following the completion of a high-profile position in the Pentagon that took most of Jillian’s life for 2.5 years, Jillian & Jeremy (J&J) decided to try their hands at being digital nomad, and pursue their passion for traveling around the world and documenting their adventures on YouTube. As a business girl and one who managed the couple’s finances, this drastic lifestyle change (not having a predictable, reliable income & company-sponsored benefits) completely terrified Jillian; however, after seeing their favorite YouTubers publish income & expense reports, and learning there was a BIG opportunity to monetize their passion, J&J took the plunge in Feb 2020, sold most of their belongings, canceled their lease, and had a plan to begin travel in in March 2020. The plan was to store what little we didn’t sell at a family beach home in Delaware and use this as “home base” in between traveling the world.
– -1b, Circumstance: certain dates you never forget. Your birthday, for example. Feb 28, 2020 is one of those days for us. Jillian’s last day at the Pentagon. March 6, 2020 was the last paycheck and when benefits ended. Then, the world effectively shut down due to COVID. There was no advance notice. No backup plan. We had movers scheduled, sold most everything we owned, and had a house sit lined up in Costa Rica starting in March, which was intended to be our first destination as travel YouTubers.
– -1c. Impact: Ultimately, the impact was a four month delay to our travel start date and thousands of unplanned dollars in rent / living expenses, Our house sit in Costa Rica was canceled and Costa Rica closed its borders. Fortunately, our landlord allowed us to extend our lease two months during the worldwide quarantine (despite not planning to spend this amount of money to be stationary). In June, we moved our belongings into our Delaware family home and continuously monitored evolving travel restrictions around the world.
– -1d. Resolution: in July 2020, we traveled to Progreso Mexico for 2.5 months. Mexico was one of the more lenient countries for COVID restrictions; however, the town we lived in (Progreso, Mexico) was mostly shut down, which made navigating an unfamiliar location even more challenging. From there, we continued on to Brazil for three months, where we faced our next challenge (see #2 below)…
2. Inability to obtain medication abroad for Jeremy’s medical issue, Hidradenitis Suppurativa, which rendered him immobile while overseas and subsequently nine months following.
–2a. Context: Jeremy has a painful auto-inflammatory disease called Hidradenitis Suppurativa (HS), which impacts up to 4% of the global population. Thus far, Jeremy managed his HS with medication, which we thought we could get overseas based on some quick internet research.
–2b, Circumstance: Turns out, this expensive medication was impossible to get in both Mexico and Brazil, and Jeremy’s health declined to the point of being immobile. Traveling home from Brazil was a feat and required he be in a wheelchair and receive lots of help from airport staff.
–2c. Impact: Once we returned to the US, Jeremy’s body rejected (built up antibodies to) his medication having been without it so long, and he was bedridden for nine months, as we worked with a team of doctor’s to find the next concoction of medications that worked. This was a very dark time, as Jeremy couldn’t do any of the things that gave him joy in life. He couldn’t even cut his food, and relied on Jillian as his caretaker. Our YouTube travel adventures were paused until he recovered.
–2d. Resolution: After nine months in bed, and a couple more months of physical therapy and LOTS of new medications, Jeremy and Jillian resumed their travel adventures in August 2021, starting with a US road trip, primarily to have the flexibility to return home quickly if Jeremy’s health declined. The medication, a low-dose type of chemo infusion, is required every eight weeks. Which means we plan our global travels around his medication / infusion schedule. Although not ideal, we are finding a way to persevere, and aspire to continue our digital nomad adventures.
3. Complete lack of understanding and knowledge on what it takes to be a full-time content creator.
–3a. Context: In a “9-5 job” you have one role and do that role daily. Everyone knows who-does-what, and you operate like a well-oiled machine. As entrepreneurs, you have 10+ roles. From researching, writing, filming, editing, sound design, SEO, algorithms, web design, accounting, travel planning…the list goes on. In general, we believe there is a significant lack of understanding on what it takes to run a small business. Coupled with the fact that Jeremy and I run three separate businesses, travel (YouTube), photography (Jeremy) and management consulting (Jillian), it’s easy to feel like you are on a hamster wheel of pumping out content without keeping your bigger picture goals in mind.
–3b, Circumstance: having never been full-time content creators, and only consumers of YouTube videos, we had absolutely no idea the amount of work required. Also, we are early 40s, not 20s and have already spent a LOT of years working 12+ hour days, and didn’t expect this new world to take up so much time and energy. The notion of being your own boss is romantic, until you quickly realize your business(es) only does as good as the amount of work you put in.
–3c. Impact: We jumped in head first to new careers without any formal training. There are a gazillion courses and other online resources, but frankly, there is SO much information, it’s overwhelming. The impact comes in the form of burnout and never feeling like you are doing enough to “move the needle” to achieve business and financial goals.
Also, focusing on the wrong things (like spending too much time researching what other people are doing) doesn’t help your bottom line.
–3d. Resolution: From time management, to developing systems that help make your workflow smooth, we are finally “getting it”, after a year (we don’t include the “false start” in 2020-2021 due to Jeremy’s health), The silver lining is that we can use our experiences to help other people. This is a new vertical we didn’t plan for (in terms of creating content), but feel so strongly about helping demystify the transition to a content creator.
Jillian & Jeremy, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?
Jeremy and Jillian run three businesses:
1) Travel YouTube Channel
–1a. how you got into…: one of our favorite travel YouTube couples shares income & expense reports on their blog. This really “clicked” with Jillian (the one who manages our finances) to realize there is a big opportunity to make a living doing what you love. Since Jillian was concluding a time-based position in the government, coupled with Jeremy’s existing photography / videography / drone skills, we decided to dip our toes in the digital nomad world. We agreed from the start that if the digital nomad / content creator life didn’t work out, we would never regret the life and travel experiences we gained along the way.
–1b: what type of products/services/creative works you provide: YouTube videos and blog posts showcasing different parts of the world, including food, culture, activities and helpful tips.
–1c: what problems you solve for your clients and/or what you think sets you apart from others: providing context (geographical, historical) and visual inspiration on each location we visit, along with information we wish we knew in advance, so others can benefit for their own travels. Coupled with our personalities (the differentiator), we like to keep it real and not put on a show. That’s taken some time to develop as we learn to be more comfortable on-camera.
–1d: What are you most proud of: the volunteer work we’ve done in each country we visit. Also, producing over 100 YouTube. videos despite a major medical setback.
–1e: What are the main things you want potential clients/followers/fans to know about you/your brand/your work/ etc.: We want our videos to be “all meat, no bun”. Meaning, we want to give people loads of information they can either use or be inspired with, not just a video diary of our personal adventures with no context.
2) Photography / Videography / Aerial Drone / Audio Engineering
–2a. how you got into your industry / business / discipline / craft etc,: Jeremy first began photographing landscapes with his iphone. As he developed an eye for creative compositions, he also began photographing band promo shots and live concerts. Jeremy’s large circle of friends and colleagues in the industry noticed his photography work and quickly fell in love with his style and creative eye, which fueled his desire to hone the craft and turn his skills into a profession, along with periodic audio engineering shows (such as iHeart Radio Festivals and the Grammys) when the schedule allows. Over the past ten years, landscape and nature photography, videography and aerial drone footage has became Jeremy’s favorite, and his background has fit wonderfully into the couple’s YouTube travel channel.
–2b: what type of products/services/creative works you provide: digital and physical photography prints, personal and commercial drone footage (FAA certified), stock footage, videography (including real-estate, where he was once the lead videographer at a real estate TV network), NFTs, and “A2” audio engineering skills for broadcast television and live sound.
–2c: what you think sets you apart from others: being color-blind, Jeremy’s unique eye for vivid colors and beauty, coupled with cutting-edge technology, gives each of his mediums unique perspective.
–2d: What are you most proud of: Having images on 2 separate occasions be published and shared by National Geographic, and being an assistant audio engineer, recording many artists, like Metallica, Roger Waters, Lady Gaga, The Eagles, Stevie Wonder, and many more.
–2e: What are the main things you want potential clients/followers/fans to know about you/your brand/your work/ etc. That I am very passionate about my work and my craft. I’m reliable, communicative, and have an extremely high attention to detail, as well as high standards. I love what I do and I put my all into my work.
3) Management Consulting
–3a. how you got into your industry / business / discipline / craft etc, : Jillian spent 15 years as a Chief of Staff within different sectors of The Boeing Company, followed by a high-level position as Director of Operations within the Pentagon, working directly for the Secretary. of Defense. These experiences armed with the knowledge to share with others as a freelance management consultant.
–3b: what type of products/services/creative works you provide: virtual and in-person management consulting for individuals, corporations and other management consulting firms on running large-scale administrations, strategy execution techniques, and chief of staff best practices.
–3c: what problems you solve for your clients and/or what you think sets you apart from others: my experience and successful career working for world class corporate, government and management consulting firms is definitely my competitive advantage.
–3d: What are you most proud of: the resilience I’ve gained from my work. history. I’m indestructible. ;-) Second would be the amazing network of professionals and friends I’ve accumulated over the last ~20 years.
–3e: What are the main things you want potential clients/followers/fans to know about you/your brand/your work/ etc.: 1) I’m extremely approachable and professional, yet fun! 2) There is no need to re-invent the wheel – go with someone who has succeeded already,
Let’s talk about resilience next – do you have a story you can share with us?
Lots from the past two questions you can use here.
What’s the most rewarding aspect of being a creative in your experience?
Jillian – Having complete control- from artistic vision, to time management, to business decisions. This is a double-edged sword, as YOU are responsible for the ultimate success (or failure) of your business.
Jeremy – For me, it’s seeing the outcome of whatever it is I’m doing, and sharing it with the world. Whether it’s composing a photo, and then editing it into some surreal scene, or setting up microphones and recording Paul McCartney or U2, just seeing the crowd’s face at these shows, or seeing people enjoy, and most importantly, be inspired by my photography, is what’s most rewarding.
Contact Info:
- Website: https://www.jillianandjeremy.com/
- Instagram: https://www.instagram.com/jillianandjeremy/
- Facebook: https://www.facebook.com/jillianandjeremy
- Linkedin: https://www.linkedin.com/in/jillianandjeremy/
- Twitter: https://twitter.com/jillian_jeremy
- Youtube: https://www.youtube.com/channel/UC2043u82GIwZ6dn0tVmdx2Q
- Other: The above is our travel YouTube info. Here are other businesses if needed: Jeremy’s Photography: https://www.sikimagery.com/ (handles on social media: IG: @sik_imagery, FB: @SiK Imagery, Twitter: @SiKImagery) Jillian’s LinkedIn: https://www.linkedin.com/in/justjillian/
Image Credits
We own all rights to every image provided.