How our small business took a sabbatical.

Author: Jen Jackson

When the prolific, English fantasy author Terry Pratchett died, he left behind a cache of unfinished works. But unlike many of his writing contemporaries, his half-baked thoughts and creations were not left to chance, interpretation, or greedy lawyers. Pratchett had slyly concocted a plan and entrusted it to his most loyal friend, Rob Wilkins. The fate of those 10 novels simmering on his hard drive? Destroy them with a steamroller. If only Harper Lee had been so prepared.

In a deadline-driven work environment, we’re often scrambling in the present moment which leaves little time for thinking ahead. But to make things like posthumous plans for a hard drive or a month-long sabbatical possible—preparation is essential. Here’s how we made our sabbaticals work.


As business owners who also happen to be sisters, a partnership like the one Kim and I have is a symbiotic relationship, which is only intensified by our shared DNA. Whether it’s decision-making, collaborating, or just lending a listening ear, we’ve come to depend on each other. But one thing we wanted our month off to be—a way to completely detach.

We spent a year planning for our sabbaticals starting with consideration of best timing for our schedules and the workload. With the summer of 2017 as our target date (Jen off in June, Kim in July), we worked backward with a checklist of what needed to happen over the next 12 months.

We started with people and processes. Rather than me shifting all of my responsibilities over to Kim, or vice versa, we empowered our team and network to keep our business flowing seamlessly. For creative direction and review, we instituted peer-reviews led by a few of our senior writers. For client and writer relations, we asked our amazing Director of Operations, Pati, to step up. For business and accounting, our finance manager, Debbie, made sure Kim and I were clued in about each other’s daily tasks so our system of checks and balances was retained. These conversations started six months out with the cross training happening three months prior to our sabbatical date. This gave us time to collaborate, troubleshoot, and iron out the kinks.

With a few months to go we notified clients, outlined our processes, and started testing some of the new assignments. Then it was review and refine time with two weeks to go. We reviewed and refined some more with one week to go. Just days before departure came the official hand off.

“To expect the unexpected shows a thoroughly modern intellect.”

—Oscar Wilde


For two partners who err on the side of optimistic, worst-case scenario projections don’t come naturally. But even with a well-laid plan, not everything will go according to it. From a few communications snafus to needing some critical passwords to simply forgetting some things, there were surprises we just didn’t anticipate.

And then came the big windfall—being awarded a new, high-profile project as Kim was walking out the door for Europe. Um…yay? Saying no to the new work was not an option, although we knew there would be some shifting and stepping up to make it happen. With the core team pretty maxed out, we turned to a super-pro writer, Leta, who happened to be new to the team, and she handled the pressure and assignment like a champ.

I’m proud to say that when the unexpected arose, we rose to the challenge. And as a result, a lot was learned about ourselves and our resolve. And the biggest takeaway: no matter what came our way, we could handle it.


Write On was born at an ah! moment during a vacation sabotaged by work—Kim and I realized working autonomously as freelancers wasn’t actually affording us the freedom we had dreamed of. As we’ve built the business, intentional choices about how to grow our writer network and the internal team are what really made our sabbaticals possible. With professional, senior writers and a highly experienced management team, we knew the business was in great hands during our respective absences. So, when it was time to walk away, there were no laptops in tow, no calendar dates to be kept. It was a clean break because of the unwavering belief in our team.

Reflecting on my month of travel, date nights with my husband, perfecting my puzzle skills, and grocery shopping with a list, I underestimated the impact of a cleared mind. I came back eager, invigorated and inspired. I came back with reaffirmed belief in living in the moment over going through the motions of life. And, contrary to Kim’s anxiety dream that my month off turned into forever, I came back.