Lessons Learned Experimenting With a Structured Sabbatical

A guest post by Jacqueline Jensen, author of Travel Isn’t the Answer: Live With a Sense of Curiosity, Passion, and Awe Anywhere and Everywhere. Jacqueline is currently on a structured sabbatical in Europe.

Americans are infamously terrible at using the paid time off they get from their jobs. Over the past fifteen years, American workers have been taking less and less vacation. Project: Time Off, an initiative to promote taking time off, found the American worker’s vacation usage had fallen to 16 — nearly a full week less than the average between 1978 and 2000.

Project: Time Off calls this time America’s Lost Week.

Our focus on demanding work and career chasing doesn’t leave much room for time off to focus on other things, much less a balanced everyday lifestyle where values like curiosity, passion, and awe are at the top of the list.

What if the best way to advance your career is to take some structured time off? Welcome to the rise of the early-career gap year. The idea of taking a sabbatical to pursue personal and professional priorities on your own time is gaining steam.

Here’s what the modern-day sabbatical looks like: Talented professionals are choosing to take a structured sabbatical in between gigs and leveraging their job security to work on passion projects full-time.

I first heard about this idea when I visited Recess Labs, an experimental entrepreneur-in-residence program in New York City for talented people working full-time on unconventional projects. Unlike a startup incubator or studio, the program doesn’t take equity from participants. Recess Fellows are provided a structured work day, demo days, collaboration sessions, and a strong culture that supports the curiosity and experimentation of its members to build their passion project, even if it isn’t a venture-backed startup.

“One of the most unique features of Recess, relative to similar entities in the startup ecosystem, is that it’s open to a wide variety of side projects,” said Sib Mahapatra, founding fellow at Recess Labs. “Some of our fellows are working on ideas in retail, cryptocurrency and logistics with the potential to be major businesses – but we also have fellows who are writing novels about tech. The point of the program is to encourage people to work on things they personally want.”

Inspired after visiting Recess Labs, I made the decision to embark on my own structured sabbatical while living in Europe. My structured sabbatical centered around three focus projects:

1. Writing my first book and launching a pre-order campaign.
2. Taking my interest in learning to code to the next level with a 5-month online Intro to Programming course.
3. Creating more space in my daily life for growth in my mental and physical health.

Initially, the idea of taking a structured sabbatical uncovered some doubts and fears:

What if I failed in my focus areas? When I returned to full-time work, would employers be ok with my time off? Would those around me think I was being lazy? Would I be able to stay on track with my goals during my structured sabbatical?

At the same time, I felt growing excitement and momentum build around trying out this idea. Leaving behind my day job to invest in myself stirred up feelings of power, innovation, and joy. How will I know if these passion projects gathering dust might be something incredible if I don’t dedicate time to try them out?

“It’s important to understand that doing your own thing doesn’t mean you’re aimlessly jumping into the ether, though ’taking a breather’ can be part of your motivation,” explained Sib. “If you have a plan, discipline, and runway to execute on it, you can custom design time to meet your goals and collect the information you need to make better long-term career decisions – and that’s a really powerful thing.”

I use three tools to keep on track and celebrate wins along the way:

1. Accountability check-ins. I have a handful of communities online that I utilize for meaningful goal-setting each week. One is a public Slack community where I post goals alongside other community members. I also have designated “accountability buddies” for more private 1-on-1 check-ins. The more accountable I am, the more progress I see in my goals and the more support I feel from those around me.
2. In-person meetings. As a digital nomad, I often find myself in a brand new city. I kicked off my structured sabbatical in Berlin, which ended up being the perfect place to connect with like-minded and creative individuals. Putting in-person meetings in my calendar each week has helped to keep me talking through my sabbatical even on days I have doubts about what I am doing. These meetings are also a key way to accelerate serendipity. I write more about that here.
3. Journaling. I started to embrace journaling a couple years ago, but I find that during my structured sabbatical, it’s one of my most powerful tools. In addition to a twice daily check-in using a 5 Minute Journal, I free-write, mind-map, and doodle in a Baron Fig Work/Play notebook.

While I think it’s a great idea for a sabbatical to have structure, I’m also finding a key for my own growth is not being so reliant on structure. I want to feel content satisfaction as often as I can, not like I have successfully checked off a to-do list. It was a big adjustment for me to leave a full-time job where I was seeing success often and decide instead to venture a bit more into the unknown by working on projects where I may fail.

“Being daring is all about trusting yourself to handle the results,” writes the team at First Round Capital. “A shocking number of people in tech know they’re brilliant, know they’re capable, but don’t trust themselves to know what to do if they get fired, fail spectacularly or just want to switch gears towards a more fulfilling path. Shifting your confidence from one area of your life to another gives you the safety net you need to take more chances.”

I am in the first weeks of my structured sabbatical. So far, I can see a lot of growth in myself and I am proud of the work on each of my projects. I still have room to go further in shedding my attachment to traditional career growth for validation. It’s a process and I am allowing myself to try out new ways of thinking.

If you aren’t in a place to spend months on a structured sabbatical, how can you reclaim more of the time you have now for passion projects? How can you get connected to a space of experimentation, play, and even welcomed failure? I’d love to hear from you!

Jacqueline Jensen is a digital nomad, former venture-backed startup founder, speaker, and recognized community builder. Jacqueline’s next ambitious project is publishing her first book. Watch her TEDx talk “Playing nicely with fellow entrepreneurs pays off.” Jacqueline’s interests include travel, yoga, entrepreneurism, startups, and learning to code. You can connect with her at @JackieMJensen or on LinkedIn.