Written by Jacqueline Jensen – digital nomad, former startup founder, and speaker
When I was 14 years old, I landed my first job working at a flower store.
I worked for 6 hours every Saturday watering the plants in the storefront, mopping floors, and cleaning the shop’s giant glass windows facing the bustling street.
Although I didn’t walk away from that job with many skills that I use today – I have never been able to keep a plant alive for more than 2 weeks – I walked away with a simple, but powerful, idea in my pocket:
Working gives you a paycheck.
And a paycheck is the ticket to independence.
Flash forward to nearly 2 decades later – the concept of working for a paycheck stuck with me and was a primary driver in my life. Even during my time as a startup founder, the biggest early challenge I faced was weighing how taking the risk of creating my own company would affect my wallet.
I placed a lot of value in the security of a paycheck.
I remember the day our founding team decided to pay salaries to ourselves. It turned out that knowing exactly how much would be coming in each month gave me a sense of ease to tackle other challenges in the business.
Over time, the power money held over me would keep me playing small time and time again. If I found myself in an unfulfilling role, I would worry about not being able to find work and rationalize why staying put was the safer bet. I was diligent about saving, but I was afraid to ever withdraw.
I always felt like I was at war with the feeling of security that money seemed to promise.
While visiting New York City, I learned more about a project a friend was working on. Dubbed Recess Labs, it’s an experimental entrepreneur-in-residence program in New York City for talented people working full-time on unconventional projects.
The idea of taking a structured sabbatical to work on something unconventional intrigued me.
I wasn’t unlike many entrepreneurs and former founders I knew – we all had a list of unconventional projects we’d love to try. But after talks with those I admired, I began to notice there was one thing that seemed to make me different.
There was something that held me back from actually exploring projects on my list.
For the three years after my startup shut down, I had decided to hang up my entrepreneurial hat to work as an employee at startups. The primary reason was that I liked the steady paycheck. I found a sense of security in the idea of not having to hustle, scrap, or be let down on the financial front.
I did great work. I got paid. It seemed my fears around money were put to rest.
When I stopped to think through the reasons I placed so much value in a steady paycheck, they seemed a bit silly. A paycheck was just a bandaid – the fear was still there and not serving me.
I realized maybe it was time to let go of my 14-year-old beliefs.
What if the idea that a paycheck is the ticket to independence was wrong all along?
One of the things that interested me most about Recess Labs was that their fellowship program was open to a wide variety of side projects. A structured sabbatical didn’t need to have anything to do with a viable business idea – it could just be to scratch a curiosity itch.
“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,” said Sib Mahapatra, founding fellow at Recess Labs. “The point of the program is to encourage people to work on things they personally want.”
While a traditional sabbatical is usually taken by academics or paid for by a company, this new kind of sabbatical felt more like, well, recess. It’s what you do when you can do anything you want.
Launching My Structured Sabbatical
I found myself thinking about what was happening at Recess Labs for weeks after I left New York City. Things at my job had felt stagnant and not aligned with my values or growth. What if rather than seeking a new role at another startup, I took a structured sabbatical?
At first, the idea seemed whimsical, irresponsible, and even a bit lazy.
In this time of my life, aren’t I supposed to be working and advancing my career? When I decided to get back into the startup world, how would I explain this gap in time?
I decided to do some research about sabbaticals to learn more. Why do people take them? And what impact do they have?
In the book Reboot Your Life by Catherine Allen et al., they interviewed over 200 people who had taken sabbaticals lasting anywhere from one month to two years and the results showed that not one person regretted the decision to take a break.
I read study after study which found sabbaticals promote well-being, decrease stress, and provide opportunities to acquire new knowledge and skills. The return on investment is strong.
So many leaders shared how they came back to their career with new ways of innovative thinking. There was even one person in particular who wasn’t a strong writer, but ended up writing a prize-winning essay on their sabbatical!
One study found that those who spent their sabbatical in another country enjoyed bigger gains in well-being than did those who merely worked on different projects but from the same location.
Months earlier, I had booked travel plans in Europe for four months. I decided to use my time abroad as my sabbatical springboard!
It was important to me to have structure for my sabbatical, but at the same time be open to shedding the intense goal-focused mindset I had been clinging to for years.
Each day, I think of my sabbatical in terms of three focus areas:
Overcoming my fear around money falls under the third focus area. Of all the projects, I am most excited about the progress I am making on this one in particular.
Carefully untangling this fear had uncovered an addiction to work that developed over years. It also gives me the opportunity to try new things to manage fear like stepping up my meditation and presence practice.
The best tactic for having a successful sabbatical?
So far for me, it’s been to embrace the new change of pace. Trying out a new speed has been life-changing for me. Each day, I find myself feeling more confident, more at ease, and becoming excited about the opportunities for growth ahead.
Guest Written by Jacqueline Jensen
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! Her interests include travel, yoga, entrepreneuriship, startups, and learning to code.