Sabbatical Stories

Winston’s Family Sabbatical

Winston set out on a year-long family sabbatical after ten years at the same data management company to think about what he wanted to do next, pick up some hobbies, and spend more quality time with his children. He was able to use this time to build not only his relationships with his children and self, but also the app that would become his post-sabbatical career. When he left the small Norwegian island where spent this year, Winston had gained not only a new job, but a new outlook on the relationship between life and work, risk-taking, and financial stability.

Opportunity Arises for a Family Sabbatical

While Winston had taken short breaks before, including a month-long trip to Norway where he met his wife, none of them had been a “proper sabbatical.” Once he was certain that he wanted to leave his company, Winston started bouncing around ideas about what to do next. He was intrigued by a Ted Talk he had listened to by Stefan Sagmeister, who discussed “borrowing” 5 years of time off from your retirement and sprinkling them into your life.

Because his children were young (3 and 4) and his wife was looking for a transition back into the workforce, this seemed like the perfect time for a year away. After explaining these desires to a Norwegian friend, she suggested moving to Rødøy, an island above the Arctic Circle and working as a teacher. This aligned with the desires Winston and his wife had for their sabbatical, including their personal goal of having their kids be fluent in Norwegian. 


“Taking a year off forces you to be more intentional about how you spend your time.”

To achieve his goals, Winston developed a three-part weekly schedule for himself that included family time, free time for himself, and professional time. Having this segmentation gave him this necessary focused time, while also ensuring that he didn’t constantly feel like he needed to be doing something else. 

For hobbies, Winston’s plans included learning how to catch and prepare fish, and to play ukulele. 

One of his most treasured memories from his sabbatical was the tradition of “daddy days,” which was time he spent doing projects one-on-one with each of his children. While he was working back in Boston, Winston worried that he wasn’t spending enough time with his children. Taking this sabbatical allowed him to foster these relationships without the external pressures and demands of his full time job. 

Financing a Family Sabbatical

“It’s empowering to know that, if our income suddenly drops significantly, we can live pretty happily on a very limited income.” 

To finance the sabbatical, Winston and his wife decided that they would live off of his wife’s salary from teaching on the island. Despite this only being a fraction of his earnings as a tech exec, they were able to follow this plan and avoid dipping into their savings. They had to live more frugally than they did in Boston, but learned that their family could live pretty happily on a limited income. 

northern lights from their small village
A view of the Northern Lights from their small village

Creativity During the Arctic Winter

“Going on sabbatical increases your chance of being creative because you’re not surrounded by distractions.”

As the days got shorter and the temperature got colder, Winston found himself spending more and more time indoors. This prompted him to return to an old skill of his—coding. He came up with the idea for a text-to-speech smartphone app and spent the rest of the winter developing it, publishing it on the app store come spring under the name Voice Dream.

“Finding meaning in your work often times requires a close connection to the people that you’re helping”

One major difference between his regular work and this new project was that it allowed him to get much closer to customers. After launching the product by himself during sabbatical, Winston would read each email, giving him a sense of how his customers are using the product and info about any bugs to fix. He found this experience exhilarating.

It showed Winston that his product was meeting a need in the market, affirming his programming skills and addressing the problem of collaborative work while living far away. Before working on the app, Winston had attempted to start other ventures, but found the mechanics of starting a business difficult from his remote location. His app, while starting as a passion project, let him overcome this problem due to his ability to work on it alone.

Going Forward

The ultimate byproduct of my sabbatical is that I no longer need to compartmentalize work from having fun and making a difference.

When Winston and his family returned to Boston, he became an entrepreneur in residence for Matrix Partners, intending to launch his own venture-backed startup, but continued spending half of his time working on Voice Dream. As app sales steadily increased, Winston and his wife decided that he was going to make the app his work and stop doing anything additional. 

Post-sabbatical, Winston instituted a “summers off” policy in his company, to both align with his wife’s teaching schedule and to offer his employees significantly more vacation than traditional office jobs. His sabbatical also helped him redefine the relationship between work and play, allowing him to be creative and take the risk to develop Voice Dream.

“I hope we seek these experiences out in life, not because of the memories, but how it changes you as a person.”

family sabbatical meal time!
A family sabbatical meal with a view

Interested in more examples of family sabbatical? Read about Justin and Allison (and their 4 kids) here.

Read more about Winston’s sabbatical in his interview on NPR here.

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