How A Sabbatical Can Radically Hack Productivity

Elizabeth Schwartz’s five-month hike on the Pacific Crest Trail was an exercise in letting go and trusting that work would still be there when she got back.

How A Sabbatical Can Radically Hack Productivity
[Photo: Bob Wick/BLM/Flickr]

“Sometimes the best way to improve your work is to stop working,” says Elizabeth Schwartz. She should know. The chief operating officer at Austin-based software startup Square Root took a five month sabbatical to hike the Pacific Crest Trail in 2016, after working at the company for six years.


During her talk at SXSW this week, Schwartz revealed that the motivation for hitting the trail (not informed at all by Cheryl Strayed’s Wild) was more about the burst of inspiration to do it that continued to keep her up at night, and the serendipity of her brother getting laid off and having the time to start the hike with her. “There’s never a right time to take a sabbatical” Schwartz explained. Especially when your job is as all-encompassing as hers.

But she made the case to her boss, Square Root’s founder and CEO, Chris Taylor, and he granted her the leave, which was only partially paid. Before she left, Schwartz, a self-professed planner, mapped out all of her job’s responsibilities on a spreadsheet and started to delegate “up, down, and sideways” across the organization.

Although she wasn’t totally out of touch while on the trail, Schwartz started realizing she didn’t need to constantly check in with the staff. Trust in people to do their jobs, she said, was key to having them step up and be accountable–not to mention more engaged and productive.

And that’s what so many organizations struggle with. Companies that attempt to one-up each other to attract and engage employees are rolling out amazing perks like massages, pet cloning, and paid international travel, among other things. This may be successful in the short term, but even unlimited vacation is just theoretical if the culture doesn’t support and encourage employees to take advantage of it. For several years of tracking, Gallup’s poll numbers remain stubbornly stuck on engagement. Only about a third of American workers are engaged on the job.

The upshot, Schwartz maintained, is that leadership needs to model the behaviors that reinforce their trust in staff to do their jobs well. Although she admitted that Square Root hasn’t had another person take a long sabbatical, she as an executive modeled how it could be done. And acceptance and flexibility (especially to work remotely) are crucial to building a company where people want to work.

For Schwartz, taking an extended leave reset her perspective and transformed her leadership style to one that was more hands-off. Taking inventory of her daily tasks helped her see what she could delegate and what needed more focus. That’s arguably the biggest productivity hack of all.

About the author

Lydia Dishman is a reporter writing about the intersection of tech, leadership, and innovation. She is a regular contributor to Fast Company and has written for CBS Moneywatch, Fortune, The Guardian, Popular Science, and the New York Times, among others.