Why and How to Take a Sabbatical

For those who have the financial means to do so, I highly recommend taking a sabbatical every few years to ensure you’re aligned with your goals, see the big picture, and refresh to get ready for your next challenge.

I love early stage start-ups, but they can also be all consuming as it’s like raising a baby each time. You get to know every aspect of the business from the ground up. You feel like you can’t get away as things really depend on you. You’re tapping into every aspect of your energy and brainpower, often mulling over things even after the workday is “done.” You’re emotionally tied into the roller coaster of successes and pitfalls.

That is why after my past two start-ups, I’ve deliberately chosen to taken a sabbatical. Each time I’ve re-emerged more sure, energize, and invigorated to jump into my next challenge.

Why take a sabbatical?

Before taking a sabbatical, understand your goals for it. For some, it is to do something different, like train to be a yoga teacher or to write a book. For me, it is to gain a fresh perspective on the market and to have some more “sit on the bench and think time.” I wanted to figure out where I should invest my time into next, where the market was going, what are some trends in the industry.

It is also often, of course, to relax, spend time with family, take vacation, and recharge.

Is it risky?

It can seem daunting to be “without a job.” True, there is a bit of a question from recruiters when you’re not working, but this can be mitigated in various ways:

  • Take up active consulting roles and talk about what you’re doing, this is also a great way to find your next opportunity
  • Be active in thought leadership / writing, the quality of your content should attract those who are looking for your specific talent
  • Have strong references from your previous roles
  • Consider taking a sabbatical within the same company
  • Devise a plan for what to do so you won’t be too busy being worried

A sample way to plan for your sabbatical

I received this list from a friend who worked with a coach while planning her sabbatical, and received permission to share it as it was extremely helpful for me

1) Visioning

Made a visioning board of what an amazing sabbatical would look like. Literally cutting out things from magazines, writing down words that came to mind etc. or do this on Pinterest

2) Laundry list

Write down a list of things you want to do, feel free to let this be super random — from some books to read to watching a movie on a Tuesday morning in bed while eating chocolate :-)

3) Some formal training / class

Perhaps a yoga-teacher training class? coding class? art history class? Goal is to get a different part of the brain going and learning.

4) Digital detox -

X weeks without opening laptop, be more present and creative with those around you, works especially well in spending time with kids

5) Personal training / fitness

6) Assessments (as a way to collect data — look at all those assessments at once; here’s a sampling some of those tests, and they do change over time)



Myers Briggs


Michael Hyatt Lifescore




Highland Assessment Battery — quite expensive but really cool. 3 hours in depth online tests and then having a psychologist (phd) play back to you what that means for ideal work, life environment.


7) Go back to people you haven’t worked with for a while and ask them what they remember the most helpful thing you did was and the least helpful [with benefit of hindsight and some distance]

Landit is a great tool for doing this if you want to put some tech behind it

8) Lastly: Making sure you have time every week without any plan.

Getting back to work

For friends of mine, they wanted time to be fully off before starting to look for a job, and then once they were ready, they went into full time job search mode. For me, I found advising and consulting for early stage companies in the spaces I was interested in was a great way to “expand my mind” while having a lighter load. It could also possibly turn into my next role, without the pressure of needing to find my next job when you’re engaging with people. For many start-ups, it’s also a great way to really feel the fit of a potential senior candidate into the culture and how much value they can bring. This is a bit easier if you’re looking into early stage companies, as many large companies can be more rigid.

Your timeline will depend on your goals and also your budget. I had a longer timeline than I actually took, but was open to jumping back early to a full time opportunity if I found the right fit. This allowed me to really look for something I wanted to invest in for the next season of my life, rather than being compelled to “find a job.”

During my first sabbatical in 2016, I spent time consulting for various companies in the AI space, and got to understand it’s many winters and summers. One of the companies I worked with (or really the two co-founders) was Subtle Medical, a start-up using AI applied to medical imaging, which I ultimately joined and led the commercial team up to its recent Series A.

During my recent sabbatical in 2021, I initially took a step back to look at overall trends in healthcare: data, precision medicine, real world evidence, chronic disease management, early detection, and remote care. I got a chance to advise various start-ups through Astia, USCF Rosenman Institute, and my network. I took two meetings a week on Lunchclub, and lurked on various sessions on Clubhouse. I re-connected with friends. I wrote. I figured out what “skills” I was good at— which I initially found hard to articulate since it was something I did everyday, so advising start-ups helped me figure out what questions I was answering repeatedly. Our family traveled during the window post vaccination and before travel became crazy, visiting the Big Island of Hawaii, Scottsdale / Sedona / Grand Canyon, and Yosemite.

I am excited to announce the end of my sabbatical to join Nanome, a VR platform for the next generation of science, starting with drug discovery. I am energized by the young team of passionate founders. Like with AI four years ago, I am bullish at the inflection point of VR/AR and mixed reality as the future of work and collaboration, though admittedly it’s a bit earlier in the trajectory, but clearly out of the woods with all the major tech players: FB, Apple, HTC, Microsoft, Sony, Lenovo, NVIDIA, and others investing in the next generation hardware.

I hope you’ll have a chance to take a sabbatical yourself, and I am excited to share more about Nanome with you in the future.



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