Planning a Sabbatical

As of today, I am embarking on a ~6-month sabbatical. High-level, we are on the verge of a big move and the pent-up energy of the pandemic combined with projects wrapping up at work offers a good opportunity to take it on–and enjoy some extended vacation time while we’re at it.

This is an overview of why I decided to take time off and what I plan on doing.

Why Take a Sabbatical?

The thought of taking a sabbatical is intimidating: forgoing income, breaking a continuous job history, and all that extra time. But there are numerous reasons you might want to step away from work. A handful that come to mind:

  • Travel - see new places, visit family & friends, enjoy nature
  • Input - time to learn new things, read, enjoy more music/movies/museums/arts
  • Output - time to write, work on personal projects, build something for fun
  • Reflection - reflect on the past, think about the future, consider your career path
  • Space - to do nothing, get away from routines, clean things up

Sabbaticals also benefit the companies that implement them as a benefit for employees. I saw this first hand at Autodesk, and many established Bay Area tech companies have embraced a 4-5 year sabbatical cadence as part of their culture. Folks in academia are accustomed to the practice. Much has been written about this elsewhere, so I will focus on my journey below.

Why Now?

Bouncing Back from the Pandemic

As the memories fade it may be hard to believe this in the future, but the coronavirus pandemic has been a major impetus in my personal decision. We’ve seen droves of workers leaving their jobs, so many that it has been dubbed “The Great Resignation.” Of course, there are many reasons behind this, and over the past two years everyone has had unique and challenging experiences. I was fortunate to be able to work through it, but it came with stresses that left me feeling burnt out when all was said and done.

On the positive side, the world is opening back up. Concerts & events are back, and people are hungry for travel & socialization. There’s even a bit of hope that we might still see a Roaring 20’s decade. Having been heads down for much of the past two years, I’m ready to travel, visit friends & family, and enjoy cultural events…then jump back into building software when I am re-energized.

Inflections at Work

I also find myself at convenient crossroads in work.

With the recent spring release, Brightidea Whiteboard feels like a complete v1 product and I am delighted & impressed with what the team has accomplished. As a broader product development team, we’ve honed our quarterly release cadence and have been shipping software predictively & reliably. The immediate product team has grown by three in the past year, and everyone is up-to-speed making strong contributions. It’s one of the rare times when everything comes together, and nothing feels “undone.”

Personally, I passed my fourth anniversary which feels simultaneously like it flew by & a silicon valley eternity. I’m reflecting on where I am in my career and thinking about how to distill and bring together the things I enjoy and am good at. I’d somehow like to integrate more hands-on involvement in designing and making things than I’ve had recently, but I do enjoy the influence & scale, motivating a team to accomplish big goals, and working at a systems & architecture level.

I’ve worked at startups and a big company, and need to think deeply about how I want to spend my next deployment. Having worked with corporate innovators while at Brightidea, being a 0-1 intrapreneur also has some appeal as a blend of both worlds (with compromises of course). I had exposure to this at Autodesk working with Emerging Products & Technologies but was never able to get above 10-20% of my time focused on disruptive innovation.

I Decided Seven Years Ago

As alluded to above, I have previously taken a sabbatical while at Autodesk, although on a smaller scale and without leaving my job. For every four years of service, employees received a 6-week sabbatical. This was a refreshing break that came with a reset at work and the opportunity to do more than a 1-2 week vacation allows, so I decided that I would try to make this a recurring event for myself through my career. It’s been nearly seven years since I decided this, so I’m feeling overdue.

What Will I Do with the Time?

Travel and Learn Spanish

I know I will be spending at least a month in Spain, hopefully longer. TBD whether we travel elsewhere in Europe, but will be checking out a bunch of towns from the beaches to the mountains. I will be enjoying time with family & friends over good food & summer festivities.

In the meantime, I will be studying Spanish. Though I’ve been to Spain a few times, I am very much a beginner at the language. I never took Spanish in school and wasn’t exposed to it growing up so it’s been tough to pick up. I’m hoping it will be easier when my mind is emptier.

Leave San Francisco

I will be leaving San Francisco and likely California. Won’t go into all the details here, but suffice it to say the quality of life in the city has drastically declined over the past couple of years, while cost-of-living is again rising.

This will likely also come with a transition to automobile life. I’ve been car-less for several years now, relying mostly on my commuter bike and occasionally public transportation or Zipcar. It will be a lifestyle shift, and seems like a tough time to be in the market for a car (new or used), but maybe things will change.

Hobbies and Activities

I’ve been enjoying getting back into reading science fiction. While reading fiction can sometimes feel like escapism, I love getting pulled into sci-fi for the societal & technological ideas combined with the humanity that comes across in a well-written novel. I already have several books loaded on my Kindle and will be leaning into reading for enjoyment.

If reading is input, I plan to maintain output by writing. Generative creativity & communication is a core part of my professional work and a part that I thoroughly enjoy–writing, presentations, wireframes, workflows, and various product artifacts to name a few. I’d like to focus that energy in my free time on writing things to share more widely on the internet, including on this blog which has been neglected. I also have some creative design ideas to potentially execute in Figma.

Last point here: I will spend more time outdoors at the beach, on the trails, and riding my bike. What I do will depend on where I am and what I have access to, but you’ll find me outside. I did manage to prioritize health and fitness during the pandemic–by cooking at home, doing calisthenics a few times a week, and getting out for solo endurance training every couple of days–so I hope to maintain these healthy habits going forward, especially when settling after the move.

Physical & Digital Cleanup

Moving will offer an opportunity to prioritize getting rid of accumulated objects and redundancies. Will keep it brief, but I know I have a lot of clothes I haven’t worn since pre-pandemic. I also have a bunch of outdoor gear that may or may not be practical, depending on where I end up. I will be reducing a combination of bikes/surfboard/bodyboards/camping gear/etc. before moving.

On the digital front, I have been lugging around a growing box of hard drives & storage devices that need to be processed and disposed of. Among other things, I have a huge music archive and tens (hundreds?) of thousands of photos that need to be organized and deduped. I plan to get this all on a single NAS with online backups.

Reconciling personal notes, ideas, and research across local files, Trello, Notion, Evernote, Google Drive, etc. would also be nice, but is a lower priority.

Job Prep

I expect towards the end of the year I’ll be ready to get back into working full-time. I haven’t laid it all out, but this will eventually become the-job-before-the-job:

  • Refresh my website & portfolio to capture the last five years
  • Update my resume, LinkedIn, etc. for the role I am targeting
  • Get plugged into a new local tech & startup scene
  • Make progress and document any side projects

In the meantime, if you have any part-time opportunities or need a hand with product & design please reach out!

Doing Nothing

Overall it seems like I will be quite occupied. And I could even go on and name a bunch of other things I’d like to do. But finally, it will be important to prioritize–and be okay with–doing nothing. In an always-on connected world full of dopamine traps competing for our attention, stillness and silence are the real scarce resources to cherish during this time.

I’m pretty bad at doing nothing so I will have to ease into this one (several weeks in Spain should help!). It is worth naming explicitly as an ongoing reminder.


Want to learn more about taking a sabbatical? These resources are a good place to start. Also, feel free to reach out if you have any questions!

The Sabbatical Project

Cool site I discovered with tons of info and inspiration:

Ted Talk by Stefan Sagmeister