Planning a Sabbatical

Today, I’m starting a 6-month sabbatical. We’re on the verge of a big move and the pandemic’s accumulated energy combined with work projects concluding offers a good opportunity to take it on and enjoy an extended vacation.

This is an overview of why I decided to take time off and my plans.

Why Take a Sabbatical?

Taking a sabbatical is intimidating. You have to forgo income, break a job history, and deal with all that extra time. But there are numerous reasons to step away from work.

• Travel to see new places, visit family and friends, and enjoy nature.
• Time to learn, read, and enjoy more music, movies, museums, and arts.
• Creativity opens up to write, work on projects, and build something fun.
• Reflection on the past, consider your career, and plan your future.
• Space to do nothing, escape routines, and clean up.

Sabbaticals benefit companies that offer them. I saw this firsthand at Autodesk, and many Bay Area tech companies have embraced a 4-5 year sabbatical cadence. Academia is accustomed to this practice. Much has been written about this, so I’ll focus on my journey.

Why Now?

Recovering from the Pandemic

As memories fade, it may be hard to believe this in the future, but the coronavirus pandemic has significantly influenced my decision. We’ve seen droves of workers leaving their jobs, dubbed “The Great Resignation.” There are many reasons behind this, and over the past two years, everyone has had unique experiences. I was fortunate to work through it, but it came with stresses that left me feeling exhausted.

On the positive side, the world is reopening. Concerts and events are back, and people want to travel and socialize. There’s hope for a Roaring 20s decade. After being focused on work and personal fitness for the past two years, I’m ready to travel, visit friends and family, and enjoy cultural events. Then, I will resume building software when I am re-energized from being offline.

Inflections at Work

I find myself at a convenient intersection in work.

With the recent release, Brightidea Whiteboard feels like a complete v1 product. I’m delighted and impressed with our team’s accomplishments. As a broader product development team, we’ve honed our quarterly release cadence and ship software predictively and reliably. The immediate product team has grown by three in the past year, and everyone is up to speed making strong contributions. It’s a rare time when everything comes together, and nothing feels “undone.” A natural pause.

I just passed my fourth anniversary, which feels like it flew by and a Silicon Valley eternity. I’m reflecting on my career and how to combine what I enjoy and excel at. I’d like more hands-on involvement in designing and making things again, but I enjoy the scale of influence, motivating a team to achieve significant objectives, and working at a system architecture level.

I’ve worked at startups and a big company and need to consider my next deployment. Having collaborated with corporate innovators at Brightidea, being a 0-1 intrapreneur blends both worlds (with compromises). I had exposure to this at Autodesk working with Emerging Products & Technologies but couldn’t dedicate more than 10-20% of my time on disruptive innovation.

I Decided Seven Years Ago

I’ve previously taken a smaller sabbatical at Autodesk without leaving my job. After four years, employees receive a 6-week break. This was a refreshing experience that came with a reset at work and the opportunity to do more than a 1-2 week vacation allows. I decided to make this a recurring event in my career. It’s been nearly seven years since, so I’m overdue.

What Will I Do with the Time?

Travel and Learn Spanish

I’ll spend at least a month in Spain, longer if possible. TBD if we travel elsewhere in Europe, but I’ll explore towns from the beaches to the mountains. I’ll enjoy time with family and friends over good food and summer festivities.

In the meantime, I’ll be studying Spanish. I’ve been to Spain a few times, but I’m still a beginner at the language. I never took it in school or was exposed to it growing up, so it’s been tough. I hope it will be easier when my mind is less occupied.

Leave San Francisco

I’m leaving San Francisco and California. The city’s quality of life has drastically declined in the past few years, while the cost of living is rising. I love the weather and natural beauty, but I also need to be nearer to family.

Hobbies and Activities

I’ve been enjoying getting back into reading science fiction. While it can feel like escapism in these times, I love getting pulled into sci-fi for the societal and technological ideas combined with the humanity in a well-crafted novel. I have several books loaded on my Kindle and will be reading for enjoyment.

If reading is input, I plan to maintain output by writing. Generative creativity and communication are core to my work and something I enjoy—writing, presentations, wireframes, workflows, and product-shaping artifacts. I’d like to focus that limited and newly available energy on writing on the internet, including this neglected blog.

Lastly, I’ll spend more time outdoors at the beach, on trails, and cycling. My activities will depend on my location and access, but I’ll be outside. During the pandemic, I prioritized health and fitness by cooking at home, doing calisthenics, and solo endurance training, so I hope to build on these habits.

Physical & Digital Cleanup

Things have become cluttered.

Moving will allow me to prioritize getting rid of accumulated objects and redundancies, physical and digital. I have unworn clothes since pre-pandemic and outdoor gear that may not be practical depending on my new location. I’ll be reducing bikes, surfboard, bodyboards, camping gear, etc.

I’ve been carrying a growing box of hard drives and storage devices to process and dispose, plus several online backup services. I have a music archive and tens (hundreds?) of thousands of photos to organize and dedupe. I plan to get this all on a single NAS with online backups.

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

Job Prep

I expect to be ready for full-time work by the end of the year. This will eventually become the job-before-the-job:

• Refresh my website and portfolio to reflect the last five years.
• Update my resume and LinkedIn for the targeted role.
• Plug into a new local tech and startup scene.
• Make progress and document side projects.

Please reach out if you have part-time opportunities or need help with product and design!

Doing Nothing

I’ll be occupied and could list other things I’d like to do. But it’s important to prioritize andbe 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 bad at doing nothing, so I need to ease into this. Several weeks in Spain should help! It’s worth mentioning as a reminder.

Resources

Want to learn more about taking a sabbatical? These resources are a good starting point. Reach out if you have questions!

The Sabbatical Project

I found a cool site with tons of info and inspiration: https://thesabbaticalproject.org/

Ted Talk by Stefan Sagmeister