The Case for Sabbaticals: Why I Plan on Taking One Every Five Years
Plus How I Think and Plan For These Strategic Breaks
I still remember the moment I woke up in my Carmel-by-the-Sea rental house on the first morning of my sabbatical in the summer four years ago. The sun was shining brightly, warm but not too hot, tempered by the fresh Pacific Ocean air. My breath was flowing, breaking free from the anxiety-blocked breathing I’ve held and known for years as a Silicon Valley tech lawyer and privacy officer.
That first day of freedom was a stark contrast to the already-scaled-down-but-still-hectic daily life I was accustomed to: often up by 5 am to exercise, in the office by 6 am, a couple of hours of substantive work, followed by back-to-back meetings all day until 6 pm, a brief dinner, and then more work at night until 10 pm, sometimes later.
That first day of my sabbatical, I finally had a blank slate to create and explore. The past decade and a half were spent laser-focused on my career, which I loved and was very passionate about. But I always had a nagging feeling that there’s more to life and living than work. Whatever that was had been beyond reach given my 60-hour workweeks in Silicon Valley, which, to be fair, weren’t as bad as my 70-80-hour workweeks in Big Law. I had so many things I had wanted to pursue throughout the years: write, teach law school, start my own business, explore one or two of my many interests outside of my career in privacy, cybersecurity, tech, and law, and gain more freedom and flexibility overall …
Sabbaticals are often perceived as an indulgence for the few, and I recognize that I am privileged to have been in a position to even consider them. That said, sabbaticals are vastly misunderstood, underrated, and underutilized. Detaching ourselves from work for an extended period might seem like an unnecessary luxury or an impractical proposition. However, the benefits of this pause can transform not only us as individuals but also the culture of our workplaces. As someone who has lived through the transformative power of this extended hiatus, I am convinced that sabbaticals are not only beneficial for individuals but are equally instrumental in fostering a more productive workforce, vibrant economy, and well-rounded society.
The Good Sabbaticals Can Do
Sabbaticals offer an essential respite from our work-centric lives, providing us with the opportunity to replenish our mental and physical health. Research in the Journal of Applied Psychology indicates that sabbaticals lead to reduced stress levels and better overall health. My own experiences resonated with these findings as I found myself returning to work rejuvenated, with a clear mind and a revived spirit.
Furthermore, sabbaticals can serve as a catalyst for creativity. The break from routine, coupled with exposure to new environments, perspectives, and experiences, can stimulate fresh ideas and innovative thinking. Sabbaticals, by providing relaxation, change of environment, and mindfulness, stimulate creativity. Personally, my sabbatical gave me the newfound environment, space, and time to think, sparking new insights that I was able to apply to my professional endeavors.
Moreover, sabbaticals provide an opportunity for skill enhancement and personal growth. As professionals, we often get so caught up in our specific roles that we neglect the chance to learn new skills or pursue different interests. A sabbatical allows time for that. My own sabbatical was a testament to this, as I rediscovered a penchant for writing, a skill that significantly enriches my work.
Despite the compelling benefits, the adoption of sabbaticals in our work culture remains low, often due to misconceptions about their impact on career progression and the lack of supportive policies. Yet, as our understanding of work-life balance evolves, it is high time that we reconsider the potential of the sabbatical. Employers need to understand that a well-rested, mentally healthy, and creatively stimulated employee is more likely to contribute positively to the organization in the long run.
The Criticisms from Sabbatical Naysayers
Critics argue that sabbaticals pose significant costs to businesses, including the loss of output, costs of temporary replacements, and the disruption of team dynamics. But to see these short-term disruptions as substantial costs is to overlook the long-term gains of a workforce that returns revitalized, rejuvenated, and ready to contribute more creatively and productively to the organization. As noted by the Harvard Business Review, employees who take sabbaticals often return with an increased output.
Moreover, sabbaticals can foster talent. Sabbaticals can provide senior leadership the opportunity to succession plan; junior employees, the room to step into more challenging roles, encouraging growth and fostering a culture of internal promotion. This approach can serve to bolster motivation and increase the overall productivity of the team.
As for disrupting team dynamics, it is essential to remember that teams are not static entities. They evolve, adapt, and reshape in response to different situations, a fundamental characteristic that makes them successful. Sabbaticals can be seen as opportunities for teams to refine their resilience and adaptability, thus strengthening the group in the long run.
To be fair, the fear of career stagnation and financial constraints are real and valid. But a well-planned sabbatical, preferably with financial support from the employer, can be an investment in one’s career rather than a hindrance.
Indeed, the fear of skill decay is one that looms large in the mind of any professional considering a sabbatical. However, this fear neglects to consider the breadth of skills that can be acquired during a sabbatical. Learning new languages, taking on new projects and endeavors, understanding different cultures, developing new hobbies, or even just improving the ability to adapt and be resilient - all these skills picked up during a sabbatical can often be transferred to the workplace, fostering a more innovative and adaptable workforce.
How I Planned My Own Sabbatical
My sabbatical sprung out of a necessity. I had been operating on autopilot for decades, laser-focused towards my goals: getting into and finishing law school; passing the bar exam, building a Fortune 500 privacy program from the ground up; advising 100+ Fortune, tech, and multinational companies; and building more privacy programs for Silicon Valley tech companies.
And then, one evening, I sat staring at the phosphorescent glow of my work computer, negotiating the privacy and security contract terms of another deal in the hundreds of millions. While that work would’ve been thrilling to many, I realized that after years of doing it, I was burnt out and no longer enjoyed my then career and life path. So then and there, I decided to embark on a sabbatical. Not an impromptu vacation, but a deliberate departure from my daily grind, an opportunity to reboot, recalibrate, and recharge.
Here’s how I turned the daunting prospect into an adventure of self-discovery.
Seamless Succession & Transition
Because I didn’t want to burn any bridges at work, I was determined to set up my former company for success. This required careful consideration of my duties, responsibilities, and existing projects. A thoroughly planned and executed succession ensured that my team could function effectively and efficiently when I left.
In the months leading up to my sabbatical, I identified internal and external candidates who could potentially replace me. I went out of my way to make their hiring happen. I also began working closely with existing team members, sharing not just the projects, but also my thought processes, strategies, and insights. To me, the transition period wasn’t just about transferring—it was about enabling growth for other as I set out to embark on my own growth journey.
Facing My Fears
The idea of taking a sabbatical felt daunting, and the chorus of fearful whispers threatened to become a cacophonous symphony of anxiety.
But I knew that having fears are normal, and they can be managed with clear-eyed risk assessment exercise known as “fear setting.” With fear-setting, I was able to name my sabbatical-related fears, an important first step to dealing with them. I put each fear onto paper, turning those nebulous anxieties into tangible challenges. I then meticulously planned a strategic counterattack for each one, transforming my worries into manageable molehills. I confront4r each fear, assessed its validity and likelihood, and then planned mitigation strategies. For example, fears of financial insecurity, career plateau, and the undefined contours of an uncertain future loomed large. [I’ve enclosed a sample fear-setting template at the bottom of this article for my subscribers.]
Saving for a Safety Net
To assuage my fears, I planned my voyage to a sabbatical with a solid foundation of financial planning. A carefully nurtured nest egg was my lifeline, a safety net for unpredictable storms and unforeseen costs. I meticulously charted out my sabbatical budget, accounting for basic sustenance and room for error. I committed to a savings goal that stood as a testament to my discipline and determination. [I’ve also enclosed a sample monthly sabbatical budget tracker template at the bottom of this article for my subscribers.]
A Seasoned Sounding Board
My transition from the habitual daily grind to the unknown was emotionally charged. Navigating this tumultuous sea called for some help: my therapist. They became a sounding board for my uncertainties and guilt, and a guide through the labyrinth of emotions that surfaced during this period.
My therapist helped me focus on the positives, reminding me of the importance of self-care and its long-term benefits. Additionally, my therapist helped me set personal goals for the sabbatical. This gave me structure and purpose, turning my time off from work into a proactive journey of self-improvement and self-discovery rather than just an escape from daily responsibilities.
Our sessions fostered my mental readiness, allowing me to see the sabbatical as an opportunity for rejuvenation and self-growth rather than an indulgence.
Rallying an Army of Allies
My sabbatical wasn’t a solo journey, but a communal effort that relied on the support of my loved ones. In addition to 1) my therapist and 2) my partner, I found my “army of allies” in 3) my family, 4) my friends, and even 5) my old colleagues, some of whom visited me during my sabbatical.
Although many of them didn’t fully understand, their unwavering faith in my decision and their heartening cheers transformed my moments of doubt into stepping-stones towards courage and conviction. They were my cheerleaders, encouraging me when I faltered, celebrating my steps forward, and offering me support during my sabbatical.
A Setting by the Sea
I spent the summer of my sabbatical living in the Pacific town of Carmel-by-the-Sea, my days filled with reading for pleasure (vs. work), walking the beach with my dog, thinking in the bath tub, meeting new people I would never have met in my daily grind, and exploring hidden gems in Carmel Valley, Monterey, and Big Sur.
Because my sabbatical goals were to rest, think, and plan the next stage of my life and career, I intentionally did not travel until the end of my sabbatical. I did go to Europe--London, Amsterdam, and Rome--but by then, I had already articulated and put into motion my goals to start my own business, teach law school, and write.
Charting the course for my sabbatical was akin to meticulously planning an expedition to a new world. The investment of time, effort, and willpower paid off. My sabbatical emerged not as a mere respite from work but as a classroom for life, resilience, and personal growth. The next stage of my life began at the end of my comfort zone.
What Came Out of My Sabbatical
During my sabbatical, I discovered a profound clarity of thought that I had long thought lost in the feverish tempo of modern living.
My mental health, once a pendulum oscillating between the high-pressure stakes of my career as a Silicon Valley lawyer and the complex challenges of life, found a steady balance. I had traded the gritty noise of the San Francisco Bay Area for the serene ambiance of a tiny beach house and the decision bore an unexpected fruit: a richer career that basked in the light of newfound freedom and creativity.
Following my sabbatical, I designed and taught a one-of-its-kind experiential law school course on Privacy & Technology at Santa Clara Law’s leading privacy law program, holding court with eager law students, the next generation of privacy leaders.
The glimmering jewel in the crown of my achievement was my writing: countless pages in the form articles, whitepapers, and even a draft manuscript of my first book.
Then the audacious world of privacy tech start-ups called to me, and I answered, venturing into the exciting frontier of privacy, technology, and entrepreneurship. I founded The Rise of Privacy Tech (TROPT), a venture dedicated to fueling privacy tech and innovation. I joined the boards of several privacy tech and Web 3.0 startups. I even Angel invested in several startups and became a fractional CPO in others.
However, my most poignant success lay in the reinforced bonds of my relationships. Friendships, once weathered by time and distance, were revitalized in shared laughter and long conversations; whereas, my family ties, formerly strained by my ambitious and workaholic tendencies, now stood stronger than ever. Away from the hubbub of Silicon Valley, I found a sense of connection that I hadn't realized I was missing.
“When you see someone often flashing their rank or position, or someone whose name is often bandied about in public, don't be envious; such things are bought at the expense of life. ... Some die on the first rungs of the ladder of success, others before they can reach the top, and the few that make it to the top of their ambition through a thousand indignities realize at the end it's only for an inscription on their gravestone.” -Seneca, On the Brevity of Life
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In sum, sabbaticals are more than just an extended vacation; they are the reset button our work-driven lives need. They are strategic investments in our workforce and in ourselves. After all, the human brain is not designed to work relentlessly. It needs a pause, a break, a moment to breathe and recharge. And sabbaticals offer just that. So, here’s to advocating for a healthier, more productive, and more innovative society. A society that embraces the power of the pause.
Select Sabbatical Planning Templates & Resources
Below, I’m sharing with my subscribers my sabbatical planning templates and resources.
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