The importance of a mid-career sabbatical (especially for Type A Millennials like myself) and how to make the most of it towards Ikigai

Massimiliano Hasan
7 min readJul 7, 2021

I recently embarked upon a new chapter of my life: a mid-career sabbatical AKA professional hiatus AKA work break. This is the first time I’ve done such a thing and I’d like to use this post to share how I came to make this decision, as well as how I plan to make the most of it as I pursue Ikigai, a concept that is

“… culturally defined in the society of Japan as a comprehensive concept describing subjective well-being. It is considered to be related to life-satisfaction, self-esteem, morale, happiness as well as evaluation towards meaning of one’s life” [reference]

Ego, Enmeshment & Burnout

The odd-numbered years of my 20s are marked with the ambitious Type A archetype’s laundry list of bragging rights…

  • 21: awarded an academic merit scholarship to pursue a Master’s degree at a top business school
  • 23: graduate with high distinction and start working in Silicon Valley at one of the largest technology companies in the world
  • 25: get promoted, stock options and a six figure income to ensure that I can actually afford the San Francisco Bay Area lifestyle
  • 27: former employer IPOs, while I head multiple functions and hire/manage over a dozen people at my new employer
  • 29: attain VP & Chief of Staff roles and accepted into the top university to study & research development economics under Nobel laureate professors

A superficial scan of these 5 achievements would suggest that I’m happily chugging along the success train; yet, despite these milestones, I was beginning to feel adrift and unfulfilled as I close out my twenties. The global pandemic and the loss of my grandfather didn’t help either. My initial response to this was to pursue a yoga teacher training (while still working) to cultivate more mindfulness by deep-diving into a moving meditation practice. However I failed in 2 key ways: I wasn’t able to truly introspect because I was still so caught up in my day-to-day work responsibilities and—more importantly—I still tied my identity to my professional achievements, a psychological phenomenon known as “enmeshment” which this HBR article on career and identity describes so well:

Many people with high-pressure jobs find themselves unhappy with their careers, despite working hard their whole lives to get to their current position. Hating your job is one thing — but what happens if you identify so closely with your work that hating your job means hating yourself? Psychologists use the term “enmeshment” to describe a situation where the boundaries between people become blurred, and individual identities lose importance. Enmeshment prevents the development of a stable, independent sense of self. While identifying closely with your career isn’t necessarily bad, it makes you vulnerable to a painful identity crisis if you burn out, get laid off, or retire. Individuals in these situations frequently suffer anxiety, depression, and despair. By claiming back some time for yourself and diversifying your activities and relationships, you can build a more balanced and robust identity in line with your values.

This corporate burnout is not uncommon and the sabbatical is certainly one antidote that seems to be growing in popularity anecdotally.

Realization, Sabbaticals & Ikigai

As not only a “Type A” Millennial but also the eldest son and grandson as well as a Capricorn (for those who believe in that astrology stuff), it was hard for me to put aside my subconscious familial expectations, workaholic tendencies, and achievement anxieties to really embrace the idea of a sabbatical. Coming to this realization was not something that came naturally to me and only began recently after reconnecting with my former leaders—three of whom are currently on sabbaticals themselves as well—wherein the idea of taking a career sabbatical became de-stigmatized to me…

There’s an excellent podcast from my former leader and sabbatical evangelist, Pak Djemi who credits sabbaticals with realigning his career with a sense of spiritual purpose; and there’s ample evidence to argue that his sabbaticals yielded great success, given that he launched several impactful businesses such as Jenius, BTPN Syariah, BTPN Wow!, and Daya after coming back from his hiatus. Similarly, another former leader of mine and sabbatical frequentist, Aldi, credits his breaks with major pivot points in his career, including launching Mapan. Finally, my former manager and mentor, Ben, has coached me and demonstrated that one can still be engaged professionally in a lighter-touch way throughout a sabbatical via advisory roles.

If these three highly successful individuals (all of whom I have the privilege of calling former bosses) could decouple their identities from their professional lives in pursuit of more introspection and mindfulness via a sabbatical then why couldn’t I? Thus, I finally felt emboldened to pursue one myself with the intention of ascertaining the ever elusive Ikigai in my next professional role by focusing on academics and mindfulness.

When I reflect on the above chart, I realize that I’ve spent a lot of time meandering near the desirable Ikigai center but not quite ever reaching it. For instance, when I was at Kiva my passion and mission were aligned but I couldn’t quite build wealth there. Furthermore, at Gojek I started off within the overlap of mission and vocation, wherein I quietly dealt with impostor syndrome while working on products that were solving real high impact issues for a large set of users. Then, as I got better at my job and as the organization evolved, it was more around the overlap of profession and vocation. Despite never fully achieving Ikigai, I consider myself tremendously lucky that I got so close at a relatively young age. While I have a rough idea of what my Ikigai looks like by combining my professional skills in data & analytics, with my passion and societal need for poverty alleviation, I have yet to figure out precisely what that looks like in practice. Hence, I do realize that in order to progress closer towards that desirable center, I need to slow down and introspect first…

There’s nothing wrong with pressing the pause button to scratch intellectual itches and/or explore other passions because of the fact that we spend 3/4ths of our adult life working. If we spend all of our time blindly climbing the corporate ladder, we might inadvertently lose sight of what keeps us grounded with a sense purpose. Because we spend so much time working, shouldn’t we pursue an occupation that is a passion, a mission, a vocation as well as a profession? Isn’t that worth reflecting on?

Guidelines & personal OKRs for effective sabbaticals

So how does one Sabbatical-ize effectively? Sabbatical veteran Pak Djemi summarizes 3 key tips for having a successful sabbatical:

  1. Clarify your goals and questions that you aim to answer (ideally these include spiritual ones as well)
  2. Ensure that you have a companion to guide you through this period (ideally someone who has gone through it before)
  3. Set a time limit (ideally 6 months or more)

My ENTJ interpretation of how to do this effectively was to leverage Objectives & Key Results (OKRs)!

For those unfamiliar with OKRs, they are a goal-setting framework popularized by Andy Grove, John Doerr, and Google (great reference here). Typically they are used in a professional setting, but can be used for, well… anything! This was was actually the first time that I set OKRs outside of work but it was helpful in framing my goals and putting structure around what would be an otherwise unstructured career hiatus…

The link is here if you’d like to explore in detail.

While my friends might roll their eyes and dismiss these OKRs as “such a Max thing to do” I actually hope that this framework can inspire others with my personality quirks to consider as a tool for better articulating and measuring their personal goals—whether within the scope of a career sabbatical or not.

To close, I think it’s important to note that even thinking and intending to embark on a career sabbatical in pursuit of Ikigai is certainly only reserved for those with a degree of privilege as it takes resources (financial, mental, etc.) to even ponder such questions. The vast majority of humanity will most likely never reach the center of those 4 concentric circles. This is actually a big reason why: A) I hesitated to even embark on a career sabbatical to begin with & B) I am so keen to deep dive on studying poverty alleviation, since such a reality wherein most individuals are unable to realize meaning and purpose through their life’s work is inherently unjust in my eyes.

I am excited to see what I am able to achieve in the next year of refocusing my energies on my academic, intellectual itches while balancing such ambitions with a healthy dose of activities that manifest my physical, mental and spiritual health in parallel.

I hope that this piece was inspirational and informative!

If you’d like to connect with me while I embark on this journey to chat further, you can reach me at my personal email: or academic email: