Why I Took a Mid-Career Sabbatical and Why You Should Too

One thing that the world of startups (and/or being poor) teaches you; is efficiency. How to do more with less, and how to make the absolute most of what you’ve got, be it time, money, or leverage. And while a 6-month sabbatical in the middle stages of your career might sound like a terribly inefficient thing to do, in the grand scheme of things - it is the most efficient thing you can do for your career. The most successful people I’ve met understand?—?it is not simply how hard you work, but rather what you work on that has the biggest impact on your success.

Thus, a career recalibration, or purpose recalibration?—?is an imperative activity to re-centre, re-focus, and fuel your greatest strengths (ideally backed by a clear purpose) into a singular high-impact stream of work.

Why Carrer Recalibrations are Necessary

Many people start in a career or industry that they were convinced into by their parents, friends, society, or themselves, and end up hating it but feel that they are too far in to change course. The reality is it’s never too late, but it does get harder to re-learn, and pivot the older one becomes, this is why I don’t believe people should wait till their comfortable 50s to take a sabbatical.

“Life happens to us, until we decide to take a step back and put real intention into designing the life we want?—?then we make life happen for us.” I think me?

Most people live a life so full of work, followed by distraction, that they have no time to ever think, reflect, or go deep inside themselves. Extroverts are at higher risk of this than introverts due to the amount of their time spent outside of solitude. Men are at higher risk than Women, naturally being less self-reflective and (GENERALLY) less in touch with themselves and who they truly are.

I would urge people to consider this curated recalibration period as a strategic long-term investment in their overall quality of life.

Attention GenZ: Please do not take a sabbatical after working for 2 years because you don’t LIVE, LAUGH, LOVE your job.

Our Addiction to Productivity

I must admit, I fell into the trap. After years of subscribing to the American, hustle culture, I became another career-obsessed robot, where my worth and purpose were tied solely to the success of my career pursuits. I became a person so far off from who I was and what I was.

And this is not even the world I was raised in by my parents, quite the opposite (a Hassidic group which encouraged very little secular education). So one can’t imagine how ingrained this identity-crushing societal phenomenon is for people who were raised through the modern secular system.

I only truly realized this when I couldn’t believe how hard it was for me to not be productive on my sabbatical. Initially, I could barely go a day without some form of productivity, even if it was reading non-fiction or doing an online course - there simply couldn’t be a day of pure leisure (aside from Saturday) #jewishguilt?;). I had to challenge myself to attempt to have a day that did not include some type of work, be it self-development or educational.

From a psychologist’s couch, this may be diagnosed as a ‘lack of self-worth’, and from the mat of a Buddhist, it may be described as ‘attachment to the external’. The common theme, however, is the phenomenon that the modern world is all too familiar with, and that is?—?your worth is defined by your productivity.

Now while I am still a capitalist, albeit more of a ‘hippie capitalist’, I do believe it is important to make a distinction between one’s market worth in the world of work, and one’s worth as a human being.

We seem to have conveniently conflated the two.

Note: For ambitious types like msyelf, this can also be an internal need to create and produce which is a good thing, but has to be managed and channeled correctly during times of rest.

What it is, and What it is?Not

I believe it would be a grave shame to spend your sabbatical just watching your favourite TV shows and being a couch potato. I also believe that for a sabbatical to be effective, it must include some degree of solitude. You don’t have to go as extreme as me and meditate in the wilderness without human contact, but when we are surrounded by others constantly, it is harder to truly discover ourselves.

And when it comes to career or any other type of life recalibration?—?the first step is to understand oneself deeply. No small task.

“Your fullest life, then, is one where your loves and your work flow in an infinite loop,”. “The energy of one fuels the energy of the other. Thus, the only way you’ll make a lasting contribution in life is to deeply understand what it is that you love. And the inverse: you’ll never live a life you love unless you deeply understand how to contribute to others.”

Marcus Buckingham in Love and Work

The reality is, that what spurs one into a sabbatical will ultimately determine the type of sabbatical they take. As with most things in life, the intention is where the outcome begins.

Hence why I strongly suggest hiring a coach who will help you uncover your deeper desires, generate clarity, and partner with you to make the experience as impactful as possible in the long term. (This doesn’t indicate an inability to do it alone but indicates your proclivity to efficiency, self-growth, and purposeful living).

Harvard’s research on The Transformative Power of Sabbaticals?—?includes three different types of sabbaticals and content on their effectiveness:

1. Working Holidays

People who were pulled into this type of sabbatical did so to work on a passion project (for example, to volunteer for a think tank or found a start-up). During a working holiday, they alternated between intense periods of work and dedicated breaks to rest and rekindle long-neglected relationships. For instance, one interviewee interspersed hunkering down upstate to write a novel with visiting New York City to have fun, connect, and decompress.

2. Free Dives

People who fell into this category were pulled into their sabbaticals by wanderlust. Having read inspiring memoirs or having heard friends’ stories, they reached the point where they “needed an adventure and a kind of a soul reset.” As one told us: “It’s now or never.”

3. Quests?

The third group had the most dramatic transformations. Questers weren’t pulled into projects or adventures but pushed out of work by unsustainable expectations and toxic organizational cultures. Exhausted and burned out, the sabbatical was a last resort because continuing on their current path was untenable.

My Sabbatical Journey

My quest, or ‘creative sabbatical’ as I called it, was both spurred by the closure of my startup company, as well as my burnout after not taking a holiday for nearly four years. There was also another important task that I had to attend to, and that was focusing on strengthening my recovery and tending to my mental health using more natural and holistic methods. This meant a good part of my sabbatical was emotionally draining and mentally painful, but luckily I did not have the pressures of work and I had positioned myself in beautiful nature which made it more bearable.

I called it a creative sabbatical because I was going to focus on my long-lost artistic side?—?the side I nearly pursued before going into the world of tech and business. It was a creative rebirth or ‘creative recovery’ of sorts (for this I may recommend The Artists Way by Julia Cameron). I essentially fast-tracked what I was going to revisit after retirement or after my first exit. In my early twenties, I had attended a prestigious theatre school in NYC and was seriously stuck between a career in the arts or business. In the end, I chose business for many reasons, namely because I always planned to build a family and the probability of ‘making it’ through film-making or screenwriting was too low, compared to business.

Here are some creative projects I started during the sabbatical.

1. Docu-Series; Depicting the psychological links between extreme religious groups, addiction and creativity - told through the lens of a Jew, Muslim, Jehova’s Witness and Amish.
2. Podcast; with my good friend, mentor (and trained psychologist), talking about the deeper things in life with a bit of banter sprinkled in. (since taken this down and paused publishing)
3. Standup Comedy: I performed my first standup show at Hotel Cafe in North Hollywood after revisiting all my years of written material and doing some open mics and improv.
4. Blog/Vlog: I started to edit and publish some of my journals, and also joined Instagram where I started talking about things that are important to me; topics like mental health, entrepreneurship, creative expression and life in general.
5. Playscript: I started writing a one-man show called “Mini-Me” which was inspired by my 15-year mental health battle, where I ultimately found peace through meditation and not medication.

In addition to the creative projects and the addiction recovery work, I spent time journalling/reconciling a lot about my life and my choices, trying to understand my journey until then on a deeper level. Not for the purpose of rumination, but rather to rediscover my authentic purpose. Part of that of course was to start thinking about my future and which career to pursue after learning that being a tech CEO wasn’t the one I actually wanted.

When the Fun Ends (or Begins)…

The first three months I actually vowed to not think about my future career, however as fate would have it, two months later I found myself on a 13-hour train ride in the middle of Ukraine listening to the sounds of drunken soldiers and the symphony of war playing in the background. No, I never became a mercenary, I was visiting factories to export Ukranian products to the UK on what I thought was perhaps a part of my new purpose as the opportunity was a truly serendipitous one.

Although I sketched up about five new potential businesses, the one that formed which was most aligned with my purpose and beliefs was Africovery. A vehicle by which to bring more people to the African wilderness (safari) to heal, to reset, and to find their purpose. Through this, I can also do my part in supporting the fight against Rhino-poaching in Southern Africa.

I also decided to qualify as a coach with the ICF and AIP, blending both my highly pragmatic side and my spiritual side - to craft an offering aimed at helping other entrepreneurs, executives and creatives.

My Sabbatical Recommendations:

• Goal-focused sabbaticals?—?for me, it was important that I felt proud at the end of it, that I had accomplished something, internally or externally. You want to look back and think, “wow that was a beneficial period of my life”, whether it produced the clarity you needed, gave you back your energy, or you produced something you always dreamed of.
• Hire a coach for the period?—?I am a big believer in the power of coaching (hence why I decided to qualify as one), and for a sabbatical / recalibration period, coaching is a powerful force multiplier.
• Build routine and discipline?—?Make sure to set a schedule and routine to stay disciplined. I took on a challenge to get in shape during this period and to go alcohol-free which produced some incredible (and difficult) results!
• Don’t simply return to the old life?—?I vowed to continue some of my creative projects on the side and stay committed to a more balanced life going forward no matter how uncomfortable it may be inside.

Conclusion

Through this journey, I learned a few things. Firstly, it’s f*cking hard to just sit by yourself for hours on end?—?but SUPER rewarding in the end. I learned just how important the concept of ‘clarity’ is in life (and how powerful journalling can be in its pursuit). Most importantly, I learned that all the answers are within. Depending on how disconnected we are from ourselves, the deeper we may have to dig?—?but they are there. Trust.

“Knowing others is intelligence; knowing yourself is true?wisdom.” Lao Tzu

Only once we cease to operate on default, swayed by what happens around us or ‘to us’, do we take back control. And it feels incredible. It is a lonely and uncertain place at first, but as you rebuild and maintain the courage to stay committed to this new path, you find that the internal wisdom inside will guide you toward your higher self and authentic living.

Much love and I will leave you with this…??

FAQ

• Doesn’t this require a lot of money? I managed to pull it off for not that much, given that I am quite low maintenance in terms of budget, and the majority of it was done in South Africa which is about 70% cheaper than the US. Also through By the Grace of God, I stumbled upon a website that is a platform for housesitting in some beautiful homes and locations all over the world, in exchange for looking after their pets. Also, a special shoutout to the US government and JP Morgan who both gave me a chunk of change after the startup went under that lasted me about a year. But you’ll see when you have more time to cook for yourself, and when you spend time outside the city, you spend much less money. Also worth checking out is Workaways for the adventurous.
• Will it devalue my market worth? I believe if done right it should actually increase your market worth. Here’s how: firstly, if you work as an employee, usually when you switch over to a new company you earn more as opposed to staying with the same company for years and years. Many people rebrand during this time which increases their market worth, and many re-evaluate what they want to be doing in the first place. However, if the inner work is done, there is a high chance that your self-worth will increase after this experience, and ultimately it is YOU who dictates your worth to the market. If the people who are going to hire you think well, they will see you took a career break in order to work on yourself which shows you have a higher propensity to upskill, to continuously learn and grow, and thus provide even more value to them as an employer.

Resources

The Sabbatical Project: https://thesabbaticalproject.org/

Books

• REST
• Work and Love, Marcus Buckingham
• So Good they can’t ignore you, Cal Newport (good for re-purposing careers, not good for following your passion;)

Articles

• https://hbr.org/2023/02/research-the-transformative-power-of-sabbaticals
• Mine on Career fulfillment
• https://thetigersjourney.com/the-bizarre-story-creative-sabbatical/