This very week 7 years ago was momentous for me. After 13 years at Microsoft I took my first prolonged break from work.

It was a true “sabbatical” which according to Google is defined as a sustained period of paid leave for every seven years worked. I was overdue by almost double! My intent was to resign, not out of anger or spite, but based on an insight that it was time to step off the corporate track and live in a different way.

My boss, who was remarkably wise, talked me out of it, encouraging me to take a paid work break that I’d earned, with the option to return to a new leadership role after a few months. Microsoft, my employer, did allow sabbaticals for people who were strong performers at a certain level and tenure at the company. Most people I knew never took them. It never occurred to me that it was even an option until it was presented. To me a sabbatical always unconsciously felt like a career failure. I was very wrong.

Taking The Leap

Looking back on that day in September, as I said goodbye to my team (it took about a month to transition my work and team management responsibilities to a new leader) I ventured out for what was to be three months of unplanned living. It was my first experience in life with such an uncharted road ahead.

Even as a child, summers came with the specter of the impending start of the next grade. From the ninth grade onward, summers were spent at a regional college campus, cramming in more knowledge to get me ahead of the pack academically. I vividly recall sitting in a college-level introductory computer science course during an intolerably hot summer at Syracuse University, all of 15 years old, thinking “What the hell am I doing here, I should be at Darien Lake with my friends!“. During college, I was always working – focused on landing strong internships that would set me up for the inevitable career ahead.

This time, I really didn’t know what would be next. I would need to carve out a new role at Microsoft, should I return. Very quickly, it became clear that I needed more time away and stepped away from Microsoft permanently.

This began a lengthy journey of exploration, travel and wonder – punctuated by prolonged moments of “Oh shit, did I just throw away most of my life savings and a career I worked so hard to gain!” Side note: For those that aren’t aware of how compensation works at most technology companies, for those who are rising steadily up the ranks, there is the frequent doling out of “restricted stock units”, that are both enticing but also serve to keep one attached and loyal to the firm as they only “vest” (are accessible) over several years. When I resigned, I also said goodbye to most of my net worth as it sat dormant as unvested RSUs.

It’s now been seven years since that day I went on my sabbatical. Since that time I’ve had over 100 (yes, I keep track!) conversation with former colleagues, friends, friends of friends and complete strangers about their interest in taking career breaks. I’ve coached plenty of people through this process as well. In some cases, they fell back in love with their work. In others, they realize that breaks are natural, and take the leap into the unknown for prolonged periods of exploration and getting back in touch with what it’s like to wake up on Monday’s without a “daily standup” on the calendar or executive reviews to prepare for!

I’d like to share a few thoughts on sabbaticals, as I’ve experienced a lengthy one myself and many more vicariously through the eyes of clients.

Breaks Are Natural, And Vital

There is a sadistic life plan that goes something like this: Study hard for 20 years so you can get a great job. Work hard at the job for another 30-40 years so you can retire. Then, cram in all the things you are inspired to do while your joints, lungs, heart and brain are still functioning. Hope your life partner is still healthy enough to do the same. This is a deferred life plan. It’s barbaric when stated as such. Yet, it’s exactly what modern society considers normal.

News flash, life doesn’t operate mechanistically. Machines work consistently, for prolonged periods. Life isn’t mechanistic. It’s organic. Explore any organism or ecosystem and you will realize that there is always a period of rest interleaved with periods of effort. I’m typing these words in late September. Out my window I can see the trees preparing to shed their leaves. Regeneration will soon follow. Wounds will be healed. Preparations will be made, deep inside the root systems, for a flurry of growth come spring.

For humans, winter never comes. It’s perennial summer. We broil under the intense heat of such a life.

Wherever You Go, There You Are

There is no escaping one’s mind. You can be happy as a clam in a busy office and pissed off on a tropical beach. I’ve experienced this personally.

A few months into my sabbatical, I officially said goody to Microsoft and turned in my “blue badge”. My wife and I started what we thought would be 6 months of travel, mostly overseas. A few months in, while galavanting around Southeast Asia, without a supposed care in the world, I realized that I was utterly miserable.

What’s wrong? My wife asked.

Me: I’m trying to figure out what we are going to do when we get home in a few months. We’ve rented out our house for the year. Where are we going to live? How much money can we afford to blow through? When will we need to start work again? What should I do for work? We have been here for a while, where should we go next? I’m trying to figure all this out and I feel like I’m going crazy!

Wife: Maybe we should just relax and trust that we’ll figure it out, just like we always have…

Me: [not saying anything for a long time, but silently stewing in my mind, coming to the realization that I was treating my sabbatical like a product to be designed and reverse-engineered instead of an exploration to be enjoyed and trusted]…

Me: You’re right, I need to chill out…

There is no force in the universe as powerful as the human mind. I’m not speaking hyperbole. We are literally creating the universe through the quality and content of our mind in each moment. Taking a break from work is no guarantee that your mind will obligingly follow along and bring never-ending joy and relaxation to the table. In my experience, the state of mind that one carries in their daily work will persist, and often be amplified, during a sabbatical.

The great meditation teacher John Cabot-Zinn has a wonderful book titled, “Wherever You Go, There You Are.” That pretty much sums up what I’m trying to say.

If you are contemplating a career break, and it’s coming from a profound sense of stress, start by learning how to cultivate a more intimate and productive relationship with your state of mind. Learn how your mind is completely defining your experience of life. This goes well-beyond meditation, though such a practice can help.

If you cannot find a way to cultivate a peaceful state of mind before taking a career break, make sure you’re at least continuing to invest in such an exploration as you pursue your sabbatical.

Success (or whatever you’re after) Can’t Be Planned

I kept a journal during my sabbatical. This documented my thoughts about where we should live and what I should be doing for work. It’s astonishing to think how wrong my initial impulses were regarding what I thought my new career would be. Beyond career, I was wrong about a lot of things. When I first went on sabbatical, I seriously thought I’d move back to Seattle after a bit of travel – returning to the home we just bought before leaving town (we rented it out for the time we were traveling). I thought I’d be working as a “head of product” at a tech company (not Microsoft, but perhaps a startup or another large tech company).

I thought I knew what I really wanted. Turns out this was just my ego playing games.

As time went by, more clarity emerged, both regarding what I wanted and what I didn’t want. I wanted sunshine and more of an outdoor lifestyle. I wanted the capacity to directly impact people’s lives. I wanted a greater sense of freedom for my work, where I wasn’t chained to a building or desk for a set number of hours per week. I also wanted to be on a learning curve that was innately challenging and interesting. I wanted just enough money to not worry about it.

In hindsight, these words seem so clear to me. However, the journey itself was not so clear when I was on it. As Steve Jobs said in his often cited commencement speech about living an inspired life, “you can’t connect the dots looking forward, you can only connect them looking backward”.

Clarity does emerge, though it takes the capacity to listen deeply to oneself and notice where innate interest and desire is showing up. 6 months after leaving my job I was pretty clueless. After 12 months I was gaining clarity, enough so that I started seriously exploring coaching as a profession. Within 18 months, we had chosen a new location to live and I had several clients and was officially “in business” with more than a career, an actual vocation. Life was moving ahead in a new direction.

Perhaps the biggest mistake I see with people taking sabbaticals is the “preemptive close”. Living in uncertainty can be uncomfortable, to the extent that people prefer to be administered guaranteed electric shocks than deal with the uncertainty of having only a slight chance of getting zapped. However, with the proper state of mind, it’s also the very place from which deeper insights about how you wish to live and work can emerge. If you can help it, don’t rush to make a snap judgement about what you are going to do next. Allow the insights to emerge organically while simultaneous learning how to listen to the signal amidst the noise.

Ask Bigger Questions

If you want more clarity, pay attention to the quality of the questions you are asking consciously and subconsciously. The more clear I became (along with my wife!) regarding what a “great life” looked like, the more clear I was able to be regarding what “meaningful work” looked like. “What does a great life look like?” can appear to be a frivolous question, relevant only to the most sheltered and entitled of humans. I completely disagree. This is a vital question that everyone should be sincerely asking and exploring for themselves (and together with their families) regardless of socioeconomic status or age.

When I struggled with my answer to “What do I want to do for work?” I shifted attention to making sure I was living a life that was interesting and joyful. While it’s true that one can realize deep insights through pain and suffering, it is not required. In my opinion, the more skillful humans become at getting back in touch with living a life full of aliveness and connection, the more obvious the question of work becomes.

A great career, over the long term, must fit into a great life. I’ve never seen a wonderful career perennially blossom in the midst of a garbage heap of life piled high with stress, regret and indignation.

Learn To Trust Yourself

I’m saving the most important lesson learned for last. Trust in oneself is the antidote for insecurity in a career transition.

As it became clear that my future work would look very different than what I did prior to my sabbatical, there were only two logical responses. One was to respond with my intellect, which has the tendency to plan, deconstruct and reverse engineer a path to safety. There is a temporary comfort that the intellect can offer, but it’s transient in the same way that a hot bath can feel good, but eventually, you need to walk around the world with your clothes on! Trying to sort out the solution to a non-linear problem (like how to redesign one’s life!) is going to be a painful experience when the intellect is leading the charge.

The other path, and what I chose, was to trust something far deeper than my intellect to get me through the uncertainty. There are many moments, where trust played a paramount role in my journey from Microsoft to whatever you call me now (independent Executive Coach for the time being!). The more we look to society (including friends and family) to tell us what to do, we will continue to be swayed by insecurity. There is a quiet power in being present to the world and listening to others, while simultaneously allowing that small and still voice within to shine. As hokey as it seems, trust in one’s capacity to navigate life well is the only lifeline we need.

I hope that this post has inspired you to at least consider the option of a career break. It is not the right answer for everyone. You might love your job. You might be in the midst of an important project that demands your commitment. You might need to keep up with a steady paycheck.

I get it. I’m not trying to get anyone to jump ship, but instead, to realize that breaks are important, and when done well, can reorient you to life in a way that helps you bring more of your full capacities as a human being to work.