On the Eight Stages of Sabbaticals — Part 1

sabbatical[NOTE: This series of posts first started in 2013 on a different blog, Free Agent Economics, which is now no longer online. I am re-posting here, with a few updates, for all those friends and interested folks who’ve asked me about my sabbatical approach.]

When Walter White of ‘Breaking Bad‘ (US TV series) needed to start a lucrative new career, all it took was an enterprising young partner with the appropriate connections, some easy-to-acquire lab equipment and a lone Winnebago out in the desert. For the rest of us trying to switch to new careers/ventures – lucrative or not – things are not quite so, well, serendipitous or easy (unless, I suppose, you’re considering a similar line of work to White’s, which, for the record, I do not recommend).

Some time ago, I left a longstanding corporate career to take a break and head into a new direction. These days, when I meet new people, there are often many questions as they learn about my life changes. No, this does not bother me at all. On the contrary, I find it most interesting that a majority of these people sigh wistfully about how they’d love to take some time out and pursue a passion, start a business, travel or just take a break. So, I don’t respond with a glib “Why don’t you then?” because I know how difficult it must be for them to not give in to this urge — as it was for me to even consider it, let alone plan it and then do it.

Additionally, the slowly-growing prevalence of companies offering sabbaticals to employees as part of their benefits packages (I have worked for two such firms), has begun to make this a more socially-accepted norm beyond the traditional field of academia.

Based on the questions I’m asked often, I thought it might help to share specifics of how my personal sabbatical experience became possible, particularly for those looking for more than a how-to (although, yes, I am framing my posts in the latter context). I do not claim any sort of expertise in sabbaticals and there are definitely plenty of books/resources out there (a set of useful links will be included in the final post of this series). That said, when I was wavering on the edge, it was the personal stories of a couple of other sabbatical-takers that helped me more than any books/sites, so this series of posts is in that spirit of personal sharing to pay it forward.

The Eight Stages

sabbatical airplane

Let’s break this down into a few stages. In hindsight, things did not unfold quite so neatly for me when they were actually happening (coherence and causality usually become clearer in the aftermath of tumultuous events, don’t you think?) and I wish I’d thought of a way to understand/develop these stages much earlier. Let’s also use the analogy of an airplane journey to define specific sabbatical stages as follows:

-2 Decision — This pre-sabbatical stage requires 4 key sub-decisions – the reason(s) for and the type of preferred sabbatical, the physical location(s), timing and desired length.

-1 Preparation for Boarding — The pre-sabbatical financial, logistical and relational steps needed to get ready to take off.

0 Lift-off — Starting the sabbatical and figuring out various initial and necessary changes in lifestyle, habits and identity.

1 Altitude — The first few weeks/months of the sabbatical where the required ongoing adjustments to lifestyle, habits and identity drive/determine pace, satisfaction and future vector and acceleration.

2 Cruising — This is where things should be settling in somewhat and going well. But, there are, potentially, some new things to watch out for so that we can maintain our set pace, vector and acceleration and manage any unexpected turbulence.

3 Preparation for Landing — As with all journeys, preparing for a smooth wheels-on-ground requires various checks and a revisit to the financial, logistical and relational steps of Stage -1, but from a slightly different angle.

4 Landing — Getting back on solid ground and taxi-ing in to our destination, whatever that might be. And, as we begin to close out this transformational journey, we have to decide what we take with us, what we leave behind and where we need to go next to make the most of what we’ve gained (or lost, as the case may be).

5 Post-landing — We’re there – whatever “there” means to each of us. We’re still watchful but we’re also very hopeful at this stage. So, we need to balance the cautiousness with the hopefulness (both for ourselves as well as for those around us that matter or have taken this journey with us) to avoid getting mired in the same old, same old problems we faced prior to our journey.

Each of these stages merits individual blog posts and I anticipate adding/updating these over time based on comments and feedback. Today’s post will focus on pre-sabbatical Stage -2.

Stage -2: Decision Stage

sabbatical decision

In addition to the type of sabbatical and your reasons for them, it is helpful to figure out the physical location(s), timing and the desired length as well. Having clear ideas for these sets you up better for the subsequent stages of the journey. But, more importantly, the thinking-through gives definition, clarity and shape to your aspirations.

1) Reason(s) for and the Preferred Type of Sabbatical

People come to this life-changing decision in different ways and for different reasons. Designer Stefan Sagmeister once explained how and why he takes sabbaticals every few years. is an excellent resource site and offers a list and descriptions of various types of sabbaticals. There’s also this interesting trend being called “early retirement” but is really just another sabbatical (Please. Who retires at thirty-two and says they expect to have many more retirements? Excuse me for getting tied up in semantics here, but it is rather misleading). It could be simply a sort of temporary escape. Or, perhaps a way to get through your personal bucket list. Whatever your reasons might be, at the very least, you need to get clear about them. This is easier said than done, particularly if you are operating with a more-than-full slate of professional and personal obligations that are draining both your physical and intellectual resources. Figuring out the type of sabbatical you want is a good starting point. Sticking with the flight analogy, it’s like deciding which airline you’re going to fly with for your desired journey, given the multiple choices/routes they may offer.

2) Physical Location(s) for Sabbatical

If you’re going to travel or start a new study program or a new business, you will need to determine where in the world you want to do any of these things. While finances, family and other ties, lifestyle preferences and mobility may restrict the physical location(s) you are able to consider, I strongly encourage exploring possibilities beyond your usual and comfortable boundaries. This is a big life change for most people and, to make it truly worthwhile, it ought to be somewhat transformational. The world is not as big and daunting a place as it once was. Evolving mobile, local and social technologies continue to enable increasingly efficient and functional virtual lives. Do look beyond your usual environment.

My biggest regret about my sabbatical is not having spent enough time on this pre-sabbatical sub-decision — not having pushed my existing boundaries enough, given my personal circumstances. So, I’ve had to make a few course corrections mid-stream, and they’ve required some rather intricate maneuvering.

So, invest more time here, research more, talk with others who are doing or have done what you’re considering (it is easy to find such people outside your regular network these days via various social networking sites or search engines). Just don’t get too far down the road such that you get stuck in a direction you don’t much like/enjoy. It bears worth repeating — this is too big of a life change to not make it truly worthwhile.

3) Timing of Sabbatical

When to take a sabbatical is another ponderous question. While it is deeply inter-connected with the other sub-decisions here, it is likely the hardest because sabbaticals are still not mainstream enough to be considered a normal phase of life. I often joke about how Shakespeare’s Seven Ages of Man do not include breaks between the ages and would be that much better if they did, at least in our century. That said, in studying and talking with those who have been successful (in terms of getting to where they wanted to) with their sabbaticals, the most common deciding factor centered around having enough financial stability through a combination of savings, passive source(s) of income, or a supporting and high-earning spouse/partner. I would add that, after financial criteria are satisfied, it might help to pick a time in life after one has earned a few battle scars which, hopefully, have helped develop a requisite amount of emotional intelligence and fortitude to weather upcoming turbulence.

4) Length of Sabbatical

There are different schools of thought here as well. I know some who decided to take their break in 6-week increments (re-assessing at the end of each period whether they needed/wanted to continue on) and some who did not have any end-dates whatsoever. While, for the most part, your selected sabbatical type will dictate the time required, I’ve found this Buddhist parable very apt when trying to answer this question:

Long ago, in T’ang China, there was an old monk going on a pilgrimage to Mount Wu-t’ai, the abode of Manjusri, the Bodhisattva of Wisdom. Aged and weak, he was treading the long dusty road alone, seeking alms along the way. After many long months, one morning, he gazed upward and saw the majestic mountain in the distance.

By the roadside, there was an old woman working the field. “Please tell me,” he asked, “how much longer I must proceed before reaching Mount Wu-t’ai?” The woman just looked at him, uttered a guttural sound and returned to her hoeing. He repeated the question a second and third time, but, still, there was no answer.

Thinking that the woman must be deaf, he decided to push on. After he had taken a few dozen steps, he heard the woman call out to him, “Two more days. It will take you two more days.” Somewhat annoyed, the monk responded, “I thought you were deaf. Why didn’t you answer my question earlier?” The woman replied, “You asked the question while you were standing put, Master. I had to see how fast your pace was, how determined your walk.”

So, as you see, the decision-making process is not simple and, most certainly, it is uniquely different for everyone. For some, these 4 sub-decisions alone took 1-2 years. For others, like me, they happened over a matter of weeks (although the sense of needing a radical change had been building up over a longer period). If you can afford the time, I advocate a slow-thinking approach, having adopted a faster one myself. A huge part of this thinking/deciding approach is also about gearing up for monumental and difficult-to-foresee changes in lifestyle, habits and identity — something I found myself doing AFTER I’d already started my break, when the changes were already underway. So, yes, this is causing a lot of course-correction as I go along and is not entirely conducive to a smooth ride.

One Last Point About Stage -2

sabbatical success

There is a lot of varying good-and-bad advice out there. Some, like Michael Wolfe, a serial startup founder and serial sabbatical-taker, recommend not having goals/plans and staying mostly unstructured. While I do like his Barcelona sabbatical plan and can totally see myself doing something similar (someday, somewhere, sometime), I personally needed to clearly-define my “there” so that I will be able to recognize it when I get to it. It’s not about creating and checking off to-dos or racking up accomplishments. You have to define, clearly and specifically, what success/arrival will mean for you with such a transition/journey. And, if you’re taking this sabbatical with a significant other or family, then you all have to agree on this definition of success/arrival.

For me, it was about finding a new and interesting professional field in which to learn/grow and, possibly, start my own business. Along the way, I’ve had to course-correct quite a bit due to rushing through this first pre- sabbatical stage, as I mentioned earlier.

Another example: A friend told me her sabbatical aims were threefold: 1) to re-connect with many of the close friends and family members she had fallen out of touch with over the years by having them visit her or visiting them; 2) help her immediate family get more organized (she’s a big proponent of David Allen’s Getting Things Done system); and 3) figure out what she wants to do next.

Your “there” can be as low or high in ambition as you like. It can be a simple high-level list like Wolfe’s, a specific goal like mine or a more personal aims like my friend’s. Just make sure you know what and where “there” is so you get that sense of personal satisfaction and completion when you finally experience it.

Stay tuned for the next Stage. As always, I would love to discuss this further with you in the Comments section below, so, please do share your thoughts.


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