Life Sabbatical Series 2: Tactical and Oh Shit Questions to Ask Yourself When Planning a Life Sabbatical

Thanks to everyone who read and shared and commented and reached out in response to the first post I shared in the Life Sabbatical-ing series, What’s a life sabbatical and who is “allowed” to take one?  Your feedback has really encouraged me to keep exploring and sharing on this topic. Please keep the feedback coming!

One excellent result of sharing the first blog post has been connecting with some other folks who are planning or have taken a life sabbatical (even if they didn’t call their experience a "life sabbatical"). And it's been awesome to talk with people of different demographic backgrounds and who are at different life stages about how they approach taking a period of dedicated time to reflect on key questions they have about their lives as well as how they wanted to use the answers they discover to  shape of their life going forward.   As the blog series continues, I’m looking forward to asking some questions to these folks about their experiences of life sabbatical-ing and sharing their stories here.

Speaking of questions, that’s what this post is all about.  Something I have learned over the years is that there are many types of questions.  Some are factual ones that enable the sharing of information (“What time is it?”), others are opinions disguised as questions (“You think he’s smart, right?”), and others are big and juicy enough to frame months or years of learning and action (“How might we shape an equitable future for our city?”) 

When planning for a life sabbatical, I’d offer that there are two types of questions to consider: the tactical ones and the “oh shit” ones.


Tactical Questions

Let’s start with the tactical questions. Tactical questions yield specific answers and will help you build the scaffolding on which you’ll design your life sabbatical.  You may not have the answers to the tactical questions today, but if you spend some time and energy, you know that you’ll be able to come up with them. A notable quality of tactical questions is that they do not change who you are, but they may change what you do for a specific period of time. Another is that the answers may not be static, especially once you actually embark on your life sabbatical.

When it comes to planning for your life sabbatical, here are two, core tactical questions to consider:

Detail of Street Art in Raval, Barcelona, Spain

Detail of Street Art in Raval, Barcelona, Spain

  1. Who is my support structure for my life sabbatical?  Said another way, who will be my people, my cheerleaders and thought partners? Who will show me love and empathy when I am worn down or questioning my decision to life sabbatical?
  2. What resources am I willing and able to invest in my life sabbatical?   Yes, money and time are important, but there are other things to consider like comfort, relationships, and sense of identity.  Like question 1, the answer to this isn’t static and will likely change while sabbatical-ing.


Oh Shit Questions

For me, an "oh shit question" (henceforth also called an OSQ) can fall into one of two categories – it can be a query that’s so insightful that I’ve never even thought to ask it before, or it’s a question that has hit on a subject that is so important that it scares me or seems like too much work and I’ve been avoiding it.

The other characteristic of an OSQ is that no matter how good a talker you are (and I’m a pretty good talker) you can’t just think really hard and answer it.  Whereas tactical questions might change some behaviors in the short term, OSQs are big and perspective changing types of questions.  They get at the core of who you are and want to be and ask you to learn about yourself and, potentially, grow and change behavior for the rest of your life.

Angels, Madonna, Child, and Post-it Note, Florence, Italy.  If you can't make it out, the note says "Believe!"

Angels, Madonna, Child, and Post-it Note, Florence, Italy.  If you can't make it out, the note says "Believe!"

If the prospect of OSQs is anxiety-producing, you're not alone.  Growth and change can be beautiful, but it can also be hard.  I'll share with you some of the wisdom that my coach Melissa Maher shared after posing a mind-bending OSQ to me: don’t even try to answer this question right now. Write it on a post-it note, and put it somewhere that you’ll see it every day.  Read the question out loud each morning and set an intention to notice what you are experiencing in your life that relates to that question.  Don’t force it, our brains do powerful work even when we’re not paying specific attention. When the answer emerges, you will know.   

As a high-achieving, type-A person, I was skeptical. But I trusted my coach and the process and realized that I couldn’t schedule when I would have the answers.  And when they did emerge, it was something entirely new to me.  The answers were fully formed, and I was very clear and confident and excited about what I needed to do.

So, just as there are two core tactical questions for planning a life sabbatical, I also believe that there are two essential OSQs:

Being open to the world (and scouting for a pack of elephants), Okavango Delta, Botswana

Being open to the world (and scouting for a pack of elephants), Okavango Delta, Botswana

  1. What am I trying to learn or explore through my life sabbatical?  If you are anything like me, you will identify 2-3 questions that will be foundational to how you design your approach. These are oh shit questions that are inspiring you or weighing on you or which you feel called to answer.
  2. Where or in what contexts am I most open to the world?  Where, doing what, and with whom are you most joyful, energized, and/or curious?  Reflective, challenged and/or surprised? Most willing to accept feedback, criticism, or be uncomfortable?  Notice these people, places, and activities, because you’ll definitely want to make them part of your life sabbatical experience.

If the answers to the tactical questions provide a scaffolding, the answers to these OSQs will help you to design the life sabbatical experience for which that scaffolding provides support.

And if this is feeling too theoretical, don’t worry.  In future blog posts (which I'm going to try and do bi-weekly), I’m going to go deeper and share concrete examples from my own experience relating to each question I posed today. Stay tuned...

Let me know which of the four questions you’d like me to explore in my next post!  And if you are planning or you’ve taken a “life sabbatical” are you interested in being interviewed for the site?  Leave a comment, or get in touch via emailTwitterInstagram, or LinkedIn.

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