What I’m Thinking About As I Embark on a Sabbatical

For the last week I’ve been on sabbatical from The Ready. I have approximately 15 more weeks to go. What follows is a slightly cleaned up and elaborated version of an ICBD* exercise I shared with my colleagues before I signed off for the next few months. We generally use it with teams who are preparing to embark on some kind of new project or endeavor together, but it struck me as a potentially useful solo writing exercise, too. The idea is simple, ask yourself the following questions and you’ll probably feel much clearer about what you’re going to do and how you’re going to do it:

  1. What are your intentions for this? Why are you here? Why do you want to be a part of this?
  2. What are your concerns? What are you worried about?
  3. What boundaries do you need? What will help alleviate some of your concerns?
  4. What’s the dream outcome of this endeavor? What will it feel like? What will it look like?


My first day of sabbatical was Monday, June 28th. My last day of sabbatical will be October 15th. I’m not 100% sure what’s going to happen between those two dates and I’m trying to be okay with that ambiguity.

There are obviously multiple very different paths available to me. I could really lean into not having any sort of structure or project and just see where my nose takes me over the next couple months. I’ll undoubtedly find some interesting things to do, read, and explore that I’d otherwise be incredibly unlikely to find in the course of my “regular life.”

I could pick one major project, like writing a book, and use my sabbatical to dive deep into it. It would come, potentially, at the cost of having more relaxation or unstructured time. But when would I have a better chance to focus on something like this?

Obviously, this is a false dichotomy. I’ll probably inhabit both of these ways of being — and others — over the course of these four months. The main thing that I’m holding myself accountable to is simply being deliberate with how I decide to use the time. That doesn’t mean I need to be super productive. I can be deliberate about playing video games, sitting by the pool, or going for long walks. What I don’t want to happen, though, is floating through my sabbatical without ever making any decisions about what I want my moment-to-moment experience to be.

I’m up for some really focused and deep work (for example, I’m sitting down and writing this article) and I’m up for some extremely unstructured exploration. I’ll read. I’ll play some video games. I’ll go for walks. I’ll golf. I’ll probably go work on my brother’s farm for a little bit. I’m trying to hold it all very lightly… yet deliberately.

In broad strokes, though, my intention with this sabbatical is to get Healthy, Happy, and Hungry again. I intend to eat well and move my body such that the version of me that comes out the other end of this sabbatical in October feels and looks healthier than the version who went into the sabbatical in June. I intend to do things that restore my spirit and my outlook on my work and life. And finally, I want to come out of this sabbatical just yearning to get back into the work of my lifetime with The Ready. I want to be champing at the bit to get back into the mix of things and bring my newly restored self to the difficult work of transforming organizations and building a company capable of putting a dent in the universe.


I could write an entire article only about my concerns. I’ll do my best to distill them to the most cogent and urgent.

In some ways, this sabbatical and the fact that I feel like I need it, and maybe have actually earned it, feels shameful. It’s an incredibly generous benefit. I’m already well paid and I sit inside an air conditioned room and mostly look at computers all day. There are so many people who are more deserving of a massive break from work. Why do I get this? What about people like my parents? My fiancee? My brothers? Or folks in truly essential yet low paid jobs that are 10x more physically draining than mine?

I’ve been around since the very beginning of The Ready. I was the first employee so I’ve been in the mix with everything that has happened… and now I’m going to be away for awhile. Will I still have a good reputation when I return? Will I be the only one who ever partakes in this policy and I’ll wear some kind of scarlet letter for the rest of my time there? What cool projects, moments, and things are going to happen while I’m gone?

I’m concerned I’ll feel too much pressure to make my sabbatical “worth it” and dive deep into some kind of work-adjacent project so that I can point to something at the end of it to justify the expense to the company. We explicitly didn’t write detailed expectations into the sabbatical policy but I know that one way I’ll try to soothe feelings of psychic distress and guilt is to make something so amazing and important that everyone thinks, “Wow! Sam sure did a good job on his sabbatical.”

And then, on the other side of that continuum, I’m worried I’ll under plan my sabbatical so drastically that I’ll just kind of float through it, get to the end, and realize I never really did anything worthwhile or truly restored myself. While I know I don’t want to make my sabbatical a super planned and rigid endeavor, I do know that I want to be deliberate about how I spend my time. There are things I want to think about, write, and explore that won’t “just happen.” I’ll need to make them happen if they’re going to happen at all.

Lastly, work has been my primary identity for… basically my entire adult life? I’ve either been working or going to school — or commonly, both — since 2004. I’ve never not worked. I worked through undergrad. When I graduated, I spent the first part of my twenties hustling to make a teaching career work while having graduated into the Great Recession. After beating my head against that intention, often while holding multiple jobs at once, I spent the rest of my twenties going to graduate school while working as a teaching and research assistant and while still writing my website and still taking on coaching clients and trying to start a consulting company and taking on freelance consulting gigs. Then, blessedly, The Ready. And continuing my PhD work while also being the first employee at a company in an industry I desperately wanted to be in but had no experience (cue the imposter syndrome and the manic sprint to self-educate myself into some feelings of competence). And throughout all of this my area of focus has been on the experience of work for other people. How can organizations be better? Are there better ways of working? What does the future of work look like?

So, yeah, I think about work a lot. If I’m not working, or helping other people work, then who exactly am I?


I made it clear to my colleagues (and implicitly, myself) that I’m going to try to take this sabbatical as seriously as possible. Which means I’m not going to hang out on Slack or be checking my work email. Both of those things have been excised from my phone and require some deliberate effort to log back into on my computer.

Although I don’t know the exact shape that this sabbatical will take (and I’m sure it’ll morph over time), I’m committing to sticking to my normal rhythms related to review and planning. Specifically, that means continuing to do my Sunday afternoon weekly review and planning sessions as well as my monthly sessions. They will probably be much shorter and less involved than when I’m working full-time, but they are at least some built-in checkpoints where I can ask myself how things are going and whether I want to make any changes to how I’ve been operating.

I’m also going to keep a very simple daily Sabbatical Log where I jot down what I did each day. I suspect it’ll be an interesting thing to look back on in the future and the act of having to write a few bullet points each evening will help me keep my attention deliberately engaged.

I’m sure I’ll come up with more boundaries over time, but I’ve generally found that the fewer and clearer there are the more useful they end up being.


Luckily, I can think of several different dream scenarios that will leave me feeling like I treated this sabbatical with the respect it deserves and gave me the outcomes I need. I don’t need one specific outcome to feel like I got what I needed from this. As I mentioned in the Intentions section, the pithy one-liner for this sabbatical is “get Healthy, Happy, and Hungry.”

Some characteristics of the dream scenario for Healthy:

  • Lose around 10 pounds
  • Get my cholesterol and triglycerides lowered
  • Get my food sensitivities and allergies sorted
  • Run, cycle, and walk consistently
  • Meditate consistently

Some characteristics of the dream scenario for Happy:

  • Play a bunch of golf and drastically improve
  • Play a bunch of Starcraft 2 and treat it as an arena for deliberate practice
  • Read fiction
  • Spend a significant amount of time in contemplation and writing in my journal

Some characteristics of the dream scenario for Hungry:

  • Use this non-distracted time to develop my skills in concentration, focus, and deep work while learning about a bunch of organizational, consulting, and adjacent topics
  • Develop a bunch of the amorphous ideas that have been bouncing around in my head for years into coherent pieces of writing
  • Deliberately develop surprising and creative connections between my various interests and the domain of organizational design and transformation

I hope it’s not a cop out and I hope I’m not abusing the word… but truly the dream scenario of this sabbatical is that I can look back at how I spent my time over the last four months and say that whatever I decided to do I did it deliberately. I’m open to the idea that this sabbatical may take an unexpected left turn at some point. I’m open to the idea that I may decide to throw away all my intentions except one. I’m open to the idea that I may decide to do a bunch of things that are currently not even on my radar. The only thing I’m holding myself to is staying conscious, intentional, and deliberate through it all.

If you’ve done something like this in the past and have any advice you think I should hear, please shoot me an email or send me a message on Twitter. If you’d like to follow along, might I suggest subscribing to my newsletter or following me on Twitter?

*This is an exercise that was developed by my former colleague, Bob Gower, and his wife, Alexandra Jamieson. If you’re interested in learning more about it, check out their book Radical Alignment and their company The Alignment Company.



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