I am a little more than halfway through my sabbatical, and I get two questions more than any others (after "are you actually working?"). Did you make a plan? And what are you actually doing? This post answers both, and it borrows from a new book on sabbaticals, Big Time Off by DJ DiDonna, that helped me understand the part I did not plan for. The post-sabbatical post will come later, once there is a "post" to write about.
So, did I make a plan?
Yes. A thorough one. It is a seven-page working document with five parts: a north star, a short list of priorities, milestones with dates, a list of open decisions, and a daily log where I record what shipped, what moved, and what is stuck. Every project I care about is on it, and so are three writing retreats, each with exactly one deliverable.
The north star is the next step in my career, the full-professor case, and every priority has to serve it in some way. That sounds rigid, but it is the most useful line in the whole document. When something new shows up (and something new always shows up), I can ask whether it serves the north star or just looks interesting.
So, what is in the plan?
First, the research. I have nine (yes, nine) open papers, and I picked two to be the flagships: a theory paper on product-form strategy and a paper on how institutional voids shape fragmented healthcare markets. The rest moved to the pipeline, which is my polite word for "when there is time."
Next, the work that is not research. An AI teaching playbook and two teaching cases built from my classes. The website, a signature talk, and the Creator Summit at Kogod. A weekly accomplishments log, because I know that by December I will not remember what I did in June.
Then, the milestones, with dates, and the retreats. Finally, the open decisions, meaning the things I was not ready to decide yet, like whether to swap one of the US retreats for Mexico, or which of three larger projects (a book proposal, a policy brief, or an AI and healthcare project) gets started this year. Writing those down meant I stopped re-deciding them every week.
So, what am I actually doing?
Working the plan, mostly. The healthcare paper is the first one out the door, the theory paper is in its deep draft, and the playbook and cases are on the calendar for this fall. The retreats are happening, and the log is being kept (so far).
But I am also doing something I did not expect to do. I am slowing down and making margin in the plan.
Why?
Well, because the plan was full. Every week had a purpose, and there was no room for things I did not know would come up. And things came up. First, in October, I am attending Cloudflare Connect in San Francisco. Next, in November, I am going to Thesis 2027, Every's one-day conference in Brooklyn on what great human work looks like after automation (a question I have opinions about). Finally, the ESSEC visit I mentioned in my first post is now confirmed: I am going to Singapore to see how they run things and to give a talk in their Luxury Branding Seminar. On top of that, a whole new research question on health influencers (see my last post) showed up that was not in the proposal.
None of that was in the plan, and all of it serves the north star. So the plan had to give. Some pipeline papers moved later. Some "nice to have" milestones came off the list. I am learning to leave white space on the calendar on purpose, which, for me, is harder than filling it.
So, what does the book say?
Well, DiDonna is a lecturer at Harvard Business School who took his own sabbatical after burning out running a fintech company, then spent the better part of a decade interviewing hundreds of people about theirs. His central claim is that "the most important moments of your life rarely happen at a desk."
He found that sabbaticals tend to move through three phases. Recover, where you unplug and stop being your workday self. Explore, where you try on new interests. Practice, where you stick with one of them long enough to find out if it could become a real change. He also describes three archetypes based on how people move through the phases: the working holiday (recovery and practice), the free dive (recovery and exploration), and the quest, which runs through all three and, he argues, produces the biggest transformation.
What was the most important point in the book for me?
Well, it was not the phases or the archetypes. It was a simpler question he asks early on: why do we save all of our retirement years for the end? Why not take some of them now, while we can still use them? It does not have to be a year, or even six months. What about three or four months? What about six weeks? I think anything less than that does not work, because you spend the first week or two just coming down, but six weeks is enough to get somewhere.
I want to be careful here, because a sabbatical is a huge privilege. In academia it usually comes after years of work and a record of publications, and it is meant for studying new and interesting problems. For me, that problem is AI in marketing, which is obviously shifting the world as we know it, and is shifting the world of higher education right along with it. Most people will never get a sabbatical handed to them. That does not mean the question does not apply.
Where do I agree with him?
On recovery, completely, and I say that as someone whose plan did not have a recovery phase in it. It went straight from "submit the healthcare paper" to "writing retreat." His interviewees needed six to eight weeks just to stop being their workday selves. I did not budget any, and looking back, the margin I am now making in the plan is the recovery phase asking for the time it was owed.
I also agree that part of recovery has to be physical. Not a metaphor, an actual body. For me that has meant gardening, yoga, pilates, long walks, and Solidcore, which I am struggling through and which, I will admit, is scary. None of it is in the seven-page plan. All of it is what makes the seven-page plan possible. If you take nothing else from this post, take that: you cannot recharge from the neck up.
Where do I differ?
An academic sabbatical is not quite the sabbatical DiDonna is describing. His subjects quit jobs, sold companies, or negotiated leave with no specific outcome required. Mine comes with a proposal on file and a report due at the end. By his taxonomy, I am an Achiever on a working holiday, and I would argue that eight months of uninterrupted deep work is its own form of recovery from a department chair's calendar.
Which brings me to the part of his framework that does not fit at all: re-entry. In January, I come back as department chair. There is no soft landing. I will need to hit the ground running, and so the last stretch of the plan, November and December, is not exploration. It is chair preparation. That is the post I will write once I am on the other side of it.
Did I make a plan? Yes. Did I plan too much? Also yes. Will I tell you how re-entry goes? That is the next post, and I will write it after I have actually come back.
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