If you are an academic whose semester has recently ended and you are suddenly struggling in dealing with unstructured time, pull up a chair, I’ve got some advice based on my experience of trying to juggle simultaneous (but not necessarily complementary) careers in teaching and writing
My progression over the years:
1. Teaching a full-time load while cramming as much writing as possible into the tiny fissures of “free” time.
2. Teaching a single course which somehow expanded like a gas to take up almost as much time as teaching full-time while writing as much as possible with the increased “free” time.
3. Writing full-time.
Each step has required me to change my relationship to unstructured time and revealed to me an eternal truth, it will always be a struggle.
When I was teaching full-time, to try to get into a productive frame of mind in the summer offseason right after the semester is over was always supremely difficult.
Without that structure, it’s easy to drift, and as we drift, the anxiety over the drifting becomes more and more oppressive as those big goals seem increasingly unattainable, and as those big goals seem increasingly unattainable, the motivation to write drains away. Soon enough, the semester looms, course planning must be done and the big goals get pushed to the indefinite future.
I was often more productive with my writing during the semester than during the summer, as the structure of classes forced me into good habits.
Once summer came around, those habits would not follow, absent the structure of school.
When I was at Virginia Tech (2004) I secured a book contract for an unwritten manuscript with 14 months to turn it in, including a full summer on the front end.
Naturally, I did almost nothing on the book that summer, spending far more time playing Grand Theft Auto and luxuriating in having so much time to finish the book than actually working on the book. I ended up writing 85% of it in the last three months, and while I think the book turned out well, the process was not so good, not so healthy, also not sustainable.
When I stopped teaching this year, my solution to unstructured time was to pile on assignments with deadlines to the point I was “hair on fire” busy.
It worked! I wrote two book manuscripts between May 2017 and December 2018.
It worked because I simply had no other choice but to grind away on the books plus my regular freelance assignments which pay the day-to-day bills. I worked every day, including weekends, and in the final push for the second book, even spent more than six hours working on Christmas Day and New Year’s Eve/New Year’s Day. This will endear you to your family, let me tell you.
As you’re probably intuiting, this is also unsustainable. I was threatening to break myself permanently. Even though my total hours worked when I was balancing teaching and writing was about the same when I was writing full-time, spending the entirety of my time writing had me identifying with Jack Nicholson’s character in The Shining.
I did not drive an axe through any of the doors in my house, but I can’t say I didn’t consider it, just as a stress relief.
I have employed every bit of advice others recommend to deal with unstructured time, setting a schedule, daily goals, weekly goals, monthly goals, denying myself things if I didn’t produce, rewarding myself if I did produce.
Things that worked like a charm one week suddenly failed the next. I had days where I would produce 5000 words and feel unbeatable followed by days of nothing, where I could not muster anything salvageable.
While I actually do enjoy the process of writing, I ended many days feeling a kind of desperation, even despair as I feared I was always behind whatever curve I should’ve been ahead of.
But when I look back on last year, I see plenty of productivity, not just those two books, but 100,000 words on this blog, another 40,000 for my newspaper column, and even a (possibly unsellable, but still…) draft of a short novel (45,000 words). All told, that’s around 300,000 words of useable writing.
Clearly, something had happened, even if I had many weeks where it felt the opposite and could endlessly flog myself for what seem like bad practices and habits.
So my advice, in addition to all the good stuff about schedules and rewards and punishments and using the pomodoro technique is to maybe, just maybe, lighten up on yourself.
Piling on the work so you have no choice but to grind away is a particularly bad idea for your summer “break” (I know, “break,” ha ha ha ha ha ha). Summer should allow for some time for decompression, for reflection, for recharging. Of course for most some work must be accomplished, but summer should not be a sprint. It’s not healthy.
If you’re an academic and you’re dedicated to your job, you’re likely working harder than anyone can know, including yourself.
It’s easy to lose sight of that.
 On top of everything else, from spending so much time deskbound, I developed a moderate case of “frozen shoulder,” an affliction more associated with the geriatric. I needed six weeks of physical therapy to get the thing back to a normal level of middle-aged creakiness.
 Useable, not necessarily finished, as in steps on the way towards finished, though obviously some of it is also finished.