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How to design a sabbatical

Originally published on Substack in Issue #61: How to design a sabbatical

A Word on Being a Multi-Hyphenate

Today I thought I’d walk you through how I got here and where I hope to go, as there are a number of readers here who are multi-hyphenates of their own sort (i.e.: you need multiple hyphens to explain what you do).

The short version goes like this: I’m passionate about many types of work, inquiry and contribution and after a long period juggling a lot of work, I needed to give myself some time to recover and go deep on less things.

I had my first experience juggling multiple, similar-but-different jobs in 2011, when I worked both at a book publisher and design studio after college. This was not unlike my college experience, where my time felt evenly split between running our school magazine and managing classes.

That first year in NYC, my weeks were split in to 2.5 days per place. At the design studio, I helped with projects and wrote about the intersection of design and education. At the publisher, I spent time in the slush pile and learned to edit.

My favorite days were the ones cut in half, when I would begin my day in Soho from 9am to 1pm and end it in Morningside Heights from 2pm to 6pm. While I had been socialized to look for a nice, full-time desk job like my peers and benefits would have been nice, working this way felt natural to me. I could never focus on anything for more than 4 hours a day, I didn’t like small-talk and didn’t have much interest in office chitchat or downtime. Most importantly, I liked to finish things. I loved the feeling of needing to get something done by a certain time and I learned how to work fast.

In the 12 years since, I have worked a single job, full-time, only twice, for a total of 2 years. For the other 10, I have always worked some combination of project and client-based work that exercised different parts of my brain and personality. There were years with teaching gigs in the morning and reporting in the afternoon, years with production and strategy splitting a week in half, and years where I had to go deep for a deliverable for a solid few months before moving onto the next.

The pros of working this way were that there was absolutely no fluff in my day. I learned to deliver high volumes of work quickly and gain expertise laterally, in multiple industries at the same time. The cons were that after a while, it became exhausting. I rarely had the chance to decompress, miss a deadline or take sick days without risking a domino effect. And still, I loved it.

As my professional network grew, however, I never fully felt like I could relate to the hustle of freelancing (I mostly had long-term contracts) or the demands of consulting (I produced for myself as much as clients). The only name that resonated with me was multi-hyphenate, which came out of the entertainment industry but has expanded to include anyone who is a worker of many kinds, often around content. I would like to see the boundaries pushed on what hyphens we carry, starting with my own.

Thus, for a long while, I’ve considered taking a sabbatical, which is a real privilege, if you’re able to take a brief rest from the need to earn income, and also a real anxiety-provoker, for someone who is used to a highly scheduled, high speed work life.

But here we are.

My intention is to take the time to develop craft skills as a writer and researcher, as well as figure out what kind of storytelling I believe in, particularly what kind of long-form. I’ve written a lot about my thoughts on the news industry but I haven’t thought too much about the future of long-form storytelling, which is what I love the most. I’ve also considered doing a doctorate many many times but ultimately found happiness in my own independent research. I wonder what avenues exist for people like me (see Nadia’s essay in the inspiration list below).

I’m also curious about the way in which I need to work in the future and what life skills I’ll need to manage my professional life, because whether I like it or not, being a working woman of a certain age who intends to have a family requires real planning and resource adjustment if I can give my best to both work and care. Skills like time management, household management, long-term financial planning, self-care, and authentic and holistic investment in my adult friendships.

What is a sabbatical?

You probably know the term sabbatical from the academic context, which, according to Oxford Languages and Google, is a”period of paid leave granted to a university teacher or other worker for study or travel, traditionally one year for every seven years worked.” The term itself comes from the sabbath, not the day of rest kind but the year of rest mentioned in Leviticus that refers to a year of agricultural rest for land after 6 years of sowing and pruning.

But in recent years it’s been extended as a benefit in a number of workplaces and colloquially used by artists and workers taking a break.

The idea is that you don’t do your usual work, which for me, means producing work for others on deadline. I began inching my way towards total temporary freedom in early May at a writing residency with the Future of Local News Network at Blue Mountain Center and getting to just think and write away from home for a few days was so freeing. I’ve since realized I need to toss most of what I wrote there and even that feels freeing.

How I’m designing mine:

My intention is both to rest and study hard, which seem kind of opposite. But I’ve found that the trick is to remove the promise of too many deliverables from the equation and let my intuition guide the rest. That, and learn from mistakes.

Mistakes I’ve made so far:

  • Trying to structure time rather than follow inspiration. I very much am not trying to make a direct swap of work hours for others into work hours for me. And yet that’s what I’ve found myself doing, and at the end of each week feeling incredibly unproductive.
  • Establishing too many deadlines for myself. This will be important, eventually, but I don’t have a product in mind that I need to deliver in 6 months. I have proposals, ideas, and streams I need to follow, and all that deadlines have done so far is get missed and sap inspiration.
  • Considering audience too early: As much as I love the readers here, and I have to explain who I’m writing for to my agent, the fastest way to kill a great story is by writing for an audience you’re not even sure you care to serve yet. Craft is not business.

What is working:

  • Starting small: Deciding what I’ll do in a day instead of in a week is going well.
  • Accepting exhaustion: Sometimes just a few hours of deep work can be exhausting and that’s a sign that it is enough.
  • The pomodoro technique: When I need to get something done (like this newsletter, that I’ve been putting off!) using the 25 min on, 5 minutes off timer technique is the only way through.
  • Write or do nothing. This is a famous tidbit from Neil Gaiman’s writing routine, where the only alternative he gives himself at his designated writing time is to write, or to do absolutely nothing. Ultimately, just sitting there and thinking tends to be boring enough that you’ll get some writing done. I’m trying this out in small chunks at a designated time and so far, writing at a higher volume than I ever have, even if most of it ends up being garbage :)

What I’ve been inspired by:

And finally, the fun part. Before embarking on this journey, I’ve taken inspiration from a lot of folks. Here are a few that have stayed with me.

On Working:

On Life vs. Work: