#1 - How to spend your time?

This article is part of my Sabbatical series. It builds on the previous piece. If you have not read the last essay, you can read it here.

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Getting six weeks of paid time off from work, in addition to your four weeks of regularly accrued PTO (plus ten sick days), is a massive perk. Six additional, previously unaccounted for weeks in a year. The last time I had six weeks off was right after graduating college and right before starting work. I was a different type of human back then! What would this new person do? What I share ahead outlines how I went about thinking about my sabbatical time. This is not a recipe for how everyone should think of their sabbatical but I hope you find something in here helpful!

The Question (or, The Corruption of Sabbath)

Even since my first day at Etsy, the sabbatical was coveted. There were many who had already taken their sabbatical, there were folks who were hitting three or four year marks who were being reminded how close they were to their sabbatical. The pro advice from those who’d done it before was to start planning it at least a year in advance. So even as early as your first year, you start a countdown to year five. You plan and re-plan and discard and re-shape, then maneuver, both, your ideas and yourself, of what you’d do once you have these six weeks available to you.

Dream vacations are the most common use case. I heard of people doing incredible things in beautiful places - three weeks in Japan; biking through the Korean back country; beach hopping in southern Italy; renting a ski-in/ski-out, you name it. All extremely inspiring! What you did during the time off (maybe more importantly what you get to tell others you did) becomes more important than the act of “sabbath,” the act of “resting”, itself. Doing “nothing” sounds boring so you actively try to avoid that. It’s a weird corruption of the idea of a break (from work) but one we’re all susceptible to. What is not evident when you ask someone “what are you doing for your sabbatical?” is a question beneath that question - “what is your intention with your sabbatical?” Any answer is valid - “just unplug from work”, “I’ve always wanted to go to Albania since my PhD thesis on Kosovar Albanians” or anything in between - but I believe the question is important.

Beginnings of an Answer

After I made it through four years at work, I started thinking more strongly about what my sabbatical would look like. One of my closest friends, Luis, was going to go on sabbatical six months before me. When I asked him what he was doing, he said, essentially “nothing.” His plan was to stay in New York and be a tourist in his own city. I asked him didn’t he have any big trips he wanted to take? He told me he did but filling six weeks only with travel felt antithetical to the idea of taking a break from work. As much as you like your job, you’re often doing it for others. Travel is something you can still do if you take your paid time off (PTO). This break is for yourself! Luis’ decision helped me take away my performative pressure to travel. Like I said last time, I believe travel is vitally important. It’s just this time, it didn’t feel like the right choice for me. At least not travel for the sake of you-must-travel-during-your-sabbatical.

So, if not travel, then what? This thinking was happening during my training for the NYC Marathon. Me and my friend, Ashley, at the end of a 13 mile run were ruminating on sabbatical plans (Ashley was due for a sabbatical five months after I was so these thoughts were on her mind too). Ashley, incidentally, introduced me to Luis so we’d both heard about Luis’ plans by then. In talking out loud with Ashley, I remembered The Last Lecture by Randy Pausch. Dr. Pausch in his lecture is trying to share a template of how to live your life and what legacy you want to leave behind. Specifically, he outlines a list of his childhood dreams and how they either came about or didn’t in his adulthood. When I first saw The Last Lecture in college, I was already feeling the pull of adulthood, and my childhood dreams were starting to take a backseat to adult responsibilities. Back then, I wrote down a list of my childhood dreams I wanted to make sure I do. The sabbatical forced me to think back to that list and see if there were unfulfilled dreams I wanted to pursue. The idea of sabbatical-for-childhood-dreams felt right.

(Don’t) Go Climb a Mountain

I went back into my old diaries looking for my childhood dreams, only to find I had either fulfilled some of them, or that the dreams had changed.

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  Open a food truck ✅ - My wife, a brilliant chef, had done a couple of pop-up supper clubs in New York. Having assisted her in pulling these off (very successfully), the food truck dream felt fulfilled.

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  Experience ZeroG ¯\_(ツ)_/¯ - I think I straight up stole this from Dr. Pausch. I was not being very imaginative. I did skydive however so if I wanted to fly, I did.

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  Eat at a Michelin 3-starred restaurant ✅ - This was born straight out of watching a LOT of MasterChef Australia when I was 14. My wife and I had the privilege of dining at Central for our honeymoon (as a gift from my brother)

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  Run a marathon ✅ - When I wrote this, I wasn’t even a runner. I’ve now run two!

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  Speak at TED Global ❌ - Back then, I think I liked the idea or prestige that came with being a TED speaker more than the craft that would get me invited to be one. This didn’t resonate with my current belief system anymore.

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  Work at Googleplex ✅ - Again, this was one of those childhood dreams where I liked the idea of working at a fancy campus with massage chairs and sleeping pods more than the work that the company was doing. I did, however, have an offer to work at Google which I rejected to join Etsy. So the fact that I could’ve worked at the Google campus but chose not to makes this feel complete.

There was one more thing though that I didn’t write down. When I was 16, I heard that a friend’s brother went to climb Kilimanjaro. This guy was also an ultramarthon runner (no surprise where I got my running dreams from) so I was clearly enamored with this dude. And the idea of climbing this mountain stayed with me.

As I evaluated childhood dreams, Kilimanjaro shot up to the top of the list. I started researching Kilimanjaro climbing routes, preparation guides and travel outfitters. A typical climb would take between 7-9 days with a few days before and after to acclimate and relax. It felt like the kind of thing you could do on PTO but also one that fit the idea of a sabbatical. I was still falling prey to the what-you-get-to-tell-others problem, now disguised in the garb of childhood dreams. Not invalid, but still performative.

The more I sat on Kilimanjaro, the more unsettled I felt with it. It was great in theory but if you asked me why I wanted to climb, I couldn’t really give you a why other than because.

There were two more reasons, one more vulnerable than the other, that made committing to Kili difficult.

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   My dog, Oreo, is 11 this year. He’s in great health but the thought of spending too much time away from him especially when I can give him undivided time felt wrong.

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   At the time of this decision, my wife and I had been married three years. We had always said we’d give each other our full attention for three years and then think about starting a family. Depending on when I took the sabbatical and when we decided to climb Kili, it would delay any family planning we wanted to start.

The more I thought about why Kilimanjaro felt wrong, the more I realized I was falling back into old patterns - choosing something because it sounded impressive rather than because it served a deeper purpose. That's when I remembered what had actually anchored me during those difficult years in Seattle.

People (Over Experiences (Over Things))

So if not travel, not childhood dreams, then what?

I mentioned in my previous post that a lot of life happened in the last five years. Some friends and family passed away. Some I didn’t get a chance to say goodbye. Life got busier, some days, weeks and months felt extremely myopic. These six weeks felt like a good way to zoom out and focus on what matters.

I was at a friend’s Bachelor Party a month ago and found myself answering a surprisingly profound F*ck/Marry/Kill question. F/M/K - Connection with Others, Self-Awareness, Self-Acceptance? Without even thinking, my answer was:

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  Marry - Connection with Others

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  F*ck - Self-Acceptance

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  Kill - Self-Awareness

And that’s what I wanted to focus on for these six weeks. Connection with Others. I wanted this time to be spent focusing on people - family, friends, friends’ parents even. Get back to friends I hadn’t seen in a long time, hadn’t spoken to who had moved to different parts of the world. Reach out to friends’ parents who had lost their children untimely. Spend time with Oreo and give him the attention he deserves.

There is a little travel baked in also but it’s not travel for travel’s sake, it’s still in service of connection with others. My cousins and I have always wanted to take a trip together. Our families vacationed together every summer when we were growing up. As adults, we wanted to rekindle that connection, and it seems like everyone is available, so we’re spending 10 days together in Taiwan (arbitrary bucket list destination where visas aren’t required for everyone).

In addition to connection, I want to spend time creating. The things that took a backseat - storytelling, writing, painting. Read more, play squash more, run more. I’ve always been too much of a planner so part of the challenge here is to go into my sabbatical without too much of a plan. Give myself the space and freedom to explore how I choose to spend this time. And addressing The Need to feel productive during this time, I hope to live by John Green’s words:

You will always struggle with not feeling productive until you accept that your own joy can be something you produce. It is not the only thing you will make, nor should it be, but it is something valuable and beautiful.

Again, this was my framework. Your answers may be travel and/or childhood dreams and/or people. My only hope is that you make this decision with intention - not for the story you'll tell afterward, but for the person you want to be during. 😊