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One of the coolest perks of working at Automattic is the sabbatical.

Every Automattician, after reaching the five-year anniversary milestone, is eligible to take up to 90 days off from work to completely disconnect, recharge, and do anything they like.

At the start date of your sabbatical, your access to the super admin tools is removed. Not only are you not expected to work, but you’re also actively barred from working.

How you spend your sabbatical is entirely up to you. You can dedicate this time fully to tending to your families and loved ones. You can take up a course and skill up in the areas you’re interested in. You can take up a new hobby or finally dedicate time to the one you’ve been putting off. You can even travel the world if your heart desires.

Or you can just relax, tend to the garden, and enjoy time in serenity.

My five-year anniversary at Automattic was in May 2020, a terrible year to reach the five-year milestone in. However, because I hadn’t planned for it in advance, I wasn’t able to take the sabbatical last year.

In hindsight, I’m glad I didn’t have to take it then, for obvious reasons. Something about Steve Jobs’ ‘connecting the dots looking backwards‘ comes to mind.

sabbatical slack message
My Slack status for the next three months.

I eventually set November 1, 2021, as the start date of my first sabbatical. This, unfortunately, means that my second sabbatical will be delayed, as I will only be eligible for my next sabbatical five years from the end of my first one, but the trade-off is worth it. It would have been a wasted sabbatical if it had to be spent at home.

My plan was to spend my sabbatical traveling to a few different countries. For a while, I was seriously considering a trip to Antarctica (After watching this, who wouldn’t!). It would have been expensive, but the experience would have been one to remember for a lifetime.

I also had planned to visit the US and take a long, cross-country road trip from New York to L.A., going through historic cities and landmarks. I’m no stranger to taking solo road trips in the states. So I was really looking forward to it.

Unfortunately, due to the current situation of the world, and the vaccine politics [of some countries not accepting some vaccines] that’s going on (more on that on my latest issue of Letter), it’s uncertain whether I will end up taking that road trip across the US. But I still have plans to take a series of trips at home. And if things get better, I might take a road trip abroad as well.

I’ve received different suggestions from colleagues who have been on sabbaticals before. Some suggested taking the time to completely disconnect from all things tech. Some suggested meticulously planning every day so that I can make the best use of this time. Some have even suggested doing absolutely nothing and letting myself be bored.

I think I’ll end up with a combination of the three. Some days, I’ll work toward my personal goals. Some days, I’ll be traveling. And some other days, I’ll let myself be bored.

I’m deliberately not giving myself measurable goals for this time. I find myself overthinking almost daily. I’ll allow myself to do what I feel like doing (which isn’t always sleeping 😛 ) and see what I get when I come out on the other side.

If you’d like to keep up with what I’m doing without overloading your inbox, I welcome you to subscribe to my newsletter where I publish at most twice a month about remote work, cars, tech, and daily life. (Here’s the latest issue that I just sent out today.)

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