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How I Pulled Off a (Mostly) Stress-Free 3-Week Vacation

“If this isn’t time-sensitive, feel free to resend this email in July once I’m regularly checking emails again.”


“Yet so many of us today — I’m speaking of those fortunate enough to have the resources and the vacation days — remain slavishly attached to our 24/7 connectivity and take only a week at a time, maybe two!, off work.”

This is a quote from Jynne Dilling from a New York Times article titled, “In Defense of the Three-Week Vacation,” which I just happened to read a few days before I embarked on — you guessed it — a three-week vacation. It was to be the longest vacation I’ve ever taken while working full-time.

With that said, I’m someone who likes to travel, who uses my vacation days when I’m working, and who takes advantage of spare time when I have that. But, since two weeks is what I’ve typically been given for paid vacation, I’ve never attempted to go away for longer. As Dilling points out, few of us have or do.

For my recent honeymoon, however, my husband and I decided that if we were going to go to Japan, our destination of choice, we wanted to do it right. To us, that meant taking more than the standard — and, I’d add, respected — two weeks. But that decision also meant getting organized — like never before. I’ve always been a to-do list person, but planning this trip (without affecting my reputation) would put my skills to the test.

28 Weeks Before Departure

“You have unlimited vacation, right?” my husband eagerly asked me as we started planning the trip.

“Well, yeah, but…” I began before I gathered my courage and went to my boss with the uncommon request.

I sat down with her, made the ask, and then quickly interrupted myself to say that I fully expected to work late nights, and maybe even some weekends leading up to the trip — all of which I sincerely meant. But my boss not only said I should go, but also said that coming in on Saturdays was ridiculous and unnecessary — instead we’d come up with a plan that worked for both of us, putting minimal extra work on either of our plates.

This conversation could’ve easily gone another way, despite my having a good relationship with my manager and being aware of our company’s policies. By looping her into the conversation before we finalized any plans, I was telling her that I respected her decision regardless (though, obviously, I went into it looking for a specific outcome). And by making it clear that I wasn’t planning to peace out for 15 days without doing any extra work beforehand, I made it clear that I was willing to sacrifice to make this dream trip a reality.

I went home that evening feeling really good, the stress and nervousness I’d felt going into the meeting replaced with a new confidence. Why shouldn’t we take a three-week honeymoon? It was a once-in-a-lifetime sojourn. We both worked hard and deserved the break. Years from now, would I regret missing 15 days of work, or would I wonder why we’d settled for two weeks and a far limited picture of the country we were about to explore?

That’s a rhetorical question, obviously.

10 Weeks Before Departure

In the months leading up to the trip, I began planning ahead. Although my manager didn’t expect me to work double-time before the trip, I knew the only way to not make that a reality would be to be as organized as possible and add a little bit more to each day leading up to our departure.

The first step was working backwards to create a realistic, yet reasonable timeline. I laid out all my upcoming deadlines, both for articles and projects, and split them into three categories: I can do in advance before leaving, I can push back until my return, I can delegate to other people on my team.

Obviously, this is easier said than done. Because as an editor, this meant, first and foremost, changing my writers’ deadlines. If I wanted to stay true to our editorial calendar and have their articles published while I was away, I’d need them to turn in their drafts well in advance of my vacation start date. And to be fair to their schedules, I’d need to give them plenty of notice. (This is where having a reverse timeline comes in handy!)

As soon as I’d set the modified due dates, I sent out a simple email with the deadline bolded. I was frank in my reasoning because I believe in transparency. Every single one first congratulated me on my nuptials, and then each agreed to work ahead of schedule to accommodate my needs.

While you may not (and are probably not) an editor, the biggest lesson you take from this one example is the importance of having good relationships with the people you work with. If I hadn’t been accommodating and kind in the past when similar requests came up, they could’ve easily responded to my request with, “Sorry, that doesn’t work for me.”

2 to 4 Weeks Before Departure

As the departure date neared, my manager and I communicated regularly about what I had coming up, what I anticipated happening while I was gone, and how I planned to tackle my assignments before I packed my bags and left the country. This list changed from meeting to meeting as so much of my list depended on other people, and it required both of us to be somewhat flexible.

There were a couple larger-scale projects that, in a perfect world, I would’ve dealt with before leaving, but rather than finish them hastily and risk turning in sub-par work, I decided to put them on my radar upon my return. Letting the appropriate parties know where things stood, I forced myself not to stress about it.

Being honest with my over-achieving self wasn’t easy. I hate leaving work for other people to wrap up and I hate not following through 100%. But in this situation, I had no choice but to be honest — lest my teammates found out that I’d fudged the facts while I was two weeks into my trip and completely out of touch.

After all, the underlying reason so many people fear their co-workers going on long vacations is because they’re scared that it’ll lead to project backlogs, missed deadlines, and additional work on their plate. By addressing this fear head-on before being asked, I alleviated many of those fears.

1 Day Before Departure

On my last day, I emailed my boss a final status update and wrote an out-of-office email intended to give an appreciative nod to work-life balance, as well as a reminder to people that’d be out for a while. Because I’d made my impending absence known to everyone I worked with, I didn’t actually expect to receive that many messages while I was gone.

I also borrowed a trick from one of my co-workers, who, not long ago, had closed a recent out-of-office message with the following line: “If this isn’t time sensitive, feel free to resend this email in July once I’m regularly checking emails again.”

Insert Several Thousand Words on How Awesome My Honeymoon in Japan Was

7 Days Since Returning

I’ve been back a little over a week and am happy to report that I’m surviving with minimal stress! The jet lag was worse than I expected and for the first few days, I worried that every time I opened my mouth, I was uttering incoherent thoughts.

But, I didn’t have time to overthink that. I threw myself back into my work with the help of a lot of coffee and the pleasant feeling that I was actually happy to be back. Even though the honeymoon wasn’t nonstop beaches, pina coladas, and long afternoon siestas, I returned feeling refreshed, grounded, and perhaps, most significantly, excited to return to the office. I loved my trip, but I’d missed my work — and as cliché as that sounds, that feeling is priceless.

The best surprise upon my return? By communicating with everyone so clearly before leaving (and in my OOO message), I didn’t return to an overwhelming inbox. There was a lot of stuff I could discard immediately — old newsletters, outdated office news, press releases on things that had already happened — and there was a lot that I needed to respond to soon but not ASAP-soon. If I was confused by anything, I marked it as unread with a note on my to-do list to follow up with the relevant parties about it.

Speaking of that to-do list, I revised it right after I went through my email. By looking at the priorities I had lined up for my return and checking those against the editorial calendar and my new inbox action items, I quickly put a plan in place for my first few days back. I should note that I found it helpful to ease back into things by returning mid-week. Just when I started to feel overwhelmed, the weekend arrived to save me. Then, that following Monday was back to business as usual.

Before I left and co-workers asked me about my upcoming honeymoon, they almost always, without fail, said, “Two weeks, right?” It was understandable for them to make this assumption. People take long weekends, many won’t think twice about a full week, and many others take a two-week vacation every year but never anything more than that. But, three weeks? I honestly didn’t know anyone else doing it, not even for a special occasion like a honeymoon. I’d be lying if I didn’t say that I felt anxious going into it — and even at points on my trip. I couldn’t help feeling bad about the time, time which society basically doesn’t regard as standard or acceptable.

But, whenever I felt that way, I kept going back to this line Dilling said about her experience traveling in Thailand for several weeks, “This kind of travel requires more time, but the gift is an acute awakening of all the senses.” My work, in all its challenges, thought-provoking moments, and peccadillos, would be there for me when I got back. And I was just as grateful for that as I was grateful for the three-week vacation.


Originally published at www.themuse.com on September 27, 2016.

Originally published at medium.com

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