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How to plan the ultimate working vacation (work-cation!)

Everything notable I’ve done over the past year happened while taking a working vacation. Aka: a work-cation!

I came up with the concept for my OBSESSED class — and outlined the entire curriculum — while vacationing in rural Sweden in an adorable cabin with one of my besties. With no wifi or phone. While eating my body weight in smoked salmon.

I wrote my first screenplay while in Los Angeles. Solo-cationing. Blissfully alone. In an adorable AirBnB rental house. In between stalking all the places the gossip mags tell me Ben Affleck is supposed to be even though he never seems to show up. (Hello, Ben? I’ll be at the Country Mart. Or the pumpkin patch. Whenever you’re ready.)

I wrote a boatload of blog content while visiting Maui with a group of girlfriends in between frolicking over to the hot tub, sunbathing at the beach, and searching for the perfect souvenir tank top. Thanks to that burst of productivity, I’ve got blog content scheduled out months ahead of time and I never have to stress about missing a post. (Feels sooo good to be ahead of the game!)

If you pop by this blog on the regular, you know that I’m all about blending “work” and “pleasure,” so it’s no surprise that I’m a big fan of taking regular work-cations. 🙂

How about you? Have you ever fantasized about doing one? Wondering how to plan your trip so that it’s equal parts playtime and productivity?

Here are my tips on how to plan the ultimate work-cation. Warning: you might be fervently scrolling through hotel and flight options before reaching the end of this post.

Step 1. Choose your adventure.

Are you lusting after a European adventure?

A mountainous retreat in a tree house?

An island-beach getaway?

Or maybe you want to keep things low key and stay closer-to-home, checking into a swanky local hotel for the weekend?

Got zero ideas? Need some direction?

The Tablet Hotels website— which curates unique, boutique hotels from around the world — is a major inspiration portal.

These travel wishlists curated by the staff at AirBnB are completely dreamy, too.

Want to get out of town —on a specific budget? Try Kayak Explore. Enter how much you want to spend and a few details about your dream destination and see where you can fly…for how much!

Step 2. Make the big decision: solo or with friends?

If you already know that you prefer to work and travel alone, then go ahead and rock your work-cation solo.

If you thrive in a more collaborative environment, like to bounce around ideas out loud, or just prefer to have the company of other people when you’re traveling, consider inviting one (or more) folks along for the ride.

Choose your work-cation companions wisely. These should be people who inspire you. People you respect and admire. People who light up your brain (think: “OMG, every time we hang out I leave with a zillion brilliant ideas! I heart yooou!”)

I highly recommend choosing people that you have traveled with — or have spent plenty of time with — in the past. There’s nothing worse than trudging through a work-cation with someone who turns out to be a life- and creativity-sucking vampire. Ungh.

Ideally, choose people who also have projects that they want to get done, just like you. It will be a pretty awkward work-cation if only one person in the group wants to work!

Step 3. Create a loose, happy structure.

You might be thinking: I love the idea of a work-cation, but seriously: if I am traveling somewhere gorgeous and exciting, how the hell am I going to do any work? Ill be so tempted and distracted by other things.

That’s a valid concern, but with a tiny bit of planning, you really can make this work.

I suggest taking the beginning of your work-cation to just… play. Sleep in if you want to. Get a pampering massage or salt-scrub body treatment. Frolic down a cobblestone street in that oh-so-cute outfit that for some reason you never wear at home. Savor long meals and scintillating conversations with friends… or friendly strangers. People watch and sip an iced tea on a park bench. Or just sit and admire the beach, mountains, forest, bustling cityscape, or whatever kind of landscape you’re in.

For the beginning of your work-cation, give yourself permission to do absolutely nothing related to work (that’s when your best ideas tend to arrive, anyway!). Shut off your strategic, analytical business-brain. Let the world beyond business flow through you. Open those channels.

After a couple days of playtime, you’ll probably be brimming with new ideas and itching to get to work!

For the remainder of your work-cation, I recommend structuring each day with a nice, balanced blend of work and play.

It might go something like this:

8am: hike/yoga/run/walk

9am: breakfast

10am: morning work sesh

1pm: lunch

2pm: afternoon activity (lounging in hot tubs, spa time, sight seeing, whatever sounds fun!)

4pm: evening work sesh

7pm: dinner and evening festivities!

Try to align with your natural creative rhythm. For example: if you get your best work done first thing in the morning (6am, sharp!) but tend to be totally brain dead after 4pm, plan accordingly. This is your work-cation, after all. It can flow however you want!

Try not to get overly rigid with your schedule. That’s always a recipe for disappointment. You never know what’s going to come up during your work-cation – an idea for a romance novel that you simply must write (even though you’ve never written fiction before), your next bestselling product concept, or even a surprising kink in your plans that throws everything else on hold for a while.

For example: when I work-cationed in Sweden with a friend last year we had a super loose, happy schedule that basically went: breakfast…work…lunch…sunbathing and rowing boats like Ryan Gosling in The Notebook (while crying out, “It wasn’t over… It STILL ISN’T OVER!!!”)…trip into town for coffee and more work…dinner…evening swim in the lake.

But there were plenty of days where that exact agenda didn’t happen. At all. Like the night in Stockholm when I stayed up all night on our little terrace, bathed in moonlight, typing so fast my little fingers couldn’t keep up with all the ideas flowing. (Then I was a totally unproductive zombie the next day while my friend fed me cheese from our Viking-sized smorgasbord platter.)

Or the day when my friend got violently sick with food poisoning and I had to get her to the emergency room. At 4am. In rural Sweden. With no map, no directions, no internet, no phone service. On the flip side: Swedish hospitals are amazing and feature super fast wifi, coffee machines that are better than Starbucks baristas, and legit hiking trails. #besthospitalever

Bottom line? Rigidity and perfectionism will murder your work-cation. If you can’t “let go”— don’t go.

OK, work-cationista. Tell me where you wanna go! In the comments below, share your dream work-cation plans. And if you’ve taken a work-cation in the past, tell everybody where you went! Let’s make this blog post like a bomb travel guide for getting shit done. Awwww yeah.