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last updated:
April 14, 2022


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Reading time: 8 min.

Honesty hour: I get nervous about starting a new project. If I’m overwhelmed by the size of a project, or I am worried that I’m not going totally rock it, I freeze. I’ll find other things to do. I know I have to get that big project out, but… it’s scary, right??

Have y’all ever been there? (Please say yes, so I don’t feel so alone in this!)

Usually, when I get to this point, I know it’s time to pull out of my best business tools: The Workcation. If you’re not sure what a workcation is, or how to plan one to help you get stuff done, you’re in luck! Keep reading (or watch the video below) to hear more about how to plan a workcation so you can get over that procrastination hump and move things forward in your business.

What’s a workcation?

Simply put, a workcation is an environmental hack to help you get stuff done. It’s all about changing your environment so you can push through and get that big project done — you know, the one you’ve been procrastinating on?

I first learned about workcations when reading Cal Newport’s book, Deep Work. In that book, he talks about something he calls “The Grand Gesture.” He tells a story about JK Rowling, when she was struggling to get out her last Harry Potter book, Harry Potter and the Deathly Hallows. She was overwhelmed by the distractions at home and just couldn’t bring herself to focus on the chapters she needed to write (sound familiar??). So she checked herself into a 5-star hotel down the street from her own home for a night — and she kept coming back because she was so darn productive.

While you don’t have to book a 5-star hotel to have a successful workcation, I do think there are so many best practices we can pull from Cal’s story here. 

“By leveraging a radical change to your normal environment, coupled with perhaps a significant investment of effort or money, all dedicated to supporting a deep work task, you increase the perceived value of the task.” – Cal Newport

When you’re in a new space, especially one chosen to support focus and execution, you can reduce your mind’s instinct to procrastinate, and get a much-needed boost of motivation and energy. 

Of course, workcations are just one way to introduce grand gestures into your work. I love a good pen, for example, or paper products you only use when you work on a specific project. Candles are also a must-have for deep focus. But a workcation is the ultimate example of a grand gesture.

Heading off for one day or two is absolutely magical, especially if you’re a business owner with kiddos, a partner, a house to run (why do repair guys always come when you need to focus??), and so on. But how do you get ready for a workcation? I’ve got you, boo!

How to prepare to take a workcation

Believe it or not, I don’t typically plan my workcations with a ton of foresight. They come as an antidote to solve a problem that comes up unexpectedly — and they usually happen during the week when I need to hunker down and get something done. These definitely aren’t week-long or even weekend getaways. They’re just to get work done in a short amount of time.

While they may come up unexpectedly, I can also usually tell when I might need a workcation in this quarter — because I know I have a big project (or projects) on the calendar. When I see this coming, I look ahead at my calendar, our family calendar, and my husband’s shifts to make sure that I can get away. If needed, I may also look at pulling the grandparents in for help, but I’m not usually gone for more than a day or two. 

Those are the times that I know I’ll need a workcation, but y’all… sometimes I just need it when I need it. When that happens, I’ll work with my husband to get the logistics down and get things rolling as soon as I can. As a mama of two and a business owner, this isn’t usually instant, but it can be done with a couple of weeks’ foresight.

Once I know I need to get a workcation on the books, my next step is to find the perfect, *chef’s kiss* location.

Location is everything 

Where should you book your workcation? I don’t typically go very far, but you may decide that you need a whole new change of scenery (as in, a whole new state). 

I actually focus on the hotel room more than the location — I want a room that looks magical to stay in because I’ll be in there about 80% of the time. My best tip? Judge a hotel from its guest picture reviews. They’re wayyyyy more accurate than the listing photos. 

I also look for low-key, calm locations. One time I almost booked a workcation in Palm Beach and realized that would be a terrible idea because… who can focus when there’s a gorgeous pool and beach within sight?? 

Find the perfect hotel 

You read that right. I said hotel, not Air BnB or VRBO. I like hotels for my workcations because they have fluffy down beds, fluffy robes, and other amenities that other places don’t. They also have: 

  • Fitness studios (hello, mid-day brain boost!)
  • Strong wifi (this is non-negotiable for a workcation!)
  • Room service (late nights = brain food!)

I also look for hotels that have: 

  • Proximity to other work spots (cafes, bookstores, etc.)
  • Tech support nearby (for computer troubles)

Honestly, college towns are my favorites for workcations. They have strong-like-southern-sweet-tea wifi, are within walking distance to coffee shops and bookstores, and they have Apple stores and tech stores when your tech fails you (it happens!).

Now that we’ve got the where of your workcation sorted out, let’s talk about what you’ll be doing on this trip. 

What should you work on during your workcation?

When I am planning a workcation, sometimes I have ONE specific, in-depth project that I need to get done. But sometimes, I take a workcation with two to three projects in mind, depending on their size and urgency. I usually tell my team or my husband — “Make sure I don’t come back home until I get this thing done.”

Once I’m at the hotel and have my butt in the desk chair (or, more honestly, tucked into the fluffy down comforter bed), I am much more able to enter “work mode” and focus on the projects I’ve been procrastinating on.

But I don’t just do a workcation to get some small tasks checked off — no ma’am. Instead, I focus on the project that leads to important financial results. This is not the trip for a vanity project or a creative endeavor that I kinda want to dabble in. This is the time to work on a project that will make the business money in the next 60 or 90 days.

Why do I focus on financially relevant projects? Because workcations cost money. I’m paying to be out of the office, to travel to a hotel and a new city. So what I do on these trips better make me money back — otherwise, it’s just a boring personal trip, right?? 

I’ve used my workcations to…

Writing this, though, I realized something important: I didn’t take a workcation before my 2 maternity leaves. But in hindsight, that would’ve been a really good time to take one, so I could have the space to focus on what needed to be done before I went out. This is also a great idea for projects that need done before your wedding and honeymoon, a big trip or sabbatical, a surgery, and so on.

If you want to hear more about how I did plan for my maternity leaves, though, you can read all about that here.

What to pack for your workcation

I love a good packing list, and this workcation packing list is one I’ve refined myself over the last few years. Here’s what you’ll want to bring with you: 

  1. Breakfast food and energy-boosting snacks
  2. Bottle(s) of wine so you can save on room service
  3. Books that you haven’t finished, especially if you’re flying or taking a train to your location 
  4. Candles!*
  5. Planners, goal-setting materials, pens, highlighters, stationery, notebooks, etc. any tools that you use for brainstorming
  6. Anything you need for filming if you need that (filming equipment, clothing changes, makeup, etc.)

Of course, you’ll want to pack your other essentials, like toiletries (I love a good self-care moment on these workcations, so bring the fancy facial stuff!), comfy clothes, a swimsuit for a hot tub break, and so on.

*  I only light my “focus candles” if I’m working on specific projects because they put me in the zone. I am not allowed to burn that candle except for when I’m getting those projects done! Sense of smell is tied to memory, after all, and when I light those candles, the muscle memory kicks in and I KNOW I’m in work mode.

Create a schedule for your workcation

You want to have a schedule for your workcation or you’ll just end up bingeing bad hotel cable TV… or at least, I would. I’ll share my workcation schedule below, but of course, I don’t expect this to work for everyone! 

During my workcation, I am working and my team is, too. No out-of-office auto-responder is needed and I’m usually available for responses and team communications.

However, I am focused solely on the specific project(s) I came for, and I like to break those deep focus sessions into 2-3 blocks during my day. Usually, these are in the early morning, afternoon, and night. 

I get up super early and get a morning sprint done and out of the way. Then, I plan for a workout in the late morning/early afternoon. I also change locations often and hop between the hotel room, the lounge, a coffee shop, etc. If there’s someone in the area who I know, I’ll also schedule a friendly chat over coffee or dinner! 

I also only plan to be on my workcation for 2 days. After that, my brain is pretty well fried. Again, this is just what works for me — it helps to know how long you can focus, how many “sprints” you can get done in a day, and the environments where you can focus the most. If you’re a people watcher, probably avoid the busy coffee shop next to the hotel, ok?! 

The #1 tool I use to stay productive on my workcations

If you’re a veteran AW reader, you probably have seen me write about the Focus Keeper App (you can grab it at the Apple Store or Google Play Store). I love this app because it keeps me focused without getting too sucked into a project that I forget to move, eat, or take potty breaks.

It runs on the concept of Pomodoro sprints — 25 minutes of focus and then you get a 5-minute rest period. If you use this app consistently, you will get the 25-minute sprint, 5 min break, and repeat that 3 times before you get a longer 30-minute break. I particularly love this app because I can hear it ticking down the time, and it’s this auditory reminder to stay on task.

If you use something like this on your workcation, you can absolutely bet that you’ll get a lot done. Of course, I’d love to hear how you make your workcation your own — and what kind of project(s) you’ll be working on when you get to that lovely hotel room.

Reading Time: 7 Minutes Reading time: 8 min. Honesty hour: I get nervous about starting a new project. If I’m overwhelmed by the size of a project, or I am worried that I’m not going totally rock it, I freeze. I’ll find other things to do. I know I have to get that big project out, but… it’s scary, […]


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