Can’t Relax? Read This to Plan Your First Resting Sabbatical

Jenna Kutcher 

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January 17, 2020


I feel like people sorta think I’m crazy when I tell them about my family’s routine month-long sabbaticals. Crazy, or that I just won the lottery. I mean, how else can someone take a month almost totally off of work and not go broke, nuts, or stir-crazy? I get it… Old me from 10 years ago probably would’ve thought the same thing. I used to believe that I was incapable of rest. That I just operated at a higher level and didn’t have the option to shut off. “I just CAN’T relax,” I’d say, when in reality work was just my natural go-to.

And here’s the thing, I still love, live for, and drool over my work. It fuels me, and my brain is always scheming and dreaming the next big biz plan, so I’ve realized that work is my autopilot and rest is actually the thing that takes work — sounds counterproductive, right? Or, maybe you’re sitting there nodding along like, Girl, I feel you. BIG time.

I was at a workshop years ago when I heard someone teach about putting imagery behind your dreams and goals. She asked us to define success and I said: Success to me would look like living somewhere else for one month a year with my husband and kids, enjoying a world outside of our norm. Funny thing? I didn’t have kids yet, but why the heck was I waiting to live out my definition of success until I had a family?

That next week, I found that notebook with those notes in it and asked Drew where he’d want to spend a full month if we could go anywhere, out of curiosity. He said Hawaii. That night I Googled flights, browsed Airbnb, and started jotting down what it would cost us if we made this dream a reality. (By the way, you can see the full cost breakdown right here of our sabbaticals in Hawaii pre-The Kutcher Condo days when we rented places on the islands instead.)

Fast forward to today. Right now, we’re on our 8th month-long sabbatical, and now it’s become a part of our plan, our life, and our reality.  I’ve done the extreme version of not logging into work at all but have found I rest better when I do little check-ins and feel like I know what’s going on in my biz. And it lessens the avalanche of responses, action items, and to-do lists when I do return to the office (or in this case, my couch in Minnesota).

So maybe you’re a bit like me: you can’t relax, you’re obsessed with work, yet your idea of freedom is doing things on your own terms, exploring, and stepping outside of your bubble. You’re a walking, talking conundrum — hello, hi, same here. We could be sisters, you and me.

Let me ask you something. Have you considered planning your own resting sabbatical? It doesn’t need to be a month. It doesn’t need to be on a tropical island. But the idea is to fully step away from your norm, your routine, and plug into a new culture, new experiences, and — DUN DUN DUN — to finally relax a little. On your own terms.

I think you could do it, and here’s the roadmap you need to make it happen.

01. Plan ahead for your work.

Sabbaticals look different depending on the type of business you work for or own. If you work in a traditional office, check your PTO and check-in with your team and superior to make sure you’re good to go for a few weeks to a month. You might think about offering to do a weekly check-in if you want to plan a long-ish sabbatical.

If you’re a solo or entrepreneur, it’s on you to work ahead (or prep your team) for at least the span of the sabbatical, and probably even a week longer to keep things running smoothly and to avoid a major stack up of work the second you return home. So, if you’re planning a 3-week sabbatical, then you’ll want to work at least 4 weeks ahead.

I know, I know, the thought of prepping an entire month of work might make you overwhelmed AF. But you can break it on down into small bits to check off week by week in the months leading up. You don’t have to double up on your work; you just need to plan ahead a bit. Read this post about batch-working to make this process easier on you. A few things to consider as you prep include:

  • Setting up an autoresponder for email to answer common questions, communicate when you’ll be back in touch, let emailers know who they can reach in your absence, and provide links to commonly asked-for resources.
  • Planning and scheduling out your social media posts, blog posts, emails, and any other content that will need to go out while you’re OOO.
  • For solopreneurs, consider bringing on a temporary virtual assistant or someone who can help keep things running while you’re away, especially if you run a product-based biz that needs to continue shipping even when you’re gone. Who knows? You might end up loving the support and decide to keep your VA long-term!
  • Tying up any extra loose strings before heading out: pay outstanding invoices, respond to lingering emails, fill in your business partners (sponsors, agencies, etc.) about your plans, and get everyone what they need before you leave.

02. Prepare for the expenses.

You might think a month-long trip would cost you a year (or more) of income, but you can actually do it in a way that’s smart and savvy for your budget. Yes, it’ll cost you more money than a normal month at home, but if you know what you’re getting into ahead of time, then you’ll be more than ready to save for your trip and still enjoy yourself guilt-free.

The three things you want to look at and research most in-depth are airfare, lodging, and transportation (public transport or car rental fees). We always like to stay in Airbnb rentals for longer trips because we can save money on food by being able to buy, store, and cook our own meals rather than eating out all the time like you have to in a hotel. Another thing: you may be surprised but renting a car long-term isn’t enormously pricey if you rent and return it at the same location. It only gets costly when you need to return it in a different town or state.

Plan to book your flights 3 months out for the best fares, and book on obscure days if you can. Thursday through Sunday are of course going to be the most expensive days to fly because that’s when people travel for their weekend vacays, so if you can fly Monday through Wednesday, you’ll likely snag cheaper flights.

Other than travel and lodging, plan to eat out for some meals and explore the area a bit, but you can even do that on a budget! Museums, parks, beaches, hiking, walking to meals, and long drives are all affordable (or free!) ways to explore new areas. Pack your own snacks, eat at least 2 out of 3 meals a day at your Airbnb (or all 3 on some days), and shop local markets for food and goodies to save a buck or two.

An important side note: when you’re away from your home and routine, it’s easy to let things slip. If you’re going to be gone when bills, rent, or other important payments are due, get those taken care of or scheduled before leaving town. You do NOT want extra expenses of late fees stacked on top of your trip cost.

03. Create a vision for your sabbatical!

Sabbaticals are respites from the noise and chaos of our day-to-day lives — they’re not a regular kick-back-and-relax vacation. They’re meant to have a deeper purpose, and it’s my personal opinion that everyone should take one at LEAST once in their lives. Get away from it all, unplug, and intentionally disconnect from busyness to reconnect with your soul, your family, and your vision.

To do that best, create a vision for the sabbatical itself! How do you want to spend this time? Maybe it’s simply to learn to quiet your mind, and you finally get back into meditating once a day. Or maybe it’s to learn a new skill, and you take a cooking class to fall back in love with working with your hands. It could be embracing the time and space you never usually have to read — and bringing a stack of your favorite author’s novels along with you.

The beauty of sabbaticals are that they are time JUST for you, to play, to learn, to slow down, to breathe, to connect with what matters. To — dare I say? — REST. Yes, even for us rest-averse worker bees. I can’t wait to see where you go.

Photo by: Tehani Bella Photography 

Want to stay at The Kutcher Condo for your sabbatical?

Find availability, rates, and our fav Hawaiian pitstops all right here!

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  1. Chelsea Rose says:

    Loved this post Jenna! I think we all take for granted how important rest is, whatever your version may be. Thanks for reminding me to not feel guilty to take a break!


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A small town Minnesota photographer, podcaster, educator and puppy rescuer, my happiest days are spent behind my computer screen sharing my secrets with the world. I'm glad you're here.

I’m an expert at online marketing, a nerd when it comes to the numbers, and my obsession is teaching others how to make a living doing what they love (without it taking over their life). 

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