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Oh Sierra


Tips for Working While You Travel

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Welcome to our first instalment of WORK+PLAY. An ongoing, honest, retelling of adventures, balance, and what it’s really like to take our business on the road.

We always approach life with a glass-half-full attitude – but it isn’t without its overwhelm, imposter syndrome, doubt, and insecurity. For a long time, our consistent travels were one of our greatest sources of guilt (sometimes brought on by external voices, but more often, by internal ones). But, as our business grows (and our travel plans, along with it) it’s time to make a shift. So, instead of jetting off and shutting down to hide from potential judgement, we want to let you in. We want to shine a light on the part of our world that we have worked the hardest to build: life, but as a vacation.

Consider this not a lesson in travelling responsibly, but more of an ongoing memoir of our experience as entrepreneurs who don’t love to be in one place all the time (especially if that place has winter). We actively seek a world where work and play can live in harmony — it doesn’t always work out (that’s the fun part!) but when it does, it’s glorious (also, the fun part). To kick off, we want to share a handful of travel tips that completely changed the way we approach work and play while travelling, and helped us to live our adventure with a little less fear and a lot more passion.

Travel Tips That Change The Game

Visualize Your Workspace
While booking your accommodations, actually imagine yourself working in them, and while you’re at it, be realistic about how different your travel-self can be from your home-self. Examples (from experience):

Are you hoping to work outside (and will you still be down with that in 45-degree Mexico)?

Are you totally comfortable working from bed (even if you’re in Vegas and that bed is littered with In-N-Out wrappers)?

Would a dining table suffice (even if it’s a tiny Montreal Airbnb and all you have for counter space is that dining table and suddenly that’s where your wine has to live)?

We were once accustomed to booking based on the thread count and the coffee provided, but now the excitement kicks in when we see the ever-elusive DOUBLE DESK pop up in a listing photo.

Don’t Be Afraid to Unplug
Let me preface this by saying — we are TERRIFIED to unplug. We use our phones for up to 2h of work every single morning, are attached to a keyboard for the rest of it, and if we’re not behind the screen, we’re behind a camera. Even when we’re not on the clock, Xanthe lives in constant fear of missing a photo-op, and Frank will never leave home without his phone because of that time we got locked out and had to wait outside until a delivery guy came to the building let us in. What? Anyway, on our most recent trip to Tulum, the networks were spotty outside of the Airbnb, and it quickly became a nuisance to carry around our phones with no real use for them (we got our work done in the morning, which is another thing we recommend). Enter: MENTAL INSPIRATION BANK. This was an experiment, but it worked. Apparently, our brains can remember things without us keeping them in our Notes. Once we had left our phones at home for a few days in a row, we decided we’d just head out on our last day to revisit some of our favourite spots to snag pics of anything we really wanted to take home with us.

Don’t Force Creativity at the Expense of Your Experience
Speeaaaaking of photographs, more often than not, we actually DON’T bring our professional cameras with us on vacation unless we need them for a specific purpose. We get excited at the idea of bringing one along to document places and things for future content (ahem, we mean memories…), but traveling with expensive camera equipment can be nerve wracking and cumbersome. It means being ultra-careful at the beach, planning our days around keeping them safe, and finding time to pop home to drop them off in between swimming/adventuring, leaving little room for spontaneity. The moral of the story: It’s okay to love your work and also recognize when it gets in the way of your PLAY.

Find Your Pain Points (But Don’t Let Them Kill You)
Over time, we’ve been able to pinpoint what specific things cause us the most anxiety while travelling and #1 by a long-shot = our email inbox. We’ve done it both ways — checked email everyday, all day, stopping everything to react and stay on-top of things, or ignored it completely for days until we cracked. The happy medium? OUT OF OFFICE RESPONSES. Looking back on it, implementing this seems so obvious but was a significant mental hurdle for us. So long as we weren’t “out of office,” we were on the clock, and it alleviated some of our guilt about enjoying ourselves while still running our business. If our “out of office,” was on, it made us feel like we wouldn’t be perceived as working. Silly Appleyards! Our business can continue as usual without being slaves to our inbox. This way, we can scan our email each day to make sure there’s no emergencies (we also leave a phone number in case of that, though!) with the knowledge that everyone else has received a reply automatically and knows what we’re up to.

Find a Home Base with Strong Wifi
Seeeems obvious, but it’s not as simple as wifi being included in the description. We spent almost two weeks last year with a “high-speed internet connection,” that resulted in us using the restaurant down the street ft. some adorable beach dogs trying to steal our quesadillas. LIFE! We highly recommend reading the reviews of a hotel or Airbnb to see what people are saying about the quality of the internet — while it’s totally cute and “immersive” to head to a local cafe, it’s also SUPER nice to have the option to check your email in your jammies and leave the laptop locked up for the day.

Don’t Overpromise
We saved the best for last, because this is the #1 biggest lesson we have learned to date. While we all love to imagine we are unbothered by things like time zones, new sounds, the promise of craft cocktails outside our door, and at the ready to grind out a full work day anywhere in the world — we’re not functioning at our highest working capacity when we’re not in a stable work environment. And honestly, if we were working 8 hours a day every day while traveling, what would even be the point?! Coming to terms with this concept truly changed the way we do business on the road. Rather than planning to start new projects while we’re away, or saying “yes” to unexpected requests while we’re on the go, we try (and we say “try” because, REALITY) to plan ahead by recognizing the exact tasks we will need to complete on our trip and — this one is very important — we make sure our clients are on board with these expectations, ahead of time. There have been many adventures when we’ve agreed to get WAY too much done, and find ourselves feeling rushed, frustrated, and uninspired. There IS a world in which we don’t have to choose between our work and our experience — and thaaaat, friends, is WORK+PLAY.

Coming soon to WORK+PLAY:

• Road trip to Florida for Christmas
• March spent in California
• And a few unexpected adventures in between, if we have anything to say about it…

Follow along @ohsierracreative, and subscribe for ongoing updates, resources, and tips here.

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About The Appleyards

We Are Passionate Community Cultivators, Partners in Life and Business, And Firm Believers That Work Should Feel Like Play.

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