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Pru Chapman
OC Founder + Head Hustler

Pru Chapman is the Founder + Head Hustler at Owners Collective, a dedicated digital community and global online resource hub for early-stage entrepreneurs. Pru gets giddy supporting business owners to create meaningful, sustainable + profitable business. She loves nothing more than bulletproof coffee, her pooch Maverick, and an empty mountain hiking trail.

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Hurling down the Italian freeway at 160 clicks an hour juggling a croissant in one hand, and my laptop in the other, I remind myself that I’m living the dream. I mean here I am, the peak of the European summer, and with little more than a high-speed wifi dongle I’ve transported both myself and my business to the land of never ending carbs and free flowing  Aperol Spritz.

This IS the dream. It’s just not quite as…. well ….. relaxing as I had pictured it. Come to think of it the ‘laptop lifestyle’ I had pictured in my mind had indeed featured my mac, but the actual work component had hardly a supporting role. The reality of that has hit me harder and faster than the Italian freeway tolls, as I realise that there is actually work to do.

Fast forward three weeks later and there are some finer details of this Italian picture I’ve ironed out. So if you’re planning a similar soirée that ain’t all carbonara and limoncello, here are my top tips for balancing out work and play on your next holiday:


1. Get your wifi sorted before you go

The Pièce de résistance of the working holiday. Get this sorted before you go and you’ve solved 98% of your problems straight up. Some mobile phone providers have sweet deals for the intrepid traveller (hello Vodafone), while others totally fall short (I’m looking at you Optus). Check with your local provider first and you might be pleasantly surprised, but failing that you have a few options. Firstly, you can organise a SIM card with included data on arrival, which is by far the most popular option. Personally however, I’m a closet control freak, so I like landing and being ready to go. I’ve found an awesome little option in the form of MyWebspot, an iPhone sized hotspot that gives you super fast 4G across the vast majority of Western Europe. These guys deliver this little piece of magic directly to your arrival hotel complete with phone chargers, spare battery and return pre-paid envelope for when you leave. There is a daily limit, but I’ve run coaching calls, webinars, and video challenges from Mykonos to Portugal and everywhere in between on one of these bad boys, and can’t fault them.


2. Tell the people you’re going with that you’ll be doing a spot of work

I’ve done it both ways. Firstly, pretending that I’m not working and secretly getting up at 5am to get a few hours in before everyone rises and I pretending that I’m already wired from an early morning walk. More recently I’ve started telling my family and friends what I need to do and why, then follow it up by how long I’ll expect to need each day. If you take one thing away from this blog, let it be that option B here is the way to go.


3. Utilise transit time for working

You’re on holidays for a reason, don’t forget so when you find your feet in a new place you want to get out and explore it! The last thing on your agenda should be work, so where to fit it in? In transit is the place. My pocket wifi mentioned earlier lets me work from pretty much anywhere and everywhere. Trains (not planes), and automobiles included. If you’re taking a holiday, chances are that you’ll probably be on the road fairly regularly, so get tapping and you can easily knock over your ‘must-do’s’ for the day.


4. Only do the things the ‘super essentials’ to while you’re away

Holidays are not about emails. So if you’ve got things that you need to do or make happen while you’re away be super clear on what those are, and do only those things. Here’s to NOT sitting on email all day.


5.  Share it yo!

This is an awesome time to connect with your community and not only share the journey but also give them a BTS view of why and how you travel. Essentially I’m a ‘flashpacker’. I love nothing more than a clean well-lit Airbnb, where I can feel like a local and cook my own dinner (outside of Italy of course). Fancy hotels make me feel uncomfortable and disconnected, so I rarely go near them. All these adventures I share on our Instagram, and whenever I do our engagement goes off the charts #winwin.


6.  Be prepared for things not to work – and be ok with that

Your wifi will fail, your mac will run out of battery, emails will fail to send, and uploading will be near impossible at times. Take it as a sign that you should get offline and go and enjoy this glorious place you’ve brought yourself to. After a long walk, a lick of gelato and a thousand photographs, everything will work better, promise.


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