• Business, Travels & Adventures

    Work & Travel As a Digital Nomad, Glamorous or a Pain in the Ass?

    Work & Travel, is it glamorous or a giant pain in the ass? In this guest post, Brooke is breaking down the honest truth of what it's like to work AND travel -- The Quirky Pineapple Studio

    From what Instagram would have us believe, the existing concept of travel as a “digital nomad” is a genetically enhanced individual who takes their laptop to destinations they can’t possibly afford on a seemingly eternal basis, doing no work whatsoever.

    In other words, by the current definition, digital nomads are full of sh*t.

    Me? I’m part of the new generation of location independent entrepreneurs. We’re the ones building their dream businesses from the ground up and working their asses off to make it viable, sustainable, and flexible.

    Does that mean I travel 365 days a year? No – because I live in the real world where there’s rent to pay, work to do and a life to live.

    Does it mean I had the autonomy to travel to 15 countries in the past year – including a month-long adventure in India – without having to ask anyone’s permission to get any approvals? To travel for the joy of it rather than as an escape from my miserable 9-5 cubicle life? You bet your ass it does.

    I know what you’re thinking…

    Work & Travel As a Digital Nomad

    “That’s not possible”. “You’re so lucky”. “I wish I could do that”.

    Luck has absolutely nothing to do with it. Let’s just get that straight. I’m also not some trust fund baby, nor do I have money to burn.

    I work hard, I book early, I drive places – I just DO things.

    If you feel like it’s your time to do something, then there are a few ground rules for making a location independent business viable (and enjoyable) for you and, more importantly, for your clients:

    Get Smart

    Your business is only as intelligent as you make it. Make sure every system you implement is online and can be accessed from anywhere, any time. This means your accounting software, project management system, onboarding and client management, marketing, project delivery (Google Docs) – everything. You have to be able to adapt if your laptop is swiped by a random in a train station, and you need visibility over your business at all times. 

    Some of the tools I use to make my business work ‘smarter’:

    Dubsado – CRM of the gods. Amazing for templates, accounting, lead captures – and they’re adding new features every day. It can accept invoice payments, automate workflows, and even gives each client their own portal login to view any documents, email trails, and invoices. The ultimate in professionalism, simplicity, and productivity. And I’ve even arranged a link to get you 20% off the first month.

    N26 – If you’re still traveling and your card gets swiped, you need to be able to lock that sh*t down real fast before your hard earned cash goes down the drain. N26 is all across Europe and is soon opening in the UK and US. Everything – and I do mean everything – can be done right from the app. It’s clean. It’s intelligent. It’s simple. It takes 8 minutes to set up. Oh, and it’s free.

    Trello – I can’t possibly say enough about this app so I’ll give it to you straight – you will never find a better project management tool than Trello. I categorise my “boards” as a workflow – Pipeline, Open projects, In Review, Complete and To Be Invoices, Finalised. With notifications on any changes, additions or comments made by you or the client you share it with, an iOS/Android app that is flawless, and “power-up” integrations with all your favourites including Google Docs, you will know exactly where every project is at wherever you are. Get on board.

    Get Serious

    If you want to be taken seriously in business, you need to be damned sure you’re taking your business seriously.

    Your clients should never have to suffer simply because you feel like working by the beach. In fact, if you’re truly location independent, your clients shouldn’t know the difference between you working from your home office or while on a 20-hour train ride across India. Get realistic about managing client workloads, under promise and always, always, overdeliver.

    This also means investing in yourself and your business. No, that doesn’t mean getting an upgrade for your next hotel booking. It means you have to give your business the tools it needs to survive and thrive.

    Buy the computer. Subscribe to the software. Educate yourself. These things will follow you wherever you are in the world and are the cornerstones for your business’s success.

    Get Mobile

    I went to India for a month in April. I was too paranoid about breaking or losing my beloved MacBook Air, so I took my shitty old 2008 iPad 2. I downloaded Google Docs, Trello, and set up my emails, thinking I was so clever taking a smaller, lighter, less expensive tablet that I didn’t mind losing.

    Un. Til. My. Tab. Let. Star. Ted. Typ. Ing. As. Slow. As. You’re. Rea. Ding. This.

    This is not good when you write for a living. My productivity plummetted, it took me 10 times longer to finish projects, and caused me more stress than I needed on an already hectic adventure.

    You and your laptop are one. Where you go, it goes. Get it insured. Get a good case. Keep an eye on it. But do not – I repeat, DO NOT – leave the best asset your business has behind. Your work will suffer, your clients will suffer, and without these, you’re no longer a ‘digital nomad’, you’re just some unemployed dude sitting on a beach.

    Get a portable charger. A big one. Take the right adapters. And never underestimate the power of a pen and paper. When technology fails, your notebook will not. Ideas come thick and fast when you travel, and they’ll be gone before you can put them to use unless you write them down.


    The moral of the story? The only way to work and travel as a digital nomad and for it to not be a pain in the ass when running a business is if you establish a business that’s designed to travel with you.

    Also, notice that I keep saying “travel” rather than “holiday.” Holidays are things you do to escape responsibilities and live in a fantasy bubble of joblessness for as long as your budget will allow. Traveling is experiencing all the glorious, challenging, and unique places this world has to offer while remaining completely committed to the hustle.

    Be prepared. Manage your time. Lay your foundations. Live the hustle.


    Meet Brooke Ermogenis – @brookeinnez Brooke Ermogenis

    Copywriter, expat, and straight talker

    Founder + Director of Occa Inc
    Founder + Director of The Expat Hustle

    Copywriter by trade, I’ve built my business while living as an expat in Germany over the past year – building a client base, navigating crazy bureaucracy in a language I don’t understand, and creating a business that I truly love. Soon launching The Expat Hustle – an online community and resource designed for expat hustlers just like you.


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    Work & Travel, is it glamorous or a giant pain in the ass? In this guest post, Brooke is breaking down the honest truth of what it's like to work AND travel! -- The Quirky Pineapple Studio

    So, is it worth it to work AND travel at the same time?