Quitting Your Job is Not the Right Answer

Big Dreams Need Bigger Plans

I hear it every time I tell someone I’m a digital nomad. When you talk to people who dream of indefinite international travel they will invariably tell you that they wish they could quit their jobs and do what you do. Many people with office jobs are only now starting to understand what remote work is. Frankly, it’s crazy that we live in a time where this is possible Having said that, there’s something  I want to shout from the top of Everest whenever I hear defeat in someone’s voice:

Remote work is amazing BUT you shouldn’t quit your job!

If you’re working a job, today, that’s accomplished primarily through a screen, there’s a very good chance that you can transition into the remote lifestyle.

But Caro, don’t I need to build my own company to be a Digital Nomad? 🤔

No! Many digital nomads do own their own businesses providing services, consulting, or a digital or physical product offering through, let’s say, dropshipping. This is perfectly valid and a real way of making remote income.  If that step seems a little more jarring than exciting, that’s okay. This article is all about keeping you in your current work ecosystem: you get to keep your job, keep your money and see the world.

Carolina overlooking Machu Picchu July 2017 | Happened while working a remote 9-5 job. 

Transition to Remote

Your biggest obstacle to transitioning your existing job to a remote position is building trust with your management team. It’s that simple, and that hard. If this is your dream, are you going to let a group of people who determine your income stop you? Work with them to get you what you need to live your best life.

Hit your metrics, communicate your goals and build their confidence that you can succeed in a new workflow. It’s going to take more than your enthusiasm to convince them that you’ll keep up with your workload while you’re out of office. If you’ve never worked remotely before, don’t worry.

Try It On For Size

Dip your toe into the pool – manage 1 or 2 remote days a week. Then work up to 1 week a month. The big jump will be from 2 weeks remote to a full month out of office. Develop a schedule that works for both you and your management team. This gets them comfortable with the reality of you not being in the office, as well as you delivering work when you’re not there for them to remind you of your deadlines.

Communication is hard. This is the real challenge, maintaining those lines of clarity on your deadlines and deliverables so you can collect those consistent pay cheques and keep their trust. You also want to see what your coworkers are like when you’re not there and you’re solely interacting with them via text or video calls.

It’s Okay if it’s Not for You

You can travel the world without going digital nomad. Without quitting your job. It’s also possible that you find yourself 4 months into your remote lifestyle, working from a neighbouring city, let alone another country that’s 12 hours ahead of your work timezone, and come to the realization that this isn’t for me.

I’ve put so much time and energy, I’m literally living the dream,
“How is this not for me?”

You might just be a perfectly healthy person with a strong family, social and professional network at home. Living nomadically is incredibly stressful. There’s a reason why ancient people built communities and started farming instead of constantly following the herd. Digital nomads have a lot of autonomy in their lives, but not knowing where you’re going to be in the next 6 months, or even next month, can make even the most disciplined of us anxious. Our physical and mental health is always our #1 priority, and making a lifelong commitment to a lifestyle that isn’t healthy for us is not a recommended action for your professional, or personal life.

The only way that you’ll find out if the digital nomad lifestyle is for you is to actually try it out. Take the risk for yourself. Learn something new about yourself, even if that something new is where your boundaries are.

Building Something Anyway

You’ve done what seems to be the impossible and you’ve got a stellar Instagram to prove it. You’ve learned that building solid relationships with your friends and family is deeply important to you and you need them in your daily life. These accomplishments and revelations don’t need to stop you from building a life that allows you to travel whenever you want.

Jonathan taking a photo at Machu Picchu July 2017 

Build the online dropping store anyway. Work towards getting that corner office that comes with work-related travel and negotiate for more vacation time as a perk.

You can do this while working remotely. You can do this working from your kitchen table in your apartment after work. It’s about building something that’s fully yours and you don’t have to ask anyone’s permission if you want to leave the office early or go see a friend in a different city, or country, for a week or two. There’s nothing more digital nomad than that.

Thanks for reading!
– Carolina & Jonathan

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2 thoughts on “Quitting Your Job is Not the Right Answer

  1. Great article! We lived abroad for several years and at the time we were mostly not digital nomads (typically worked from offices in foreign countries). One of the biggest challenges is forming a new community, which typically gets harder as you get older.

    We’ve also been digital nomads after earning the trust of an employer. Really like the way you wrote this – that’s an amazing opportunity that many employees can earn, but certainly not for everyone. Like how you highlted th office dynamic too – which can change when an employee goes remote.


    1. Thank you!

      It’s definitely something that has to be carefully considered. Lots of new remote workers are really excited to travel, but it’s so easy to lose everything we built during this time. Remote life is amazing, but also something to maintain!


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