How to Plan Your Exit: Going From Office Desk to Digital Nomad

Leaving the comfort and salary of a steady office job for the uncertainty of life as a self-employed digital nomad is a huge change, both personally and professionally. I did it myself in 2021 when I left my job as a lawyer in London. Overall, it was an amazing decision and I’m infinitely happier than … Read more

The post How to Plan Your Exit: Going From Office Desk to Digital Nomad appeared first on Goats On The Road.

Leaving the comfort and salary of a steady office job for the uncertainty of life as a self-employed digital nomad is a huge change, both personally and professionally. I did it myself in 2021 when I left my job as a lawyer in London.

Overall, it was an amazing decision and I’m infinitely happier than I was before. But, it’s not all roses and sunshine. It can be hard at times, but ultimately, I think the challenges are worth the huge upsides.

Here are the steps that helped me go from office-bound and miserable to location-independent and free. These tips all come from my own personal experience. I hope they’re useful and help you pull off your own escape.

How to Plan Your Exit: Going From Office Desk to Digital Nomad

Whether you’re craving freedom, adventure, unlimited travel, better weather, or simply a life outside the corporate box (for me, it was all of those things), here are a few things I highly recommend you do first. This will help set yourself up for success, before taking the plunge.

Dariece Pool Madiera

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Reflect on Your Why and Goals

Goats On The Road, Dariece, in a hammock at a hostel in quilotoa loop isinlivi
Relaxing in Isinlivi before hiking the next morning

Before you write your resignation letter, take a step back and ask yourself why you want to become a digital nomad. What’s driving this decision? Whether it’s the freedom to explore new places, the chance to work on your own terms, or just wanting to escape office life, understanding your motivation is key.

For me, it was the frustration of being stuck in a rigid routine, and the stuffiness of the legal profession. I realized I wanted a lifestyle that prioritized flexibility and adventure. This “why” still gives me clarity and motivation to this day, and helps me stay focused when times get tough.

Write down your goals – both personal and professional. Do you want to see specific countries? Learn new skills? A new language? Create a sustainable income online? Build a mighty business empire? Having clear objectives will help guide your decisions and keep you motivated.

Build Financial Stability and Security

Nick & Dariece Goats On The Road enjoying some much deserved down time with drinks in an outdoor restaurant

Money stress is one of the worst parts of being a freelancer. That’s why creating a solid financial safety net is essential before you hand in your notice. You’ll need savings to cover at least a few months of living expenses, plus an emergency fund, and a plan for steady income going forward.

My business took almost a year to start making any money. Being in Central America for the first few months of my nomad life certainly helped make the money I had saved go further. But, if I hadn’t built up a pot of savings before I quit my job, I would’ve soon run out.

Before leaving your job, make a budget, cut unnecessary expenses, and try to save as much money as possible. You don’t need to have already built up a business to the point of profitability before you hit the road, but the closer you are to this stage, the less risky it will be.

Develop Remote Work Skills

Remote worker Alex working from beautiful location. Working on laptop from desk with surrounding mountain views

One of the things I love most about being a digital nomad is the ability to travel as much as you like. But, like it or not, you’ll still probably need to spend a large chunk of your time working – even if you can nip off for a cheeky surf between meetings.

As many of us learned during the pandemic, remote work requires quite a different mindset than working in the office. You need personal discipline, solid communication skills, and the ability to manage your time effectively without having a boss looking over your shoulder.

I find this much easier working on my own business that I care deeply about. But, don’t underestimate how different the experience is. If you aren’t already, get familiar with tools such as Slack and Teams, and consider taking online courses or enrolling in a coaching program to help you upskill.

Research Potential Destinations

Nick Working Blogging

Not all destinations are created equal for digital nomads. Some places (like Thailand and Portugal) are known for their low cost of living, lightning-fast internet, welcoming attitude to nomads, and thriving communities of remote workers. Other places are more challenging.

Picking the right destination for your lifestyle and budget can make or break your experience. Keep in mind your own priorities. Do you want year-round sunshine? Easy access to coworking spaces? A low-key vibe or a busy social scene? Rural or urban? Is the time zone likely to be an issue?

Your first destination doesn’t have to be perfect. I spent a month in Chiapas, Mexico when I first started out. It’s an absolutely stunning place, but it wasn’t ideal for remote working, with regular power cuts and ropey internet. I also managed to catch dengue and the flu at the same time – rough.

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