My Journey to Working From Anywhere
And 6 essential tips that helped me achieve the lifestyle I wanted so badly — Part 2
Dear friends,
Last week, I shared how I took my first steps in the remote work/'work from anywhere' space three years ago. In case you missed it, you can catch up here:
Today, I will share the second part of my story, along with tips and tricks that helped me secure a job that are still relevant today. As always, your feedback is welcome, along with any questions or doubts you might have.
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After scouring all the main remote work job boards every day with the discipline of an admiral (don't let me fool you: I was also shedding an insane amount of tears from fear, frustration, and imposter syndrome), I managed to secure a handful of interviews.
Some of the main job boards I used were Dynamite Jobs, We Work Remotely, and remote.co. There are more (just type ‘remote job boards’ into Google), although not all of them are as high quality.
Here were the results of my search after roughly three months and countless applications:
One turned out not to be a real job;
One ghosted me after the first interview;
One rejected me after the first interview;
One rejected me after two interviews;
One ended up selecting me after three interviews. However, during a final phone call, I discovered that it didn’t provide the geographic flexibility I was looking for, so I declined;
Finally, one selected me and offered the location independence I was seeking.
Yay!!!
This meant I could have finally started working and traveling for up to six months a year.
For the following two years, I traveled and worked from various countries, collaborating with colleagues spread out in just as many places.
Was it The Perfect Job™️? No, but it served its purpose by allowing me to live the lifestyle I was seeking.
Thanks to it, I had the chance to work from coffee shops in South Korea, sipping amazing cold brew coffee, take a swim in the sea during my lunch breaks while in my hometown on the Italian coast, hang out with friends after work in exciting New York City nights, or take an overnight ferry to Croatia.
All this while being able to not take PTO days if I didn’t want to.
How did I do it?
Looking back, these very practical tips helped me tremendously in my search:
Tip #1: Set an alert for when a job in your field is posted on your chosen remote job boards.
Subscribe to the job board’s newsletter, select the job categories of interest, and choose the newsletter frequency that best fits your search needs. This allows you to get ahead of many other applicants by applying as soon as the job is posted.
Tip #2: Investigate companies’ remote work policies.
It can be disheartening to discover that even when job ads state “This is a fully remote position” or “Work from home (or wherever),” they usually mean you can work remotely... from your country of residence. Understanding the companies’ work-from-abroad policies might require additional investigation, such as checking all the corners of the company’s website or asking a recruiter directly on LinkedIn.
Tip #3: Get crystal clear on your employment goals, specifically the lifestyle you aspire to.
If possible, avoid accepting roles whose policies you don’t align with, as it could end up being a waste of time. I understand that a scarcity mindset might kick in during moments of discouragement, but ask yourself whether accepting similar roles would actually bring you closer to your goals of working & traveling.
Tip #4: Keep in mind that it’s very difficult (if not impossible) to get a job as an employee that perfectly matches all the aspects: great job satisfaction, a good salary, and perfect time- and location-independence.
Especially at the beginning of your career when you don’t have an extensive work history, you’ll need to be open to starting with less exciting roles in favor of a better lifestyle. It’s a tradeoff. Once you have a foothold in the company, though, you'll be able to grow and better refine your position.
Tip #5: Small companies, especially tech startups, are more likely to have informal remote work policies. Big companies that allow remote work are more likely to have formal processes in place.
Both are worth considering.
Tip #6: Have an impressive amount of grit and perseverance.
Remind yourself that you’re seeking a setup that is anything but mainstream, and finding it will be anything but an easy and smooth ride. As the motto goes, "Outstanding results require outstanding efforts.”
Over to you:
Have you ever embarked on a quest to find a fully remote job? How did it go?
What obstacles did you encounter along the way?
Let me know!
Until next week,
Yours,
Caterina