This Certified Mindset Coach and 6-Figure Copywriter Is Living Her Best Life Across Europe

What really happens when wanderlust meets work? Welcome to Digital Nomad Diaries, where we ask women to get real about the joys and challenges of remote work. Because even though this lifestyle is definitely a privilege, that doesn't mean it's not without its challenges and trade-offs.

Name: Dayana Aleksandrova
Industry: Copywriting & Mindfulness Coach
Countries/Cities You've Worked From: Spain, the Canary Islands, Portugal and Costa Rica.

When did you first start working remotely? Did the pandemic make this possible for you or were you way ahead of the game? Tell us about your first remote work experience?

I first started working remotely in the summer of 2017. I quit my last-ever 9 to 5 job at a tech startup and decided I was going to make money online but didn't know how. So to minimize my risks and give this a shot, I landed a volunteer position as a social media manager and blogger at a treehouse hotel in the Dominican Republic. They gave me free housing and meals, and I spent all of my free time applying for gigs online. I landed a $1,120 per month writing retainer for an HR company and this put the start to my remote career!

The close-second experience I got was in the fall of 2017 when Matador Network, an online travel publication hired me part-time to manage their app for travel planning. The company (to my delight) was 100% remote and has never made me go to an office once in 5 years.

What were the practical considerations of remote work? (Did you sublet your place, have to find a pet-sitter, make any arrangements with your workplace?)

I sublet the room I was renting and set out on the road. At first, I was earning very little so I would go on various websites to find hotels and resorts looking for volunteers. I lived in the Dominican Republic twice and in Tenerife for free in exchange for writing. I also entrusted my plants to my roommate. Any of my belongings that my roommate didn't want to be responsible for or had no room to keep, I stuffed in boxes and mailed to my mom's house.

Where have you worked around the world? Where did you spend the bulk of your time?

Having lived in New England for high school and college and being originally from Bulgaria, I was sick of cold weather and snow. My dream was to live somewhere cheap with tons of culture, good food, beaches, and palm trees.

This is why I made Barcelona, Spain my homebase for 3 years. As the city has an extremely well-connected airport, I'd take a week and go work from Curaçao, Hungary, and Italy.

I've also lived in Malaga, Tarifa (Spain), the Canary Islands, including Tenerife, Fuerteventura, Gran Canaria, and Lanzarote. I have been fully-nomadic since the beginning of 2021. I am currently in Portugal and moving to Costa Rica next.

What was the time difference adjustment like? Do you pick your destinations with this in mind?

I work in increments around the clock because I have teammates in Asia, Europe, and the US and Canada. I don't work for 8 hours straight. Instead, I wake up around 6am and work for 3 hours to get all the Asia tasks done, then take a 5-hour break, and come back in the afternoon to work with my US team.

I do consider timezones sometimes but I would rather tell my clients that this is my lifestyle and ask them to include me in as few live meetings as possible so that my changing timezone isn't a problem. So far, they have all been very understanding.

For you, what are the costs of working remote? (Rent, co-working space, flights). Would you say that this cost you more than working at home, less or about the same?

Honestly, rent is the most expensive piece of all. I live with my boyfriend out of Airbnbs for the majority of the time. We spend anywhere from $2,000-3,000 per month and split cost. I don't typically opt for a co-working space because I either do live coaching sessions or write and I get very distracted if there are people around me.

As a digital nomad in Europe, I spend more than what I would spend living on location. In Barcelona and Tenerife, my average long-term rent was $800 per month. One thing to consider when switching Airbnbs is that you want a place that has great internet and a nice, minimalist decor because you want to maintain a good brand presence on your calls. All of that comes at an extra cost.

But as a digital nomad in the Caribbean, I spend way less. I've rented a one-befroom apartment for as little as $450. And if I am to spend $2,000 for a place in Costa Rica, I'm getting something way nicer that I ever would in Europe.

My boyfriend and I traveled by car for the last year to avoid crammed airports and have recently begun flying again. Thanks to the flexibility we have to travel during the week, we've managed to save money on flights. For example, traveling to Mexico is a lot cheaper on a Wednesday than it is on a Saturday. So having that freedom has been very helpful in minimizing living costs.

I also save money from physical memberships. Instead of going to the gym, I work out with a resistance band on my balcony and watch YouTube videos. My only memberships right now are virtual, such as my coaching and marketing masterminds.

Any unexpected costs?

Health insurance! I did not bother buying a global plan and when I found myself sick with plenumonia in Tenerife, I had to pay out of pocket for a visit to the ER. Instead of getting help for free, I shelled out $500.

What are the best parts of working remote? Worst parts and frustrations?

I absolutely love the freedom of remote work. To me, life is short and I want to see as much of the world as I possibly can. I get itchy feet so to speak when I live in the same place for too long. Working remotely has allowed me to travel as much as I want and I even manifested my soulmate on a small, off-the-beaten path island!

I also love the little things such as waking up as early or as late as I like, taking an afternoon nap, going for a walk whenever I want, playing music while I work (and dancing to it sometimes), and going to pee as many times as I want! This last one sounds silly but I used to work at Bank of America in Boston and I had to log all my bathroom breaks.

The worst part about working remote is that it takes a way above-average level of discipline and internal motivation to get things done. It's easy to slack off and just spend 2 hours scrolling through Instagram or leaving the house at 2PM and not bothering to finish your work, only to scramble to meet a deadline at midnight.

Loneliness is a factor of remote work, too. By being a digital nomad who moves around often, I haven't been able to build a solid network of friends and dating was a pure nightmare before I met my boyfriend.

Also, I miss having a home where I can create a comfortable workspace with an ergonomic chair, a desk setup, and have a closet to store all my clothes and shelves for my books. I have a Nespresso machine that I travel with because most of the time, it's hard to find places that make good coffee so I make my own flat white. But as you can imagine, traveling with appliances is annoying and I often have to leave things behind that I love such as my juicer.

Another frustration is that every time I move locations, I seem to lose something! It might be a boot or a T-shirt from the Weeknd tour, or a handbag that I love. It's very annoying.

Did you find that you were fully able to enjoy being abroad while working?

Yes! I make it my priority to experience a destination and so I'm very strict when it comes to my calendar and minimizing Zoom meetings as well as not working on weekends. I also take day trips during the week when I don't have calls and work from new beaches or coffee shops.

How does remote work affect your productivity?

I'm highly-motivated because I grew up with really strict parents so I've got a solid morning routine that helps with my productivity. I wake up around 6AM, work, then do my workout, go for a long walk or a hike, return to work for a few hours, and take the evening off. I'm really experienced by now since I've been remote for 5 years, but my boyfriend who is new at this still struggles at times.

My biggest tip for anyone who's new at remote work is to take your time and organize your calendar. Put in your workouts, lunch, coffee breaks and deadlines so you don't miss anything. Make sure to schedule your rest time so you don't burn out. And if you're able to physically—I highly recommend that you wake up as early as 5-6 a.m. Trust me, when you wake up early, you feel like you live two lives! You're in control of your day and you're not running around putting out fires.

With all of your experience now, what are your current thoughts on remote work? Would you do it forever/indefinitely?

I strongly believe that remote work is the future. I would do it all day, every day for the rest of my life. It's crazy to be limited to four walls and an eight-hour schedule. I saw people getting a taste of remote work in the last two years, and now that employers are asking them to come back, they simply say no. I think for the majority of people, once you work remotely - you never want to go back to the status quo.

I would work remotely forever because I just can't imagine being told what time to wake up, work, and go home. Plus, as someone who's protective of her energy, I love the freedom of controlling my environment and who's in my space.