Going into 2021, I will be celebrating 4 years working remotely. It’s crazy to think it has been this much time now since I began my journey working from anywhere. I’ll go through why I started and how it happened, how I’ve been able to sustain living a life a travel (with ideas you can take away for yourself), and what it’s looked like for me to continue to build a successful career while working remotely (so you can see you can do it too!).

How I started working remotely

A brief background of my career before working remotely

In 2016, I had been living in NYC for a few years working in tech. I started out in web design and development, working at a tech startup, transitioned to UI/UX Design at another tech startup, and eventually moved up to managing the design team in the same company pretty quickly.

Halfway through 2016 my husband and I became frustrated with the fact of having such limited time off(that we mostly had to use to visit family instead of taking real vacations!). We were working our butts off, doing well and the things “expected us”: having a cool apartment downtown in Greenwich village, having good jobs at cool companies, a busy social life, and all things one expects or assumes for a post-grad young professional in the city. I talk a lot about this in my YouTube video here.

I was working so hard and doing well yet couldn’t do the one thing that mattered so much to me: travel.  I had always traveled as much as I possibly could one I turned 18, working all summer long each break between school and college. I’d save up to take a trip to a new country every school break, saved up to study abroad in Italy etc.

The problem was: I was extremely career driven too. Unlike a lot of ‘digital nomads’, I’m not the type that “hates the office life” or the 9 to 5. I love structure and use it to my advantage. I work well in team settings. I am goal oriented and achievement has always been one of my strengths. I was lucky in the fact that I was able to figure out a field of work I really enjoyed doing (I can be on the computer for 12 hours and not be bothered haha0.

What didn’t sit with me was the perception of “traveling the world” (unless just on a vacation) that I was used to seeing was always reserved to those “not doing anything with their life” (or atleast, that’s what other people described those who were doing that as). I hated the fact that I had to choose one or the other.  WHY could I not have both? WHY did I have to choose?

What I realized about my career

A few things occurred to me in 2016: I had successfully transitioned into the UI and UX field (which doubled my income from just web design and development) and guess where I learned what I needed to make that transition: online.

Not only did I NOT need to go get a new degree to double my income and expedite my career, I was able to learn everything for it online. And what did I notice about those I was learning from? Both the companies and individuals that I was learning from in this relatively new field from all worked remotely. And not just random individuals, but those who were leaders in this field.

I realized in 2016 that in fact, I do NOT need to live and work in one place in order to

1. Keep working in my field and continue to grow my career

2. Become a leader in my industry

This suddenly opened the door for me to realize I do not need to leave my career behind to travel the world too.

What triggered me to finally take action to start working remotely

About halfway through 2016 my husband and I had booked a trip to Morocco for the following February (it was a bucketlist surf destination for him). The thing was, we only booked the flight there… The nature of my husband’s job at the time was that he wasn’t sure he could take off 1 week or 2 and wouldn’t know until less than a month ahead of time so we’d book the flight back once we knew.

Well, after we booked that one way flight, we started joking ‘What if we just didn’t come back?’

But the thought terrified me.  My life and career was in NYC at that point. I wasn’t ready to give everything up.

But we kept joking about it. And the more we joked about, the more I started to realize: Maybe we actually could do it. But I didn’t want to quit my job either. You can imagine the debate going back and forth in my head.

The end of 2016, the company I was working for was having trouble with finances and funding and the future seemed extremely uncertain for my position (and everyone’s for that matter) at the company.

Should I find a new job in the city? But from what ‘everyone’ had told me, getting a ‘regular’ job has proven no less stable and secure. Here I was, still facing the fact that I could lose my job with hardly a week’s notice because they couldn’t afford to pay any employees anymore. At the end of the day, I realized there is no ‘real’ security and only YOU can create it – you can still lose your job and all the benefits that go with it at a moment’s notice (no matter how valuable you become to a company). Yes, certainly there are industries that have ‘more security’, but in the end, only YOU have the complete control of your future.

Realizing this, combined with discovering the ability that I could continue and shape my career from anywhere, this idea of ‘not coming back’ no longer was so scary. What was scary was losing my job on a moment’s notice and not being able to pay the next month’s insane NYC rent.

Transitioning my full-time job to be remote

We made the decision at the beginning of December 2016: we would move out of our NYC apartment, spend the holidays with family, and then spend 2 months in Costa Rica and Panama, 1 month in Morocco and figure it out from there.

Making this decision, I felt like a giant pressure lifted from my chest. Suddenly the idea that I could lose my job was no longer scary.  I felt out of control by the situation of the company I worked for, I felt out of control by the cost of living in NYC with losing that job and not having enough time to prepare for another position.

When I decided  to do what was best for ME,  I suddenly felt in control again. That my future was now truly up to me, and not reliant on anyone else. That if I did lose my job, at least I’d be somewhere warm, and somewhere I was excited to be.  The worst case scenario suddenly was an “oh well I’ll be fine now”.

But here’s the catch: I still didn’t want to quit my job, even with the uncertain future.  I loved my job, managing the design team, my coworkers and teammates, working in tech, I loved creating and problem solving every day. I loved spending hours on my computer on end.

While I loved my job, my husband was not happy with his career direction, even though he was brilliant at it, and desperately wanted a change. He 100% planned to quit, which he did, and his bosses of course were bummed to see him go. So I prepared to tell my boss what was up, what my husband and I planned to do and what was best for us personally.

I slacked my boss that I needed to talk to him about something. I was soooo nervous. I  loved working for the company and what we did! I also still wasn’t quite ready to leave NYC, I loved the city, but I still needed to do what was best for me, for my marriage, and our general life path.

We went into a conference room and I told him everything: our plans to move out of our apartment, that we would be traveling for a few months, my husband quitting his job, etc.

The first thing he asked is if I’d like to work remotely. I was sooo relieved! This was what I was hoping for because I didn’t want to quit. I just wanted both. And a part of me knew that it was very possible because I knew as much as I enjoyed the work that I did, my team also needed me to. I always prioritized my work above almost anything else, stayed late most nights, came early most days, and did everything I could to go above and beyond in my role. All of that effort not only amounts to my quick promotions into management, but now this: being an asset to the company and our team.

At the end of 2016, going into 2017, I started working remotely. I had my same job, same salary (things got better financially for the company I was working at), same hours, just now I would log on and work 10-6 from wherever I was in the world. I even grew our design team and made hires remotely, with occasional visits back to NYC to work in office with the team. I made sure I was always available during EST working hours, and did whatever I could to make sure my output and quality was no different from when I was in the office.

From then on, I was hooked.

What I’ve gained and learned from working remotely

Fast forward to today, I’ll now be celebrating 4 years working remotely. I continued to be fully employed remotely for 2 years up until the end of 2018 when I started working for myself, contracting in tech in UI/UX and now also working as a content creator and influencer.

And what’s happened since working remotely? These are the biggest 3 things;

• I started making more money (especially once I started working for myself and I could balance more opportunities)
• I started traveling way more
• I have been able to live abroad
• I have spent way more time with family and friends

The list could go on but these are the biggest, which really is just an overall huge increase in my quality of life.

Now, of course there are downsides to working remotely (there are downsides to everything), but overall, I am so glad I started. And with a little bit of courage, a strong digital skill set, and determination, you can do it too. In these last 4 years, I have seen more than ever the growth of working remotely, not just the benefits. The future of work is online and even industries you would never think to have an online component are starting to.

I hope that my story can inspire you and show you that it is more than possible to work remotely, to travel, to have your cake and eat it too. If you are feeling stuck, feeling uninspired, or feeling trapped, you can watch a few of my youtube tutorials on figuring out a good path for remote work for yourself so you can discover this freedom, while also building a successful career.

Don’t forget to grab my work anywhere starter kit to dive into exactly what you need to do to start your work anywhere career, explore your options, and have all the tools and guides to start!

Ready to take YOUR job and life remote? Get everything you need to work from anywhere inside my starter kit!