Remote Work: What It’s Like Working For A Distributed Company

What Is It Like Doing Remote Work

What it’s like working for a remote company and living a remote lifestyle – but more importantly, doing the research and taking a leap of faith to get there!

As the wave of technology continues to shape the world in which we live, it is important to have the opportunity to understand what is out there for you.

On a personal level, many people are well aware of what they are capable of and what they can do within their means. That said, many still do not fully understand what is out there for them professionally. 

One thing many are still learning is the fact that there are new options available to them professionally. These options may ultimately lead to happier and healthier lifestyles, by offering them geographic freedom.

In comes the professional wave of remote work (also known as telecommuting) – allowing professionals to be exposed to a new variety of employment options that allow them to decide their geographic boundaries.

Over the past three years, I have had the privilege of transitioning to a fully remote lifestyle thanks to forward-thinking employers and taking a leap of faith.

For some this means traveling the world, for others, it means working from the comfort of home and spending more time with their families.

Whatever “working remotely” means to you, start discovering where the opportunities lie and how you hope to spend your days when the time comes… the shift isn’t going anywhere as Business Insider projects that 50% of the United States workforce will be working remotely as early as 2020.

Here is my story of remote work…

Part One: Becoming a Remote Worker

A Desire for Change

It’s hard to believe that only three short years ago I was sitting at home contemplating where the next steps in my career would take me. I had just spent a few months in Europe traveling through seven different countries and experiencing new cultures. The previous six years would be spent navigating corporate structure and grinding the phones from a cubicle – also known as the “bullpen”.

Reflecting on these experiences I ended up realizing that sometimes it was a negative work environment that resulted in a lack of fulfillment, but also I was no longer feeling inspired and creative in my surroundings.

I realized my happiest moments in the past few months were outside of my comfort zone, exploring what the world had to offer. Then came the Google search that would end up changing my life forever….

“How to get paid while travelling the world.”

Pictured Above: My home city, where I completed University and spent the early part of my career. Saskatoon, Saskatchewan, Canada

Takeaway: Don’t be afraid to conduct a little research, the world is changing so fast that there may be possibilities that you have yet to uncover!

Many people, including myself, become complacent for fear of change – when in reality it is an incredible thing to embrace.

The Eye-Opening Opportunity

Of course, that Google search was just a pipe dream, and unfortunately, I didn’t find a get rich quick scheme or magically have money show up to pay the expenses of traveling…

…but what I did find was a whole network of forward-thinking professionals reshaping the way their professional lives were lived and the way their geographic surroundings looked. 

My exploration led me to a company called Remote Year, at first I was considering going on one of their travel programs. The tough part was at the time, I didn’t have the role that would allow me to work remotely outside of my geographic boundary – even though I was working from home.

Through this realization, I was led to simply asking an individual within the company who I was speaking with if they would recommend me for one of their internal openings.

Long ago I learned one simple rule, if you never ask, the answer is always – no.

Simply going for it would eventually change my outlook on life. The opportunities for adventure, at the time, would be unimaginable. This individual, who would later become my good friend, ended up recommending me for the role – which I would get and my remote work life was set to begin.

Takeaway: Use your network, take a leap of faith – and don’t forget to thank those who help change your life for the better. For networking, LinkedIn has been one of the greatest opportunity finders that I have utilized during my career.

Working in a Remote Company for the First Time

The Cultural Curve

The day I received a call letting me know I would be offered a position in my first fully remote role is one that I will never forget. Realizing the opportunity to fully change your lifestyle, to one that you only dreamt of, is an incredible feeling that most do not receive.

For that, I will always be grateful… listening to a call asking if you can move to Mexico City for training in two weeks was quite the adrenaline rush.

So, it began!

Going into my first fully remote role was definitely a big learning curve. There are a few things I wish I had done differently or at least taken the time to educate myself on in advance.

That said, moving to a new country and experiencing the culture, while needing to start a new language from scratch, were some of the most rewarding experiences – outside of the working environment. 

Professional Development

From a professional sense, however, it is really important to prepare mentally and continue with an element of structure.

Remote work has an incredible amount of trust involved, therefore you need to ensure you have your structure in place in order to stay accountable to yourself and the organization.

Next, you will be introduced to an array of different software systems that will allow you to conduct your work from anywhere with a WIFI connection.

If you are interested in learning more about which tools I like to use, you can find that here

Once you develop the right skill set, you ultimately open up to more remote opportunities.

Many remote-based organizations are utilizing overlapping software and skillsets. Therefore, once you better understand the inner workings of remote companies and develop skills of appropriate time management and accountability, you can search for the right organizational fit.

Pictured Above: View from We Work Torre Reforma. Latino, Mexico City, Mexico

Takeaway: Working remotely is essentially an education curve in itself. Of course, accepting the opportunity of a lifetime is amazing, just ensure that you are prepared for the changes in accountability and time management that it may bring.

Searching for the Right Organizational Fit

The Travel Bug

From the beginning, I knew that remote work was the new wave for me in my professional future. The first organization, as indicated above, was Remote Year – a travel company that fosters remote work and travel programs to cities around the world. An amazing opportunity for myself looking to break into the remote work world, but furthermore, a desire to see the world and make the most of my professional freedom.

I loved the company, however, I did not particularly enjoy my role specifically. In saying that, I would highly recommend the Remote Year travel programs if you are already working remotely, or are looking to make that transition. It is an amazing experience filled with forward-thinking individuals breaking out of traditional lifestyles. 

Entry into the World of Software

This would bring on my next challenge, I had a desire to work in software – while of course keeping on course with the remote lifestyle. I joined a small tech startup that was focused on software that was associated with Amazon. In such a small organization, I would end up being hired as a Sales Executive and eventually transition into a customer-facing Product Manager role.

Being in a small organization, it’s amazing the amount of different skills you can learn across several avenues – this was one of the largest professional leaps I was able to take, all while continuing to learn about remote lifestyles.

The company would end up being taken over by a larger entity and thus, my path to find the perfect spot continued.

Feeling at Home with Dropified

Sticking with my goals of fully remote work and working in the software industry I was able to utilize different resources to come across Dropified (those remote job board resources are found below). My current organization has been an amazing fit for a variety of reasons.

First off, I have an opportunity to work with very diverse clients that have a great appreciation for our software. Being able to work alongside something you believe in is a huge difference-maker in finding that perfect role.

Next, our leadership team is always on top of the game, whether it be through competitive analysis or capitalizing on new opportunities and ventures there is always something exciting on tap for our team.

Finally, they have hired a team of professionals and experts in their fields – allowing them to work independently with confidence, towards a common goal.

Remote Work Job Board Resources

Full Time Positions
We Work Remotely
Working Nomads
Remote Job Hub

Takeaway: Fully remote organizations are filled with forward-thinking and talented leadership making amazing cultures common. That said, don’t forget that your daily duties are your primary focus and indicator of enjoyment – so ensure to find your most compatible fit!

Part Two: Living a Remote Lifestyle

The atmosphere in a Remote Work Organization

One of the most important aspects of a remote work organization is the development of an amazing culture. When all of the individuals are primarily working from various locations alone, the organization's culture is what holds them together, staying motivated towards that common goal.

Since I have started working in remote organizations, I have noticed five main trends that shape the atmosphere within them. 

Access to Global Talent

This is the one component that most organizations recognize as their biggest strength when transitioning to a remote workforce. With geographic restrictions, comes access to only the talent within that local population.

By becoming borderless, organizations have a virtually unlimited talent pool that they can select from, resulting in some of the top professionals of their craft, coming together on projects within the organization.

Cultural Diversity

Developing from the topic above, I have had the privilege to work with individuals coming from all areas of the globe – except Antarctica. Whether it be North or South America, Europe, Asia, Africa or Australia – I have had the privilege to develop friendships with professionals of such diverse cultural backgrounds.

The best part of this is the increasing cultural understanding, especially in global organizations. It also brings an aspect of learning that happens organically and often can't be replicated in the office setting.

Freedom to Perform

The reason most people join remote organizations; the freedom to work with flexibility in regards to where and what hours. That said, we will alter the quote a little – “with great freedom comes great responsibility.” As mentioned earlier, accountability and time management becomes paramount.

You know what you need to do, and so does your employer – get the job done!

Lend a Helping Hand

If you’ve never experienced remote work, you may have thought that it is more challenging due to not having a team around you for quick access to assistance on whatever the matter may be.

Through my experience, everyone within the organization has a desire to help out if they have the expertise on what you are looking for. Through technology like Slack, people are quick to respond to your inquiries and often times a solution arrives quicker than in the traditional office space.

Overcoming Loneliness

Even though you will always have connections to people digitally, it isn’t uncommon for remote workers to feel a sense of loneliness during the workday. This is where your workday structure and lifestyle must accommodate physical connection as well.

One way to combat this is to utilize your schedule freedom to get some physical activity during the day, or, find a co-working space near you loaded with professionals who have this aspect in common.

Takeaway: Access to global talent and continuous learning through cultural diversity allow remote organizations to create a very welcoming atmosphere where everyone is willing to help out. However, by having the freedom to work remotely, you may face loneliness during the workday. Due to this, it is important to get out there and find the place where you feel innovative and inspired by your surroundings!

Co-working Spaces and Diverse Offices…

Workspaces of the World

If you’ve never been to a co-working space – it is a must in my personal opinion. I’ve met some great people through co-working spaces, as well as felt the most inspired in certain circumstances. They come in all shapes and sizes and have an array of activities to break up the workday as well.

Whether it’s a game of pool, ping pong, post-work beer on tap or simply staring at the beautiful artwork on the walls – some of the world’s most innovative spaces are built to break up the traditional mold.

A few of my favorite co-working spaces are We Work and Selina. These are two of the fastest-growing in the world – and for good reason.


“Home” Based Office

For some people, the traveling aspect may not be the reason for a desire to transition to remote work. The most important thing is having a comfortable space where you feel productive.

Currently, I am no longer going to co-working spaces simply because I wanted to stay home more often. That said, I made sure that my new home had space where I was excited to take my coffee every morning and felt as though I could replicate co-working spaces or traditional office spaces.

Lucky enough for me, I was able to find a complex that has an office space within. 

WIFI Chasers – Office of the Nomad

By far my favorite category of work spaces, since at times it can get a little ridiculous – but there's WIFI!

A common theme in this article is freedom through remote work. If you're the type that is looking to take advantage of those travel plans you have been putting off; be sure to check the WIFI quality in advance before venturing out.

Personally, when working from an amazing space with a great WIFI connection, I can feel myself becoming more energized and that transmits through my work and across to my clients.

Pictured Above: Nomad Life in Bacalar, Mexico

Takeaway: Co-working spaces are some of the greatest places to meet other professionals from around the world, in an amazing work setting. They are very innovative when it comes to creating an environment that you enjoy coming to and staying at. That said, since work can be done from anywhere – don’t forget to take advantage of that.

Genuine Work-Life Balance

Never Miss a Moment

In the beginning, I got into remote work in order for a bit of an escape. It wasn’t until after doing it for a while that I realized this important advantage.

Working remotely has allowed me to live in different countries around the world, however, more importantly, it has allowed me to be with the people I love in the moments that matter even when living and working abroad.

With flexibility, you shouldn’t have to miss your friend’s wedding or your children’s sporting events because of geographic restrictions, not having enough holidays or requirements of being in the office. Not only can memories be made in new and exciting cultures, but you can also make sure you never regret missing a moment. 

Pictured Above: My family at my cousin's wedding in Saskatchewan, Canada

Digital Nomads

Depending on the point you are at in your life and what your true desires are when seeking remote work, becoming a digital nomad is one of the most rewarding experiences you can have.

Experiencing diverse cultures and living in different countries cannot be understated when it comes to personal growth. I’ve been lucky enough to live a nomadic life as well as that of working from home in an environment where I am happy and productive.

If you choose to travel, your life essentially becomes a holiday. There’s no more waiting for that week of vacation you booked three months from now. Your weekends become experiences others dream of and your evenings allow you to see what your new cities and countries have to offer.

Sometimes it can be scary, sometimes you may get homesick, but you always come away with learning something new and experiencing something that may change your life for the better.

Teotihuacan, Mexico
Catedral de Sal, Zipaquira, Colombia

Machu Picchu, Peru

Run Those Errands

When it comes to having to make time to conduct normal everyday things as well, you have the opportunity to do so. For some people, keeping up with physical and mental health is very important.

With flexibility in the schedule, you may want to go to the gym at a time that feels the best for your body. Other times you may need to schedule doctor’s appointments in the middle of the day, or simply get groceries for tonight’s dinner with the family.

Whatever it is, remote work provides the flexibility to conduct everyday things at the convenience of your schedule. In saying that, the next topic comes up rather consistently since you may use portions of a traditional workday for your errands.

Pictured Above: Late nights making up for the daytime missed, wherever and whenever – get the job done!

Biggest Myth

Even though you have the freedom to live your life as you choose, oftentimes with all of the beautiful photos and amazing experiences – your friends and family may question whether or not you truly work.

The truth is, sometimes there is great difficulty switching off. Since your office travels with you, often times you will see yourself working from anywhere at any time.

My recommendation is to ultimately focus on set hours, even though those hours may be at odd times of the day.

Takeaway: Genuine work-life balance is the main reason most people get into remote work. Depending on the person, that might mean traveling the world and for others, spending quality time with their loved ones. Whatever it is, achieving this is a life aspect many people don’t have the opportunity to get – soak it in and never take it for granted.

Final Thoughts and Recommendations

As mentioned in the beginning, remote work is here to stay not only due to technological advancements but from the workforce’s desire to break traditional molds.

For some, remote work means seeking out jobs that allow you to work from wherever. It could also mean starting up a new location independent business such as thousands of our successful customers here at Dropified have built to accomplish those same desires.

For me, the biggest thing was the happiness and mental healthiness that came about due to making the transition to a remote lifestyle. The feeling of freedom and the allowance to live where I felt most comfortable (while being uncomfortable) was the biggest reward I could ask for.

Ultimately, I encourage anyone considering the change to remote work to take that leap of faith and go for it! The only regret I will ever have is wishing I made that leap sooner.

If you’re ever looking for guidance or more stories on this lifestyle, don’t hesitate to research or reach out. Best of luck – and happy freedom searching!

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