The Cocoa Nomad shares his remote (work) journey over 10+ years

1. Hey, can you please introduce yourself?

Hi, I’m Alondo Brewington, a location independent software developer, with a current focus on mobile applications. I grew up in Georgia (Atlanta) and the Carolinas (Charleston, Goldsboro) and spent most of my life moving between those three states. As a military brat, relocation was a normal occurrence. Adding the remote work component would take many years but in hindsight, it makes perfect sense that it’s the lifestyle that I’ve chosen.

I have now been working remotely for almost 10 years. In  2016, I joined the Remote Year program and traveled to 12 countries in the span of 12 months. Since then I’ve traveled to/ worked from more than 30 countries.  My work experience has run the gamut from full-time employment to freelance/ contract work to entrepreneurship so I’ve experienced various organizational dynamics. 

Below is a photo of me enjoying a day at a co-working space in Koh Phangan, Thailand. It’s a tongue in cheek look at how remote work is promoted on social media 😝 but in reality, this was the most productive month I had that year. (My only time in that hammock was for this photo).


2. What motivated you to choose remote working?

My first remote work experience was in 2003 when I was doing small data projects in Crystal Reports for a hospital in Georgia while I spent a few months in Malaga, Spain. I got my first taste of international travel but I wouldn’t consider it as a full-time option until after another trip during graduate school in 2007. 

At the time, remote work was still in its infancy and only thought of by most people in terms of call centers and offshoring. I worked a long-term contract engagement at Atlanta Public Schools, which briefly experimented with allowing some team members to work remotely.  Although, it was quickly shuttered by the new CTO shortly after my arrival, I got an opportunity to confirm that my skills and productivity were not location dependent 😎. From there it was easy for me to start thinking about pursuing remote work as the norm, rather than the exception.


3. What were your initial months like? Did it live up to your expectations?

When I  joined a  freelance iOS app development project in 2010, I wasn’t sure what to expect. Since my team was colocated and we spent much of our time together at a co-working space, it didn’t feel like remote work. We would visit the client site for occasional meetings and product demos so it felt more like a vendor relationship. Our next project was for a client in Florida and the physical distance started to make some of the remote work elements readily apparent.

Soon I transitioned into working on my own as our team members started taking advantage of the flexibility and relocated to various cities.

I benefited from a more gradual movement into remote work and I believe that it helped me make a smoother transition as I dealt with fewer disruptive elements at a time.

4. How did you find remote working roles?

All of my remote work has been found via my professional network. The work predominantly comes from previous clients or employers and word of mouth. My most recent project came via my travel network, as I’m working with a fellow Remote Year alum. 

That said, I’ve done a very poor job of business development and am working on improving in this area. My old ties from the US bore fruit for so long that I ignored the need to cultivate new ones until very recently. It’s easy to get stagnant when the work is coming in steadily.

It’s important to maintain a pipeline of communication within your network. Keep people updated on your current projects and your availability. I’ve started by updating my social media profiles to ensure that I’m clear about the type of projects I’m interested in and the ways that I can help others. 

It’s also important to connect with those around you physically. If you are traveling, consider going to a local co-working space, particularly one that has an active community. Search online on sites like Meetup or FB groups around your desired location/areas of interest to find out where people are. You can also do this organically. I’ve made connections with people who frequently work from places like Starbucks, Dunkin Donuts and Panera Bread.

Another part of my new process will include proactively looking/bidding for projects on sites such as Upwork,, and AngelList. I don’t have much experience with having to bid on projects but I believe the skill-building alone will make it worthwhile.

5. What have been the best, good and worst aspects of remote working for you?

The flexibility to work where/ when I’m at my best has been life-changing. I’m healthier and more fulfilled with increased clarity about my path forward. I believe that this comes through the quality of work I’m able to provide for others. 

While I’ve always been a “good” worker in a traditional environment, I always found myself struggling to fit within 9 to 5, brick and mortar framework. With the transition to remote work, I can work on things at my optimal periods (early morning & evenings). Because I can rest when needed regardless of time, I can take advantage of creative spurts and capture insights when they occur (which happen more frequently). It’s also provided a new way of measuring my productivity,  based on outcomes/value instead of mere physical presence/time spent. 

While working remotely work has been largely positive, it can be very isolating and lonely. If you are not mindful of its effects, you can develop some bad habits that could negatively impact your well being.

Physical and mental health are incredibly important. I would encourage everyone to make time for fostering community and self-care while working remotely.

6. What tools do you swear by while working remotely?

My tools and processes are always in flux as I like to experiment with various techniques to make sure I’m using what works best at a given time. That said, I have found a few that have been consistently valuable over the years. 

I’m a huge fan of Trello for managing my work projects.  While I’ve used other project management tools (Jira, BaseCamp, Rally, Pivotal), I find that Trello’s simplicity and ease of use provides a non-intrusive way of getting things done. I also use the Pomodoro Technique to focus on tasks and kickstart deep work. I don’t use a specific tool for timing myself (I am building one that integrates with my workflow).

In a digital world, I still find pen and paper highly effective. I tend to start with note taking in small composition notebook with multi-colored pencils and pens (Pilot G-2 0.7 is my favorite). From there, I transcribe the information into a digital notebook (I currently use Day One for MacOS). If you’re using Windows, I find that One Note is just as useful for this purpose.

7. Your most exciting/ hilarious experience since you started working remotely.

My initial experience in Spain was pretty exciting. I was enjoying the ability to follow a passion (learning Spanish) while still being able to work for a client in the US. Back then, internet access wasn’t available in lots of places, so I would take my laptop to an internet cafe to process data/send reports back to the client. There were already workstations there, so to accommodate me, the staff would have to move furniture so that I could connect (they were slightly annoyed) and I worked under a bucket that was used to catch water leaking from the roof 🤕!

I didn’t experience anything like that again until my time in La Paz, Bolivia in 2016. It was the first part of the full-time journey where I felt that I’d really stepped out of my travel comfort zone. There was a 2-day internet outage (Bolivia was down, not just the workspace). Those experiences, though almost 15 years apart, taught me a valuable lesson about making technical assumptions and being prepared.


8. What is your golden advice to a new remote worker?

In the same way that a new business needs to have a strong handle on cash flow, a new remote worker has to develop a mastery over workflow. This includes time/attention management, effective communication and having an accountability/feedback structure.

Traditional office work structures often hide poor habits and it’s not until you’re out of that setting that those deficiencies become apparent. Removing the traditional work schedule requires new remote workers to be mindful not to allow work to bleed over into their personal time and places the onus on team members to challenge old notions on productivity metrics.

Without being physically present, it’s even more important to keep others updated on your status, be mindful of others’ schedules when collaboration is needed and give/ provide feedback to ensure that all team members are moving in the right direction.

I achieve this by conducting personal retrospectives outside of team meetings that are tied to the outcomes that have been decided by the group. In addition, I have designated days/ times for projects/ tasks to ensure that each receives the proper amount of time and attention. During progress meetings, I make sure to not only update the team on my current status but review the path forward. It’s easy for a change to get lost in an email/chat thread that may impact a deliverable. Don’t be afraid to ask if what you’re doing still makes sense.

9. How do you see your career shaping up and your goals?

I’m currently developing training/ teaching materials to help others become successful in transitioning to remote work. I’ve found through conversations that my experiences can be of value and I simply need to get these thoughts and tips into a format that people can access from wherever they are. 

The market is full of information on the technical logistics of remote work but not enough on organizational impact at both the team and individual levels. Often, companies simply aren’t ready to make the move and need guidance at each phase of the transition process.  This represents a huge change for my career as I have been focused on product implementation for the better part of a decade. While I doubt that I’ll ever move away from coding completely, its role in my career will most likely shift to the form of tools that support improved team workflows and communication.

10. How do you expect remote working to evolve in the future?

I think that more companies will embrace remote work as the benefits become more apparent, organizational competency improves and the competition for talented people intensifies. Remote work is not a panacea, however, and will not completely replace traditional work environments. We’ll see more hybrid approaches as companies find and implement remote work where it’s advantageous and makes the most sense.

11. Where can we follow you on?

Web: ,

Twitter: @abrewing @thecocoanomad

Instagram: @thecocoanomad 

You can listen to the Cocoa Nomad Podcast on the following services:

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