How I’ve made over 300k on Upwork while being a digital nomad

Eight Proven steps to follow

Andrea A. Bailly
The Cult
4 min readJul 15, 2022

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Photo by Antoni Shkraba from Pexels
Photo by Antoni Shkraba from Pexels

It all started one night in an Airbnb apartment in Madrid; I finished a two-month Spanish/Portugal road trip and was ready to work.

How it all started; my first client

The first thing I did was look for freelancing platforms. I found two that I liked; the first one was called people per hour, and the second one was called Upwork. So I started looking for job postings that were fit for me. Luckily I landed my first client on people per hour. It was an online clothing store from the UK that needed help redesigning its site; they wanted a new look and were also looking for help with their newsletter; this client was my jumpstart to the world of freelancing.

My Journey

To give you a little background, I studied graphic design in college and always liked the fashion industry; when I graduated, I worked in a newspaper magazine as an intern and focused on the magazine's fashion section.

After I finished the internship, I moved to West Hollywood, Los Angeles. I worked for twentieth-century fox, designing posters for tv series. I lived a few blocks from Melrose Place; the weather was always great. I had an excellent farmers market on the weekends, enjoyed breakfast at Joan’s on Third, ate the best Mexican food in the country, went to the movies every week, and took great road trips with my husband in his 1976 Porsche 911 S Targa.

Then decided to move to the desert Palm Springs CA, one of my favorite places in the world. Nothing compares to the smell of hot earth at night and a full sky of stars. We used to love to take night drives, stop in the middle of nowhere, take the car top off, and just sit there in silence, smelling and feeling the desert at night is an actual high. There is something extremely mystical about it.

Marilyn Monroe statue 2012 Photo by Andrea Bailly

My husband and I found this perfect condo where Marilyn Monroe used to stay when she came to Palm Springs and rented the place. We had a great swimming pool that we would use every day, especially in the evenings. After six months, we felt we needed a change and moved to Bellingham, Washington. That’s when my freelancing journey started.

Failure is a stepping stone to success

I decided to open an online boutique, but that project failed; I was pretty disappointed with the outcome. I had spent many months of energy and dedication creating this fashionable website. I put all of my design style and knowledge into this website. Hence, it was very “me.” It was my trademark style.

Little did I know that I was working on a portfolio that would help me show my trademark style as a freelancer.

And that’s how my dream portfolio was born; from a failed project, a butterfly was born, I was proud of how the site looked, and that’s how it all started. My clients would see that work and want the same look and feel (it’s like I had created this secret formula that my clients longed for).

Once I started with the first client, my portfolio built itself up to what it is today, and whenever I acquire new clients, it all starts with a look at my portfolio.

Here are eight proven steps I followed to successfully freelancing:

  • Create a good portfolio and continue to upload work you feel proud of. I suggest using Behance or Adobe Portfolio.
  • Write a strong cover letter that you can reuse and tweak based on each potential client.
  • Believe in yourself and be confident when speaking on the phone or video with your potential client.
  • Have a specific niche you want to focus on; for example, mine has always been fashion, but you can focus on whatever your interest is.
  • Be consistent with your style.
  • Pick and choose your clients, don’t accept any client/job; always stay within your niche. If you do what you like, you have a much higher probability of succeeding.
  • Never stop learning; always continue to educate yourself; there are a lot of free online resources, for example, youtube tutorials.

Focus on one platform and then move on to the next

Master one freelancing platform at a time, and then move on to the next when you are up and running. My favorite freelancing sites are:

  • Upwork
  • People per hour
  • Fiverr

Conclusion

You can do anything you set your mind; I think the secret is to love what you do, be passionate about it, and never stop learning.

If you enjoyed this article please like and share. To learn more about tips on freelancing, design, and a nomadic lifestyle, you can follow me on Twitter and LinkedIn.

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Thank you for reading this piece.

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Andrea A. Bailly
The Cult

Transforming dreams into action | Designer focused on entrepreneurship, digital wealth-building, productivity, self-improvement, art, and design.