How to Use Upwork to Transition to Full-Time Remote Work

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A couple months ago, Christina Shults posted in our private Facebook community a huge win: She found a way to fund her travels using Her post in our Facebook group had such a phenomenal response, we asked her to give us more insight on how to use Upwork to build a remote freelance business.

If you haven’t heard of it, Upwork is a marketplace for freelancers in graphic design, web dev, writing, virtual assistance, sales and more. If you’re looking to find remote freelance gigs, read Christina’s success story. You can learn more about Christina on her website:

With one month left until our full-time travel departure date (don’t judge), I signed onto Upwork hoping for the best.

Fast forward a few months, and I love the way my design career is going. I have enough work to support me and my travels for quite a while.

A big chunk of my design work has come from Upwork – and no, I’m not being paid $5 an hour.

How I spent the past few years is what set me up for success. The two biggest things that made a career as a remote graphic designer through Upwork possible are:

1) design education & experience, and

2) learning the business side to freelance work

Design education and experience

I can’t recommend these enough.

You don’t have to have a 4-year degree anymore to be successful in this field – there are tons of online resources and internships out there for you to learn the foundations and intermediate skills (don’t just rely on Skillshare and the like).

Take those skills and do some work for other companies. I learned more about being a designer in my first job than I ever did in college. Without real life experience, you’ll have a hard time finding good clients right off the bat on Upwork.

Learning the business side to freelance

I worked a few full-time design jobs during my time in Buffalo. While working the 8–5 life, I was dreaming of having more freedom and being able to work during the hours I felt most productive. Does anyone else hate afternoons or is it just me?

I didn’t want to stop working – I just wanted more flexibility, more time to travel and less time driving through a snow storm in 5PM traffic.

So I started reading a million articles on working remotely and the ever-so-awesome digital nomad life… which wouldn’t stop for 3 years. During this time, I kept a handful of freelance projects going. I learned so much about working for myself and how to balance my time that the eventual shift to full-time freelance was easy.

I didn’t turn to Upwork to start gaining my first freelance clients. I felt that because I was new I would make connections quicker, have more luck, and gain more experience working with local people and agencies. I realize this may not be true for everyone.

I used:

  • Thumbtack
    It’s not the best, I’ll admit. Jobs cost credits to bid on and the person hiring doesn’t have to pick a freelancer in the end. But I decided to use the free credits you’re given when you first sign up and found my first freelance gigs. One ended up being with me for a year. I did not use Thumbtack after my credits ran out.


  • Craigslist
    Guys, Craigslist isn’t that sketchy. I scanned the creative & computer gigs section in the local area for any design gigs I could find. Through this method, I ended up working part-time and long-term for a local small agency. While not all jobs I’ve completed for them are portfolio-worthy, I gained so much knowledge in how to balance projects, invoicing, and freelance taxes. Plus, I made a lifelong connection.

Pro Tip: allows you to do a multiple state-wide search through whatever section on Craigslist you’d like. Although, I’ve found way more success when reaching out to local people. It turns out people posting jobs think freelancers on Craigslist are just as sketchy 😉

How this has led to success with Upwork…

The first part of 2017 was dedicated to renovating our travel trailer to meet our mid-April departure date. The free time I had to build my freelance business suffered as a result. With one month to go, I was started to freak out a little when I came across a few Upwork success stories. Reading about Upwork in a new light made be feel confident I might be able to succeed with this platform.

The key was to treat Upwork as a way to connect with companies and individuals for long-term work.

If I’m focusing on racking up a large number of small quick jobs, Upwork becomes tiring and not worth the effort. Once you learn to weed out the bad jobs, you’ll find that there are a lot of people hiring quality designers.

I hopped on Upwork, filled out my profile and portfolio thoroughly and started bidding away with all this new knowledge on proposal techniques. I knew I needed one 5-star review to get the ball rolling. Soon after, I landed a gig designing an educational eBook. It wasn’t much money, but she was a great client.

At this point, I had enough freelancing experience and confidence in my design skills to turn this project around quickly and beautifully. She was happy and I got my awesome review.

About 2 weeks before we were set to leave, I received an invitation to a corporate logo design job. He invited me for an interview and asked to pay for my time to submit a proposal before I was granted the job. He loved the proposal and I’ve been working for him since.

A few weeks later when my boyfriend was freshly new into his workamping gig for the summer, I received another Upwork invitation. He said he found me on Upwork, liked the educational eBook I completed (that was won through Upwork) along with my overall style. This led me to taking on a branding job for his education platform.

Invitations are key to Upwork success!

I have landed two long-term positions that will support me to the end of the year. With those jobs and my other side gigs come referrals and next thing I know, I’m proving to everyone that it’s totally possible to work remotely on the road. Now my only issues are worrying about high-speed internet and not enough hours in the day to complete all this work 🙂

In summary, fill your portfolio with real world work and learn how to freelance successfully first. Translating these skills and experience to Upwork gave me what I need to have success with this platform quickly.

Key Takeaways:

  • Learn your chosen skill with education AND experience
  • Take the time to learn how to run a business (invoicing, taxes, time management–these are just as crucial as the skills you’re marketing!)
  • Build your portfolio and skills BEFORE relying primarily on sites like Upwork for income
  • Get your first 5-star review quick to get more views on your profile
  • Referrals are a great way to keep new jobs coming your way

Have you ever tried a site like Upwork for freelance work? Let us know your experience in the comments!

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