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  • TT&W Team

UpWork - a (Potential) Path to Remote Freelancing

Updated: Jan 28

Freelancing in Turkey
Freelancing in Turkey

When we tell people about our plans to travel for a year, one of the most common questions we get is, “how can you afford to take a year off?”  

Welp, we can’t, which is why we decided to name our blog They Travel & Work, not just They Travel.  

But, tongue-in-cheek comments aside, this is absolutely a valid question.  And, while we outline the bigger picture strategy we settled on here, it’s definitely worth discussing UpWork, one of the key tools we’ve used for finding remote work while traveling.  

It’s not for everyone, but it’s certainly worth exploring the option.  

Interested in heading overseas? Check out our international travel checklist here!

So What is UpWork? 

Per the company’s website, it’s “the world’s largest remote talent platform.”  What does that actually mean?  Put simply, it links companies with freelancers, meeting the market for A) companies to find contractors, and B) contractors to find gigs in their respective fields (e.g. accounting, web design, law, admin support, etc). 

From the horse's mouth: UpWork's sales pitch to potential freelancers (
From the horse's mouth: UpWork's sales pitch to potential freelancers (

And, there’s a level of formality and security that takes this platform beyond the found-a-random-guy-who-says-he-knows-computers-on-Craigslist approach.  Think AirBnB- or Yelp-style reviews, but applied to employers and independent contractors.  In other words, when a company hires someone, that person has been both verified by UpWork security via a government-issued ID video verification, and his or her prior work performance is publicly available in the form of post-contract reviews.  

For the contractors, they can also see the same level of public review for the employers, so before you accept a job, you know if the person hiring you is a flake or not.  And, once the freelancer and employer agree to a contract, the funds for that contract (or specific milestones if long-term) are deposited into an escrow account with UpWork.  

Bottom line, for our purposes – and that of other folks looking to head overseas for a bit – it’s an awesome platform to find contract work while traveling. 

Testing the Market

Prior to actually applying for posted jobs as a freelancer, you need to create an UpWork profile/resume, pitching yourself as a subject-matter expert in a particular field.  

For Chipp, fresh off passing the CPA exam, it seemed logical to apply for accounting jobs.  Well, turns out becoming a CPA just means you know a little bit about a lot of things – certainly good for cocktail party conversation, but not great for finding freelance work. 

After a dozen or so non-responses or straight rejections, it became readily apparent that a change of course was necessary.  

Adjusting and the Importance of Persistence

Not going to lie, the first week of applying to gigs without luck can be disheartening.  You read the description of a posted job, think, “wow, I’d be perfect for that,” then apply, submitting a cover letter of sorts and, occasionally, answering some other job-specific questions.  

Quickly realizing that actual accounting was out of the cards, Chipp looked for another option and quickly realized that a huge market exists for people hiring freelancers to write about accounting – and real estate.

Knowing the vocabulary of accounting – and with a solid foundation in commercial real estate – Chipp tweaked his UpWork profile and began applying for jobs writing online content for real estate and accounting firms.  

After successfully completing one article – and receiving the associated positive, public review – a barrier seemed to break.  He was now a known entity on the site – not just some other random person who may or not actually have the ability to support his resume/skill claims.  At this point, the job offers dramatically increased.  

Building Long-term Relationships

As with any work, it’s far easier having an established relationship with a core group of clients than hustling for new gigs every day.  By starting this process a month prior to actually leaving the States, that happened. 

Between completing his first UpWork profile (the failed, accounting-specific one) to changing tack and embracing a writing niche to leaving for the first overseas leg of travels, Chipp was able to put together a handful of long-term contracts, ideal for travel.  

Basically, each client has a long list of article topics that need to be written, and by writing a few a week for each client (with the only deadline being the end of the week), you can create your own schedule.  So long as you get your work done to standard, it doesn’t matter if you wake up, have some coffee overlooking Istanbul, and fire out a few articles - or go explore all day and write after dinner.  

Your routine is your own.

It’s hard to better summarize a central goal of our travels than with these five words.  

It’s not Binary - Start Early  

Hollywood and Instagram make international travel seem like a 100 percent impulse decision - just get up and go one day.  

Contract work and full-time employment aren’t mutually exclusive.  Thinking about freelance gigs?  You don’t need to just up and quit your job one day.  Test the waters.  See if it works.  Build a client base.  

Having the emotional and financial comfort of a full-time job makes building a freelance book far more approachable.  Maybe it turns out your skillset doesn’t align with jobs posted on UpWork.  Starting this process while still working a regular job gives you the opportunity to shift course - or maybe retrain yourself into a more freelance-relevant field.  

Bottom line, not going all-in on freelancing shouldn’t be an excuse not to try it.  Worst case scenario, you learn how the UpWork platform works but don’t get a job.  Best case scenario, you build an income stream not tied to a single geographic area.  To slightly modify the words of the New York Lottery: 

Hey, you never know - until you try.  


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