3 Tips For Navigating Freelance Work While Traveling Through The Pandemic

3 Tips For Navigating Freelance Work While Traveling Through The Pandemic

Looking in the rearview mirror, 2020 was quite an obstacle course for traditional employees, freelancers, and contractors.  The pandemic’s resultant financial tsunami overwhelmed many brick and mortar businesses and tossed many of us overboard to tread water or drown in debt. For example, you might be negotiating requests from clients who want a rate reduction or simply not finding clients at all; in basic economic theory terms, there is a geometric increase in competition (supply), and the (clients) demand for these workers did not increase.

This “sink or swim” dearth for both existing remote workers and new freelancers is quite daunting but do not lose faith- all hope is not lost!

Because contrary to the above statement, Flexjobs.com has stated the number of “remote postings on their site have increased by 12% from July to August alone.” Furthermore, Upwork released the results of its second 2020 Future Workforce Pulse Report and found that “41.8% of the American workforce continues to work remotely, an estimated 26.7% will still be working from home through 2021, and 36.2% million Americans will be working remotely by 2025.”

Upwork Chief Economist Adam Ozimek says, “As many businesses adapt and learn from this remote work experiment, many will alter their long-term plans to accommodate this way of working. On work marketplaces like Upwork, we can already see this shift underway with increased demand for remote professionals.”

This 87% increase in the number of remote workers since the pandemic’s onset means a doubling in the available remote and freelance workers in the near-term future.

 That said, my opinion (based on the increase of remote job postings on LinkedIn, Indeed, etc., and employees I’ve spoken with during my travels) is that the demand for these freelancers will have a parallel increase too.

And although the global pandemic financially debilitated businesses and their employees, it simultaneously accelerated this “working from home” transformation-  now, there are many office workers who morphed into remote workers. Ultimately, gaining better work flexibility and more freedom.

Why “freedom”?  

As Matt Ridley opines in his new book “How Innovation Works: And Why It Flourishes in Freedom,” freedom means the opportunity to “Exchange, experiment, imagine, invest, and fail. “

If you are reading this article and working from home or packing your laptop into a suitcase and seeking suggestions to find freelance work – here are three tips to help you find these opportunities.


Tip #1: Dive into DMs (Network, Network, Network)

When you have little experience in a field … OK, no experience… you need to create and then expand your options. You cannot build a portfolio to evidence your skill level unless someone offers you a job. But most people won’t pay you to work if they can’t view any samples of your previous projects.

How can you liberate yourself from this vicious circle?

I suggest taking advantage of free resources. For example, if you are on Twitter, send out tweets to prospective employers or offer your services for gratis in exchange for a testimonial.

If you are on Facebook, join groups like Digital Nomads Around The World, Remote Jobseekers,  Virtual Assistant Hiring- Homebased Jobs, as well as more specific groups designed for your (potential) niche.

If you are on Instagram or Tik Tok- start diving into direct messages to communicate with the individuals you consider “titans” in your industry. Maybe, create a product and then message them with your final piece- showcase your skills!

You never know who might respond…. right now, or in the future.

If you are on LinkedIn, start building connections to establish a network in your field- And if you already have a network, reach out to your former teammates. Such “cold messaging” will help you nurture prospective clients, job growth, and career-changing opportunities.

Didn’t someone say, “Who you know might be more important than what you know?


Tip #2: Teach English To Stay Afloat

I recommend teaching English to generate revenue- Gird your loins and use teaching as an income stream.

If your native language is English, seize the opportunity to leverage.  All you need is a bachelor’s degree, a 120-hour TESOL certification ($20) to apply, and a few hours per week to work. Listed below are five companies you can check out:





Magic Ears

You can earn between $20-$26 an hour, and if you work 20-25 hours a week- that’s approximately $1600-$2600 gross per month. You can sustain yourself, depending on the currency conversion of the country you live in or travel to.

Waiting for your portfolio to become more marketable and your “pro bono” clients to evolve into “income-generating clients” can be excruciating when you need to pay bills right now… But this is why you should teach English!

Ultimately, you can produce a steady income while waiting for your financial orchard to bear fruit.

Plato once said, “Our need will be the real creator.”


Tip #3: Hire A Virtual Assistant

Many people have difficulty adjusting to the entrepreneurial nature of this career path. Spending your days applying for jobs, reaching out to clients, creating proposals/email scripts, making spec ads or samples (besides working) is time- consuming.

Even if an individual intellectually acknowledges the tediousness of such prospecting, they may have trouble coping with the emotionally dulling, or outright chilling, effects of being repeatedly rejected.

At the end of the day, we all know many of the hiring managers we speak with, the editors we direct message, and LinkedIn jobs we apply to will not respond or will openly reject our applications (which is OK).

Essentially, it is a numbers game- for every few dozen projects you apply for (chances are), you will get rejected from the majority of them- that’s our statistical reality, so don’t let it dampen your spirit!

One of the main issues (if it isn’t already an issue) will be your limited time frame for applying to these opportunities. You will be working on your other assignments, handling outreach, sending out emails to prospects etc.… you are running a business.

However, despite knowing these odds, you can still focus on the quality of your submissions while increasing the number of your proposals, applications, and samples by hiring a virtual assistant to take care of your laborious tasks for a low cost, fixed price (if you can afford it).

Virtual Assistants (V.A) from developing countries will run approximately $5-20 (U.S.) per hour, and their counterparts from the U.S. or Canada will be in the $25-$100 price range. You can teach these VAs how to perform simpler time-consuming tasks (such as answering your phone calls, or emails, scheduling your meetings etc.) so you have more free time to reach out to clients and apply to job listings.

Just remember, before investing in a Virtual Assistant, you will need to look at the cost-benefit. For example, if your V.A. costs $10 per hour but requires “babysitting,”- they are not making your life easier and, therefore, are not worth your investment. On the other hand, if they can get the job done correctly or improve your methods/products, they will be worth the costs because they will yield revenue.

If you want to learn more about the different types of virtual assistants, costs associated with them, etc., please click here.

While you are applying for work, they will be freeing up hours for you. Over the long-term, this can help double or triple the number of applications you can send out. Thus, increasing your chances for successfully finding freelance work.

Gary Vee once said, “You should focus on quality AND quantity.” 


Final Thoughts  

Build the foundation for your upward progress as a freelancer (at any level) by maximizing your resources and time while using a backup plan to sustain yourself financially. If 2020 has shown has us anything, it’s that working remotely from your home, a café, beach, or fill-in-your-own-destination, is the new normal and backup plans are necessary- so, as my Okinawan grandmother would say, get to work, Gambatte!


About Max Hsu

After graduating in May 2018 with a B.S. in Cyber Security, Max Takaesu Hsu decided to explore untrod paths. He became a highly competent travel hacker who is a freelance content writer on Upwork with crackerjack SEO experience. This digital nomad goes by the nom de plume, the Wandering Warrior Poet and, is currently working from Serbia. This year alone, he traveled through three different continents while financially sustaining himself. You can follow the Wandering Warrior Poet on Instagram and Twitter.

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