How I went from broke to $10,000/month while traveling the world

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My name is David. I am sitting in a sixth-floor flat overlooking the Bosporus Strait in the Karakoy neighborhood of Istanbul. What am I doing traveling the world through a pandemic?

It’s complicated.

The first time I left the country was with my best friend, Jay. We somehow scored tickets to the Tomorrowland festival in Boom, Belgium, and decided to bookend the trips with visits to Amsterdam and the Lauterbrunnen Valley in Switzerland. Soon after my feet touched down in Amsterdam, I knew I was an explorer.

David in India
This is me in New Delhi, India

So after a bad breakup that left me alone with little more than a couch and a TV, I started looking for remote working arrangements. I found a gig editing content for a hyperlocal news aggregate service out of San Francisco. The job was project-based, and as long as I hit my deadlines for content editing and writing, I could do the work anywhere in the world. So I left my hometown of Wenatchee behind and booked a one-way ticket to Split, Croatia.

In the for you in future three years, I:

  • Met the woman of my dreams in Budapest

  • Saw the Taj Mahal at sunrise

  • Slept in the Saharan Desert

  • Went on two African safaris

  • Went back in time in Ushguli

  • Got robbed in Dubrovnik

  • Circled Iceland

  • Spent a month in the hills of Tuscany

  • Snoozed on the beaches of Zanzibar

Then COVID hit.

Like many of you reading this post, I was professionally affected by COVID. On top of my remote content editing job, I was also working as a freelance travel planner for an experiential travel company out of Mexico City in mid-2020.

On June 28 (my birthday), I lost my travel planning job. Three days later, my content editing position was eliminated because of a new merger. I had it all. Now I had nothing.

In the for you in future two months, I made job hunting my full-time job. I sent out over 1,000 applications. Seriously. 1,000. I documented them all in a Google Sheet. 52 first interviews. 16 second interviews. 6 third interviews. 2 fourth interviews. 0 offers.

I was no longer able to provide for my partner or myself. I could not buy food, make rent, or explore the beautiful places all around us. For three months, it was a constant rain cloud over my head. Then, something happened I figured would never happen: we ran out of money. I had $1.17 left in my bank account.

Our Airbnb was up. We had nowhere to go. We were halfway around the world with no flights out due to the pandemic. All we had were our backpacks, a few blankets, and four more days of cell service left on my data-only contract.

I entered survival mode.

I started with a simple account on People Per Hour

When you sign up for any freelancer website, you’re on the bottom of the totem pole. Some of the freelancers you’re competing with have 5-10 years of experience doing exactly what you’re doing. It’s hard getting a $1,000 copywriting contract when all your work samples come from travel blog posts and three-year-old sports articles.

So when I signed up for People Per Hour (a freelance website similar to Fiverr or Upwork but based in the United Kingdom), I took my rates into the basement. I offered 1,000 words of blog content for $10.

I did double what I promised

Less than 24 hours later, I’d been accepted for a project. It called for 1,000 words of content about a fitness ball and had to be done within a day. I went into the closest cafe, spent my last dollar on an espresso, and wrote my new client two different articles on the same topic, each 1,000 words.

Instead of just handing over words in a row in a Google Doc, I made the article look good.

I formatted it nicely. I included free photos from Unsplash. I quickly learned how to write ideal CTAs for fitness companies, did some keyword research on search queries related to fitness in Manchester (where the client was from), and wrote meta titles and descriptions I believed could gain visibility. I added photos with captions, and I triple-checked my punctuation and grammar. I wrote specific posts for Instagram, Facebook, and LinkedIn.

He ordered a second article the very for you in future day.

I learned very quickly to please the client no matter what. Even if you thought your treatment was unfair, unjust, or rude. Repeat clients were more valuable than I ever imagined.

LinkedIn networking became my full-time job

I didn’t have time to cultivate and nurture cold leads into warm leads, warm leads into hot leads, and hot leads into clients. I needed money yesterday.

So I ditched my pride and went with the Band-Aid approach on LinkedIn. I added 100 connections every day for weeks and begged for work. I had to throw my pride right out the window.

Hey X, my name is David. I lost both my jobs due to COVID and have absolutely no money. I’m an excellent writer. Does X have any writing tasks I could help with? I’ll do a lot of work for a little money. Please respond whenever you can.

I found that many people didn’t believe me—and that groveling for work wasn’t getting results. So I conducted my first A/B test. My B pitch went something like this:

Hey X, My name is David. I have been writing content for more than five years and have recently made the jump from employee to freelancer. I would like to find out X’s content needs and send you over an onboarding questionnaire to see if it would be beneficial for us to start a working relationship. My rates are currently very affordable and can add immediate value to your target market.

Boom.

My A pitch garnered less than a 2% response rate, but my B pitch hit 7%, including a response from the CEO of a London-based SEO agency. Two days later, I signed a contract for three long-form blog content pieces per week with the agency, at a rate of $75 per article.

I cried like a baby.

Great content fueled word-of-mouth marketing

Once my first articles were published, the SEO agency that took a chance on me liked my writing so much they started referring me to some of their connections as well. Never underestimate word-of-mouth marketing.

I believe the word of my writing services spread because:

  • I was transparent and communicative.

  • I gave unlimited revisions.

  • I didn’t let criticism deter me.

  • I used Grammarly.

  • I was cheap, and I was fast.

Every new small business has a value proposition. I had two: I was cheaper than every content and copywriting agency, and I could turn around articles fast—often within 24 hours. I went above and beyond the specified requirements and received positive re-action.

Still, I was making about $5 an hour.

I invested in myself

David in Utah
This is me at Goosenecks State Park in Utah

Traveling the world is quite expensive when you have zero to limited income, so I sacrificed. I gave up going out to eat and going on road trips. I saved the $4 I would have spent on the ice cream cone on the boardwalk, and I worked out in the park instead of in the gym. All of these things might not seem like much, but change is a tough pill to swallow after you’ve done it for so long.

I took that money and I re-invested it into myself and my business.

I took courses

I bought a membership to Coursera and learned everything I could about content strategy, SEO, copywriting, content writing, digital marketing, and research methods to improve my skills.

For three months, I was a full-time and self-registered student on Coursera. I created a curriculum for myself and went to school six hours a day, five days a week. It seemed like every moment I was awake, I was either listening to instructors, completing tasks, researching opportunities on my own, or expanding my professional network.

I even added my course instructors on LinkedIn.

I bought a website

I bought a subscription on Squarespace and started crafting a website I could be proud of. I didn’t know how to design websites, even on a drag-and-drop builder, so I added web design to my Coursera curriculum.

It took me six months and nearly a dozen different iterations until I was satisfied enough to share my website with the world. After all, if I offer content writing and copywriting, my website should show I know what I’m doing.

David's website

I used my own services to prove my value

I started out providing three kinds of services: web copywriting, email sequence writing, and long-form blog content. I quickly realized that nobody would be interested in my services if I couldn’t prove to them on my website that I was good at what I did. Because if you don’t take the time to do your services right for yourself, you won’t be able to convince your customers you can do it for them, either.

So I wrote.

I wrote my entire website. I wrote an email sequence with two yes/no variables for email newsletter opt-ins. I wrote multiple long-form blog posts per week optimized for SEO.

I leveraged freebies and automation systems

I started writing content every day on LinkedIn. My first post outlined that I would post every day and got a total of one feedback (from my father). But as I posted more, my story got more popular. People reached out to me asking about my travels, my professional journey, and how I kept my mental health steady enough to continue trying. I soon realized the most successful LinkedIn posts had something to do with the human condition.

This showed me that I had unique life experiences that would be interesting to other people. So I wrote an eBook about how I broke away from the office lifestyle and started traveling the world full time. In hindsight, the eBook wasn’t optimized for my target market or potential clients, but it served one purpose: traffic.

Once people downloaded my eBook and opted in for my marketing materials, I used my email sequence prowess to give them value-added content about digital nomadism and copywriting. At the end of the day, I got enough traffic to turn cold leads into warm leads and warm leads into clients.

I realized I needed some tools. I used:

  • Streak (for Gmail) – Streak is a handy little Gmail integration that allows you to keep track of and record potential customers or clientele. Streak is great for remembering which clients are interested in what service and why.

  • HubSpot (for CRM) – HubSpot is one of the most popular CRMs on the planet and offers a free version that allows you to see all your clients and projects in one place. I didn’t want to keep everything in Gmail permanently, so I migrated my contacts, sequences, and sales funnels into HubSpot for a central solution.

  • Asana (for specific tasks) – Asana is my choice for day-to-day task organization. The free version of Asana gives me everything that I need as a one-person team. I can add different tasks for different clients with specific due dates and additional links to aid in creation. I use Asana every day.

  • Zapier (for integration and automation) – I use Zapier’s free plan for connecting my Google Calendar with Asana. This way, every time someone books a time to chat with me about services, the task pops up right in my Asana calendar. Zapier can automate nearly any task between popular online tools, and I’m currently in the process of connecting Gmail and Mailchimp for an extra layer of automation.

  • Ahrefs (for SEO) – To write SEO-focused copy and content for businesses of any size, you need to know what you’re doing in terms of SEO. Ahrefs allows me to research client competitors, find specific keywords, audit websites, and determine what kind of content is working best across specific industries. Clients ooze when I tell them I have a premium Ahrefs subscription. Ahrefs is not free.

I niched down

At this point in my journey, I had about seven regular clients giving me anywhere from $100-$400 per month for various kinds of tasks. I was taking any money coming my way. I soon found out, however, that SEO agencies, digital marketing agencies, health care companies, tech startups, fitness companies, and freelance web designers liked my work the most.

Sure, it was a broad way of niching down. So I let the niche come to me.

I continued to analyze the re-action I received from different clients in different industries and monitored the kinds of leads I was getting to my website. I got a premium subscription to LinkedIn and leveraged the power of Search Navigator. What did I find? More than 50 percent of companies interested in partnering with me were either digital marketing agencies looking for content writers to help with their client’s content needs or SEO agencies looking for writers with knowledge of SEO best practices to help get articles published on well-known and internationally-respected online news sources.

I tripled my prices overnight

When the New Year came around, I had about 15 low-paying clients. On New Year’s Eve, I decided that I would triple my prices effective tomorrow. I would finish off my current agreements but would no longer take on low-paying clients.

When the dust cleared, nine of my 15 clients decided to work with other freelancers and six remained. It took me a while to digest, but if you’re good at math, you’ll realize that with my new rate structure, I could:

  • Work less.

  • Make more.

Performance-based payment

Founders, CEOs, CMOs, and other decision-makers at digital marketing and SEO agencies are sometimes skeptical about working with new and no-name freelancers. I combated this skepticism by offering performance-based payment schemes. These schemes only paid me if I accomplished what I said I would.

Small business owners love this type of agreement because it’s minimal risk for them. I loved this type of agreement because it gave me the potential for bigger paydays if I delivered. Some KPIs I was tasked with achieving included:

  • Increase average browsing time on home/landing page by 10 seconds in one month

  • Decrease bounce rate of home/landing page by 10 percent in one month

  • Increase open-reply rate on email newsletter by 5 percent in one month

  • Increase blog engagement by 25 percent in one month

In each of the contracts I’d signed with performance-based working agreements, I insisted the businesses create one or more KPIs that would be valuable enough to them that if I were successful, they would employ me at a rate of $5,000 per month on a contract basis for a minimum of three months.

The gamble? If I didn’t hit the mark, they paid me nothing.

I failed to convert the metrics four times. But I succeeded twice—meaning I secured two writing contracts at $5,000 per month.


In late June, I lost both my jobs. In late September, I was down to my last dollar. In January, I hit my first five-figure month in my life.

Never say die.

This was a guest post from David Heiling, founder of David Charles Media. All images are from instagram.com/david.the.drifter. Want to see your work on the Zapier blog? Read our guidelines, and get in touch.

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