Box full of cash

How I earned $10,000 on Upwork

The other day I checked my email and realized I got a congratulations email from Upwork. “You earned your first $10,000 on Upwork!” I hadn’t even really been paying much attention to earnings so I was surprised.

Oh wow not bad. But it looks like I’ve been at for three years or so now.

These days I work full time and still do freelance on the side with Upwork and Fiverr to earn extra cash to invest. If you keep up at it, it starts to add up after a while.

So How Do You Do It?

The secret is you need to invest some time into building reviews and a reputation so new clients will feel comfortable taking the risk of hiring you. As such you can’t really expect to make much in the early stages. Note that it took me three years to get where I am.

How the Heck Do You Get Your First Client?

It can be very difficult getting those first clients so the secret to doing that is to provide an almost too good to be true offering at the lowest price you can go.

Some of my initial gigs involved cold calling through a list of potential sales customers for cheap. I worked hard and over-delivered to be sure I’d get good feedback.

It’s a bit of supply and demand to get that initial business. If you provide rock star service for dirt cheap, it’s very tempting for clients to want to hire you and see if you can deliver well for them. Everyone loves a discounted amazing service.

How many monitors does it take to freelance properly? Only you can decide.

So you do this for a while and as you build good feedback you can start to raise your prices and the complexity of projects you’ll work on.

I can understand why some might feel like working for the lowest wage possible in the beginning feels like a suckers bet but you should consider it as simply investing time into building your business.

Oh yeah…Upwork Takes Their Cut

To anyone interested in trying it, you probably have a question of how much Upwork charges to be a freelancer. They generally take 20% of your earnings.

I’m sure some might say this is horribly unfair. After all, you’re doing all the work so why should they get 20%?

20% is reasonable

I believe a 20% commission is reasonable. Here are a few reasons why.

  1. They brought you the business saving you a ton in advertising and all the financial risk that comes with an unsuccessful marketing campaign.
  2. They provide escrow service to help make sure you get paid and they have a feedback system to make sure you get good clients that will treat you fairly.
  3. They handle billing and time tracking or project tracking with their own system

Consider the risk involved in launching your own service. You could spend quite a bit on marketing your freelance services before securing a client. You risk nothing but your time by bidding for gigs on Upwork.

Where would you work if you can work anywhere? Here’s the scene in Ho Chi Minh, Vietnam around District 3 if I recall.

I’ve heard horror stories of freelancers spending weeks on a project and delivering their services only to be left in limbo trying to chase down their pay. This is much less likely on Upwork if you choose a client with a good reputation.

You will also spend less time and effort tracking your hours and typing up invoices since Upwork does all this for you.

What’s your ideal place to freelance? I had to fire up the laptop in a Louisa coffee in Taiwan. A great place. Also, check out Cama coffee if you visit. Maybe a bit too close to Wuhan province these days. Stay safe Asia.

Why Are You Promoting Them?

You would think I’m getting paid making some affiliate dough promoting Upwork but as far as I know, they have no affiliate program. I’m just sharing tips because I think it would be helpful for people starring out and I’m all for more freelancers and trying to change the work environment to get us out of offices.

CAMP AIS coworking Space

Digital Nomad Life for Non-Programmers

Oh, you’re a location independent software engineer that travels the world living the digital nomad life with a six-figure salary, living on 15K a year? Good for you, but what about the rest of us? Why should programmers and software engineers have all the fun while the rest of us are stuck in cubicles?

I get it. Learning to code and develop isn’t exactly easy and it’s a high demand skillset. But surely programming isn’t the only skillset that lends itself to location independence. How can nonprogrammers live the digital nomad life? And why would we want to?

Why Asia for Digital Nomad Life

After spending the winter in Taiwan, I was close to the end of the 90 day limit of my visa exempt stay, so it was time to head out. Next, I posted up in Chiang Mai, Thailand.

Chiang Mai is one of the most popular spots for low-cost living and digital nomad life. It’s easy to see why. Why did I decide to spend a few weeks here?

Delicious Thai food

Chiang Mai has delicious food at wildly low cost. Pad Thai, Pad Se Ewe, Tom Yum, Curried chicken and Pork and Papaya salad a just a few popular Thai dishes you’ll find. Chiang Mai has their very own signature dish Khoi Soi.

Khao Soi and drink
Khao Soi is a dish with egg noodles and curry plus pork or chicken
Lay's Cooling Chips
Feel hot? Eat some mentholated chips to cool off.

And there’s a surprising selection of Western style food in Chiang Mai, still at a reasonable price.

Cheap Internet. Fast Internet.

You can get 6 gigs of data and voice for about $16 for the month. (But I just beat that in Ho Chi Minh, Vietnam with a 5 gig SIM for about $4.50 US.) And I’ve seen some blazing fast internet speeds in Chiang Mai. Here’s a speedtest I saw using the Wi-Fi at a place called “The Funky Dog Cafe”

Cheap Housing

Should you stay at least a month, you can find very nice apartments for around $300 to $450 USD a month. Some of these hotels are rented out on Airbnb. (Click the link to get $40 off a home booking of $75 or more and $15 off an experience of $50 or more.) The one I picked was about $18 a night. I booked it on Air BNB. Unfortunately, there were more mosquitoes than I could handle, but the host was nice enough to allow me to change my reservation and not get charged for the full time.

I switched to a nicer hotel in Nimman area, the trendy upscale area in Chiang Mai. My room was about $30 for a moderatley luxurious mosquito free place.

S17 Nimman hotel in Chiang Mai.

Warm Weather Year Round

If you’re looking to avoid a midwest freezing winter or a cold winter anywhere, digital nomad life will let you go where you want. Plenty of cheap warm destinations to hide away from December to April.

Cheap Transportation

If you go to Thailand, understand Uber is not available. However, you can sign up for the SE Asia equivalent of Uber which is called “Grab. Sign up for discounts when you take Grab. My girlfriend and I were able to taxis around most spots throughout the city for around $1.60 to $3.00 USD.

Cool Cheap Coworking Spaces

Camp Coworking Space
Fast Internet, snacks, and open 24 hours. Digital Nomad central at the top of Maya Mall.

Shopping Experiences

Wild Shopping deals on multiple levels at the Chinatown market in Chiang Mai.

How to Do It

Well if you want to join what Tim Ferris has referred to as “The New Rich” that work location independent and keep cost low with geo arbitrage you need to generate location independent income.

Generate Location Independent Income

You can generate location independent income in many ways. Here’s a few.

Fiver Gigs

Sign up to do gigs on Fiverr. Fiverr is a website where people from all over the world post “gigs” that they will do for prices starting at, as you may have guessed, five dollars. A gig can be almost anything. It could be something as common as a logo or website design, to something more obscure like dance in a monkey suit and sing a song and provide a video of this performance.

So you can choose to do any type of work on Fiverr. You could proofread resumes. Perhaps you could sing jingles. Or maybe you could be a hand model. But the bottom line is you don’t need to be a programmer.

The secret to getting work on Fiverr is having good reviews. It’s not easy to get business initially until you’ve built trust. Here’s how you do it. Start off charging bargain basement prices and increase your gig price as you get good reviews. You have to pay your dues.

Use Fiverr as just one channel to advertise your business. If business comes in through Fiverr, sure you’ll need to pay them 20% but it’s risk-free. Think of their fee as an upfront advertising cost that you only pay if you get business. That’s something you won’t get from Facebook ads or any other advertising.

You can use Fiverr as your place to vet business ideas with zero advertising cost. Once your business proof of concept has shown an idea is viable consider developing your own website to try marketing your service on your own terms. Once your site is built advertise it with a marketing avenue that works. Facebook is popular to do very targeted marketing.

Fiver isn’t just a place to earn online. As you build your business, you’ll eventually want help and expertise of others. Other freelancers can help you build your business. Need a logo or a whole WordPress site? Get 20% off Fiverr gig purchases when you sign up for Fiverr here.


Upwork is similar to Fiverr in that it’s a community of workers willing to help you with projects or a network you can join to do work yourself. You could say Upwork might be viewed as the somewhat more “grown-up” version of Fiverr. Sign up to do larger projects on Upwork.

The same as Fiverr, the secret to success on Upwork is offeirng top tier service at ultra low prices until you have some good reviews under your belt to inspire trust from new potential customers.

If you sign up for customer service related work before April 15th, 2019 you will receive 1 month free of Freelancer Plus at Upwork.

After Chiang Mai, I took off for Ho Chi Minh, Vietnam, another popular low-cost living spot in Asia. More on that later. But here’s a preview of a serviced apartment you can get for around $30 a night. Another Airbnb find.

Once you are earning some location income you can dramatically lower your cost of living and get by on around $1,500 a month if you’re interested in living the digital nomad life. Come back to this site and consider subscribing if you’d like to know more about ditching the office.

This post contains affilate links for Grab, Agoda, Airbnbn, Upwork and Fiverr. I may be paid a commission for sales generated from clicking these links at no cost to you. I only establish affilate partnerships with companies that offer brands or services I use and believe are a good value.