My First Contract — The Dumb Way to Start Freelancing

My First Contract — The Dumb Way to Start Freelancing

We learn most by our mistakes, in business and in life more generally. I learned a lot in the very brief time I tried contracting on Fiverr and UpWork.

Fiverr and UpWork are sites that facilitate the contracting of various, normally internet-based and most often technical, services, usually for a fairly cheap price compared to “legacy” contracting and consulting companies. Of course, you get what you pay for, and much of the content churned out by contractors on Fiverr and UpWork is fairly basic, with some sellers offering higher-grade services and products for higher prices but most churning out basic products and service packages that are easily automated.

You can purchase just about anything on Fiverr and UpWork, from logo design to penetration testing services… though the latter service offering is a bit more questionable than the former. These sites are also advertised as the stomping ground for aspiring contract software developers and consultants seeking to kickstart their portfolio with some client work. It is supposedly quick and easy money that forms a sort of flywheel of new clients as you niche down and get positive reviews, and YouTube is full of developers talking fairly big money and fairly low overhead required.

I’m sure you’ve already guessed, but I decided to give it a shot. This is what I learned after a couple of months of giving Fiverr and UpWork an honest go.


Why give Fiverr and UpWork a try in the first place?

I’ve kept it fairly hush hush with a couple of hints here and there on Twitter and LinkedIn, but I’m spinning up a consulting company focused on data collection and software engineering for growing businesses and startups. This effort has been in the works for quite some time, but I’m putting the final touches on the consultancy’s landing page as I write this article, so the efforts will finally show fruit.


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Several months ago, though, while fleshing out my business offering, I figured I might want to find a way to build out a decent portfolio to help accelerate the process a bit. I looked around, very quietly asked a handful of people in my network and didn’t find much of note, so I decided to move to Fiverr and UpWork to see if there was anything worth working on there.

There are attractive aspects to Fiverr, UpWork and other similar freelancing sites. For one thing, it always behooves smaller creators and entrepreneurs to take advantage of recommendation algorithms as much as humanly possible for the purpose of increasing discoverability. It can be incredibly difficult to get discovered without a third-party algorithm putting your content, service offering or profile in front of faces.

It is also a “target rich environment.” Most of the people browsing the Fiverr and UpWork feeds are actively looking for something. You’re much more likely to find a potential client on UpWork than putting feelers out on Twitter.

Finally, Fiverr and UpWork handle some of the annoying parts about freelancing, namely getting paid. For a fee, they handle all of the payment processing, disputes and deposits themselves and let you focus on providing the services.

So, before the angry commenters tell me I’m being too harsh on Fiverr or UpWork, know that I spent at least one chapter talking specifically about the benefits of those sites. To be clear, I’m sure plenty of people have made good money on Fiverr and UpWork…

But just as many, at the very least, have had experiences similar to mine.


Normally, the first month or so on freelancing sites is pretty dead. You spin your wheels writing proposals, tweaking your profile and offerings and trying to land your first gig or two. I found very little success in the first month or so, and went quite a while without even checking my inbox aside from tweaking my profile and changing the wording on a couple of my service offerings.

My message inbox wasn’t a barren wasteland, however… I received an absolute deluge of spam.

This is perhaps the biggest and most common complaint by freelancers on Fiverr, UpWork and other sites. There is a constant stream of fake accounts sending templated spam requests, mostly trying to get you to open a Google Doc that supposedly contains a business proposal. The most common scam I saw was one seeking to persuade the victim to create a bogus profile on a freelancing site for the scammer in exchange for a cut of their income.

Obviously, I never followed through on any of this spam, and it got bad enough to where I stopped visiting the sites entirely, causing them to ultimately suspend my profile. I would say that spam and scams easily made up 80–90% of my incoming messages on the sites.

Of the remaining 10–20% of messages, these “legitimate” requests were further divided into two more categories: legitimate and actionable requests, and legitimate and unethical requests.


Aside from spam, one of the more prevalent issues on a lot of these contracting sites is the amount of unethical service offerings and requests on the site.

I was specifically offering web scraping services, consultations and development. Of the legitimate requests I received, a fairly large majority were people straight up just asking for me to create massive email lists, presumably for spam, by scraping the web in bulk searching for contact info from as many sites as possible.

Several others smelled strongly of cyber stalking behavior with an obsessive bent, requesting a social media user’s posts be scraped at an incredibly frequent interval and their alt profiles found and scraped as well.

Many others simply requested that we move the conversation to Telegram or WhatsApp, presumably because their request was something that would break Fiverr or UpWork’s Terms of Service.

One only has to search “penetration testing services” or “mobile hacker” to find a host of sketchy looking “security researchers” offering various services with only the thinnest veneer of “trust us, we’re ethical” excusatory language. Hackers-for-hire is a shady (and academically interesting) world, but the script-kiddy version of that world is lying right in front of our noses on sites like Fiverr.


Of the dozens of messages I received on both platforms, I ended up closing on a total of one gig. I set up a consultation, billed the client for a $5 consultation… and they ghosted.

The gig was fairly boring, essentially scraping retail sites and dumping price and item metadata into a Discord channel for the purpose of retail arbitrage. The client was creating a paid community for people interested in retail arbitrage and requested that I create the data scraping function.

Luckily, I only wasted about 45 minutes of time on the contract total, and a bit more trying to chase down the client who ghosted me. After I severed the gig via a sternly but professionally worded message, I closed the tab to Fiverr and haven’t been back on the site since.

Now I realize that these freelancing sites are not necessarily the shortcut to freelancing opportunity that they are often advertised as. There is potential for earnings there, but there is a lot of chaffe to sift through to find it.

Now I am focusing on building a real client base via content marketing and speaking to people in my growing network. Fiverr and UpWork, for me, were major wastes of time, but they did kickstart my motivation to get my own consultancy going…

This time, the right way.

Interested in data collection and software engineering services for your growing business or startup?

I offer a decade of software development expertise and a wealth of experience in data collection and analytics for scrappy, growing startups and small businesses. If you need access to the data necessary for your organization to thrive, feel free to reach out and let’s talk about what I can do to grow your business and empower data-driven decisionmaking.