My time as a freelancer was short. Very short. About 1 year, in fact. And for good reason.

In that very short year, I ended up in 3 very bizzare scenarios. So much so that I feel it's worthy of it's own writeup.

Freelancing can be fantastic. You get a lot of benefits, namely,

  • You are your own boss.
  • You can make your own schedule.
  • You can work from anywhere.

But wait... this sounds great! What could POSSIBLY go wr-

Client #1

Let's meet our first client. Since popular freelance sites like UpWork were, and still probably are, out of my league, I had to resort to finding listings on Craigslist and Kijiji. The bowels of internet classified.

After 15 minutes of searching, I stumbled across a suitable posting and reached out. The job was to do some simple web and mobile design for a small business.

We hop on the phone, talk about requirements, and a week later I sent over the final revision. I get paid the day after, and all is well! My first client, what a great feeling!

I know, wholesome, right? Just wait.

Fast forward 6 months. I have a small break from school, and reach out to Client #1 to see if they have any work I can pick up. You know, 🌈 building relationships and whatnot.

The first email

Soon enough, I get a response.

The second email

Uh, okay. Gotta cut the numbers in half. Maybe their company is having a sale? You know, how retailers say that the clothes are 50% off, but really they just doubled the original price? Yeah, that's probably it.

I open the picture, and see...


... a paystub. A paystub for an employee of Client #1's business. And I'm supposed to cut all the numbers in half?

Now, I'm no accountant, but... does Client #1 want me to help them commit TAX FRAUD?

Turns out pay stub fraud is actually quite common - and most definitely illegal.

At this point, I'm in a tough situation. Do I refuse to do this work and lose a client, which don't come easy for a freelancer just starting out? I definitely wasn't prepared to be an accomplice, that's for sure.

I didn't know what to do. Am I obliged to report this? I had plans the following week, and jail would make attending a bit complicated. So, the next day, I went to Derek Rayside's office in confusion.

After about 30 minutes of wondering and researching the IEEE Code of Ethics, we came to the conclusion that I should probably just stop working with this client.

And that was the last of Client #1. My first freelancing experience. Surely, it can only go up from here?

Client #2

Ah, Client #2. Fresh off the disappointment of Client #1, I was excited to work with Client #2. The posting seemed right up my alley.

After some initial exchanges, I get a really long email. I've removed the uninteresting parts.

Client 2 First Email

Clearly, this person did not realize that I was a student. But, the more interesting thing happened when I clicked on the Google Drive link.

Client 2 Folder

I kid you not, there was a document in the Mockups folder called Passwords. Naturally, I opened it (with no malicious intent, right Client #1?).

Sure enough, every single password you could dream of was in this document. Bank accounts, passport information, their SSN, social media passwords - the whole lot.

Why was this in a public mockups folder? How many people has Client #2 shared this with? Why is their Twitter password mypassword? And why did they need to write that down to remember it?

To whomever is reading this, please use a password manager. Don't be Client #2.

Yes, I did let them know about the password document. No, I didn't end up being the CTO of the next Uber. I stopped getting responses after letting them know about the passwords document, which made sense. I wouldn't want to work with someone who now knows literally everything needed to destroy my life.

That was the last of Client #2. A true classic.

Client #3

My personal favourite. I found the posting from this client deep in the depths of Craigslist.

I sent over my resume, and got a response. Backend work for a "popular website". Finally, a normal client! And for a high-traffic website - this would be a great experience.

Then, I saw their email.

Sigh. What now? Have I not been through enough?

I couldn't find anything particular online when I searched for Vodka Casino, so I decided to give them the benefit of the doubt. I got another email with project details.

Project details email from vodka casino

I opened instructions.pdf. The first line caught me by surprise:

When I type [CENSORED]🔞 in the search bar, it should...

Wait, what? Why would someone search for [CENSORED]🔞 ? Unless...

I open the website, and yup. Sure enough, I had been hired to work on an adult film website.

At this point I had decided I could not work on this. But, curiosity did strike me... how much does this industry even pay? I might as well get some information for my troubles, after all.

I tried to get a quote, but was met with a request to talk over the phone. I wasn't willing to have my phone number out in the adult film industry. Besides, how would I even address this person?

Hi Vodka, how are you?


Good afternoon, Mr. Casino.

Clearly, a phone call wasn't going to happen. That was the last of Client #3, and is the story of my brief career in the adult film industry.

My freelancing experience was eventful to say the least. Freelancing can really be great - I did end up having some successful clients in the end. It was a great way to build my skills, resume, and make some money on the side.

Yet somehow, in one year, I almost:

  1. Helped someone commit tax fraud
  2. Became the CTO of the next Uber
  3. Worked on an adult film website

Moral of the story, if you're searching the depths of Craigslist for your gigs, just be careful out there. 😅