Some freelancers are clowns. Honestly. That is the inevitable conclusion I had to make in May 2025. That month goes down in my solopreneur books as The Month of Clowns! These clown freelancers lose clients faster than you can spell ‘Pennywise’ correctly, I bet!
Let me tell you why. But first, let’s do some poetry (thanks, Mr. Nuts, my AI sidekick, and The Head of Marketing, for a perfect first draft):
They dance on deadlines, shoes too big,
Juggling drafts for a miserable gig.
A painted smile, a hopeful frown—
To paying clients, just a clown.They promised gold with sleight of hand,
But built their pitch on shifting sand.
“Where’s the magic?” clients sneer,
“Refund, please—you’re no Shakespeare.”There’s a lesson learned in circus light:
It’s not enough to just recite.
For trust is earned, not sold or spun—
Or else the show is a really quick one.
Good, huh? 🙂
Enough clownship from my side. Here’s the story, and hopefully, a couple of lessons for new freelancers. But first, a couple of words about why this all happened…
Background
As a solopreneur of the mad scientist type, I often come up with crazy ideas and try to make them a reality. I even turned it into a new service recently: The Split Test Syndicate (TS²), where my team and I science the shit out of startup ideas by testing them out in reality and by simulation – in 2 weeks!
Anyway, I was running some experiments where I needed a little piece of utility software to find certain types of people really fast, and then call them up using cold-calling specialists. And once, I just needed a good consultant for experience sharing, paid by the minute. Fun, crazy stuff!
So, I had the “pleasure” of working with plenty of freelancers and two small agencies, also. But, it turned out that the quality of freelancers has hit rock bottom! Only 3 out of 8 of my hires since April 27 were successful!
And I had the strangest discussion with one more small agency and one freelancer. Totally clueless clownship from these guys! So, that makes only 3 out of 10 being successful. That’s a 30% success rate. Or a 70% failure rate, which seems more apt in this context. Either way, these are not numbers worth mentioning to advertise the freelance sites I was a client on, namely, Upwork and Fiverr.
So, May 2025 was recorded in my books as The Month of Clowns.
What was weird was that I had just hired three really good guys. All these first three totally aced their gigs, so I was sure to get the same good stuff again. But no…
The Month of Clowns: 7 Ways freelancers lose clients
Here’s a summary so that you can avoid making the same mistakes! 7 miserable examples coming straight up!
Clown No. 1: Software project that never ends
A freelance software developer I hired on April 28th produced decent stuff… but apparently, can never finish! At the time of writing this, May 30th, i.e., more than a month later, he’s still not done!
We’re talking about a small utility program worth a petty $200. I’ve probably spent more time than him installing, uninstalling, sorting out software library conflicts, reporting bugs after bugs after bugs, and testing the program!
At some point, I wasn’t sure if I really was a client of his or if I was working for the guy as a tester. 😀
He’s a nice guy otherwise, very collaborative, and DM responses come relatively fast, but clearly, he loves doing his projects so much that he never wants to see them end. 🙂
Clown No. 2: Notes… what notes?
This was the first cold-caller. He did 100 calls and reported 0 results. Most people didn’t pick up, he claimed. He was supposed to NOT call on Mondays, Fridays, and weekends because people are not available then. That left him Tuesdays, Wednesdays, and Thursdays. Plenty of time. We went through this in the call when I was interviewing him and explaining what the job was.
One Tuesday morning, I asked when exactly he made those calls – he said last Friday and yesterday… which was Monday! Dah!!! We already knew calling on those days won’t work out!
Apparently, making notes during calls with clients is not what every freelancer does.
I got a full refund, fortunately.
Clown No. 3: These guys just ran away with the money
Another cold caller was a small agency. We had a short call where things went pretty well as the guy was smooth, suggested a good working process, a clear timeline, and a decent budget.
What I was promised to get was:
- A summary report
- Notes on each call
- Sample recordings using the dialer software they recommended, and which I subscribed to
Things went straight to execution really fast. I was kind of impressed… until I saw the result!
What I actually got was:
- A summary report with a couple of statistics only (which was not even a document, just an ugly message on Slack)
- No notes except for two calls
- No recordings
And those two supposedly successful calls… they said there was “poor connection” both times (coincidentally!), so no follow-up could be done. Zero result. And worse, there was no proof of any work done at all!
They chose to run off with the money (their quotation was not big) and keep that 1-star review I left on their Upwork profile page. Case closed. I’m happy to pay to keep that review visible to all of their future clients… and by clients, I mean poor victims.
Clown No. 4: Maybe it was a sloth, actually…?
The next cold caller promised to do 200 calls. In the 25 calendar days that we had (i.e., plenty!), she managed to do fifteen. 15 out of 200 in 25 days!!! Her excuses included (but were not limited to):
- A broken laptop
- Issues with her landlord
- Funerals
- Local community events
- The inability to update files on Dropbox (that’s super-hard, right?)
- Not figuring out how to share files using other means (even harder, apparently)
And lastly, as a bonus (wait for it):
Not making any excuses! 😀
Same thing as last time, don’t call on Fridays. On Tuesday, she promised to finish them all. Did 0, though. Also, the same promise on Thursday. On that day, she managed to do 5 calls. Wow.
But, as the success rate was really high compared to others, something decent came out of those just 15 calls! So, I was happy to pay not for 200 but for those 15 calls actually done… which was just a couple of bucks. So, at least this clown turned out to be quite cost-effective from my perspective. 😉
Clown No. 5: A true Excel wizard
The last cold caller whom I found on Fiverr did quite OK and worked relatively quickly. Only, he couldn’t figure out how to fill the Excel sheet with dates, times, and notes about each call because the texts in the previous cells block some of the cells he should fill!
I guess resizing columns wasn’t invented when he learned his Excel skills… 😀
Four revisions were needed to just do ordinary formatting of the Excel sheet in a normal way and place the right data in the right columns. OMG!
Clown No. 6: Big business competing with solo freelancers
This was perhaps the funniest one. Or the most tragicomical one. This time, instead of talking to a 2-person agency, I found myself talking to a big corporation about a tiny $100 gig. And The Boss on their side started arguing whether the size of the job was meaningful at all… for them!
Of course, as usual, the scope was already specified in the job post! I’m always very specific about mentioning it. Anyway, before I realized how big the company was, we had a call where The Boss tried to explain why the job should be bigger in terms of volume. 2.5X to be exact. (NOTE: It would still be $250 only!)
He couldn’t specify HIS budget yet, but was to “discuss it with his team.” After the call, he sent me a mile-long corporate welcome message in Upwork messages, which not only looks funny as it fills the page on my desktop, but it also doesn’t fit the format of the platform’s streamlined hiring process.
Since I had now realized that I had met a bunch of clowns once again, my brief response was: “TL;DR” with a repeated wish to see his quotation. I had asked for it twice now.
Then there was yet ANOTHER long message about something where I had to copy-paste my “TL;DR” again, and later, block the guy as I still saw some replies coming… to maintain that little sanity I still have left (which isn’t much, to be honest, at this point).
And by the way, after all these messages, there was still no number for the budget. Apparently, they hadn’t finished their internal discussion yet! 😀
Clown No. 7: A great team that doesn’t work together
This was probably the clowniest encounter I’ve ever had on Upwork as a client! EVER!
I was after a consultant. Someone with experience solving a specific problem. Wrote a job post. Got several decent proposals, interviewed several guys in DMs.
Then there was a really well-written proposal, and we had a good DM chat about it. I then noticed that it came from an agency account… Well, whoever solves my problem, I’m happy to pay that guy. I don’t care. I care about the results only.
Particularly, I was after sharing experience with certain tools so that I can save time testing all of them! It would take days and days for me. I wrote THAT WISH in the job post specifically. One paid consulting call, please.
With the guy I was chatting with, we set the expectation that it would be anything between 20 to 60 minutes of Zoom time. Like a proper consulting call, paid by the minute and tracked by the Upwork timer app, with this agenda:
- Show me what you did
- Tell me how well it went from the business perspective
- List what limitations the tool has
That was the gig. Just one call. Easy!
But, of course, these clowns messed it all up. We scheduled a call… and when the time came, the guy sent a message with a Zoom call link. But we already had a link via Upwork’s Google Calendar integration… and both seemed to be recorded meetings. “Hmmmm,” I was thinking…
Well, I got onto one of them after sending a message telling which one I’m joining. 2 people were there. Neither of them bore the name of the person I had chatted with before. I already had a feeling this won’t take too long…
These guys didn’t have video on, so we did audio only. The guy who started talking told me he was here to “gather requirements for the project”… which in MY MIND was only a short consultation! THIS CALL! There was NO OTHER PROJECT!
So, I quickly asked the person to TELL ME WHAT MY PROJECT IS ABOUT since we already went through it in the DMs (with that other guy who wasn’t on this call for some reason).
As you can already guess, he had no ***king clue what I was even talking about! Because it was a totally different guy, unprepped by the first guy! Aaaaarrrgggh!!!
He was probably hoping to get a $10K software development project, whereas EVERYTHING WE HAD DM’ed ABOUT was a CONSULTATION CALL!
I clicked on the Leave button after 34.2 seconds, saying quickly, “I’m out, bye.”
That concluded the fruitless discussion. But, look at the bright side: That 34.2 seconds was so quick no Upwork App could record even a minute of paid consultation, hahah!
Thanks, clowns. Keep dancing. Stay CLUELESS about what your teammates have already done to secure a new gig. Make your client repeat everything to each guy separately. That’s the recipe for victory. Not. Obviously.
How these guys appear in my mind.
Concluding remarks
That’s plenty of clownship now, isn’t it? But what now? Upwork and Fiverr seem to be full of clowns. I’m probably moving my hiring to LinkedIn or someplace else. Because I hate clowns. If you have good ideas, let me know on LinkedIn!
On the other hand, I see an opportunity too. What if a good professional went and joined Upwork right now… that guy would be competing with clowns only! That guy could become one of the top guys on the whole platform, owning his niche just like I did, just a year after I got my first gig.
Think about it, a huge opportunity! If this is your thinking, all you need is quite a bit of knowledge transfer, a little bit of guidance & feedback, and a moderate amount of coaching! Check out the Members section to proceed. You could beat all these clowns with your left hand. How hard could it be? 🙂
PS. In case you were wondering… EVERY SINGLE GUY was paid exactly what he/she quoted! No haggling, no negotiations. Nobody worked for peanuts. I never offer them, that I swear, as surely as CocoLord is my nickname.
