top of page

A cautionary Upwork tale

When many freelancers start out, their first method to find new clients means starting an Upwork account and bidding on jobs.

Full disclosure:

I never did this when I started my business. Why? Well, it seemed like nothing more than a way to devalue myself. And so, I started cold emailing from the get-go. And I believe that decision is at least partly responsible for my success over 3 years later.

But y’know what?

Sometime last year, I saw other freelancers praising Upwork. How it was responsible for them landing their first few clients. How they’d never be successful as a freelancer if it wasn’t for Upwork. And how it’s easy to win on Upwork when you’re better than the average freelancer you’re competing against.

I was kinda shocked by the rampant success some seemed to have using Upwork, and so I decided to give it a try for a month or two.

Before long, I landed my first Upwork gig, and thought Upwork might play a larger role in my marketing strategy. That first Upwork gig, at the time, was one of my highest paying gigs I landed—and it only required me to write something like 12 emails or so.

Since I could complete this entire project in a month’s time, I was ecstatic. I thought I was a fool for writing off Upwork when I started.


Well, this Upwork gig didn’t go as I planned.

Here’s what I mean:

It was a 12 email deal that I wanted to get done within 30 days. That’s an easy feat. In fact, my 12 emails per month tier is one of the lowest tiers I offer today.

But my Upwork clients didn’t feel the same way. In fact, they drug their feet at every opportunity they had. To date—and I’m writing this more than 12 months after accepting the Upwork gig—I have only written 10 emails. Instead of being an easy, 30-day project, it’s morphed into a ugly, 391-and-counting-day project (and I still haven’t gotten the greenlight to write the last couple emails I owe).

When I first landed the gig, I thought I’d write the best 12 emails this particular client had ever seen, and we could talk working on a monthly retainer — the same way I do with all of my other clients.

But nope.

They send out one of my emails once every few months.

The email software they use is so amateurish and incompetent that I can’t even see open rates, let alone click-through rates or revenue generated metrics.

Instead of being an opportunity which unlocked growth (both for me and my client) it’s become the bane of my existence. Sometimes I go full months without hearing a peep from my clients, which makes it harder to write emails for. I generated like 20 email ideas when we first started working together (in Dec 2021). Remembering those ideas now in January 2023 isn't a walk in the park.

And it’s completely turned me off from Upwork.


The positioning is all off too.

With this Upwork gig, I don’t come across as THE expert. I come across as a hired hand.

Plus, it messes up my taxes even more. I already use several invoicing services. Adding another one to the mix just makes it harder when I hire Peanut to go through my taxes before handing it over to my accountant.

Moral of the story?

There are two:

(Morals of the story…?)

1. If you’re a freelancer, avoid Upwork at all costs.

Not only is it hard to scale, but in my experience, it gives you the worst type of clients. Clients that don’t take your advice. Clients who don’t value your services. Clients who would rather delay your work than experience success.

As for reason numero dos…

2. If you’re a business owner, avoid Upwork at all costs.

Sure, you might be able to land a discounted freelancer. But it comes with a big cost: You’re not gonna get the best out of that relationship.

It may or may not be the freelancer’s fault. In my case, it was my clients who, instead of sending 12 emails out over the course of a month decided to send 12 emails out over the course of 13 months (and counting).

But methinks you don’t value what a freelancer can do as much as if you would if you hired them through other means.


Wanna 2x, 4x, or mayhap even 8x your impact, revenue, and freedom this year by working with a professional email copywriter who can turn cold leads into red-hot customers, and turn red-hot customers into diehard brand loyalists?


6 views0 comments

Recent Posts

See All

Unboxing the Sonos Beam Zyn sent me

I just checked my email after an extensive editing session of 24 emails and found an unusual email: UPS sent me an email saying that a package had been delivered. “Hmmmm, I don’t remember ordering a p


bottom of page