Why Freelancers And Toxic Clients Frequently Meet Up — And What You Can Do About It

Why freelancers tend to encounter bad clients over the course of their writing careers

Daniel Rosehill
5 min readJul 19, 2021
Freelancing: here’s why it can be a minefield of bad clients, especially for those new to the game. Photo by Andrea Piacquadio from Pexels

Browse through any freelancing forum on the internet — or just talk to your nearest friendly freelancer— and you’ll come across plenty of war stories from those who have been unfortunate enough to encounter clients they consider ‘toxic’ during their freelancing career.

The dynamic is so pervasive, in fact, that there’s an entire website dedicated to anonymously amassing such stories from the freelancing world.

It’s hilarious and terrible all at the same time. If you’re a chiseled veteran of the freelancing world like the author then I’m certain you’ll find much to relate to there.

During the course of my five plus year tenure in freelancing/self-employment, I’ve encountered several clients who — to my mind — fit pretty closely the definition of what I’d consider toxic.

As I spoke to other freelancers, I quickly began to understand that virtually all of us had had such experiences at some time or another. The next question I asked myself was why.

This blog provides some thoughts to answer that question.

Freelancers Encounter More Clients Than Employees Do Employers

Freelancers vary in terms of how many clients they tend to feel comfortable working with at any one time.

My preferred ‘volume’ is somewhere between five and seven. Any more than that and I start mixing up client names and forgetting who does what. But I’ve heard of freelancers who commonly work with more than ten clients simultaneously and have no problems doing so.

Given the fact that most freelancing clients are — by necessity — temporary in nature, the cumulative number of companies that your average employee and freelancer are going to encounter over the course of their career is likely to only increase over time.

In light of simple mathematics, your average self-employed freelancer/consultant is likely going to end up working with more companies than your average employee is over the course of their career. The explanation? Most salaried employees only work with one employer at a time and jobs tend to be less temporary than freelancing ‘gigs.’

There are plenty of poorly run and dysfunctional companies in the world. When you really play the field you’re bound to run into them.

To An Extent, Freelancers Self-Select For Price Shoppers

There are plenty of respectable reasons why companies turn to the freelance talent pool when they need to get a project taken care of.

Perhaps they can’t find the talent they need in their locality. In some cases, they know that the requirement is very temporary and can’t justify a full time hire. In some instances, trying out freelancers is a way of dipping their toes into a certain pool of candidates without committing to a full time hire (and it works both ways; some freelancers may ‘trial’ potential employers by starting out as freelancers with them).

But there’s also one that can’t be avoided. Many companies turn to the freelance talent pool — especially marketplaces like Upwork and Fiverr — because they want to pick up talent on the cheap. And these are precisely the type of client that you’ll want to go out of your way to avoid.

Freelancers need to remember that they can be big conspicuous targets for all manner of “price shoppers” and those intent on scoring project staffers for the lowest price possible. The solutions? Charge for value delivered and don’t compete on price. Raise rates to a level at which you’re no longer towards the bottom of the deck.

Freelancers can also:

  • Be pushed into unreasonable deals without having the experience to identify that they’re being taken for a ride.
  • Not know what reasonable boundaries might look like much less how to set them. For instance, many freelancers offer unlimited meetings on low value deliverables like small writing projects. I would argue that this doesn’t make any business sense.

Freelancers Create An Expectation That They’re Disposable

Yup.

In the cruel and sometimes heartless world of freelancing, clients know that they can pick up and ditch freelancers as their heart pleases without having to worry about pesky things like benefits.

Another important point to bear in mind is that — in many freelancing relationships — the freelancer is a remote entity who only exists as pixels on a computer screen.

It’s a lot easier to screw over Dave (freelancer) when you know that you can fire him at a moment’s notice and that you’re never going to run into him while having a drink at your local bar.

Our disposable and remote nature makes us vulnerable to exploitation and predatory clients. This is partially why having rigorous contracts is so essential.

Freelancers Can Be Lousy Salespeople — And Too Often Are

I’m looking at you, Daniel (that’s me)!

While freelancers can be very competent professionals within the areas they focus on — say writing or digital marketing — it’s rare to find a freelancer who’s a true jack of all trades in all the areas they would ideally know about.

As self-employed businesspeople, freelancers aren’t just project ‘doers’- they’re also the mangers of their own businesses. They need to market themselves in order to land work. And they need to do all those things that salespeople do in order to close out business.

Lead qualification is one of those core sales activities that it’s very easy to neglect until it’s too late. Once freelancers get past the stage of exuberance that people are reaching out to them (inbound marketing) they need to realize that the job’s only a quarter the way done.

Next comes lead qualification and making sure that the leads under management actually represent quality opportunities that are likely to yield mutually satisfactory business relationships. Finally, freelancers need to know enough about contracts to be able to come up with terms that are going to protect them in the even that expectations become misaligned and something goes wrong.

The freelancing life can be one fraught with ups and downs — and one of the most common ‘downs’ is the feeling that one is dealing with a seemingly unending litany of dubious clients.

If that’s happening to you — I’ve been there! — then take a look at how you’re presenting yourself to clients and (just as importantly) how you’re managing leads.

If you’re selling on price, find a way to sell yourself on the potential value you could deliver. But if you insist on selling by price, then at least make sure that it isn’t a cheap one.

Finally, cut yourself just a little slack.

Understand that, as a freelancer, you’ll potentially work with ten times as many companies as your friends working a 9 to 5 if you do this over the course of your career. There’s an upside so that and it’s partially what keeps freelancing interesting — you’ll get to work with lots of different companies and industries. But it also comes at a cost: you’re officially now ten times as likely to run into charlatans, dysfunctional startups, and cheapskates (or all three!) as those working in an office.

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Daniel Rosehill

Daytime: writing for other people. Nighttime: writing for me. Or the other way round. Enjoys: Linux, tech, beer, random things. https://www.danielrosehill.com