The Key To Freelancing Happiness: Not Working With Jerks

As a freelance writer of five years’ vintage, I think that I’ve figured out most of the rudiments when it comes to freelance writing.

The process has been helped — in no small measure — by documenting the journey of discovery as I go along.

If you feel like siphoning up some of the knowledge that I peter out onto the internet (for free), then check out my Medium publication about freelance writing above. There’s no ulterior motive there, profit or otherwise. It’s just the things I figure about freelance writing as I accrue experience “doing” it.

Something I haven’t talked about before — and which I thus feel is somewhat overdue — is my conscious decision not to work with jerks. It’s been a constant feature of my freelance writing live over the five years that I’ve engaged in this occupation.

Although I’ve figured out a ton about freelance writing since I started, this is actually arguably the thing that has saved my mental health the most. And while I’ve written plenty about how to charge by the word and by the hour (again, I refer those interested to the above), I’ve frequently worked with lower paying clients simply because they were pleasant to work with and treated me well.

Conversely, I’ve — on many occasions — decided not to work with clients that paid well solely because they treated me with contempt or disrespect.

Sadly, I believe that there’s a correlation between lousy companies and those that hire freelance writers.

Which isn’t to say that every company that works with freelancers is lousy. Rather that — in that large mixture — there are a good amount of operators who turn to the freelance talent pool solely because they are parsimonious characters who simply want to save a dime at all costs. Almost invariably, these are not agreeable companies to work with.

Here are some of the jerk red flags that I’ve learned to both spot and avoid. If you’re encountering these, then there’s a good chance that your freelance writing business might work better without them in your life.

Aggressive Editorial Feedback

As a freelance writer, I naturally receive — from time to time — some version of: “yeah, we really hated this draft.” It happens, I’m pretty sure, to virtually all of us.

However, there’s also an enormous difference in the way that organizations and professionals communicate this to me.

In my “good” book are editors that have an almost intrinsic knack for tact and diplomacy.

They’ll let you know that the draft wasn’t quite what they were looking for while giving the impression (at least) that they’re patiently there, in your corner, helping you to bring it to a more satisfactory state.

Others are downright blunt and nasty in the way they convey such feedback.

There are also those who just seem to relish in giving (negative) feedback for the sake of giving negative feedback. These characters typically prove themselves to be utterly implacable. Almost nothing you write within a reasonable number of drafts will be good enough for them. In my experience, it’s usually more prudent to just stop trying.

Clients that have these kinds of editor on staff are never those that I feel too bad about losing.

“You’re Freelancer 9. The Last 8 Were Kind Of Rubbish”

As a freelancer that tries to stick up for freelancing, I honestly hate hearing other freelancers being badmouthed (even though, most times,I know nothing about them).

In such instances, I’m almost always privy only to one side of the story — my client’s.

But it never casts the client in a particularly good light.

I consider any derogatory references to prior freelancers to be warning signs. There are ways with which to let a new freelancer know that they’re not the first without necessarily making obvious that you thought their predecessor was, frankly, kind of rubbish.

I’ve noticed a large correlation between clients who turn out to be jerks and those that proudly boast about having gone through a veritable litany of prior freelancing talent.

If your client is jumping up and down to tell you about how lousy their previous agency was and how quickly they got rid of them … please be forewarned that you may be next in line.

Clients That Don’t Respect (Or Get) What You Do

The final red flag that I like to keep in mind is the type of client who doesn’t really get — or value — what you do.

Sometimes it’s hard to run into this particular conundrum because … if clients don’t get what you do, they’re less likely to hire you.

Nevertheless, one does encounter clients that don’t really seem to value, much less understand, the kind of work that you do as a freelancer.

They have a go-to catchphrase too. And it’s this: “I could do this myself but … meh, I couldn’t be bothered.” (Or: “I don’t have the time.” Or: “this isn’t worth my time.”)

If you hear that from a client, take it from me, there’s a good chance that they don’t really think much about the service that you’re providing.

And when you’re disrespected as a professional, no matter how much money you’re charging, it’s hard to corral a good level of enthusiasm for that particular client.

There are myriad ways in which clients communicate that they’re likely to fall into the jerk category.

Some freelancers advocate charging a premium for the displeasure of having to put up with working for people that you loathe.

Personally — if you can afford it, and that’s, I realize, a big ‘if’ — I recommend just avoiding them entirely.

Working relationships should be, if not fun, then at least tolerable.

Being merciless about weeding out those clients who don’t treat you well — and there seem to be too many of those among the ranks who hire freelancers — has, in my experience, been highly beneficial.




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

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Daniel Rosehill

Daniel Rosehill

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

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