8 Red Flags Every Freelance Writer Should Avoid

For most people entering the full-time freelance world, the biggest concern will be finding new clients. But after being self-employed as a freelance writer and content strategist for almost three years, I can say that a better question is how to find good clients – the ones who value your work, respect your boundaries and pay you fairly. Those are the clients you want to find – and keep!  

But how do you know which clients are A-class and which are going to be pains in the A-ss before you sign a contract? I’ve developed an unofficial list of freelance red flags – little, sometimes seemingly insignificant things people do that will warn me not to accept a job, or at least outline the terms even more carefully than usual.

Here’s a list of my top 8 freelance red flags – and what I do when they pop up.

1. The subject line begins with the word “urgent!”

In the freelance writing world, most jobs are time-sensitive. But when I get an “urgent” request from someone I haven’t worked with in the past, my antenna immediately goes up – even if this person comes by way of introduction from a mutual colleague. There might be a good reason why they’re in a pinch, but more often than not, poor planning and project management play a role. Fire drills are the sort of thing that drove me nuts in the corporate world and they’re something I try to minimize now that I’m self-employed.

What I do:

Respond upon receipt with a clear sense of my availability to discuss their needs and my bandwidth for the next several days or weeks. This establishes what I am willing to commit while also giving the person an easy out if they need more support.

2. They cancel meetings at the last minute.

This one often goes hand-in-hand with the urgent requests. Someone is very eager to speak and sends a meeting request without even waiting to hear if I have interest or availability. That’s a red flag on its own.

Another one is sometimes raised about 15 minutes before the meeting is supposed to start when I get an email hastily explaining how this super urgent need has been superseded by an even more urgent need. In most cases, this change of plans is framed as a bonus to me since they are “giving me time back.”

Very nice – except in most cases, I’m not on the payroll yet. Which means I can’t bill someone for the time they’re wasting.

What I do:

I give people a pass on the first occasion – and sometimes even the second considering how upside down the world has been in recent years. But I keep a mental note of such things and tack that time on to whatever quote or contract I eventually prepare on the person’s behalf. If it happens more than twice or if the person seems completely unconcerned about the value of my time, then I pass on the opportunity.

3. Their requirements are unrealistic.

Sometimes in that introductory email, the sender will include a laundry list of all the skills and experience they “need”: 10+ years’ experience in the banking industry; 3-5 years’ experience writing social media content; basic knowledge of cloud migration strategies; ability to craft compelling PR/media narratives.

I find this wish list somewhat off-putting, especially when you consider the person is hiring for a project, not a full-time, long-term employee. Further, I find that a lot of these needs are somewhat conflicting. Show me the person who spent 10 years in the financial services arena AND has five years’ developing social media content and I will show you someone who is also a very good… storyteller.

What I do:

Like many freelancers, I am a true generalist. I have exposure to a lot of topics in many industries, but I have little in the way of in-depth experience in any given sector. When I reply, I point out which requirements on their list I fulfill and which I don’t. That’s not because I have a hard-line honesty policy so much as I find people who have specific requirements, particularly on certain topics or industries, are better off hiring a specialist.

4. They tell me they’ve been referred – but aren’t introduced by our common connection.

A referral without an introduction isn’t exactly a recommendation. When a message lands in my inbox or LinkedIn chat from a person who says they got my name from a mutual connection but aren’t introduced by that connection personally, I immediately have my suspicions. If our common link isn’t willing to drop a one-line email putting us in touch, then that often says a lot about the person who is asking or how well we might work together.

What I do:

Go back to the common connection and ask if they do, in fact, know the person in question and try to diplomatically ask them to rate the other person on a 1-10 scale, 10 being the client equivalent of the barista who gives you an extra shot and 1 being an absolute psychopath. Proceed (or don’t) based on their feedback. And if they don’t know the person? Pass.

5. They bad mouth their previous freelancer.

There is nothing more alarming to me as a freelancer than when a prospective client kicks off an exploratory call by telling me all the ways their previous freelancer fell short. Typically, this isn’t a case of missed deadlines or late delivery, but just content not to their liking or “on brand.” As someone who has no idea what this person likes or the ins-and-outs of their brand, I am not terribly sympathetic. And I know there’s a good chance that they’ll talk about me negatively at some point too.

What I do:

In situations like these, I ask for specifics about what didn’t work and ask the client to share an example of one of these stalled projects or unpublishable pieces. If what they send me seems fine in terms of the writing itself, then I know the problem probably wasn’t with the freelancer, but the direction given to the freelancer. In this case, I usually trust my gut and either walk away or bid way, way higher than usual. Then if the client turns out to be a nightmare, at least I know I’m getting paid extra to deal with it. 

6. They want me to invoice them in advance.

So this might seem like a good problem to have: Someone comes knocking on your door one morning explaining that they have budget they’re about to lose if they don’t use it right away. They aren’t ready to kick off a line of work, but they’d love to pay me in advance and then pick back up “later” when they’re “ready.”

For clients I work with regularly, I’m generally happy to accommodate those kinds of requests. But for people I don’t have direct experience with, I am very wary of such arrangements. Why? Because things change. They might think they know what they want to do with that money, but that could change “later.” And my schedule or situation could change too. There’s no telling when that person will turn back up to collect – and since they’ve already paid, they likely be way less open to working around my availability.

What I do:

I suggest that they put whatever money they have available into a third-party payment platform like Upwork or Contently. Most Finance departments consider the money spent once the purchase order is created and the money is moved, but if you transfer the money to a third-party platform, the funds don’t have to be paid until the work is actually done. That means that if and when they do actually want to hire me, I can negotiate my rate and timing based on the actual job, not their best guess at what it might be.

7. They suggest I “set aside” an existing client to get around their non-compete.   

This one sometimes goes hand-in-hand with the clients that have the laundry list of requirements. They want someone who has experience working with a company just like theirs but not actively. Has to be a lot of experience and recent experience, but not current experience. Because they have a very strict non-compete, so they can’t have someone working for them and then also working for a competitor. That’s understandable.

What’s not understandable is that when I point out the conflict, they suggest that I leave my long-term client, an account I have grown for years through meticulous relationship building, and come work for them for a limited time only instead!

What I do:

If I signed a non-compete with my current client, then I politely decline at the outset and tell them I’ll be in touch if anything changes in the future. If I don’t have a non-compete in place with my current client, then I will ask if it’s possible to get around the non-compete and sign only an NDA. That hasn’t worked yet, but I figure it’s worth a try!

8. They ask for my resume.

This is one that I come across in Europe. Even when I am referred to this person by a mutual connection, they want all the details: resume, education, portfolio. I don’t mind sending any of those materials, but I know I am unlikely to get an offer when a resume is part of the package. Why? Because on paper, I’m not qualified.

I can do the work, mind you. I can connect these people with references who will tell you as much or remind that they know someone who has already vouched for me. I can show similar work that I did in the past. But once someone wants to know about what I studied in school, what degree I hold – then I know I’m out of the running.

The one saving grace is that in all of these cases, the other person will at least tell me why. They’ve come back with notes on my credentials: I didn’t study journalism. I don’t have a master’s degree. I don’t have any experience analyzing data. In one case, the person added that someone who has stronger credentials also bills at a lower rate than I do – and while his bid came in close to where mine was, this other person would be working “more hours” for the same amount of money. I don’t need a data analysis experience to point out the flawed logic there.

What I do:

Let it pass with no hard feelings. And tell the recovering journalists I meet that they should raise their rates!

Take issue with my interpretation? Disagree with my approach? Have freelance red flags of your own to add? Let me have it!!

8 comments to “8 Red Flags Every Freelance Writer Should Avoid”
  1. I think you could change a few words here and there and have a laundry list of red flags for any freelance or self-employed person (or even those working within a company).

    The one that really hit home for me was the one about “complains about the person who worked with them previously.” That is a huge red flag for anything. That most likely means they will never be satisfied.

    • hello there! i’m sorry … i can’t believe i never responded to this. totally agree – this can apply to just about any type of freelance work and in some cases to the traditional interview experience. and yes, one of my biggest, brightest flags is the badmouthing people who held the role previously. there are so many ways to communicate a failed project without blaming one person… and also, as the hiring party, now you should know what to look for in a new person… so ask that instead of complaining about the past.

      as always, i appreciate your reading :)

  2. All excellent advice! You always impress me. I, for one, really dislike working with psychos and people who grumble about others, or give you just a little too much personal information in way of explanation for what they are asking you to do. If I get a bad vibe, I tend to trust my instincts and politely decline for that particular job. One thing I’ve discovered in working with editors, however, is that they frequently change. So the company might work out at another time. Always good to not burn bridges.

    • aw thank you so much! I appreciate this comment and i am truly sorry that i didn’t rely sooner. I seemed to have turned my notifications off.

      in any case, totally agree. trust your gut – but also if it’s possible to try out a short project to test your gut, that’s even better. sometimes clients who seem like they may be difficult to work with actually appreciate “good help” the most.

      as for the burning bridges… also true. but i am on record as saying that i am in favor of burning bridges on a personal level. a bad manager will still be a bad manager even if they work for the best company. if you do me wrong once, i’m not giving you a second chance.

  3. I subcontract some grant writing work in my consulting business. My favorite grant writer recently retired. She was SO good at her work! Really precise and kept people on task when it came to follow up and reporting. Once, a prospective client wanted my help in finding a new grant writer. They told me they hadn’t gotten along with the previous one which was this same woman, which is when I knew they probably weren’t willing to do the hard work she required of them. I confirmed this with her, and told them I couldn’t help.

    • oh i love when this happens! love it. i once had a very challenging client who wanted “big bold ideas” but couldn’t ARTICULATE any of them (the implication being that i would come up with them on my own!) send me a sample from a competitor that they liked. you know who wrote the copy they sent? ME. i told them, “yes, that is what their experts said. so that is what I wrote. what is it you’d like to say?” crickets.

      as always thanks for reading. and sorry for the delay in responding. i seemed to have turned off my notifications!

    • hellloooo. so sorry i didn’t see this comment until now. i had been on an inadvertent hiatus, partly because i am busy with other things, some of which i love and some which pay the bills. here’s to hoping that i can get back into a normal schedule now that the world is finally starting to get back to normal. hope you and yours are well and doing things you love too xx

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