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5 Annoying Situations for Freelancers and Small Business Owners and How to Respond to Them

Along with the benefits of being a freelancer, or running your own small business, come some aggravating problems. These hassles will occasionally occur, so you should be ready for them. Here are my solutions to the most common issues.

Late or No Payment

Always bill your clients promptly, as soon as you finish a project. Generally, you should expect to be paid within 30 days, so if you don’t get paid in six weeks, you need to be assertive. Follow up with an email asking when you can expect payment and reattach your original invoice.

If you still get no response, call the client. If you get voicemail and no return call, try to reach the client’s manager or the accounts payable department if the client works for a larger company. Don’t be rude; simply say you’re calling about an overdue invoice and no one has responded to your previous inquiries.

Though I haven’t done this, you can resubmit your invoice along with a late fee, say 2% of the overdue payment. That might prompt the client to at least pay the original invoice.

Last resort, in my view, if you’re willing to lose the client, you can use social media such as Twitter and call out the client, asking why your payment is late.

Unfortunately, unless you’re owed more than $5,000, hiring an attorney or going to small claims court will probably cost you more than the outstanding invoice. Of course, if you are friendly with an attorney who can request your payment on letterhead, sometimes an attorney’s letter will get you paid.

When I used this tactic, the client sent an indignant email asking why I didn’t communicate directly with him first. When I said that I had not gotten any responses to repeated emails, he finally made a direct deposit.

Unreasonable Demands

Having a detailed contract spelling out the responsibilities of both you and the client can help prevent difficulties down the road.

Sometimes if a client asks for extensive revisions of my contract, I won’t take on the client. If you can’t easily come to an agreement on the scope of a project and the payment due, that’s usually a red flag that this client will be demanding – and you can decide whether you want this particular project.

Your contract should include specifics such as:

Method of Communication

How will you communicate? Will you use the phone? Email? Short or long text? Personally, I prefer to read on a laptop and don’t want to read attachments or long texts so I usually tell my clients.


How many revisions or edits are included in the project fee? Spell out payments for additional hours, multiple revisions, phone calls or any other work that wasn’t initially anticipated.


What payment is due if the client or you cancel the agreement before the work is complete? You can say that either party can cancel the work agreement, and you are entitled to keep whatever payment has been made, along with a percentage of what you would have been paid had the project been completed.

You will have to negotiate these terms but you should definitely spell out obligations on both sides.

Missing Deadlines for No Good Reason

Obviously, you have every intention of meeting your deadlines, but what happens when your client misses deadlines?

I have found that authors don’t seem to view their delivery date as binding. I often say that a book contract is the same as any other legal agreement such as a mortgage or car loan. And it’s not just the delivery date that authors ignore.

Authors don’t return jacket copy or page proofs until I nudge and explain that if the copy isn’t returned, the pub date will be pushed back. Somehow, authors don’t think there’s an actual schedule. Remember, you can set deadlines but if your client is delinquent, all you can do is spell out the consequences.

If the client is late returning material, then you may have to establish new deadlines for your review. This relates to my earlier point of thinking about all possibilities when you’re drafting your initial agreement.

Going MIA (Missing in Action)

After one or more conversations about a new project, I email a contract. Generally, I get back a signed agreement with my initial payment, or the prospective client emails me some questions about the contract which I answer. After I receive a signed contract and an initial payment, I start to work.

Sometimes, however, after sending the agreement, I hear nothing. This is perhaps the most exasperating of all client problems.

I call or email and still get no response. I assume there is a reason for the change of heart but I simply don’t understand why people can’t say the project is cancelled or they’ve hired someone else.

Your business model must incorporate these MIA projects, which many inexperienced freelancers don’t do, according to Cynthia Zigmund, founder and president of Second City Publishing.

She will try to reach someone three times and if there is no response, she assumes the project is dead. Zigmund adds, “Do your due diligence with new clients and if there are any red flags, move on.”

Extreme Rudeness

A book I edited sells poorly. The author is obviously upset and complains, essentially blaming me for the low sales. He keeps sending me nasty emails and voicemails.

I usually write a short email explaining the speculative nature of the publishing business and offer some suggestions, although there isn’t much I can do to change the situation.

But when the author continues to harass and berate me, I stop responding. Clearly, nothing I can say will change the author’s view. If there is an intermediary – a mutual acquaintance who referred the client – as a last resort, I will let that person know the client has stepped out of bounds.

If you are a freelance worker, have you had thorny client situations? I’d love to hear your strategies on how to navigate the projects that seem to get derailed along the way. Please share them below!

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The Author

Debra W. Englander is a writer, editor and book coach based in New York. She has written for numerous publications and managed a business book program for John Wiley. She writes “The Savvy Self-Publisher” column for Poets & Writers. Follower her on Twitter @DebraEnglander.

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