Everyone likes a good story. Everyone likes a good sh*tpost (whether they'll admit it or not). Sometimes you get both.

Dealing with crappy clients

Look, there is one thing you have got to accept in this line of work is that eventually, you will deal with a basketcase client. There is no getting around it. 

Crappy client #1: Sheila

I formally resigned from my J-O-B with the Dept. of the Army back in April 2021. It was a long time coming, but my wife was making decent pay with an MLM, so we decided it was time to take the plunge.

The catalyst for the decision to walk was picking up a pair of clients on Upwork that both promised substantial, long-term work.

Sheila owned a marketing firm and was contracted to rebuild a website from a prominent aircraft maintenance vendor. I have long been the top-rated aviation writer on Upwork, and our discovery call went well, so I hopped on and quit my job. Well, that's over-simplified because I was already on my way out. But this was really my key indicator that it was now or never. 

Right off the bat, I realized Sheila was rigid. Like, not a little rigid, but a lot rigid. I get that to some extent, but it went right on past overbearing. Not just overbearing but condescending. Here's the Lord's honest truth: not only would I not take that job now because the pay was too low, but I would have ended the contract right then and there. But I was scared because I had just walked away from my career and the mortgage waits for no man. 

But here’s the catch: her communications were shaky at best despite all of her rigidity. To the extent that I misunderstood her instructions and only did half of the first assignment. I had already been around enough to know that this wasn’t a “me” thing because I don’t miss assignments. That isn't to deflect or sound condescending; Sheila isn't reading this, so I have nothing to gain. No, I want you to understand what you will eventually get into. Not exactly the same, but eventually, it's going to happen. 

You are not indispensable

Sheila was not particularly understanding about the incident and gave me a short turnaround time of about four days for eight articles. Yes, I was really jamming. And yes, I got it done. It was my first real exposure to high-pressure writing.

Well, she didn't can me after that incident. See, there is a little secret that I didn't understand yet. Despite all her blustering and scolding (she did scold me, which looking back, really pisses me off), she needed me a hell of a lot more than I needed her. 

Burn this into your brain, ESPECIALLY if you are a niche specialist: THEY NEED YOU MORE THAN YOU NEED THEM. Don't let yourself be walked on. If they treat you like shit, ditch them. No second chances. Your self-respect is worth a hell of a lot more than that. You can always pick up a 9-5 job for a while if the pay cut is too deep. Or, ideally, if you get the drift that they suck, be on the lookout for replacement clients. And always be on the lookout for replacements anyway. Generally speaking, you are under no contractual obligations at all so that a client can cut you anytime. So, always, always, always be sharpening your hook and sending out pitches. 

Anyway, back to Sheila. The thing about this was that her rigidity was a one-way street. The company she was working for was not concerned about her artificial deadlines. In fact, they weren’t really concerned with anything. She demanded things from me that were not being pushed from them; they weren’t even reading the articles in the first place.

That's not an exaggeration, either. I would jump on monthly (unpaid) status updates, and about half the time, the client hadn't even read them yet. For that, I don't blame Sheila for being disgruntled. The weird thing is that they were super chill, and when they did read my work, they loved it. There was a serious disconnect. 

Long story short, the after a few months of little to no work (after being promised monthly work), I hadn’t heard from Sheila in a while. I wasn’t all that fond of her, so I wasn’t really trying, but we were running out of money, so I shot her an email.

Parting thoughts

I don't think you should bash former clients, but I do recommend telling the world about your experiences when a client is hard to deal with. Now, there is a world of difference between a client rightfully pointing out when you aren't delivering (they are paying you), and when they are being impossible. You need to learn to identify the two. 

But here are the other key takeaways:

• Build backup plans. If you only have one client and they are terrible to work with, you have painted yourself into a corner. But this isn't a 9-5. You can and MUST always be on the hunt for new clients. Line up as many as you can handle, and then sift through which contracts are keepers. Also, use this as leverage to ask for raises. It's cutthroat but such is life.

• Make yourself more indispensable every day. Trust me; they came to you because they NEED you.

• Don't take shit if they treat you poorly. You know when you're being treated like trash. Don't take it. Find something else or someone else.

• Be careful not to overreact. Some people are harder to deal with than others. My biggest client by far is abrasive AF, but he pays really well, and we got to the point of him basically leaving me alone to get my work done.

• Broke clients are the hardest to deal with ~99% of the time. I don't make the rules. If you're writing for the poors, level up and find richer clients. They are out there, and they will not give you 1/10th the grief of a broke client.

If you are just getting started and don't know what move to make next, check out my ebook on how I built a highly profitable freelancing business using Upwork as the vehicle. It'll be the most valuable $10 you spend this week, I promise.