Dealing With Difficult Customers When You’re Self-Employed

Does Your Business Have a Difficult Customer?

Anyone who has read some of my stuff over the years probably knows that I fall into the go along/get along camp as a general rule, or to use a cliché, I do think you usually catch more flies with honey than you do with vinegar. But to every general rule, there is an exception (more on that in a minute).

Accommodating, getting along, and saying yes is not just about being a nice guy or gal; it’s often smart business, especially when your operation functions as a very tight ship.


Sometimes you do freelance business with people because you have to or because you don’t care, that is, a person or business may be offering you the best deal, or they are more convenient or have the best selection, or whatever. That is all well and good and valid.

But just as often, nay, maybe more often, we do business with someone because we want to work with that person. Whether it is hiring someone you like or contracting with a new vendor, is it not true that personality, often and surprisingly, trumps other issues?

Knowing Exactly When It’s Time to Be a Jerk

I had a pal in law school. He was not ‘law student of the year’ by any means. He didn’t have great grades, that’s for sure, but what he did have was a winning personality; people liked being around him. He ended up having his pick of jobs.

As he told me at the time, “When someone interviews you, sure, they want to know that you can do the job, but equally importantly I think, they want to see if they would like spending 10 hours a day working with you.” Those were wise words.

So yes, being a good guy usually reaps rewards. But usually is not always. The general rule is not the only rule.

Another rule is this: Sometimes you have to be a jerk. People have to know that not only are you a nice person, but that you also have a spine, that you are a businessperson, and that you mean business.

Personal example: Recently, someone was using my copyrighted content to build their business without attributing my stuff to me. I discovered it, and kindly asked them to stop. Twice they ignored my request.

So I hired a lawyer and threatened to sue. And it wasn’t just a threat. I meant it.

Two things happened as a result. First, the infringement ended, pronto. Second, they don’t like me very much anymore.

But that’s fine. We are not in business to make friends (well, at least not primarily). We are in business to make products, offer services, make a difference, make some money, and have some fun.

Preparing Yourself for Dealing With Difficult Clients

Not everyone is going to like you. Check. People may get angry when you defend yourself or your business. Check. And you may lose some business, or friends, or associates when your business priorities are in order. Checkeroo that too.

So if you have a too-tough client, if you have an employee who takes too much time, if you have business associates who have become more trouble than they are worth, and if you have tried to be reasonable, then a time comes when you should become, well, unreasonable.

To date myself, there are times in business when you just have to be like Howard Beale and stand up and say “I’m mad as hell, and I’m not going to take it anymore!”

Your livelihood just may depend on it.

Have a different opinion on whether or not it’s good to be a jerk sometimes when doing business? Share it with us!

Steve Strauss Senior small business columnist at USA TODAY and author of 15 books, including The Small Business Bible, Steve is your host at

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