I have a nasty habit of saying what’s on my mind. Actually, it’s a double-edged sword. Being fearlessly direct and opposing the status quo has played a remarkably positive role in my career. For that, I’m eternally grateful. And I highly recommend it.

But my big mouth has gotten me into trouble on more than one occasion.

A couple of weeks ago I told my wife I thought a woman we’ve been working with was attractive. Don’t ask me what I was thinking. I know it was dumb. Not because I said it to my wife. We’re pretty open and secure, always have been.

It’s what happened next that’s the problem. My wife told her. Even worse, she embellished a bit. She told her I said she was hot. Oh yes she did. Trying to stir up trouble, I guess.

Now, I don’t know if this woman is at all creeped out, but I sure am. I know the bar for making people feel uncomfortable has gotten crazy low in recent years. The last thing I want is for this woman to think “what a creep” when she sees me.

I should have known better. I used to be a highly visible executive officer of several public companies. And I’ve always had a strong work ethic and a healthy respect for individuals that kept me from crossing the line.

But that line has become increasingly blurred thanks to runaway political correctness. And with more and more of us leading entrepreneurial work lives that involve all sorts of business relationships, it’s not always clear who it’s OK to be candid with and who you need to be careful around.

So here are some practical tips to help you (and me) keep the creep factor to a minimum and stay out of trouble:

Keep those creepy impulses to yourself. Jennifer Aniston’s sex-crazed character in “Horrible Bosses” aside, this is generally a guy thing. Besides, that was a movie. Anthony Weiner’s sexting scandal is real life. And while texting lewd pictures is a far cry from telling a coworker she looks nice, be aware that mixing it up is a lot riskier than it used to be. If you’re not sure if it’s cool, it probably isn’t.

Vendors and customers are people too. Remember Mark Hurd, the former HP CEO who got into trouble over a relationship with a marketing contractor? Never mind that nothing happened between them or that third parties are not protected by the same legal statutes as employees are. There are boundaries for every professional relationship, whether you work for the same company or not.

Don’t document your stupidity. Back in the day you had to get caught red-handed to get nailed for sexual harassment or discrimination. Now, it’s remarkable how many people document their stupidity in emails, text messages, and on social networks. Remember, the internet and most of your communication is not only forever, it’s also discoverable in court.

Is it okay to date the boss? The ever-increasing work-life blur has, for many of us, turned our work into our lives. It’s where lots of us meet our better halves. So dating coworkers, employees or the boss – once taboo – is now tolerated. Sort of. How you approach it is tricky. If you have a thing for someone, try becoming friends first. Take it slow. And, if you’re a guy or the boss, it’s safer not to make the first move.

Forget the law. No, I don’t mean that literally. Of course you should know the law. Just be aware that you can be sued by anyone for just about anything. It doesn’t matter whether you did anything wrong or not; it may still cost you – and your reputation.

Think about your boss. If you’re great at what you do, your boss will do what she can to protect you. But if you do something blatant that exposes the company to legal risk, you may leave her no choice but to let you go. On the flip-side, if your performance is borderline and your job is hanging by a thread, all she needs is one good excuse to can you. Don’t be a dummy and give it to her.

How about societal norms? I despise political correctness. I think it’s taken all the fun out of work and turned our society into a bunch of thin-skinned whiners who get offended and sue if you look at them funny. Still, some company cultures are more PC than others and you’ve got to be practical. It often comes down to one question: How badly do you want to keep your job?

Look, if you find yourself parsing every word as it travels from your brain to your mouth and sounding like a robot with a screwy delay circuit, you’ve probably gone too far into the realm of the politically correct and that will hurt your career. Be direct, be genuine, be professional and have a little common sense. You’ll be fine.

A version of this post originally appeared on entrepreneur.com.

Image credit Roberto Trombetta via Flickr