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As a life coach, my friends often call me for business advice. Just recently, my pal Jason asked: “My boss took a booking from my client when I was on vacation, and now he’s claiming the commission is his… should I speak up?”

In life, when our feathers get ruffled—a relative makes a judgmental remark, an arrogant colleague takes credit for your work—we can either react or not react.

It’s that simple—and that difficult. When you see red and don’t know what to do, let these factors help you decide what to confront and what to let slide (and see how it worked out for Jason).

If money is involved…

When to Speak Up: Ever had a friend owe you money, then turn around and buy some clothes? Not OK! When it comes to your hard-earned dough not being paid back or a broke friend going too far and taking advantage of your generosity, say something!

Giving should leave you feeling blissful, not resentful.

A simple, “Hey man, I’m headed on vacation soon, and I’d love to get everything settled before I head out” or “Your turn to buy lunch!” will do. They’ll get the hint. And if not, you might want to re-evaluate how important your friendship is to that person.

When to Let It Slide: It’s a different story in a professional context. Do you want a raise? Or do you need to bring up a financial issue at work (like my friend Jason)? If so, you have to choose your timing wisely and be selective about how often you raise the topic with your manager. Being compensated fairly counts. But this has to be done sparingly so you are heard. (Jason frequently complained, and over time, his requests were drowned out.)

Choose the most important matters to speak up about. There should not be more than two serious occasions that pop up per year. In the case above, I asked Jason if this was an important enough issue to raise—given he only gets a couple of opportunities each year to contend with his boss’s decision. If it’s a yes—do it! If not, forget about it and move on (and don’t spend a single second dwelling on it). Turns out the answer in this case was the latter!

If some criticizes you or makes a joke at your expense…

When to Speak Up: If someone is unkind repeatedly, even in “jest,” it’s time to take up the issue. Is someone being passive-aggressive on purpose (and not because you’re just feeling touchy today)? The best way to confront someone who is upsetting you is openly and without a hint of anger.

First, breathe. Wait until you’re calm and ask the person if you can talk privately. Once you’re one-on-one, you can say, “Catherine, I’ve noticed you’ve made a few comments about X lately. I’ve felt it’s a bit X toward me. Am I reading this properly?”

Your kindness and openness will disarm the other person, and the less defensive you are, the more likely you will reach a resolution (and the truth).

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Likewise, if someone is being overly critical, it’s OK to lovingly say that you appreciate their advice, but you’re doing OK as you are. I love what an entrepreneur friend said to me recently: “Please check out my new website today! It’s complete, so I don’t need feedback, but would love you to leave a comment or tweet it out!”

The same goes when you see someone else who can’t or won’t stand up for themselves being treated unfairly. The world needs people who are willing to stand up for others too.

When to Let It Slide: Sometimes we can all be a little sensitive. My friend’s peer recently made a comment about her parenting that left her reeling for weeks. A different friend got upset when someone joked about her hat at dinner.

If we let a joke slide, we’re not a pushover. Heck—if we let every perceived snub, jab, or jibe bother us, I don’t know if we’d get out of bed in the morning. Just remember it’s OK to tell people when their feedback is not required.

If something unfair happens…

When to Speak Up: You get home late from a stressful day at work, and your spouse forgot to take out the trash. An employee failed to send a report on time, and now you’re late getting back to a client. Perhaps a friend returned a borrowed t-shirt or dinner platter, and it’s come back with a small stain or chip. Gah! I hear—and feel—your internal scream! You just have to ask yourself: Is this worth a fight/terse words/angry text?

Consider whether these events have become the rule versus the exception in your relationships. If you’re calm and these events still feel totally unfair, it could be worth voicing your feelings. (Just make sure your reaction isn’t unrealistic—if life were “fair,” I’d be Kendall Jenner rollin’ in my Rolls Royce). Don’t rush a rant that you might regret later and have to repair. If something still bothers you one week, two weeks, a month after it happened—it could be a sign it’s time to express yourself.

When to Let It Slide: Don’t make a hasty decision when you’re tired, annoyed, or hungry. You won’t be rational. When you’re in a calm mindset, you’ll probably realize it’s not worth the energy of an argument. Nor the potential ramifications.

Maybe your spouse is overworked too right now, so he or she forgot to take care of some chores. No big deal. Maybe your assistant is on top of things 95 percent of the time, when you consider it. And hey, didn’t you break a friend’s expensive wine glass just last month? Or still have her cardigan in your closet from last fall? These things happen! If you can, let those puppies slide, slide, slide.

Remember: Any confrontation involves some risk, so the risk has to be worth the potential reward to you—a silenced bully at work, a more reliable friend, or increased support from a partner. But the older I get, the less confrontational I become. I just don’t sweat the small stuff like I used to.

Hey, I’m in no way easy like Sunday morning. I’m uptight. I’m Type A. I’m sensitive. But I do know that people are mainly good-hearted and that life isn’t always fair—but it’s still good.


Originally featured on Greatist.

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