This is a topic I talk at length about in my book, How To Stop Feeling Like Shit: 14 Habits That Are Holding You Back From Happiness. Most people struggle with having hard conversations, as well as setting boundaries. These can be some hard lessons! Enjoy...

Let’s talk about something that doesn’t always kick ass: Tough, awkward conversations.

And I’ll start with a truth: most of us don’t have enough of them. I was just talking to a friend recently who had just moved in with her cousin and was feeling like she had no say in the space. That her cousin/roommate was messy and had her stuff everywhere. So my friend was upset and complaining at length about it.

And I asked, “So what do you plan on doing about it?” And my friend laughed and said she planned on doing nothing. Basically, just continue to complain about it. That having the conversation would be awkward and uncomfortable.

And I wonder– how many of us do this every damn day? How many of us avoid awkward conversations so often that it’s affecting our lives way more negatively that we even know?

You may think I’m nuts- but I think it’s all of us.

I’ll bet you reading this can think of at least one awkward conversation you need to have. Your mom does ____, it bugs the shit out you and you wish she’d stop. Your partner keeps joking with you about ____ and you actually don’t think it’s funny, it hurts your feelings. Your boss is ______ and you really wish she wouldn’t do that. Your best friend is always late and you need to ask her to try harder to be prompt to respect your time.

Almost every single one of my private clients over the last 8 years has had some kind of conversation that’s needed to take place that they’re avoiding. Why? Because it’s uncomfortable. Because they aren’t sure what the outcome will be. What if they other person gets mad? Says no? Gets their feelings hurt? Breaks up with them? Or (insert whatever worst-case scenario you can think of).

Now I’m not going to sit here with my pom-poms cheering you on and just telling you to go out and do it. If that’s all you needed you would have done it by now. What you need are some hard truths and a plan:

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1103: Fostering Engagement with Jim Mosquera