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But then, living with the consequences of not having a difficult conversation ain’t easy either!

And that would be reason number one: When we do not speak up for what we want or need, we do not get what we want or need!
Think carefully about that thing you really, truly dearly want. Yes, that one! Now who is going to get you what you need? Mind reading, the Lotto, fairy godmother… Nein, sorry, not gonna happen!
It is your job to ask for what you want. Not demand, especially as you cannot demand anything of true value of another, just ask.
True, they do not always understand, and sometimes they do not want to hear you.
But. You Are Not. Without. Options!!!

Reason number two: When we do not speak up for what we want or need, we get what we don’t want!
So if you sit for a moment and think about any suckiness you are currently experiencing, which part of it has been created by you not speaking up?
Uhum, yes, like that!

Mostly what we get is The Argument. The Ugly Row. The Sickening Silent Treatment.
Or the Victim or Finger Wagger.
Even Manipulation or the Anger Attack.
And if you are over any of the above, the way through is the Not So Difficult Conversation!
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Reason number three: It is not as hard as you believe! It is just like a muscle that has not been practiced in a while. Sure, you may not have been on a bicycle in a while, and that hill is steep, and the first time you go up it will be hard. But you know! You can do it and you will do it if you keep trying. Maybe the first time you will need to push, maybe you will only get half way up. But if you keep trying your muscles will get trained and it will become effortless.
And just like cycling or any other exercise, having difficult conversations can become something you get good at.