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Have The Hard Conversation

  • Writer: Week Night Wine Drunk
    Week Night Wine Drunk
  • Aug 8
  • 4 min read

The clarity that comes from the conversation you don’t want to have? That’s how you eliminate the stress of the unknown. And look, I’m not saying it’s easy because it rarely is, but you can’t move forward if you're stuck in 'maybe'. Sitting in limbo. Waiting for an answer that won't come because you never asked the damn question, is just as uncomfortable as not knowing. The difference is when you have an answer, even if it's not the one you were hoping for, you have a starting point for progress. A place to move on from. Your boss won't give you a raise if you don't ask. the guy you like won't commit if you don't ask. you won't get the new job if you don't ask. side note: read the chapter on patchouli people and how manifestation only works when you actually take some action. 


And trust me, I get it. From personal experience, I felt enormous relief after finally biting the bullet and just having the conversation. It has helped my work life, in my personal life and got me out of a marriage that was sucking the actual life out of me. I haven't always gotten the answers I wanted but once I sat with the discomfort and asked the hard stuff, I always came out the other side feeling 100% lighter.


Until you have the conversation the onus is on you to make the change. But once it’s out there, the ball’s in their court. and you will see sooner or later what their decision is. Remembering that silence is an answer too. You can no longer use "I don't know" as an excuse for inaction, it now falls on your shoulders to make the change with whatever answer you receive. You can’t control how they respond but you can control what you do next.


That doesn’t mean the road is smooth. Sometimes it’s bumpy as hell. Sometimes you need to give him a few days to pull his head out of wherever it’s stuck before you revisit the topic, but at least he knows, right? He knows how you feel. He knows he matters to you. He knows you’re willing to put in the effort. Now he gets to decide if he wants to show up for you. If he wants to be with someone who will always have his back. If he’s capable of matching that effort. And maybe he’s not. Maybe he doesn’t have the emotional maturity to step up. And that sucks but at least now you know. And it's not knowing that kills you.


Look, this advice is always easier to dish out than to take. I left way too many conversations hanging for way too long, and now I have an entire decade I refer to as my “depression era.” When you’re waking up every morning crying because you’re married to a man who squashes every bit of light inside of you, that's probably your cue to have a hard conversation. I waited and waited and waited for him to bring it up. He didn't, he was comfortable with his level of discomfort. He didn't want to rock the boat. But misery will make a person do strange things. His personality changed, He became aggressive and couldn't see how much he had shifted until I spelled it out for him. We avoided that conversation for almost 12years and it changed our entire relationship to the point that we are now divorced. Maybe if we’d the hard conversation early on things might have been different. Don't be like that, don't let the conversation fester. Infection rarely gets better on its own. If my time in the dental field has taught me anything, it's this: if you don’t remove the source of the infection, it always comes back.


I promise 90% of the time the hard conversation is worse in your head. It's like ripping off a bandaid. The anticipation is worse than the actual experience, yeah it stings for a second and the cold sweats and clammy hands might make you uncomfortable but once you hit send on that message it's out in the open and all you can do is wait for a response. If the person on the other end has any decency, the conversation will be calm and reasonable. And if it’s not—if they blow up or get nasty? Well, that’s your answer too. And believe me, you don’t want that energy in your life anyway.


And let’s not forget, hard conversations don’t just happen with other people. Sometimes the person you need to face is you. Was I really too tired to get up and go for a run this morning or was I being a little bit lazy because it was cold. Did you ignore the red flags because you like him? Were you stuck in a shitty job because you were too scared to start again? People can give you advice all day long but until you're honest with yourself you will keep repeating the hard lessons. Honestly? I probably need to have a few hard chats with myself right now. It’s awfully easy to hand out life advice, but sometimes the hardest pill to swallow is the truth you have to admit to yourself.

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