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How to Have that One Big Nightmare Conversation You Avoid

How to Have that One Big Nightmare Conversation You Avoid

Most people don’t struggle to remember their nightmares aren’t real, at least once they’ve woken up. But most of us live with another kind of waking nightmare: a confrontation we’re avoiding.

It could be something you need to say to your boss, or something you’ve always wanted to say to your mother. 

It could be about something small–something you try to sweep under the bed–but it haunts you from there. Or it could be an issue large enough to redirect your course in life, and you just can’t seem to strike up the courage. 

Either way, it troubles you. And you know you need to face it.

Here are some ideas that might help.


1. Decide–with good counsel–that the confrontation should take place. Then get their help to hold you to it.

Look, if it’s haunting you, you should do something about it. But if you’ve been avoiding the confrontation, you need more than just courage to face the person. You need wisdom to know what portion is yours–and what portion needs to be worked out through conversation.

Don’t go around to forty different people and get the advice you want to hear. Decide who you’re going to trust, tell them the whole situation, and follow through with what they say.

Having a hard time deciding where to draw on outside perspective? These are broad tips, not rules:

  1. look for someone older than you (they have the wisdom of experience, especially if they’ve walked this road before)

  2. look for someone who treats everyone with respect (they will be even with you, and they’re less likely to be ‘charmed’ by you)

  3. look for someone who walks in forgiveness (they will be impartial and they’ll inspire reconciliation in you)

Don’t even start down this road if you just want to complain and not do anything. This is called gossip, and it’s worse than lead-poisoning. 

When you’ve shared your situation, and they help you unpack just what needs to be dealt with (and which portion is yours), then let them know when you’re going to reach out–and ask them to follow up with you over making the appointment. 


2. Ask the person you need to confront for a face-to-face conversation, with enough time for both of you to share.

If you’re not confrontative by nature, you’re going to want to overestimate the time you’ll need to address the issue at hand. But in certain situations, like some workplace conflicts or simple misunderstandings, less time is needed.

Don’t be tempted to get into the issue over the phone or via text message. You don’t have to be evasive–just give the person a primer so they’re not going in blind. (Especially if it’s a big or lengthy conversation.)

Expect the other person to have as least as much to say as you will. But don’t rehearse their arguments for them. Hopefully, if both of you bring grace to the table, this isn’t going to be that kind of conversation.

Without estimating the time you need to process things, you might have to postpone the resolution. And the only thing worse than facing this confrontation is accidentally prolonging it. 

3. Take time to figure out what you need to say.

If you have the chance, take a moment to edit your thinking. Leave your legal briefcase at home: this isn’t your chance to build an argument. Instead, the goal is to winnow the problem down to its most central conflict, so you don’t get lost going down twenty or thirty dead ends. 

It’s no good to verbally vomit over the person you’re trying to address. I’m not saying you have to have Atticus Finch-level polish. But it’s unfair to them, and unhelpful to you, to figure out what the problem is mid-conversation.

There could be twenty or thirty possible roads to take, too–especially if you’re hauling around a bundle of issues. Here is the only shortcut in this whole article: genuinely forgive the other person ahead of time–and make sure you still go ahead with the meeting. Without confrontation, the issue won’t be healed between you, even if you have settled it in your heart. But forgiving the person will help you clarify the central conflict.

4. When you meet with them, be the one to begin. Keep the matter at hand to only what you perceived, and how you felt about it.

Now that you have their attention, you might want to avoid the matter again altogether. Of course there’s going to be a mild amount of small talk–but now is the time to get down to it. Don’t make them dig it out of you.

On the other hand, you might finally feel like you’re ready to pin them to the wall! Before you bust out your throwing stars and start hurling around accusations–check your heart motives.

Are you wanting to reconcile with this person, or prosecute them?

If someone has had the good faith to meet with you, then hold out hope for healing to take place. If you’ve gotten all the way to this stage and you haven’t examined your intentions, you probably got some bad counsel along the way. 

But don’t be alarmed if you’re a swirling mess of emotions–especially if this is your first Conflict Rodeo. Midway through what you have to say, you might want to punch them, and then after a few sentences you’re ready to forget the whole thing ever took place! 

Slow down, and breathe. Look them in the eyes, and remember the point of all this: there is a bridge down between their island and yours. And you are brave and willing to rebuild it, but you’re going to need their help.

(Another tip–this one from Donald Miller: keep your palms face-up on your lap while you’re speaking to them. It will help you to remember to be gentle.)

You’ve gotten all the way there. You’ve done your part–you’ve gotten the nightmare out of your head! 

Congratulations. Now don’t stick the landing.

5. Choose to remain honouring–regardless of the outcome of your confrontation.

You might not “win” this way. They might not acknowledge the issue. Perhaps they throw it back in your face and you have to listen to them accuse you and speak against you. Maybe you feel totally slimed afterward and further from resolve than when you started.

Don’t forget why you faced this fear in the first place: you’re an honourable person. And you’re becoming the kind of person who won’t let the nightmares go on.

You can’t force someone to help you fix the disconnection. But you can do your own part, and tidy up your own mind, and be resolved with the comfort that you did what you could to create peace. 

Don’t let yourself get snarky. Don’t curse them under your breath or dishonour them to others afterward. Don’t let the conflict keep getting the better of you. You faced this in the first place to uproot your fears. If you finish this with honour, and refuse to disrespect the person–even if they don’t reconcile with you–the matter will be, in a very real sense, over.

Sure, you’ll probably have to set up some new boundaries. You might have a follow-up conversation or two as well, but those will get easier and easier.

If you don’t get the opportunity to affirm the other person, and enjoy your reconnection, then just remember this one affirming truth about you:

You aren’t afraid of conflict anymore.

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