Difficult Conversations

This year I vowed to be more open with you, my readers. I promised to share more about what I’ve learned in my life that it might strike a chord and help you in your journey, too. I’ve talked a lot about dealing with other people and how to keep your emotions in check and how to protect yourself while still being open.

If you haven’t read my article on Shonda Rhimes’ book “Year of Yes”, definitely take a read through that now. I’ve referenced some relevant passages from that book and article in this post, too. I’ve read a lot of inspiring books over the past few years that have really offered me some good advice for how to deal with the curve balls life throws you. I’d also take a read through my editorial Can You Shake Off Bad Blood? as I reference a few passages from that as well.

Year of Yes – Advice Around Difficult Conversations

In my Year of Yes article I mention Shonda’s advice on difficult conversations. I’ll repeat it here for you: “Any difficult conversation, any tough issue I have sitting in the pit of my stomach, any unsaid confessions, any itchy little resentment and unpleasant business? I can talk about it. I want to talk about it. Because no matter how hard a conversation is, I know that on the other side of that difficult conversation lies peace…And the more difficult the conversation, the greater the freedom.”

“The more difficult the conversation, the greater the freedom.” – Shonda Rhimes

My Own Difficult Conversation

I’ve recently had a difficult conversation….one that was probably many years overdue, but at least two years for sure. Upon wanting to have this difficult conversation, I decided to stop waiting and write my feelings down. I thought that if I penned a letter to the person with whom I was “quarrelling” outlining my feelings in as much detail as I could muster, then at the very least this person would be able to more easily empathize and see where I was coming from. (Trust me, I went into Tom Clancy detail, but I wanted to give as clear of a picture as I could). A big part of why I did this was because this person doesn’t really know me all that well, so a bit of personal history was important to include for the sake of perspective and clarity.

I figured if it were written down – all in one place – that it would allow me to share my feelings and for that matter my “side” of the story, unencumbered and without the need to be defensive of immediate responses. I didn’t realize that the time it took for a response would be almost as difficult as getting the response itself. I’m not one for emotional purgatory – I like to deal with things swiftly and then move on. After all, life’s too short. Time certainly doesn’t heal all wounds – sometimes it makes them deeper and more sore.

When we eventually spoke, this person told me I was brave for putting my feelings out there and thanked me for the letter, but did not apologize. This person did not wish to address anything that I had written – not even my concluding statements about my hope for the future or that it gave an insight into who I am or maybe they felt they knew me better upon reading this.

I’ll be honest, I was more than a bit stunned when we finished our conversation. I didn’t hear even a half-assed “I’m sorry I made you feel that way, that was never my intention” nor an “I didn’t realize my actions were being perceived this way – I’m really sorry for hurting you” or anything like that. I’d also been told that the time it took to respond was because this person felt awkward, that this was hard to talk about and that this person didn’t know what to do. But there was no comment along the lines of “I felt especially bad not reaching out to you after learning how much I’d hurt you.”

Difficult conversations are difficult. No one questions that. The problem is, the longer they’re left undone, the more difficult they are to have.

I’m reminded of a quote from Amy Poehler’s book, YES PLEASE where she says: “A word about apologizing: It’s hard to do it without digging yourself in deeper. It’s also scary and that’s why we avoid the pain. We want so badly to plead our case and tell our story. The bad news is that everybody has a story. Everyone has a version of how things went down and how they participated.  It’s hard to untangle facts and feelings.” (p.71)

Maybe this person was afraid. Maybe they didn’t feel as if they’d done anything wrong. Maybe they truly were defending themselves because they believed that my hurt feelings were mine alone and not their problem. Maybe this is an opportunity to learn about others in our lives and how we choose to behave around them and how much of ourselves we choose to share with them. Maybe a lot of things…

A Word About Apologizing

“Your brain is not your friend when you need to apologize. Your brain and your ego and your intellect all remind you of the ‘facts’. I kept telling myself that the only thing I was guilty of was not paying attention. Sure, I was being self-absorbed and insensitive, but who isn’t? Sure, I should have been more on top of what I was saying, but wasn’t that somebody else’s job? Didn’t everyone know how busy I was? Didn’t [these people] take into consideration what a NICE PERSON I was? My brain shouted these things loud and clear. My heart quietly told a different story.” – Amy Poehler, YES PLEASE.

I was surprised to learn that this person had not empathy but blame towards me, and that by feeling hurt or upset they felt I was “nitpicking” and “holding onto things” when from their perspective I should have been letting things go. Although I hadn’t asked for an apology, I didn’t think I had to. I thought this person would know that apologizing was the right thing to do to move forward.

Like Amy Poehler, my brain shouts at me. This time it was shouting “But you lied to me! You sold me a false bill of goods! You made promises you didn’t keep, you made offers that weren’t genuine, and then you ghosted me from your life! And I’m to blame because my feelings got hurt and somehow I should still trust you?” Really??!*….what.do.you.do?

“Bandaids don’t fix bullet holes. You say ‘sorry’ just for show.”
– Taylor Swift, Bad Blood

If the apology isn’t genuine, like how Taylor Swift sings that “Bandaids don’t fix bullet holes, you say sorry just for show” (‘Bad Blood’, 1989) do you really want the apology after all? The thing about apologies is that when people know in their hearts that they should apologize, they usually do. If you have to ask for the apology, then you know it isn’t genuine.

I also think that those closest to us have the biggest capacity to hurt us – and sometimes they know that, too. But after all of the bullets have been fired – with our without apology – how do you move on? Can that trust be rebuilt or will it always be a fractured bond? You may never be able to trust someone again. Taylor also sings that “time can heal – but this won’t” (‘Bad Blood’, 1989) and maybe that means that just because you’ve moved on doesn’t mean that you’ve forgotten or that you necessarily should.

Don’t Fear The Outcome

“Saying what you think and wading into the deep end don’t always have a happy ending. Difficult conversations are somewhat of a gamble and you have to be willing to be okay with the outcome. And you have to know, going in, where you draw the line. You have to know when in the conversation you are going to say no. You have to know when you are going to say “that doesn’t work for me.” You have to know when to say, “I’m done.” You have to know when to say, “This isn’t worth it.” “You aren’t worth it.” The more I said what I thought, the more I was willing to dive into difficult conversations, the more I was willing to say yes to me, the less I was willing to allow people in my life who left me emptier and unhappier and more insecure than before I saw them.” – Shonda Rhimes, Year of Yes (p.228-229).

“Difficult conversations are somewhat of a gamble and you have to be willing to be okay with the outcome.” – Shonda Rhimes, Year of Yes

No one likes difficult conversations, but there really is something so freeing about knowing where you stand with someone. Difficult conversations and how long it takes to actually have them teach you a lot about people, too. You learn about people in an entirely different way through these conversations and this process. And isn’t it nice to just know?

I’d much rather know how someone feels about me and our relationship – good or bad. There’s so much peace and balance in knowing where you stand. You may not agree with how someone sees you or who they think you are, but that’s their deal, not yours. Without having difficult conversations, we’ll never know the truth, and the truth will set you free – believe me!

Knowing When To Move On

Who you allow to be a part of your life is something that should be taken really seriously and it’s something that should be evaluated over time as well. Share your time with those who make you feel like your best self, who you can be your real self around and not those who leave you empty inside or full of anxiety. Sometimes these conversations can be a way through the darkness with someone – they can be a way to resolve deep issues and misunderstandings and a way to find truth in a relationship and a path forward. But sometimes they don’t go well and you have to be okay with that, too.


*Kudos if you caught the “Really?!!” reference in this article. If you did, then we truly understand each other.

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Carlee Krtolica
Carlee Krtolica