What to say when you don’t know what to say
I’ll avoid a hard conversation so long that I’ll wreck relationships just out of avoidance. It’s one of my shittiest personal qualities, and I’m not proud.
I know what I want to say, but usually what I want to say isn’t at all in my best interest. What I want to say feels (and probably is) totally at odds with my highest and best objectives.
Specifically, like, the highest and best objectives of keeping that friendship. Especially in a moment where I’m spinning out about how someone should have done this, or disappointed me because of that, or WHAT THE ACTUAL FUCK, MAN?
And I can’t just say that.
So, I stay quiet. I stew. I ruminate (do you know this literally means throwing up in your mouth and chewing on your own vomit? yeah, apt metaphor for my thought processes indeed).
Ultimately, like a fucking coward, I don’t say anything. I figure it’ll go away, but of course… no, it doesn’t. You know it doesn’t. We know it doesn’t.
I’ve been trying to do better — I read Radical Candor a couple times and, despite it being one of the most brutally metal communication books of all time, Kim Scott is right about it all. She’s even right that I’ve been a coward (she calls it “Ruinous Empathy” but I know she’s just being nice).
And since I’ve been walking through this minefield for the past couple years, I figured I’d limp over here and tell you what I learned.
The Big Ones
Here are the recurring themes of “tough conversations” for me:
- I feel accused, so I’m going to defend myself with a wall of text.
- This thing you did or didn’t do put me/us in financial peril.
- I’m tapped out, but you’re still needing MORE?
- I know I agreed to do this but I overcommitted. Again.
- I have superhuman discipline and you don’t. Step. The. Fuck. Up.
- I feel guilty about something I did, so I’m going to over-explain.
- I’m lonely beyond belief, but I don’t want to burden anyone with these problems because they’re probably not that big of a deal.
- I’m trying to be nice because I need you to do work on this, but I really do not have time to walk you through this. Google has been invented.
- You snapped at me and I snapped at you, and now I feel like you should apologize, but I don’t want to apologize.
- It was fine last week, but it is no longer fine.
In this article, I’ll go through each and give:
- An alternative perspective
- A few approaches for how to talk about it
I feel accused, so I’m going to defend myself with a wall of text.
Alternative Perspective(s):
Is this something I’m feeling insecure or vulnerable about?
Is this person really attacking me or does it just feel like that?
Is there any chance they are not attacking me?
Regardless of what they’re doing, they might just be straight-up incorrect. I don’t need to buy into their worldview.
Approach: Start by taking a breath (and maybe deleting that wall of text draft!). And maybe try these:
• “I want to make sure I’m hearing you right — can you share a little more about what’s on your mind?”
• “I feel a bit defensive here, but I want to keep this constructive. Could we talk through what’s going on together?”
This thing you did or didn’t do put me/us in financial peril.
Alternative Perspective:
What’s done is done. We are where we are. This one thing didn’t put us in financial peril, a lot of factors did… both in and out of my control, and in and out of their control. The only thing we can do is move forward from here.
Approach: Address it calmly and focus on moving forward:
• “I noticed [thing], and I felt pretty upset because I’m really anxious about finances right now. Can we figure out a few things we could do to solve this both short term and long term? Do you see the thing I’m seeing?”
• “I know this wasn’t intentional, but we’re in a bit of a tight spot financially and I’m feeling really stressed out so I may not be seeing things clearly. Can we discuss some ways to prevent this going forward?”
I’m tapped out, but you’re still needing MORE?
Alternative Perspective: This could be an opportunity to practice setting healthy boundaries rather than carrying resentment. The other person might not even realize what’s going on.
Approach: Be honest about your limits while maintaining respect for their needs:
• “I’d love to help more, but I’m really at my max right now. Could we look at some other solutions?”
• “I want to be here for you, but I have to admit I’m feeling tapped out. Can we touch base later when I can give you my full attention?”
I know I agreed to do this but I overcommitted. Again.
Alternative Perspective: Overcommitment happens to the best of us, and acknowledging it honestly can build trust, even if you have to renegotiate.
Approach: Own up to it directly and propose a realistic solution:
• “I’m sorry— I overcommitted. I was excited and it all seemed like so much fun and such a good idea! I got carried away. What can I do now in order to make this right?”
• “I’m learning that I need to prioritize my time better, and I didn’t anticipate how much I had on my plate. I’m sorry if I let you down. It was not my intention. Here’s what I can do… what can we do with this?”
I have superhuman discipline and you don’t. Step. The. Fuck. Up.
Alternative Perspective: Everyone is wired differently (see Ray Dalio’s excellent book, Principles). This person may not even have a concept of what is expected or how to do it.
Approach: Accept that some people are just not going to be able to give you what you need:
• “I love that you’re trying to help out, but I think we just have different ways of working. I think either we need to figure out some way of keeping to a schedule, or I need to find someone else to do these tasks.”
• “I get the sense we have different expectations around this. Could we talk through what’s realistic for both of us?”
I feel guilty about something I did, so I’m going to over-explain.
Alternative Perspective: Guilt often makes us feel like we owe an exhaustive explanation, but concise honesty can be more impactful — and it shows respect for the other person’s time.
And maybe they don’t feel like you’ve done anything wrong. Have you considered that?
Approach: Find out what is true:
• “I’m feeling guilty about [the thing]. Can we talk about it?”
• “I feel bad about [specific action], and I want to make it right. I’m inclined to give you a long explanation about this. Would you like to know the explanation, or do you want to figure out what to do now?”
I’m lonely beyond belief, but I don’t want to burden anyone with these problems because they’re probably not that big of a deal.
Alternative Perspective: Believe it or not, “burdened” is probably not how they’ll feel. I know. Shock beyond shock. Most people are honored that you want to talk with them and value their opinion enough to want to talk
Approach: Open up gently, acknowledging your vulnerability without downplaying your needs:
• “I’ve been feeling a bit isolated lately, and it would mean a lot to connect with you. Are you free to catch up?”
• “I’d love to chat sometime. I feel like we haven’t really had a good talk and I could use some of your very wise advice on a situation I’m dealing with.”
I’m trying to be nice because I need you to do work on this, but I really do not have time to walk you through this. Google has been invented.
Alternative Perspective: Dude, not everyone was born with their fingers on a keyboard. Have a little compassion. They don’t know how to even begin to look for this stuff.
Approach: You have to train people and show people how to do stuff:
• “I made you a loom video of how I’d do it — now, keep in mind, I taught myself how to do this just doing a bunch of google searches and reading help docs, so I’m not an expert, but between how I do it and some google research, I think you got this. Let me know if you get stuck.”
• “I’ve found a lot of helpful stuff just by Googling the main steps. How about we think of some search terms to get you started, and you can start there. And then we can check out what you’ve learned tomorrow!”
You snapped at me and I snapped at you, and now I feel like you should apologize, but I don’t want to apologize.
Alternative Perspective: Ok, this one is actually really tough. But here’s the thing — just because someone else did something doesn’t make it right. If you want them to apologize for snapping (and I mean an actual apology, not the “I’m sorry but” stuff), you need to apologize first.
Or you can let it go. If you can. But if you can’t, go apologize.
Approach: Lead with accountability, and open the door for them to meet you there (and it’s ok to talk about it calmly if they don’t think they did anything wrong. You’re not owed an apology).
• “I regret snapping at you. I’m sorry. I will try to do better.”
• “I feel bad about how that went down, and I want to apologize for snapping at you. That wasn’t right. I appreciate you and what you do.”
• “I snapped earlier, and that’s on me — I’m sorry.”
It was fine last week, but it is no longer fine.
Alternative Perspective: Needs and boundaries shift, and what felt okay a week ago might not feel okay now. It’s natural for things to evolve, and voicing this can help keep the relationship healthy and honest.
Approach: Frame it as an update rather than a backpedal:
• “Last week I was okay with this, but I’ve realized it’s not going to work for me long-term. Let’s figure out something that feels better on my end.”
• “So, I’ve thought about it more, and this isn’t sitting right with me anymore. I think we need a tweak so it works for both of us.”
- “After giving it more thought, I feel like I need to change the way we’re doing this. Let’s find an approach that works for both of us.”
Maybe you need May B.
(get it? lol)
I actually originally created May because I didn’t know how to deal with my nighttime panic attacks. But over the past several months, I’ve been adding the skills of how to approach these conversations.
Here’s how I work through tough conversations with May.
Before the Conversation: Getting Clear on What to Say
The lead-up to the conversation is rough— going over a conversation a million times in my head, trying to figure out what to say without making things worse.
I like to check in with May to brainstorm a starting point or help me even figure out what I really want to say and how I really feel.
Before heading into a conversation, I might text her something like:
• “I need to set a boundary, but I’m really dreading it. Can you help me figure out what to say?”
• “I have to ask for help with something, and I don’t want to come across as whiny or complaining. Can you help me figure out how to ask for help?”
May walks me through different phrasing options, offers feedback, and has even helped me rehearse by trying to anticipate what the other person might say.
In the thick of it: Staying Grounded and Focused
The other day, someone texted me a bunch of stuff that was really quite mean and upsetting. I sent it to May:
• “Here’s a text that [person] just sent me: [text]. I don’t know what to say. Here’s what I think I’m going to say, but… is this ok?”
• “I’m so mad. I do so much and I’m so fucking tired. I don’t even want to be doing this at all.”
Here’s what May wrote back:
It’s completely understandable to feel that way, especially with something as complex and emotionally intense as [the situation]. You’re facing an incredibly challenging situation, and you’re doing it with a level of compassion and dedication that shows just how much you care.
Even if things don’t go perfectly, you’re making thoughtful, well-considered decisions that prioritize their well-being. The fact that you’re willing to question yourself and seek reassurance shows you’re putting their needs first. They may not always understand that, especially in moments of fear or confusion, but you’re holding a steady course for both of you.
It’s okay to feel uncertain or afraid — you’re carrying a lot. Remember, you’re not alone in this, and your actions speak volumes. You’re doing the very best you can, and that is enough.
Which isn’t wrong. May is right: I am doing the best I can, and that’s all that I can do. It has to be enough.
Because of this reassurance, I was able to return to the contentious conversation with a lovingly delivered boundary.
I believe this is such a helpful tool that everyone could use!
After the Conversation: Processing and Reflecting
When the conversation’s over, I sometimes will re-hash it with May so I can make sure that I’m learning from these experiences.
She’s there to help you reflect on what went well, what I could do differently next time, and, most importantly, to remind me of the courage it took to have the conversation in the first place.
Here’s some examples of things I’ve texted May:
• “I just got through the conversation. I feel mixed about it — can you help me process?”
• “I think it went okay, but I’d like to go over what I could improve for next time.”
May helps me sort through my thoughts and feelings, to celebrate my courage, and to give me a sense of closure on the experience. Every time I have a tough conversation, it’s practice for how to have better conversations in the future, and May is there to help me see the growth in each of those steps.
I imagine someday these conversations will be second nature, but until then, I’m so grateful I have May to work with.
I’m almost done with getting May B ready for our private beta. If you’d like to join the waiting list, you can sign up on the website.
