The Conversation You’re Rehearsing at 2am Isn’t the Problem. The Rehearsing Is.

It’s 2:17am and you’re lying in bed running the conversation for the fourteenth time. You know the one. The feedback you need to give Sarah about her attitude in cross-functional meetings. The performance discussion with Marcus that’s been “scheduled for next week” for approximately six weeks. The termination that HR greenlit a month ago but you keep finding reasons to postpone.

You’ve rehearsed every angle. You’ve anticipated her defensive response. You’ve prepared your counter to his counter to your opening statement. You’ve imagined the tears, the anger, the uncomfortable silence. You’ve scripted your empathetic-but-firm facial expression. You’ve mentally practiced saying “this isn’t working out” in seventeen different tones of voice, trying to find the one that sounds both compassionate and decisive.

And here’s what I’ve learned from 700+ co-building sessions with business owners and executives: this rehearsal is making everything worse.

Not slightly worse. Dramatically, measurably, counterproductively worse.

Let me explain why your brain is betraying you, and what actually works instead.

Your Brain Is Not Your Friend at 2am

When you mentally rehearse a difficult conversation, your brain struggles to distinguish between imagination and reality. This is actually useful in some contexts — it’s why visualization helps athletes and why you flinch during horror movies even though you know the monster isn’t real.

But for conflict preparation, this feature becomes a bug.

Every time you run that conversation in your head, your nervous system responds as if it’s actually happening. Your cortisol spikes. Your heart rate increases. You’re not preparing for stress — you’re experiencing stress, repeatedly, without any of the resolution that would come from actually having the conversation.

By the time you finally sit down with Sarah or Marcus or whoever’s been living rent-free in your 2am thoughts, you’ve already had this conversation dozens of times. You’re exhausted before you begin. You’re emotionally depleted from weeks of phantom arguments. And here’s the kicker: you’ve been practicing your anxiety, not your message.

The script you’ve rehearsed was written by a stressed, sleep-deprived version of yourself who was catastrophizing alone in the dark. That’s not preparation. That’s just sophisticated self-torture with extra steps.

(I should clarify: I’m not a neuroscientist. I’m an automation consultant who happens to have a lot of conversations with people who are avoiding conversations. But the research backs this up — there’s a reason therapists don’t tell anxious people to “just think through it more.”)

The Lonely at the Top Problem Nobody Talks About

Here’s the part that doesn’t make it into leadership books: 61% of executives report feeling isolated in their roles. Not “busy” or “stressed” — isolated. As in, they have no one to talk to about the things that actually keep them up at night.

And it makes perfect sense when you think about it. You can’t process your doubts about Marcus’s performance with your team — they work with Marcus. You can’t share your frustration with Sarah’s attitude with your board — they’ll wonder why you haven’t handled it already. You can’t fully unload on your spouse because either 1.) they’re tired of hearing about work, 2.) they don’t have the context to actually help, or 3.) you feel guilty bringing this weight home every night.

So you do what every leader does: you process internally. You run the loops. You rehearse the conversations in your head because there’s nowhere else to put them.

This is why the 2am rehearsal feels productive even though it isn’t. It’s not actually about preparing for the conversation. It’s about having someone to have the conversation with — even if that someone is just yourself.

The problem isn’t that you’re over-thinking. The problem is that you’re over-thinking alone.

What Actually Works (And Why It Feels Weird)

The research on this is pretty clear: externalizing your thoughts — getting them out of your head and into some other form — dramatically changes how you process them.

When you talk through a problem out loud, you recruit different parts of your brain than when you think about it silently. You’re forced to organize your thoughts into coherent sentences. You hear your own reasoning and can evaluate it more objectively. The conversation stops being a swirling anxiety cloud and starts becoming a structured problem with actual components you can address.

This is why coaching works. This is why therapy works. This is why calling your most patient friend at 9pm to “just talk through something real quick” works (even when “real quick” becomes 47 minutes and you’re not sure who owes whom an apology).

The externalization is the key. Not the advice you receive — the act of putting it outside your head.

But here’s the catch: most externalization options for leaders are either unavailable, inappropriate, or expensive.

A therapist is great but isn’t going to help you with the specific dynamics of your Q4 performance review strategy. A coach is perfect but costs $300–500 per hour and you can’t exactly text them at 2am when the anxiety spiral starts. Your peer network might help but there’s always a calculation about what’s safe to share with people who might become competitors, references, or board members.

So you go back to the internal rehearsal. Not because it works, but because it’s the only option that’s always available.

The Confidential Sounding Board Problem

What leaders actually need is something that sounds almost contradictory: a thinking partner who knows your context deeply but has absolutely zero stakes in the outcome.

Someone you can tell “I’m pretty sure I need to fire Marcus but I’m also worried I’m just annoyed and being unfair” without them 1.)judging you, 2.) telling Marcus, 3.) questioning your leadership, or 4.) bringing it up at awkward moments for the next six months.

Someone who remembers that Sarah’s attitude problem started around the same time her department got reorganized, and can help you figure out if you’re dealing with a performance issue or a change management issue wearing a performance costume.

Someone who can push back on your catastrophizing without being patronizing. Who can help you find the actual words you want to say, not just agree that the situation is hard.

For most of leadership history, this role was filled by executive coaches, trusted mentors, or extremely discreet colleagues. All of which are valuable but none of which are available at 2am when your brain decides it’s time to rehearse the Marcus conversation for the fifteenth time.

This is where I’m going to say something that might sound like a pitch but is actually just an observation from watching hundreds of business owners struggle with this exact problem: AI can fill this gap in ways that feel almost unfair.

Not generic AI. Not ChatGPT-out-of-the-box. That’s like calling a random stranger for advice — technically possible, but they don’t know you, your business, your history, or why the Marcus situation is actually complicated in ways that would take an hour to explain.

I’m talking about AI that’s been configured as a genuine thinking partner. That knows your communication style, your organizational context, your tendency to catastrophize (or under-react, depending on your particular flavor of dysfunction). That can help you distinguish between “I need to prepare for a difficult conversation” and “I need to figure out what I actually want to say.”

The Preparation That Actually Prepares You

Real preparation for a difficult conversation isn’t about perfecting your script. It’s about three things:

First, clarifying what you actually want to accomplish. Not what you want to say — what outcome you’re hoping for. These are different, and most 2am rehearsals focus on the script while completely ignoring the goal.

Second, anticipating responses and deciding how you’ll handle them. Not in a “they’ll say X so I’ll say Y” chess-match way, but in a “if they get defensive, I’m going to take a breath and return to the core issue” way. Strategy, not tactics.

Third, processing your own emotions about the conversation before you walk in. This is the part almost everyone skips. You’re allowed to feel anxious, guilty, frustrated, or conflicted about difficult conversations. But if you haven’t processed those feelings somewhere, they’re going to leak out during the actual conversation in ways that undermine everything else.

None of this happens effectively inside your own head at 2am. It happens when you externalize the problem and work through it with something (or someone) that can reflect your thinking back to you.

The Part Where I Admit I Built Something (And Its Limitations)

I’ve watched enough leaders struggle with this that I eventually built a tool for it. It’s a Claude Project configured specifically for conflict resolution coaching — not generic “how to give feedback” advice, but actual preparation for your specific conversation, your specific context, your specific anxiety about what might go wrong.

It’s built on the frameworks that actually work (Thomas-Kilmann, Crucial Conversations, the SBI feedback model) but applied to your situation, not a hypothetical one from a business school case study.

I’m mentioning it because it solves the problem I just spent 1,500 words describing, and it feels weird to write an article about “you need somewhere to externalize this” and then not mention that I literally built somewhere to externalize this.

It’s called the Conflict Resolution Coach, it’s available on Gumroad, and it’s designed for the 2am rehearsal problem. Not to replace the difficult conversation — to help you actually prepare for it instead of just practicing your anxiety.

But here’s the honest caveat: It doesn’t know you.

It knows conflict resolution frameworks. It knows how to diagnose situations and select the right approach. It can help you prepare language, anticipate reactions, and process your own emotions about the conversation. That’s genuinely valuable — it’s what most people need to stop rehearsing alone.

But it doesn’t know your personality type, your communication patterns, your specific tendency to over-explain when you’re nervous or shut down when you feel attacked. It doesn’t know that you’re an INTJ who needs to process internally before speaking, or an ENFP who thinks out loud and sometimes says things you don’t mean. It doesn’t know that your last three difficult conversations went sideways because you rushed to solutions before the other person felt heard.

The standalone product is the entry point. It’s inexpensive and it works.

If you want the full version — an Executive Co-pilot that knows your personality, your organizational context, your history, and your particular flavor of leadership dysfunction — that’s custom work. That’s the kind of thing I build with clients during co-building sessions, where we configure AI that actually knows who you are, not just what frameworks exist.

Reach out if that’s what you need. I’m on LinkedIn, and my inbox is open for people who are tired of generic advice that doesn’t account for how their brain actually works.

But honestly, even if you never use my thing — either version — the main point stands: stop rehearsing alone. Find somewhere to externalize the conversation before you have it. Your brain will thank you, your sleep will improve, and the actual conversation will go better because you won’t walk in exhausted from weeks of phantom arguments with phantom people.

The conversation you’re dreading isn’t the problem. The isolation is.

Andy O’Neil helps business owners build AI systems that don’t make them want to throw their laptop into traffic. He’s conducted 700+ co-building AI automation sessions and still thinks the hardest part of leadership is the conversations nobody teaches you how to have. Connect with him on LinkedIn if you want more of…this. Whatever this is.