Quiet Rebellion Dispatch: The Conversations We Don’t Want to Have
Notes on reclaiming your time, energy, and attention. Field reports from a life beyond the hustle and burnout.
I’ve been in a handful of difficult conversations lately.
Some with my co-founders.
Some with my partner.
Some with clients, all of whom are facing moments that require courage, clarity, and a steady nervous system.
These moments aren’t rare.
They’re everywhere.
Behind the tension in your team meeting.
In the silence between texts with a friend.
Underneath the resentment simmering at home.
Most of us aren’t trained to do this well.
Even those of us who teach it.
(I used to lead a class on this back at Google. I’ve often returned to the book Difficult Conversations: How to Discuss What Matters Most more times than I can count. Still, I find myself fumbling sometimes.)
The truth is, the hardest part isn’t what to say.
It’s getting clear on what’s really happening.
What's Under the Conversation
In Difficult Conversations, authors Douglas Stone, Bruce Patton, and Sheila Heen share a simple but profound insight:
Every tough conversation is actually three conversations happening at once.
What happened – the facts, the stories, the interpretations we hold
Feelings – often unspoken, but driving the entire interaction
Identity – what the conversation threatens in us: “Am I competent? Lovable? Good?”
These layers tangle quickly.
And when we’re not conscious of them, we spiral.
We argue over logistics when what we’re really upset about is feeling dismissed.
We come in swinging because we’re afraid of being hurt.
We shut down because we don’t know how to ask for what we need.
We talk past each other, instead of with each other.
And the systems we operate in…fast-paced work cultures, rigid roles, performance mindsets don’t exactly leave room for breath, pause, or co-regulation.
It’s Hard Because It Matters
These conversations feel high-stakes because they are.
They often ask us to be honest about something vulnerable.
They challenge the stories we tell ourselves and the people we care about.
They are also the most human thing we do.
Not just because they surface tension, but because they open the possibility for something deeper:
A new way of understanding each other.
A shift in how we hold ourselves.
An invitation to real connection.
A Practice, Not a Perfect
Here are a few reminders I’ve been returning to this week, for myself and my clients:
Map the conversation before you have it. What’s your story? What’s theirs?
Name what you're feeling. If you’re scared, say so. If you’re tender, let it show.
Start from the “third story.” That neutral frame that holds both truths.
Co-regulate. Breathe. Pause. Let your nervous system know it’s safe.
Repair, don’t perform. Say “I want to get this right with you,” and mean it.
If you’ve got a hard conversation ahead, or one that’s lingering in the rearview.
It’s ok to be imperfect.
You’re in it.
And that matters.
This is part of the work of the Quiet Rebellion.
Not just breaking free from old systems, but building new ways of being in relationship…with others and with yourself.
One reflection for your week:
What’s the conversation you’ve been avoiding, and what might become possible if you chose to have it with care?
In solidarity ✊
Nicholas Whitaker
Human BE-ing and Conscious Leadership Coach @ nicholaswhitaker.com
Co-founder @ Changing Work
🔗 Follow me on LinkedIn, BlueSky, and here on Substack
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