Undo: When Letting Go Looks Like Failure
Why release feels like loss before it becomes freedom
The Ache of Release
There’s a strange grief in doing what’s right for you.
Letting go of what no longer fits doesn’t always feel like relief at first.
It feels like guilt.
Like you’re letting everyone down, breaking some unspoken promise to keep being who they expected.
The project you stop chasing.
The relationship you stop rescuing.
The version of yourself that once made sense but no longer feels true.
We tell ourselves freedom should feel light.
But often, it begins heavy because we’re shedding identities, not tasks.
The Silence After Goodbye
When I left my director role, I expected a flood of messages.
Five years of leadership, late nights, strategy decks, and care.
But when I logged out for the last time, only three people reached out.
And then silence.
My email was cut off instantly.
Slack channels disappeared.
One moment, I was part of everything.
The next, it was like I’d never existed there at all.
The silence was deafening.
Not because I wanted fanfare, but because it revealed something deeper:
I had mistaken busyness for belonging.
The noise of constant communication had disguised how replaceable I already was.
That hurt - but it was also the truth that set me free.
The Coordinate: Undo
In the ENOUGH Compass, Undo means release what no longer fits.
It’s not destruction. It’s precision.
You’re not erasing; you’re editing.
Ask yourself:
What am I holding that once served me but now weighs me down?
What belief would I be relieved to stop defending?
Where is my effort keeping something alive that wants to end?
Undoing is how you make space for alignment to move in.
It’s not quitting. This is clearing.
The Stand-Up Stage
Before all of this, I was a stand-up comedian for over a decade.
Anything from road gigs to small clubs in the city.
I loved the rhythm of a laugh.
How it could break tension, bridge strangers, and make life lighter for five minutes at a time.
My last show was three weeks before the pandemic shut down the world.
That night was a solid set with good laughs and great energy.
Then every stage went dark, and that emptiness was the answer I’d been avoiding.
After a decade, something shifted.
The laughter stopped feeling like a connection, and it started feeling like a transaction.
I was performing intimacy instead of living it.
Comedy gave me so much: timing, courage, voice.
But it no longer held my why.
What I really wanted was to connect with people.
Not just make them laugh, but make them remember themselves.
Letting go of that stage felt like losing oxygen.
But now I can see: I wasn’t killing something.
I was clearing the air for a truer conversation.
The one I’m having with you right now.
Why Letting Go Feels Like Failing
We live in a culture that worships continuity.
Once you start, you’re supposed to keep going.
But “never quitting” is just perfectionism wearing endurance as a disguise.
Here’s the truth: endings are data.
They tell you what’s complete.
They show you what season you’re actually in.
Nature doesn’t cling to last season’s bloom.
Trees release leaves not because they’ve failed, but because they know what season they’re in.
What the Culture of More Gets Wrong
It tells you to optimize what you should release.
It sells you systems for “reinvigorating” things that have already ended.
But sometimes the most courageous improvement is the graceful exit.
You can’t curate your way out of misalignment.
You can only undo your way back to truth.
Here’s what the Culture of More won’t tell you: holding on isn’t loyalty.
It’s scarcity thinking.
More commitments. More identities. More proof you’re enough.
We accumulate and accumulate, building towers of evidence that we matter.
But sufficiency knows differently.
You don’t need to carry everything to prove your worth.
You can release what’s complete.
You can bless what served you and let it rest.
Because the freedom you’re looking for isn’t on the other side of more.
It’s on the other side of less.
Practice for the Week
Pick one small thing to release:
An unused app - that productivity tracker you downloaded six months ago
A project you’ve outgrown - the side business you keep saying you’ll revive
A story about who you need to be - “I’m the friend who’s always available”
Don’t replace it yet.
Just notice the space it leaves behind.
That emptiness isn’t absence.
It’s readiness.
That’s your compass.
You’re already holding it.
Exhale.
P.S. Tell me what did you undo this week? And what did the silence after it sound like?