Closure Is Optional
There Frank and I were at Einstein’s—bagels, orange juice, and the kind of conversation that only happens when two people stop pretending they’ve figured it all out.
We landed on a topic most entrepreneurs avoid because it forces honesty:
Letting go in order to move on.
Not in theory.
In practice.
We talked about bad decisions we’d both made—trusting the wrong people, choosing emotion over data, ignoring that quiet internal alarm screaming, “Don’t do this.”
Those mistakes weren’t the hard part.
The hard part was what came after.
When Healing Turns Into Hiding
We kept circling the same realization: after a bad decision, the most dangerous place isn’t failure—it’s comfort.
There’s a strange relief in sitting with the wound. A subtle permission slip we give ourselves to slow down, pull back, and live in the story of what went wrong.
Victimhood becomes a crutch.
At first, it feels like recovery. But over time, it turns into quicksand. Morale erodes. Energy leaks. Forward motion stalls.
Instead of falling off the trapeze, hitting the net, and climbing back up—we stay on the net. Because it feels safe.
My dad used to say something that never left me:
“It’s not how hard you hit the mat that defines you.
It’s whether—and how fast—you get back up.”
At some point, licking the wound stops being healing and starts being avoidance.
That’s when it’s time to get back in the fight.
Not Everything Needs Closure
This was the turning point in the conversation.
A lot of entrepreneurs are obsessed with closure. Final conversations. Clean endings. Proving they were right.
But most of the time, closure isn’t about resolution.
It’s about ego.
We replay conversations. Plan one last message. Wait for an apology that never comes. All while opportunities pass by unnoticed.
Here’s the truth most people don’t want to hear:
Not every situation needs closure.
Some situations need distance.
Strength isn’t getting the last word.
Strength is knowing when to walk away unfinished.
Forgiveness Is a Strategy, Not a Sentiment
We also talked about forgiveness—of ourselves and others.
Not the soft version. The practical one.
When you don’t forgive yourself, you stay tethered to the past. When you don’t forgive others, you recreate the same dynamics in new forms—new people, same problems.
It’s like the driver who cuts you off in traffic. You carry it all day. They’ve already moved on.
Forgiveness isn’t approval.
It’s release.
And release creates space—for clarity, for momentum, for better decisions.
The key is this: forgiveness only works when it’s paired with learning. If you don’t extract the lesson, you’ll end up right back where you started.
What This Really Comes Down To
Entrepreneurship guarantees mistakes. That’s not the differentiator.
The differentiator is whether you carry them or convert them.
Carry them, and they slow you down.
Convert them, and they sharpen you.
You don’t need closure to move forward.
You need honesty, discipline, and the courage to let go.
The Question Worth Sitting With
What are you still holding onto that already taught you its lesson?
Because the moment you let go—not emotionally, but decisively—you don’t just move on.
You move forward.
And that’s where the next opportunity actually lives.