I once left a pre-IPO company. Two years later, they received a $525M investment and a $2B valuation.
And I didn't blink.
If I didn't care, then it meant I made the right decision to leave.
Sometimes we stay too long in roles, sometimes we leave too early, but when we can look back later and say it was the right decision with 100% confidence, it means you timed it perfectly.
It also means you checked off all the boxes you needed to check off while in the seat, and you feel comfortable with the fact that you're not missing out on anything important. It can also mean you were fucking done, and the idea of staying another day gives you hives.
On the outside, people will turn their heads sideways, confused, and ask, "Umm, what are you doing? Why leave now? Are you crazy?!"
But only you have the answers to those questions, and frankly, you don't have to share them with anyone. As long as you can look yourself in the mirror and feel good about the decisions you made, that's all that matters.
There are societal pressures to stay in a role at a company for longer periods of time than are warranted. Sometimes it may look like we have a dream role to others, but internally, we may be dying a slow death. It could be a toxic leader, a bad environment, or it just could be that your time is up, and you need to move on with your life.
Knowing when to leave is one thing, but being clear and aware of the reasons why you are leaving is key.
When you finally get honest about those reasons, everything else gets lighter. You stop trying to justify your choice. You stop replaying conversations in your head. You stop wondering if you should have held on for another quarter or waited for the next round of equity.
The noise fades because the truth is simple: you outgrew the role, the environment, or the version of yourself that first took the job. And once you outgrow something, no amount of money or upside can make it fit again.
People love to romanticize the idea of sticking it out, grinding it out, pushing through. But staying somewhere that drains you is not loyalty. It's self-neglect. There's a difference between perseverance and punishment, and most high performers don't recognize the line until they're already deep in the burnout cycle.
And the moment you walk away, you create space for the next version of your career to show up. New energy. New clarity. New opportunities that never would have appeared if you were still clinging to a job that no longer aligned with who you are becoming. That's the part people forget. Leaving isn't an ending. It's a reset, and sometimes the reset is the exact thing that unlocks everything you've been trying to force.
So when you make a call that looks wild from the outside but feels right on the inside, trust that. Trust your timing. Trust your intuition. Trust the quiet signal that tells you it's over. You don't need permission to move on. You don't need validation from people who aren't living your life. You just need the courage to walk away when the chapter is done and the confidence to know that your career will always expand in the direction you are brave enough to go.