The Hindsight Window
On two versions of the same woman, three years apart, and the belief that finally caught up with both of them.
Dear Substack, connect me to the others who see themselves in this.
At 25, I backpacked across Europe for months with my best friend and no itinerary. We slept in hostels we couldn’t pronounce the names of, ate whatever the market stall pointed us toward, and let each day unfold instead of forcing it into a plan. For the first time in my life, I felt safe in my own body.
At 28, I was engaged to a man who told me I’d better get on the train before it left the station… a man who tried to control and stifle nearly every version of me that had come alive three years earlier. I felt like a caged animal tied to a tree, smiling for an audience that had no idea what happened behind the closed doors.
Same woman. Three years apart. Two completely different nervous systems.
For a long time, I told this story like it was about him. About the relationship. About picking the wrong person and wrong type of relationship.
It wasn’t.
It was about a belief I had been carrying since I was far too young to know I was carrying it: that anything good in my life came with a built-in expiration date. That I wasn’t “allowed” to have what other people had… not fully, not for long, not without paying for it later.
I know now that I wasn’t the only one who ever felt that. So let’s talk about why. Where the Phrase Came From
A while back, I watched a keynote by speaker and author Eric Edmeades, and he introduced a concept I have not been able to put down since: the Hindsight Window.
The idea, as I have come to understand it, is this: the sooner you can reframe something that once held you back into something that actually moves you forward, the sooner you get your life back.
Not by pretending it didn’t happen. Not by rushing past it. But by finally asking a different question about it than the one you asked in the moment.
He also named something I think most of us quietly know but rarely say out loud: trauma is sticky. It clings the way hot wax melts into fabric… it changes the texture of the thing permanently. We long to “go back to who we were before.”
But that person doesn’t fully exist anymore, not in the same shape. There’s a sticky note that’s followed me from office to office with a quote that says: “A mind, once expanded, can never shrink back to its original size.
The Hindsight Window is what opens up once you stop trying to shrink back. It’s the space where you finally get to look behind you and ask: what did this teach my system to believe, and is it still true?
I want to walk you through mine.
The Girl Who Learned Safety Meant Being Needed
I was the oldest. If you’ve been following my newsletter, you already know what that word tends means to me and my role in a family that Was always quietly cracking at the foundation: the one who holds it together.
The one who steps in when the adults can’t. The one who reads the room before she’s even old enough to read.
Somewhere in there, without ever choosing it consciously, I made a deal with myself. It went something like this: “my security, my worth, my place in this family and in this world, is tied to how needed I am. If I am not there to rescue, fix, hold emotional space for… then bad things will happen to those around me and I will no longer be safe.”
My nervous system could not handle if something ‘bad’ happened around me. So I had to be sure I was always available to fix and take care of everything (so I believed).
It was never about how happy I was or wanted to be. It was never about how free I am.
It ws about how needed I was, which meant I could control my own safety (ie. nervous system).
That deal doesn’t stay contained to childhood. It comes with you into every room you walk into as an adult, wearing a different outfit each time so you don’t recognize it. And nowhere did mine show up louder than in the relationships I chose.
Here’s what I couldn’t see back then, and can see so clearly now: I was unconsciously drawn to relationships that either had an expiration date built in, or that were never fully “real and present” to begin with.
The backpacking trip is a perfect example, and it’s a gentle one. It was never meant to be forever. It had a return flight already booked. Life living with a best friend surely had to come to an end, didn’t it?
Because it was temporary by design, some deeply buried part of me could finally exhale into it… because a season, unlike a whole life, doesn’t ask you to stay available to everyone else while you’re living it.
The engagement is the harder example. That one wasn’t temporary by design. It was supposed to be my whole life. But it required something of me that felt, underneath, strangely familiar: it required me to make myself smaller. To hand over my voice. To stop fully launching into the woman I’d started to become in Europe. And as much as that relationship hurt, some old, exiled part of me recognized the shape of it. Shrinking wasn’t safety. But it was known.
The Real Fear Underneath It
Here’s the part of this that took me the longest to uncover, and the part I think matters most for anyone reading this who leads people, teams, families, or businesses:
If I ever allowed myself to be in a real, present, fully-launched relationship… one that wasn’t racing toward an ending, and didn’t require me to keep myself small to survive it… some part of me was convinced that I would no longer be available.
I wouldn’t be available to caregive. To fix. To hold everyone else’s nervous system steady while quietly ignoring my own.
And if I was no longer available in that way, what would happen to the people who had come to rely on me being the strong one? What would happen to me, without that role to hide inside of?
This is the quiet, unspoken math a lot of high-functioning people are running without ever realizing it. We call it loyalty. We call it being a good daughter, a good partner, a good leader.
But underneath, for many of us, it’s actually a Fawn (people-pleasing) Trauma Response like Fight, Flight, Freezing and Fainting. (Check out my other articles to go deeper into the 5, not 2 types of innate trauma responses).
I was a professional at wearing a very respectable costume: If I stay useful, I stay safe. If I stay needed, I don’t get left. If I never fully arrive, I never have to find out what happens when I do.
So we pick the relationship with the return flight already booked. Or the one that needs us to be smaller so it can stay in control. Either way, we never have to test what happens if we simply… launch. Fully. Without an expiration date attached.
Looking Back Through the Window
This is where the Hindsight Window becomes so useful, because it doesn’t ask you to relive the pain. It asks you to reframe what the pain was actually protecting.
Looking back now, I don’t see a woman who kept choosing the wrong men. I see a woman whose system had made a very intelligent survival decision at a very young age, and who kept re-running that decision on autopilot until she was finally old enough, and safe enough, to question it.
The belief was never really about relationships. It was about whether I was allowed to take up my own life fully, without it costing me my usefulness to everyone else. It took years of inner work, of parts work, of sitting with the part of me that still believed good things expire, before I could finally answer that question differently.
I was allowed. I am allowed. So are you. What This Taught Me About Leadership
I don’t think this pattern stays confined to personal or intimate relationships. That’s just where it’s easiest to see, because relationships hold up a mirror we can’t look away from.
But I’ve watched this same expiration-date belief run quietly underneath boardrooms, founder journeys, and executive careers too.
The Leader who over-functions for a team that never quite reciprocates, because being indispensable feels safer than being replaceable.
The Founder who keeps the business just small enough to still control single-handedly, because scaling it would mean trusting other people to hold what she built.
The Executive who says yes to everything, not out of ambition, but because some old part of her is still convinced that the moment she stops being needed, she becomes disposable.
None of this is a character flaw.
It’s a nervous system doing exactly what it was trained to do a long time ago, in a much smaller body, in a much scarier situation. The problem isn’t that the strategy worked. The problem is that it never got the memo that the danger is over.
This is the whole premise behind Living Oak Leadership. We don’t lead from the parts of us that are still bracing for an expiration date. We lead from Self… from the version of us that has gone back, met that younger part, and finally let her know she’s allowed to stay.
A Question to Bring This Back to You
Where in your own life have you unconsciously chosen the relationship, the job, the role, or the version of yourself with the built-in expiration date… because some part of you believed that was safer than fully arriving?
Where have you mistaken being needed for being safe?
What might change if you looked back at your own story, not to relive it, but to finally ask it a better question?
I’d love to hear it. Tell me: do you have a Hindsight Window of your own?
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