Did I do enough?
Not in the sense of hours worked or deliverables shipped. I mean the other kind. Looking back across twenty years of organisations, industries, leadership rooms, difficult conversations, and deliberate silences. Did I speak up enough? Did I challenge enough? Did I push hard enough in the moments that mattered, with the right people, in the right directions?
This is not a question that arrives at the end of a bad week. It is the kind of question that surfaces when you have enough distance from enough chapters of your career to look at the whole arc and ask honestly: what did I do with what I had?
I think I picked the battles that mattered most to me. But I am less certain about all the others.
The thing that made it harder
There is a specific kind of dismissal that does not announce itself as dismissal. It arrives dressed as context. Your experience is valuable, but you do not know how we do things here. Your perspective is interesting, but this organisation has a particular history. What you did elsewhere may not apply.
What it means is: your twenty years count for less because you accumulated them somewhere else.
I have been in rooms where I knew, with the kind of clarity that only comes from having seen the same pattern play out multiple times across multiple contexts, that something was going to go wrong. And I have watched that knowledge be quietly set aside because it did not come with the right postcode. Because experience earned elsewhere was treated as a different and lesser currency.
That is a specific and particular frustration. Because you cannot fix it by working harder or speaking more clearly. The problem is not your argument. The problem is where your argument was formed.
I remember sending a friend a message around that time. “I have not spent twenty years doing this work just to be ignored. I have done it precisely so that when I say something, it carries weight.”
Did I push hard enough
This is the question I find harder to answer, and it does not get easier with more years behind you. If anything, it gets more specific.
Vocal enough with my team? Across most chapters, yes. That is the direction where speaking up felt most natural and most useful, where I could see the impact and adjust in real time.
With peers? Mostly. Though in every organisation there were moments where I read the room, made a calculation, and decided the battle was not worth the cost that day. Some of those calculations were right. Some of them I am still not sure about, years later.
With leadership above me? This is where it gets honest. There were things I saw across different organisations, at different points in my career, that I raised once, maybe twice, and then let go. Not because I stopped believing them. Because I had learned, through enough rounds of the same experience, that the return on the third attempt was not going to be different from the second. So, I picked my battles. I chose what to spend my energy on, and I let other things pass.
I did pick my battles. I am just not always sure I picked the right moment to stop fighting. (Which is a very Saara thing to still be unpacking at this point in the career.)
What twenty years actually gives you
It gives you pattern recognition that fires before you can explain why. The ability to walk into a situation and know you have seen this shape before and you know how it tends to end.
And it gives you something else that is harder to name. A read on which fights matter and which ones are noise. The ability to place your bets carefully and absorb the cost of the ones you let go.
What it does not give you is certainty that you got the calibration right. That you spoke up at the right moments in the right directions with the right force. That the battles you picked were the ones that most needed picking.
The operative word is precisely. But precision requires knowing which moments deserved the full force of what you had. And I am not always sure I knew. I don’t think I’ll ever be fully sure.
The moments I am least certain about are not the battles I lost. They are the ones where I stayed quiet and told myself I was being strategic. I was sometimes right about that. I am still not sure about the rest.
