For nearly three years, I stood on sidewalks across New York City with a plastic binder in my hand and a quota I had to hit regardless of whether it was raining, snowing, scorching, whether people wanted to talk, or whether the last person who stopped had made me feel two inches tall before walking away.
I was a grassroots canvasser for a national civil rights organization. My job was to stop strangers, make them care about something within thirty seconds, and convince them to reach into their wallets for cash or a credit card on a New York sidewalk for a cause they may never have thought about being part of before that moment.
Thirty to forty people a day, every day.
I raised more than 4,000 individual contributions and ranked in the top three nationally among a cohort of over 800 canvassers.
Not because I had a better script. I learned, faster than most, that the script was never the point.
The work was reading the person in front of you, adjusting in real time, letting go of what didn’t work before the next person was already walking toward you. You cannot afford to still be processing the last rejection when the next conversation starts. You adapt, or you go home.
I watched the revolving door take a lot of people who couldn’t figure that out. Some had more talent than I did, worked harder, and maybe even believed in the cause more deeply. But they couldn’t get out of their own way fast enough to survive the daily pace of rejection. The door revolved, and they went through it.
I was sad about it every time, and I learned from it every time.
What canvassing gave me was not resilience in the inspirational poster sense of the word.
It taught me that adaptation is a skill and not a personality trait.
You build it through repetition, through losing, through adjusting the pitch mid-sentence when you see someone’s eyes start to glaze.
You build it by accepting that what worked on the last block may not work on this one, that what moved the last person to tears might make the next person walk away faster.
The revolving door in canvassing was brutal, and it was honest.
They don’t call it the mean streets of New York for nothing.
PSA: If your organization is hiring for an entry-level role, and a street canvasser with two years or more of experience comes knocking, consider it a golden opportunity - if they can convince a New Yorker to stop on a sidewalk and talk to them, think about what else they could do!
Welcome to Code Like a Girl, the community where women in tech come to be seen, heard, and championed as they walk this path together.
When the Revolving Door Broke
I left canvassing for a role I had worked three rounds of interviews to earn, at a nonprofit I believed in. I was excelling when a board I had never met decided to restructure the entire org, and being last in meant being first out.
I was bitter, and not because of the rejection itself.
Because of the erasure.
In canvassing, rejection is feedback. You adjust the pitch and try again. But a board that doesn’t know you, making a decision that changes your life without so much as a sincere apology, is not feedback.
There is nothing to adjust for when you are simply an afterthought in someone else’s spreadsheet.
I spent an unemployed summer in Brooklyn on a meager unemployment check, applying and processing.
Then came a role with a consulate, I worked my way up, and they eventually took me out of the country to train, work I loved, skills I built quickly.
Then, years later, the same lesson was delivered a second time: operations moving elsewhere, looking for work again.
The first displacement made me bitter. The second made me stubborn.
Somewhere between those two experiences, while still living in Bushwick, Brooklyn, where ambition needed no apology, and the rough neighborhood had its own code of respect, I stopped waiting for organizations to define my value.
I knew what each version of my career had built in me, and I finally had a word for it.
Evolver.
Not just a hustler (though I was that too), not a high performer (though the numbers showed that). An evolver. Someone whose value compounds not despite disruption but because of it, who treats each displacement, each new environment, each uncomfortable role as curriculum rather than catastrophe.
The revolving door in canvassing took the people who couldn’t adapt. The revolving doors in my career tried to take me. By the time the second one came around, I understood what I was dealing with, and I refused to let it tell me who I was.
What I keep coming back to, after years in corporate and structured environments was:
Most organizations have broken their revolving doors.
The people who stopped growing don’t leave.
They stay, and they set the cultural temperature for everyone around them.
“Let’s Come Back to It”
I have sat in enough meetings to recognize a particular kind of sentence, and you probably know it too:
“That is interesting, and looks like it may really have value for us at some point. That is something we can definitely look into. Let’s come back to it.”
Read that again… slowly.
It sounds engaged and open, and it gives the person proposing the idea just enough warmth to close the conversation without starting one.
But parse it carefully, and there is not a single commitment in that entire sentence.
No owner, no timeline, no next step, no genuine curiosity about what “looking into it” might actually require.
It is the organizational equivalent of a smile that doesn’t reach the eyes.
The insidious part is that you cannot call it out. The person just said it was interesting and that we should revisit it. They are not technically resistant. They are just comprehensively unaccountable. And the culture that produces this sentence has trained everyone in the room to accept it as participation.
What this costs does not show up anywhere visible.
What it costs is the people who keep proposing change without traction: the analysts, the coordinators, the staff who stay curious longer than their organizations deserve, who keep bringing ideas to tables that were never set for them. The disillusionment that builds in them is quiet and cumulative. It also doesn’t send a calendar invite when it becomes a resignation letter.
Organizations risk losing the drivers of change when they don’t nourish curiosity intentionally.
Most organizations are not doing that.
They are doing something that looks like it from a distance, which is much worse, because it allows leadership to believe the culture is healthy right up until the moment they discover it isn’t.
The Leader Who Won’t Pick Up the Hill
The easy version of this argument is to point at the people who stopped growing and call it a talent problem. It isn’t.
There is a version of this that is harder to name because it wears a perfectly professional face.
It is not the person who is failing. It is the person who decided, somewhere along the way, that they had already become who they were going to be at work.
They show up. They deliver. They have earned, in their own accounting, the right to stop being curious.
The organization has quietly agreed. And the agreement is never spoken, which is what makes it so difficult to challenge and so expensive to ignore.
Those people exist in every organization because someone with authority decided, repeatedly, that keeping the peace was worth more than picking the hill. Leadership that avoids evolution doesn’t stay neutral; it makes an active choice, over and over, to prioritize comfort over capability, familiarity over fitness.
Pointing to a horizon and saying the journey will be complicated requires something most leadership cultures do not reward: the willingness to be visibly mid-process, not to have all the answers, and to model the very uncertainty being asked of the team.
The leaders who build evolving organizations are not the ones with the best strategy documents. They are the ones who made peace with being wrong in public, who understood that building a culture where failure is part of the named process is not weakness but the only honest description of how anything actually gets built. And they understood that “let’s come back to it,” said from the top, is not caution. It is permission for the entire organization to stop.
AI Turned the Lights On
AI did not create stagnation in organizations. It turned the lights on in rooms that were already a mess. 💡
The bad workflows were always there. The people who built their professional identity around hoarding process knowledge, who made themselves indispensable by being the only ones who knew how something worked, who said “that’s just how we’ve always done it” with the confidence of someone who has never been asked to justify it — they were always there.
What AI does is remove the places where all of that used to hide.
It surfaces what was always broken and makes visible the people who have quietly made themselves burdens to change, who become defensive when evolution is proposed because evolution implies that the way they did it was not the right way (not always true, btw), and they have been doing it that way for a very long time. That defensiveness is not about the workflow. It is about the years and the identity built around a process that is now being questioned.
Those adverse to change have become the risk. Not the technology, not the workflows that need updating. The human who decided, consciously or by slow attrition, to stop evolving.
AI is also going to surface something organizations have been mismanaging for years: accountability.
If the culture did not handle accountability effectively before, it will be more exposed now. Because AI creates evidence of what was done, how it was done, and how long it took. And evidence makes it considerably harder to let the “let’s come back to it” culture persist without consequence.
Where Do You Start?
The starting point is not a strategy session or a new initiative. It is a leader deciding what kind of organization they actually want to run, not in the mission statement, but on a Wednesday.
It means making yourself human enough to name your own gaps, because you cannot ask a team to keep growing if you have quietly exempted yourself from that same expectation.
Emulate the employee you want to exist. Try something you don’t know how to do yet.
When someone brings an idea to a meeting, give it a real next step, not a warm smile and a reschedule that never happens. Because somewhere in your organization, there is probably still one person who cares enough about the place they work to want to keep evolving it into the best version of itself.
The question is whether you have made it possible for them to stay that way.
What the Sidewalk Knew
I came up in an environment that had no patience for stagnation because it couldn’t afford any. On a New York sidewalk with a quota and a plastic binder, you either adapted in real time or you went home. No organizational politics to hide behind, no…
“let’s revisit this next quarter.”
The revolving door worked, and it was honest.
In most organizations, the revolving door is broken. The people who stopped growing don’t leave. They stay, set the cultural temperature, and outlast the people trying to move things forward. That was survivable when change was slow, when roles evolved on a five-year cycle, and expertise had a long shelf life.
We are not in that moment anymore.
In an AI-accelerated world, stagnation is not a neutral position. It is a directional choice, and the direction is backward. ⬅️
The question for your organization is not whether AI is coming, but whether the culture you built is capable of meeting it, whether the people you have protected from accountability are going to survive the exposure, and whether the curiosity of your most engaged staff is something you have nourished or something you have quietly spent down.
And the question worth asking yourself, not your team, not your board, yourself, is the same one I turned over on an unemployment check in Brooklyn, applying for the next thing and refusing to let two structural displacements tell me what I was worth:
Are you still evolving? Or have you been saying “let’s come back to it” for so long that you’ve stopped noticing?
We're grateful Uncertainty, By Design for sharing her work here. If you want AI, work, and healthcare examined by a business analyst who thinks out loud and names the things most people leave unsaid follow her publication.
This story was originally published on Uncertainty By Design.
You Belong Here
Code Like a Girl is the community for women in tech who are done proposing changes into a void and ready to be somewhere their curiosity is valued.
Subscribe for free and join our Rise Together Thursday chat. It’s a community where women in tech share their latest work, spotlight another woman’s post, and support one another through thoughtful comments and restacks.
You’ll come in with work that deserves more attention and leave feeling seen, supported, and connected.
So, I'm a guy. I learned programming on punch cards. I have a freind, my age, who, decades ago, was hired to troubleshoot a problem with some machine code for one of the US military branches. Day two of reviewing code she asked the question "Where was this variable initialized?" People in power kept her on while the engineers were saying it could not be the problem. Long story short, that fixed the problem. It's People like her, unafraid to speak up, and people like the man in charge, that change things. Keep your eye on AI as it is doing some of the same things, unveiling incompetence and exposing fraud. The world is changing. Hangman it's going to be a wild ride!