All the small things that add up to reasons to leave
I want to share a dinner that changed something in me, not because anything dramatic happened, but because what did happen was so ordinary and casual that no one else even noticed. It made me realize how deeply bias is woven into everyday work life is.
We were at an after-dinner gathering with colleagues, the kind of relaxed setting where people let their guard down and say what they really think, rather than what they say in meetings. A colleague was telling a story about their family and mentioned that some distant relatives were Black. Without missing a beat, another executive, someone senior, someone respected, someone who would absolutely describe themselves as a good person, responded with what he clearly thought was hilarious: “Well, if anything ever gets stolen from your family, you’ll know who the thief is!”
The table laughed. I didn’t.
What stuck with me after that dinner was that nobody thought twice about it. No one flinched or checked if I was okay, partly because my race isn’t obvious to most people. I’ve spent my career hearing things people might not say if they knew who was listening. But the bigger reason is that moments like these are so common and normalized in workplace culture that they barely register. They’re just the background noise of being a woman, a person of color, or anyone who doesn’t fit the default in a system built for a certain type of person.
I share that story in Not Made for You, along with many others, not because I think any single moment is what breaks someone, but because I’ve come to understand that it’s never one moment. It’s the accumulation. It’s the executive who calls a Middle Eastern business partner a terrorist, and everyone nervously laughs. It’s the assistant who says about a dark-skinned colleague, “How could you even tell he was embarrassed? He’s so Black,” while the CEO laughs along. It’s the male leader who interrupts you mid-sentence in a meeting, not once but repeatedly, and when you bring it up later, the conversation somehow becomes about your tone rather than his behavior.
None of these moments, on their own, would likely lead to a formal complaint or HR investigation. They’re too small, too easy to deny, and often dismissed as “you’re being oversensitive”, “that’s just how he is,” or”*it was just a joke, don’t take it so personally.” That’s what makes them so harmful. When something is too minor to address officially but big enough to affect how you feel about work, you end up carrying it alone. Over time, that weight is what drives people out.
This is the part we don’t talk about enough when discussing why women leave tech. We focus on big, dramatic events, lawsuits, scandals, public firings, but most women don’t leave because of one major incident. They leave because of countless small ones that no one else notices or cares about. They leave because they’re tired of being the only one who hears and feels the weight of certain comments. They leave because the gap between the company’s stated values and the real culture becomes too wide to ignore.
And here’s the impossible choice that comes with all of this, the thing I’ve wrestled with for thirty years and still don’t have a perfect answer to: when those moments happen, what do you do? If you speak up, you risk being labeled difficult, overly sensitive, not a team player, someone who makes things uncomfortable, and in a system that already wasn’t built for you, adding one more reason for people to question whether you belong is a genuine risk to your career. But if you stay quiet, if you swallow it and smile and go along to get along, you keep your seat at the table, but you lose a piece of yourself every time you do it, and over the years those pieces add up to something that’s really hard to get back.
What I’ve learned, and what I share in the book, is that there’s no single right answer for every situation. But there is a way to make these decisions more intentionally, instead of just reacting out of fear or freezing. Sometimes speaking up is best, and sometimes waiting is wiser. The real skill is knowing which to choose based on your situation, instead of always staying silent because it feels safer.
But I want to be clear: fixing this isn’t the job of those being harmed. Yes, we need tools and strategies to handle these moments, and I wrote a whole book about them, but the bigger issue is with leaders and organizations that let this culture continue while claiming to support diversity and inclusion. If you praise your culture online but ignore executives who make racist jokes, people notice. If you run mentorship programs for women but don’t address pay gaps or slow promotions, people notice. The gap between what companies say and what they allow is the biggest reason for distrust at work, and no amount of programs or branding will fix it until daily behavior changes.
So here’s what I want to leave you with: if you’ve been in those rooms, if you’ve heard those comments, if you’ve felt that specific kind of exhaustion that comes from being the only person who seems to recognize what just happened, you are not imagining it, you are not overreacting, and you are not alone. The fact that it’s normalized doesn’t mean it’s normal, and the fact that everyone else laughed doesn’t mean it was funny.
We can’t change what we don’t name. And we can’t name it if we keep pretending it doesn’t exist.