“The 33-euro hotel breakfast is too expensive.”
That was the message from my boss, delivered while I was on a business trip in Milan more than a decade ago, dressed head to toe in the pieces we sold for four- and five-figure prices.
So instead of sitting down to a proper breakfast at the hotel, I found myself standing at a bar nearby, eating a cornetto and drinking an espresso as quickly as possible before rushing to meetings. I remember proudly reporting back later that I had only spent five euros. As though this were some great victory.
I think back on that moment often, because… what?
Why was a senior employee flown halfway across the world and then guilted out of starting the day with a proper breakfast? Why was I so eager to prove I could make myself cheaper, easier?
At the time, I didn’t fully understand what was happening to me.
I do now. I was losing myself to a job.
Looks Can Be Deceiving
From the outside, my career looked glamorous. And it was. A prestigious luxury brand. Élite clients. Exclusive events in New York, Beverly Hills, Palo Alto. The most beautiful materials. The trappings of a life many women dream of. A life I had dreamt of.
But there are work environments that destabilize your relationship with yourself, and leave you looking glamorous and composed on the outside but unsettled within. It happens through accumulation. Tiny corrections. Bizarre contradictions. Constant second-guessing. Mixed messages. A slow erosion that you barely notice until you are standing in the showroom at 10 a.m., hungry because you skipped the hotel breakfast.
It started by being told, casually during my interview, that I was “expensive” — a comment that seems harmless, flattering even, until you find yourself constantly trying to justify your price.
I had worked in difficult places before. Earlier in my career, I survived a politically tumultuous company because the difficult dynamics were so universal that I never took any of it personally. Another company felt rudderless, but never altered my sense of self.
This one did. And the reason it did is worth understanding, because some version of it is probably happening to a woman reading this right now.
When One Person Sets the Emotional Weather
A leader with a strong need for control and validation can shape the emotional reality of an entire workplace. People orbit their moods, reactions, preferences, and shifting expectations.
The strangest boss I ever had hired me enthusiastically. The moment we began working together, suddenly everything I did was wrong. I would prepare careful plans based on conversations we’d had about ambitious targets, only to be told the goals were unrealistic, that we had never discussed such high figures, that they didn’t understand why this was so difficult for me.
The problem with this kind of person is not that they are obviously difficult to deal with. It’s that they erode your trust in your own perception. Conversations are rewritten. Goalposts move. You’re undermined privately but smiled at publicly. You leave meetings taking copious notes just to “cover your ass.” Over time, you become mentally exhausted from trying to orient yourself and expend the most brainpower managing the emotional climate.
If any of this sounds familiar to you, trust your recognition.
The Capability Trap
This is a trap I want every capable woman reading this to recognize.
Capable, solutions-oriented women get trapped in bad work environments precisely because we are capable. You adapt. You fix. You figure it out. You start treating dysfunction like a puzzle to solve rather than a sign to leave. And because you can endure, you often last far longer than you should.
But just because you can endure something doesn’t mean you should.
That is one of the most important lessons I have learned in both my personal and professional life. Your capability is not the same as your contentment, and your ability to endure something is not a great reason to stay in it.
The Prison With the Golden Bars
The other reason we stay too long is prestige. The company name. The title. The status attached to the role. And luxury fashion is especially seductive in this regard. But it’s the same in tech, big law, high finance, and many other fields.
You can tolerate a lot when the outside world, and you yourself, are dazzled by where you work. Walking fifteen minutes to the office, into a building that tourists take photos in front of. The catered lunches, private sales, and clothing allowance. The way eyes widen when people who get “it” hear where you work. You start treating the prestige as a fair price for the chaos. You stay because the cost of leaving feels like a step down.
This sort of thing is so common. A friend, a Harvard MBA, I might add, was telling me recently about how difficult it was to shake off the reminders of the indignities she’d endured in her last position. A woman accustomed to setting strategy was running out to buy a tie for her boss.
Complacency played a part, too, in why I didn’t make a move. Conducting a job search is exhausting. And no one wants short stints on their perfect résumé. The retail industry itself was becoming less interesting to me anyway. What to want next when I was already sitting where I had always wanted to be and wasn’t thrilled with what I’d found?
Staying somewhere mainly because it’s easier and looks good on paper is so common. I’ve had countless conversations with friends about the fear of no longer being associated with a given company or brand. A friend who features heavily on their very famous boss’s social media pages told me they often wonder who they’d be without the association.
If you relate to this, know this: Prestige does not pay you back at 2 am when you are lying awake trying to remember if a conversation actually happened the way your boss now claims it did.
These sorts of environments change people. It makes them performative, reactive, political. You stop focusing on excellence and start focusing on survival. And one day, you realize you are standing in a café in Milan, proud of yourself for skipping breakfast to save a luxury company some money.
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