A few years back I sat down and wrote a letter to the CEO of Brooks Brothers. By hand. The gist of it: it’s time — you look old and outdated, and I care enough to say so.
Nobody asked me to write it. I wasn’t owed a reply. I was a stylist in Chicago with an opinion about an American institution I genuinely loved, watching it play it safe into irrelevance. So I said the true thing, with respect, directly to the person who could do something about it — and I signed my name.
I tell this story because of what it taught me, and because the lesson runs my work now.
Most people do one of two things with a true thing. They soften it until it isn’t saying anything — feedback so polite it can’t be used. Or they say it loudly in the wrong room — the group chat, the comment section, anywhere but to the person it’s for. Both are ways of hiding.
The rare move is saying the true thing, well, in the room that matters. With care, with your name on it, to the person who can act on it. That’s harder than being nice and harder than being loud. It’s also the entire job — in a boardroom, on camera, in a letter to a CEO who has no idea who you are.
That letter didn’t change Brooks Brothers. It changed me. It’s why I still book myself — no publicist — and why my favorite clients are the ones with something true to say who need help saying it well, on the record, where it counts.
Which room are you avoiding, and what’s the true thing you’d say in it?
Questions
Did they respond?
The letter mattered for the writing of it. What came back was never the point.
Isn’t that risky in a professional setting?
Less risky than being forgettable. Said with care and your name attached, the true thing is usually received better than people fear.
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