Should I put up, or shut up?
Photo by Vitaly Gariev on Unsplash
I feel like my older coworker doesn't take me seriously at all because of my age. They're always making passive-aggressive comments about my contributions, like "That's a good idea for someone your age," or, "I'm surprised you knew that". I want to ask them wh...
by Jess Kyle โ
Apr 02, 2026
responses
say the hard things
shame resilience
Am I allowed to break up with them?
Photo by Vitaly Gariev on Unsplash
I've been dating my partner for about six months. They're kind, considerate, and seem to care about me a lot. The problem is, I want to end the relationship. They haven't done anything "wrong",ย I just know deep down that we aren't compatible. How can I break ...
by Jess Kyle โ
Mar 26, 2026
hard conversations
people pleasing
The truth about "brutal honesty"
How do I tell someone something they don't want to hear without it feeling like an attack?
I used to have pretty messed up ideas about what it meant to give someone critical feedback. For one thing, I assumed that there was a universal truth about the person that I knew but they didn't. For ano...
by Jess Kyle โ
Mar 19, 2026
feedback
hard conversations
Why does my boss avoid giving me feedback?
Iโm having trouble getting feedback at work. Even when I ask directly what I could be doing better, my boss tells me everything is fine, but his face and voice give me the feeling that Iโm not quite hitting the mark on some of my work. How can I learn from him if he wonโt tell me how to improve?...
Mar 12, 2026
hard conversations
signaling safety
What conversations are you bungling or avoiding?
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Why is it that so many of us can't bring ourselves to give a direct report critical feedback, address a moment when a coworker disrespected us, or break up with someone who's a nice person - but also not right for us? We can twist ourselves into pretzels with all kinds of justifications for av...
Mar 05, 2026
hard conversations
say the hard things