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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?
Iโ€™m 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 Iโ€™m not quite hitting the mark on some of my work. How can I learn from him if he wonโ€™t tell me how to improve?...
Mar 12, 2026 hard conversations signaling safety
What conversations are you bungling or avoiding?
ย  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

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