A few weeks ago I sent my CEO three words I hate typing: I'm really struggling.
By abbey-byfield · September 17, 2026 · Curated by George's Blog
A few weeks ago I sent my CEO three words I hate typing: I'm really struggling.
It takes a lot for me to raise that flag. Like, a LOT. Asking for help has always felt a bit like dying on my sword.
I've recently realised that I usually struggle to admit (to myself) that I'm not the expert in the room, when I feel like I am supposed to be. Or that I don't have the answers when people are looking to me for answers.
And messaging your boss to tell them you feel like you’re not meeting expectations has to be at the top of my list of things I dread.
But even though Chop and I have worked together across 3 companies over 7+ years, his response really surprised me.
He didn't rush to have a "quick fix".
He pushed back: Articulate exactly what you're struggling with before we meet, so we can actually workshop it.
And we did for multiple hours, getting to the core of it.
Sometimes you need someone to listen as you vent, sometimes you need someone to fix it, and sometimes you just need someone to sit with you in it and help you work it out.
You have to know how to ask for help when you need it, and you have to know how to ask for the type of help you need in that situation.
Support can look very different for everyone.
Good leaders meet their people where they’re at.
I’m grateful to have that kind of leadership modeled for me. It’s a reminder of the type of leader I aspire to be too.