63: Don’t Eliminate Awkwardness, Train for It

Unstuck with Jay Abbasi · Apr 21, 2025 · 53m

Meet Andy. He’s a software program manager with years of experience and a team that counts on him. But lately, he feels like he’s barely holding it together. His mornings are chaotic, he isolates himself at work, and he keeps important thoughts to himself—afraid to speak up, afraid to ask for help.

Andy is smart, capable, and well-read, but his confidence is waning. He’s stuck in the rhythm of just getting by, and his default mode has become managing everything alone. What he really wants is to lead with confidence, communicate more clearly, and engage meaningfully—but he doesn't know how to…