Episode Details

Someday is the most polite way to postpone our own life, and we’ve all got a list. We pull that word apart with equal parts humor and honesty, starting with our own “somedays” like learning guitar, traveling more, playing iconic golf courses, giving a TEDx talk, and shifting creative projects that keep getting pushed down the road. The question we keep circling is simple and uncomfortable: is “someday” optimism, or is it avoidance with better branding?

We talk through the real reasons goals stall out: perfectionism, fear of failure, fear of judgment, decision regret, money, energy, and the sneakiest one of all, identity. Sometimes the dream still matters, but sometimes it doesn’t align anymore and we’re afraid to admit it because we already told people about it. We also connect this to the startup world and “perpetual incubation,” where an idea feels exciting to talk about but terrifying to launch. Along the way, we land on practical tools that actually work: shrink the goal to the smallest possible version, ask what’s truly blocking you, and set a date so “someday” has a home on the calendar.

We close by getting real about the cost of leaving the important things undone, and what changes when you finally do the thing your soul keeps calling for. If you’ve been stuck in planning, fantasizing, or waiting for perfect timing, you’ll leave with a clearer framework for turning intention into action, plus the grace to release what was never meant to happen. Subscribe, share this with a friend who needs a nudge, and leave a review, then tell us: what are you done calling “someday”?