We’re back with another episode of Why Are We Still Doing That? — and this week, we’re talking about something that makes people squirm, triggers collective pearl-clutching, and guarantees at least one relative whispering, “But what will people think?”

We’re talking about quitting.

For a culture obsessed with grit, commitment, and “never give up,” quitting has been framed as a moral failing instead of what it often is: a brave, protective, and self-honoring choice. We’re conditioned to push through, stay loyal, and tolerate things that make our lives smaller — even when we know something is no longer healthy or aligned.

In this episode, we unpack the real reasons we avoid quitting and what opens up when we finally do.

You’ll hear:

• The cultural programming that makes quitting feel like failure — and why that script is overdue for a rewrite.

• The identity shame loop that keeps people stuck in jobs, relationships, and roles long past their expiration dates.

• Why other people panic when you choose yourself — and how your quitting often exposes where they feel trapped.

• A pivotal story from Kent’s early career that shaped our entire No Vacation Required philosophy around agency, alignment, and not waiting for permission.

All that, along with a brief musing on “cozy season” and something less cozy – ICE using Taylor Swift’s music on TikTok and the surprising silence from her normally hyper-responsive team. Like, what’s going on there?

If you’re feeling stuck in something that no longer serves you – or deserves you – you’ll want to give this listen because we’re giving you permission to quit that nonsense.

Onward + Inward,

Caanan + Kent