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The Difficulty · Complete archive

Every episode of The Difficulty.

Twice a week, plus the Working Publisher Thursday digest. Honest conversations about the choices that shape a creative life — for working writers, makers, and practitioners building real, sustainable practices.

Episode 10 June 1, 2026 Monday · the why · 40 min

On green-lighting yourself.

Legitimacy cannot be bestowed. You have to take it. On the structural reasons writers wait for permission that isn't coming, and what it actually looks like to begin without it.

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Episode 9 May 30, 2026 Saturday · the descent · 27 min

Wrestling with the self.

A Saturday essay-format episode on internal conflict — the part of the work that doesn't go away, that you have to make a working relationship with rather than solve.

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Episode 3 May 11, 2026 Monday · the why · 25 min

Resentment, avoidance, and the work that matters.

Why the work you most need to do is often the work you most resent — and what happens when you stop running from it. On the gap between the work that pays and the work that pays a different kind of debt.

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Subscribe to The Difficulty.

New episodes Monday and Thursday mornings, plus the Saturday Descent essay format. Available on Substack and the major podcast apps.