Episode
The Kind of Help that's Hard to Ask For, and the Kind of Help You Don't Know You Need
- Podcast
- The Difficulty
- Published
- May 9, 2026
- Duration seconds
- 944
- Processing state
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Summary
I almost drowned on the Ocoee River. The thing that saved me wasn’t anything I’d thought to ask for. This is the first essay in the Saturday series at The Difficulty — longer pieces from a series I’ve been writing on Substack called The Descent, about the choices that shape a creative life. Saturday is for the essays that don’t fit the news-cycle pace of the rest of the week. Today’s is about how hard it is to ask for help — and the deeper, harder thing underneath it: the surrender we resist for years before we know we’re resisting it. Drawing on David Whyte, David Hawkins, and Carl Jung’s “shoes too small” image, with a near-drowning story I haven’t told publicly before. Closing question: What am I holding onto that I already know isn’t working? — CHAPTERS 00:00 Saturday Series Intro 01:01 The Hard Word — Help 03:26 The Near-Drowning Lesson 04:52 Two Kinds of Help 06:52 Surrender vs Giving Up 07:57 Shoes Too Small 09:40 Letting Go Changes You 10:46 Readiness and Courage 12:55 Modern Ways to Give Up 14:47 The Question to Ask 15:07 Closing and Where to Find More — FREE — THE DIFFICULTY FIELD GUIDE Eight difficulties every working writer faces, and what to ask when each one shows up. → crossroadspublishing.group/assets/pdfs/The_Difficulty_Field_Guide.pdf — WHERE TO FIND ME Substack — new essays Wednesdays, the Working Publisher news digest Fridays → chadprevost.substack.com The Difficulty — Monday (the why), Thursday (the how), Saturday (essay readings) — wherever you listen to podcasts → chadprevost.com/the-difficulty Crossroads Publishing Group — publishing services, IF/THEN Books, the Iris Blackwood mystery series → crossroadspublishing.group — “The difficulty in life is the choice.” Get full access to The Descent at chadprevost.substack.com/subscribe