The Kind of Help that's Hard to Ask For, and the Kind of Help You Don't Know You Need episode artwork

EPISODE · May 9, 2026 · 15 MIN

The Kind of Help that's Hard to Ask For, and the Kind of Help You Don't Know You Need

from The Difficulty · host Crossroads Publishing Group

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?—CHAPTERS00:00 Saturday Series Intro01:01 The Hard Word — Help03:26 The Near-Drowning Lesson04:52 Two Kinds of Help06:52 Surrender vs Giving Up07:57 Shoes Too Small09:40 Letting Go Changes You10:46 Readiness and Courage12:55 Modern Ways to Give Up14:47 The Question to Ask15:07 Closing and Where to Find More—FREE — THE DIFFICULTY FIELD GUIDEEight 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 MESubstack — new essays Wednesdays, the Working Publisher news digest Fridays→ chadprevost.substack.comThe Difficulty — Monday (the why), Thursday (the how), Saturday (essay readings) — wherever you listen to podcasts→ chadprevost.com/the-difficultyCrossroads Publishing Group — publishing services, IF/THEN Books, the Iris Blackwood mystery series→ crossroadspublishing.group—“The difficulty in life is the choice.” This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit chadprevost.substack.com

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