The Writer's Round

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The Writer's Round

Kendall Cherry

8 episodes

1 month ago

In this solo episode, I dismantle the two biggest creativity killers—procrastination and perfectionism—and show you how momentum (not magical inspiration) is what makes drafts become art. Rather than coddling ideas for months or years, I walk through a practical, compassionate way to start before you feel ready, iterate fast, and let clarity emerge from the doing. Here’s what we cover: Why so many writers stall: the hidden bargains we make with perfection—and how they quietly feed procrastina...

Entrepreneurship

Business

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Entrepreneurship

Business

Episodes (8/8)

The Writer's Round

How to Be a More Confident Writer and Storyteller

In this episode, I answer a listener question from Bev about moving from email tech/strategy into paid writing, and I use my own current pivots (author, teacher, small-town creative) as a live case study in building real confidence. Rather than waiting to “feel ready,” this episode shows you how to read the invitations you’re already getting, make small aligned experiments, and let action build identity. Here’s what we cover: The real question beneath Bev’s prompt—how to shift from implemente...

1 month ago

37 minutes

The Writer's Round

Stop F*cking Procrastinating and Other Sound Advice

1 month ago

18 minutes

The Writer's Round

Energy Management for Writers and Creatives

In this solo episode, I share the mindset anchors, daily rituals, and environmental tweaks I use to keep my creative well full while running a writing business. Rather than cramming more hacks into your calendar, this is about building a few powerful habits, removing quiet drains, and planning around the forces you can’t control—so your energy becomes reliable on command. Here’s what we cover: The core mindset practices I don’t skip—guided meditations (To Be Magnetic), channeled heart-coheren...

1 month ago

1 hour 16 minutes

The Writer's Round

Why Most Writers Suck at Marketing Their Services

If you feel like you “suck at marketing,” you probably don’t. In this episode, I make the case that most writers (and founder-writers) have a sales messaging problem, not a marketing problem—and I unpack the deeper story that keeps you stuck: the starving-artist narrative. Here’s what we cover: Why marketing is the speaker, but sales messaging is the song.How “my marketing isn’t working” often means “my message isn’t selling.”The real block: fear of selling, not lack of platforms or pos...

1 month ago

28 minutes

The Writer's Round

Building the Greenhouse: My Brand New Storytelling and Sales Writing Accelerator

In this solo episode, i share the origin story and full breakdown of The Greenhouse 🌱🌻—my live, hands-on storytelling and sales writing accelerator for writers who want to charge more, sell ethically, and future-proof their work. Rather than tossing you another course to watch and forget, this program pairs deep sales literacy with real writing labs, feedback, and intimate cohorts—so your words actually convert for your premium clients. Here’s what we cover: Why I built The Greenhouse now—and...

1 month ago

1 hour 12 minutes

The Writer's Round

What I’ve Learned in 4 Years of My Ghostwriting Business

What does it really take to run a ghostwriting business—and keep it thriving—in today’s shifting creative economy? In this episode, I share the lessons, pivots, and hard-won insights from four years of building The Candid Collective® and serving clients at every stage of growth. You’ll hear the raw truths about money, clients, content, and resilience, along with encouragement for any writer or entrepreneur carving their own path. Here’s what we cover: How I accidentally became a ghostwr...

1 month ago

1 hour 4 minutes

The Writer's Round

Is AI Really Going to Replace You as a Writer?

Is AI actually coming for your writing career—or are we confusing speed with substance? In this episode, I cut through the hype to show what AI does well, where it falls flat, and how you can future-proof your craft and income. Here’s what we cover: Why AI outputs the average—and why differentiation wins.How a human voice drives retention, resonance, and conversion.The tell: converting content is rarely AI-generated.What my clients say they want from human-written work.Sales writing vs....

1 month ago

38 minutes

The Writer's Round

Welcome to The Writer's Round

Ever wish there were a corner of the internet where writers are treated like artists and business owners—without fear-mongering about AI or hustle-bro marketing? This inaugural episode sets the tone for The Writer’s Round: a candid, unvarnished, “guitar-and-a-mic” space for craft, career, and creative sovereignty. Rather than promising a one-size-fits-all blueprint, I'll offer an honest, practical look at building a writing life in 2025—where business is art, art is business, and your voice b...

1 month ago

43 minutes