The Writer's Round

Kendall Cherry
  • 0.0 (0)
  • ENTREPRENEURSHIP

A creative sanctuary for writers, business owners, and artists who are called to stay gold in this brave new world

  1. 3 DAYS AGO

    Your Content Isn’t Converting Because It’s Too Vague

    Your content is getting seen—but why isn’t it selling?  This solo episode of The Writer’s Round breaks down one of the most common (and fixable) reasons your content isn’t converting—and why being more specific is the fastest way to change that. Rather than assuming you need a brand-new strategy or more content, this episode reframes the problem entirely: vague messaging is quietly diluting your authority, your differentiation, and your ability to actually sell.  You’ll learn why specificity isn’t limiting—it’s what allows you to speak to multiple audience segments more effectively while building trust and credibility at scale. You’ll walk away with a clearer understanding of how to refine your content so it not only gets engagement, but actually drives revenue. Here’s what we cover: Why vague content feels safer—but ultimately makes you blend in and sound like everyone else.The difference between content that goes viral and content that actually converts (and why they’re rarely the same).How specificity builds trust by showing—not telling—your expertise and authority.The role of concrete examples in making your work feel structured, credible, and valuable to potential clients.Why being more specific doesn’t exclude people—and how it actually allows you to serve multiple audience segments at once.The hidden cost of high engagement content that doesn’t contribute to revenue.How specificity helps you stand out in saturated markets and against generic, AI-generated content.Simple ways to immediately make your messaging sharper, clearer, and more conversion-focused.Whether you’re a writer, service provider, or business owner trying to make your content work harder for you, this episode will help you rethink how you communicate your value—and show you that you likely don’t need more content, just more precision. CONNECT WITH KENDALL: 👩🏼‍🌾 Applications are OPEN for the inaugural cohort of The Greenhouse 🌱🌻 a 6-month accelerator to grow your writing business and transform your words into a premium product Website: candidcollective.co LinkedIn: https://www.linkedin.com/in/kendall-cherry/ Subscribe to my newsletter, Wallflower Fridays 🌻 💌 wallflowerfridays.com The Writer's Round on Substack: thewritersround.com PREMIUM SUPPORT Join The Greenhouse 🌱🌻 A 6-month accelerator to grow your writing business and transform your words into a premium product that clients love to pay you for. Apply here: findthegreenhouse.com Want to hire me to write for you? 👻✏️ Grab my services guide: candidcollective.co/services-guide © The Candid Collective

    13 min

  2. 16 APR

    Referrals Are Not a Sales Strategy

    Ever wonder why your business can feel consistent one season—and completely unpredictable the next? This solo episode of The Writer’s Round breaks down why referrals, while helpful, are not a reliable or scalable sales strategy—and how relying on them can quietly limit your income, your growth, and your ability to evolve your business.  Rather than demonizing referrals entirely, this episode offers a more grounded perspective on when they work, when they don’t, and what actually creates sustainable revenue over time. You’ll walk away with a clearer understanding of how to move beyond referral-dependency and build a sales ecosystem that gives you more control, consistency, and alignment in your business. Here’s what we cover:  Why referrals feel stable during “good” seasons—but quickly dry up in slower or uncertain economies  How referral-based businesses can experience more extreme feast-or-famine cycles  The hidden way referrals can cap your pricing, income, and overall earning potential  Why referrals make it harder to pivot, evolve, or expand your services  What you’re missing when clients come in pre-sold—and why it matters for your messaging  How relying on referrals prevents you from testing and validating your content and sales assets  The disconnect between what you actually do and what your messaging communicates (and why referrals can hide it)  Why visibility alone won’t fix your sales—and what role your sales ecosystem actually plays  How to build a more sustainable, scalable way of generating leads and closing clients Whether you’re currently running a referral-heavy business or you’ve been told that referrals are the ultimate goal, this episode offers a more nuanced perspective—one that helps you create more predictable revenue without relying on word-of-mouth alone. CONNECT WITH KENDALL: 👩🏼‍🌾 Applications are OPEN for the inaugural cohort of The Greenhouse 🌱🌻 a 6-month accelerator to grow your writing business and transform your words into a premium product Website: candidcollective.co LinkedIn: https://www.linkedin.com/in/kendall-cherry/ Subscribe to my newsletter, Wallflower Fridays 🌻 💌 wallflowerfridays.com The Writer's Round on Substack: thewritersround.com PREMIUM SUPPORT Join The Greenhouse 🌱🌻 A 6-month accelerator to grow your writing business and transform your words into a premium product that clients love to pay you for. Apply here: findthegreenhouse.com Want to hire me to write for you? 👻✏️ Grab my services guide: candidcollective.co/services-guide © The Candid Collective

    39 min

  3. 26 MAR

    How Your Inquiry Form Can Qualify Leads and Eliminate Sales Calls

    A creative sanctuary for writers, business owners, and artists who are called to stay gold in this brave new world. In this solo episode, I break down one of the most underrated pieces of a healthy sales ecosystem: your inquiry form. I explain how a thoughtfully designed form can qualify leads, speed up decision-making, and eliminate unnecessary sales calls—while still keeping the process ethical and client-centered. Instead of relying on endless discovery calls, I share how to design inquiry questions that surface the exact information you need to evaluate fit, scope projects, and move straight into proposals. Here’s what we cover: Why generic contact forms create slow sales cycles and force you to gather basic information on calls. How a strategic inquiry form helps you quickly arrive at a clear yes or no with potential clients. Why asking about project timelines reveals more than urgency—it exposes expectations and operational readiness. The role of budget transparency and how it helps you design payment plans that work for both sides. Why asking about preferred monthly payments can make pricing conversations easier and more collaborative. The underrated question I always ask: what investments someone has already made to solve this problem. How past investments reveal buying behavior, seriousness, and potential alignment with your services. Why inquiry forms help you scope projects faster by giving you early visibility into needs, goals, and constraints. How better lead qualification allows you to send proposals asynchronously—often eliminating the need for sales calls entirely. Why your inquiry form is one of the most powerful operational tools in a modern ethical sales ecosystem. Whether you’re a writer, coach, or consultant, this episode will help you rethink your inquiry process—and turn a simple form into a powerful filter that attracts better clients and saves you hours of selling time. CONNECT WITH KENDALL: 👩🏼‍🌾 Applications are OPEN for the inaugural cohort of The Greenhouse 🌱🌻 a 6-month accelerator to grow your writing business and transform your words into a premium product Website: candidcollective.co LinkedIn: https://www.linkedin.com/in/kendall-cherry/ Subscribe to my newsletter, Wallflower Fridays 🌻 💌 wallflowerfridays.com The Writer's Round on Substack: thewritersround.com PREMIUM SUPPORT Join The Greenhouse 🌱🌻 A 6-month accelerator to grow your writing business and transform your words into a premium product that clients love to pay you for. Apply here: findthegreenhouse.com Want to hire me to write for you? 👻✏️ Grab my services guide: candidcollective.co/services-guide © The Candid Collective

    20 min

  4. 19 MAR

    How I Differentiated 50+ Life Coaches Within the Same Niche

    A creative sanctuary for writers, business owners, and artists who are called to stay gold in this brave new world. In this solo episode, I pull back the curtain on one of the most fascinating realizations from teaching inside The Greenhouse—how I ended up differentiating more than 50 life coaches who were all technically serving the same audience with almost identical messaging. Instead of accepting vague positioning like “women in transition,” I explain the strategy and storytelling thinking that allowed me to transform look-alike services into distinct, compelling brands that actually sell. Here’s what we cover: Why so many coaches unknowingly use identical positioning—and how phrases like “women in transition” quietly erase your uniqueness. Why I refuse to repeat lowest-common-denominator messaging even when clients initially believe that’s their niche. The first differentiator: treating services like products so the transformation becomes clear, concrete, and sellable. Why every service needs a container—timeframes, outcomes, and defined before-and-after shifts that anchor the offer. How deep industry exposure turned my brain into a “human messaging archive,” making it easier to spot clichés and surface fresh positioning. Why differentiation often comes from reframing common outcomes instead of inventing completely new services. How subtle nuances inside a client’s real experience reveal far more specific audiences than broad demographics ever could. Why client stories are the most powerful differentiator in service businesses—and how they reveal your unique process. The cinematographer mindset for storytelling: deciding exactly what moment, insight, or transformation the audience should focus on. Why differentiation and storytelling will only become more valuable as online markets grow more crowded and content becomes more automated. Whether you’re a writer working with saturated industries or a service provider trying to stand out in a crowded niche, this episode will help you rethink positioning—and start turning everyday client stories into the clearest proof of your expertise. CONNECT WITH KENDALL: 👩🏼‍🌾 Applications are OPEN for the inaugural cohort of The Greenhouse 🌱🌻 a 6-month accelerator to grow your writing business and transform your words into a premium product Website: candidcollective.co LinkedIn: https://www.linkedin.com/in/kendall-cherry/ Subscribe to my newsletter, Wallflower Fridays 🌻 💌 wallflowerfridays.com The Writer's Round on Substack: thewritersround.com PREMIUM SUPPORT Join The Greenhouse 🌱🌻 A 6-month accelerator to grow your writing business and transform your words into a premium product that clients love to pay you for. Apply here: findthegreenhouse.com Want to hire me to write for you? 👻✏️ Grab my services guide: candidcollective.co/services-guide © The Candid Collective

    30 min

  5. 15 FEB

    How to Create a Conscious Sales Ecosystem in 2026

    A grounded, behind-the-scenes look at how sales actually work in 2026—and why the old urgency-heavy, hustle-driven tactics are quietly collapsing.  In this solo episode of The Writer’s Round, I unpack the ethos and infrastructure of a conscious sales ecosystem, why integrity is the dominant value among modern service providers, and how aligning your funnel with that shift can unclog your revenue overnight. Rather than doubling down on scarcity, cold outreach, and pressure-based calls, I break down what it looks like to sell in a way that feels spacious, empowered, and profitable—especially for writers, fractional experts, and service-based founders. Here’s what we cover: Why we’re in a trust recession—and how empowered buyers (especially women and marginalized founders) are changing the way money moves. The real reason sales cycles feel longer—and why “perfect timing” purchasing requires a new funnel structure. Integrity as the #1 business value I see across my clients—and how misalignment in your sales process silently blocks revenue. What a conscious sales ecosystem actually looks like: buyer autonomy, transparent scope, clear outcomes, and zero pressure. Why speed kills deals—and how hustle energy repels the very clients you’re trying to attract. How to gut and rebuild your proposal process so it takes 15–30 minutes instead of 2–3 hours. The inquiry form mechanics I use to pre-qualify aligned clients (and filter out energy leaks before a call ever happens). Real student wins from The Greenhouse: nine inquiries in a week and a half, renegotiated contracts, higher rates, and faster closes—all from shifting the infrastructure first. Why we rebuild the sales ecosystem in week one of The Greenhouse—and how cleaning the pipeline often leads to immediate ROI. If you’ve felt the quiet resistance to selling the “old way,” this episode will validate what you already sense: there is a different model emerging. One rooted in integrity, autonomy, and long-term trust. And when your infrastructure matches your values, the sales don’t just convert—they flow. CONNECT WITH KENDALL: 👩🏼‍🌾 Applications are OPEN for the inaugural cohort of The Greenhouse 🌱🌻 a 6-month accelerator to grow your writing business and transform your words into a premium product Website: candidcollective.co LinkedIn: https://www.linkedin.com/in/kendall-cherry/ Subscribe to my newsletter, Wallflower Fridays 🌻 💌 wallflowerfridays.com The Writer's Round on Substack: thewritersround.com PREMIUM SUPPORT Join The Greenhouse 🌱🌻 A 6-month accelerator to grow your writing business and transform your words into a premium product that clients love to pay you for. Apply here: findthegreenhouse.com Want to hire me to write for you? 👻✏️ Grab my services guide: candidcollective.co/services-guide © The Candid Collective

    43 min

  6. 5 FEB

    Intention Setting Inside The Greenhouse

    A creative sanctuary for writers, business owners, and artists who are called to stay gold in this brave new world. In this solo episode, I pull back the curtain on Week Zero inside The Greenhouse and share how intention setting becomes the foundation for sustainable growth, creative safety, and aligned sales—without hierarchy, pressure, or performance. Rather than treating goals as rigid milestones or one-time journal entries, I walk through how I use visualization, nervous system awareness, and weekly micro-actions to create real momentum for writers building premium, values-led businesses. Here’s what we cover: Why I created Week Zero and how intention setting shapes the entire arc of The Greenhouse. How peer-based learning replaces hierarchy and creates deeper trust, ownership, and follow-through. The “see yourself successful” exercise and why future visualization works better than rigid goal-setting. Why focusing on the next small step keeps momentum moving without overwhelming your nervous system. How shared fears lose power when named collectively—and why this matters for creative confidence and sales. What conscious community actually looks like inside a writing accelerator, and why safety fuels growth. How intentional sales ecosystems give writers back their time, energy, and creative bandwidth. If you’re navigating a liminal season, building something meaningful, or craving a more human way to grow your work, this episode offers a grounded look at how intention, structure, and community can work together—without burning you out or asking you to perform. CONNECT WITH KENDALL: 👩🏼‍🌾 Applications are OPEN for the inaugural cohort of The Greenhouse 🌱🌻 a 6-month accelerator to grow your writing business and transform your words into a premium product Website: candidcollective.co LinkedIn: https://www.linkedin.com/in/kendall-cherry/ Subscribe to my newsletter, Wallflower Fridays 🌻 💌 wallflowerfridays.com The Writer's Round on Substack: thewritersround.com PREMIUM SUPPORT Join The Greenhouse 🌱🌻 A 6-month accelerator to grow your writing business and transform your words into a premium product that clients love to pay you for. Apply here: findthegreenhouse.com Want to hire me to write for you? 👻✏️ Grab my services guide: candidcollective.co/services-guide © The Candid Collective

    31 min

  7. 04/12/2025

    How I Think About Teaching Storytelling and Sales Writing

    A creative sanctuary for writers, business owners, and artists who are called to stay gold in this brave new world. In this solo episode, I take you behind the scenes of my teaching philosophy—how I approach storytelling and sales writing, why I don’t believe in formulaic “plug-and-play” content, and the deeper emotional and spiritual layers that run underneath everything I teach.  From childhood chalkboards to designing The Greenhouse’s curriculum, this episode traces how teaching became the core of my craft—and why I believe great writing starts with a great lens. Here’s what we cover: Why I always knew I’d be a teacher long before I knew I’d be a writer—and how that shapes everything I create now. How The Greenhouse brought me “home” to my teacher identity and why writers need real instruction, not just templates. Why self-paced courses rarely work for storytelling and sales—and what writers actually need to get better. Why understanding the mechanics behind a story matters more than following a framework. How I think about storytelling as a camera lens—not a formula—and why your voice (not mine) is the point. Why storytelling is a skill that transcends business: from weddings to wakes to dinner tables. The spiritual undercurrent of everything I teach—and how stories help us see ourselves more clearly. Why sales writing is really self-advocacy—and why your pricing, your confidence, and your storytelling are deeply connected. How stories raise the collective “light” in the world—and why your work deserves to be shared so others can transform too. Why the ripple effect of your stories matters more than you realize. If you want to learn storytelling and sales writing in a way that’s practical, human, and deeply empowering, you can join me for The Greenhouse or start with my free workshop, How to Write a Money-Making Testimonial, happening December 11 at 11 a.m. CT. Links are in the show notes. I can’t wait to teach you—whether it’s for one hour or for six months. JOIN MY FREE WORKSHOP ON DECEMBER 11th Learn how to write a client case study in story form in my upcoming FREE workshop: How to Write a Money Makin' Testimonial.  Register here P.S. Seeing this episode after December 11, 2025? Use the link above and we'll send you the replay! CONNECT WITH KENDALL: 👩🏼‍🌾 Applications are OPEN for the inaugural cohort of The Greenhouse 🌱🌻 a 6-month accelerator to grow your writing business and transform your words into a premium product Website: candidcollective.co LinkedIn: https://www.linkedin.com/in/kendall-cherry/ Subscribe to my newsletter, Wallflower Fridays 🌻 💌 wallflowerfridays.com The Writer's Round on Substack: thewritersround.com PREMIUM SUPPORT Join The Greenhouse 🌱🌻 A 6-month accelerator to grow your writing business and transform your words into a premium product that clients love to pay you for. Apply here: findthegreenhouse.com Want to hire me to write for you? 👻✏️ Grab my services guide: candidcollective.co/services-guide © The Candid Collective

    32 min

  8. 04/12/2025

    Why Client Case Study Stories Convert Like Crazy

    A creative sanctuary for writers, business owners, and artists who are called to stay gold in this brave new world. In this solo episode, I break down why client case study stories are the most profitable, trust-building, conversion-boosting stories in your entire business—and why so many of us still avoid sharing them.  These aren’t just “testimonials”; they are narrative proof of your value, your process, and the real transformation you facilitate. Case studies help your audience see themselves inside the work. They let people understand not only what you do, but how it works—and whether your approach is right for them.  And in a market where buyers are more cautious, more informed, and doing more research than ever, these stories matter. Here’s what we cover: Why stopping to reflect on your client work is essential—not optional—if you want predictable monthly or quarterly sales. The problem with the “five gold stars + screenshot” testimonial trend—and how it trains your audience to scroll right past your wins. Why story-driven case studies outperform static testimonials every single time. Why “I don’t know enough details” is a cop-out—and why you have more of the story than you think. The user behavior most people miss: why audiences don’t actually read screenshot testimonials and what to do instead. How to write case studies that introduce nuance, speak to different buyer segments, and mirror the emotional and practical value of your offer. Why today’s customers require more information, more safety, and more transparency before they ever invest—and how case studies deliver exactly that. How case studies de-pressurize the sales cycle by answering questions before someone ever gets on a call with you. Why qualitative wins (clarity, confidence, momentum, relief) matter just as much as revenue data—and how to tell those stories well. Why these stories are your highest-converting sales assets—and why they’re also the least shared. Want to turn client wins into stories that sell? Join my free workshop Dec 11 at 11am CT: How to Write a Money-Making Testimonial. I'll share my method, examples, and tools for archiving your best stories. If you're listening after Dec 11, the replay is waiting for you. Just use the link in the show notes. Access it anytime, whether it's next week or next year. Case studies are the highest-ROI stories you can tell. Let’s make sure you’re actually telling them. JOIN MY FREE WORKSHOP ON DECEMBER 11th Learn how to write a client case study in story form in my upcoming FREE workshop: How to Write a Money Makin' Testimonial.  Register here CONNECT WITH KENDALL: 👩🏼‍🌾 Applications are OPEN for the inaugural cohort of The Greenhouse 🌱🌻 a 6-month accelerator to grow your writing business and transform your words into a premium product Website: candidcollective.co LinkedIn: https://www.linkedin.com/in/kendall-cherry/ Subscribe to my newsletter, Wallflower Fridays 🌻 💌 wallflowerfridays.com The Writer's Round on Substack: thewritersround.com PREMIUM SUPPORT Join The Greenhouse 🌱🌻 A 6-month accelerator to grow your writing business and transform your words into a premium product that clients love to pay you for. Apply here: findthegreenhouse.com Want to hire me to write for you? 👻✏️ Grab my services guide: candidcollective.co/services-guide © The Candid Collective

    17 min
See All (20)

About

A creative sanctuary for writers, business owners, and artists who are called to stay gold in this brave new world

Information

  • Creator
    Kendall Cherry
  • Years Active
    2025 - 2026
  • Episodes
    20
  • Rating
    Explicit
  • Copyright
    © 2026 The Candid Collective
  • Show Website
    The Writer's Round
  • Provider