From cringe to confidence: how to make selling feel good episode artwork

EPISODE · May 14, 2026 · 36 MIN

From cringe to confidence: how to make selling feel good

from Flying Solo · host Flying Solo

Does the thought of sales and selling make you squirm? You’re not the only one. Yet, selling a part and parcel of doing business, so how can you get over the ick? To help us reframe our thinking and banish that cringe factor for good  we're joined by Kate Toon. Kate is an ,award-winning business mentor, digital marketing coach,and author of the bestselling "Six Figures" series, including her latest, "Six Figures in Sales." We discuss what it really takes to sell without sleaze, why honesty trumps hype, how to price your services with confidence, and why building genuine rapport is your greatest sales asset—whether online, offline, or somewhere in between. If you’ve ever struggled with selling, this episode is packed with practical wisdom to help you find a sales style that actually feels good. Time stamped overview 00:00 Applying advertising skills to small business 03:56 Criticism of Meta advertising platforms 09:27 Setting freelance income goals 10:56 Discussing pricing strategies 15:28 Understanding Google's EEAT criteria 18:00 Challenges of running a bookshop 22:35 Importance of honesty in sales 23:38 The impact of brand connection 28:06 Improving your website's about page 30:17 The importance of strong writing skills 33:29 Focusing on emotional appeal Key topics 1. Mindset Shift in Selling ·     Selling  is not inherently "pushy," but simply about matching solutions to the people who need them and overcoming objections rather than convincing uninterested parties (05:12). ·     Highlighting that discomfort with selling often comes from a misconception—it becomes easier and less "cringe" when you know your audience genuinely wants or needs what you offer (05:35). ·      Moving away from "bro marketing" and push tactics, Kate Toon advocates for honesty, conversation, and real rapport with potential clients (00:48, 08:31). 2. Pricing and Value Perception ·     Accurate pricing starts with logical, unemotional calculation understanding minimum viable income, realistic billable hours, and tiered income goals (09:27). ·     Price is rarely the main objection in sales; most clients can afford the service or product but are concerned about value and outcome (14:10). ·     Transparent communication about what is feasible within a client's budget and honest conversations about the value provided are crucial for long-term trust (12:21, 13:38). 3. Building Trust and Reputation ·     The "EEAT" (Experience, Expertise, Authority, Trust) acronym from SEO as vital for any business's digital and real-world reputation (15:28). ·     Consistent branding and authentic rapport—both online and offline—help potential customers feel confident, acknowledged, and valued (19:11). ·     Testimonials, peer recommendations, and clear evidence of qualifications play a pivotal role in building the authority and trust that drive conversion (16:43, 28:24). 4. Human-Centric Digital Marketing (Beyond Ads) ·     Kate Toon advocates for organic methods over paid advertising, emphasizing SEO, content quality, and relationship-building (04:53, 27:01). ·      Businesses should build extensive and authentic about pages, accumulating third-party endorsements and trust signals to enhance their digital footprint (28:24). ·     Content—especially copywriting—should be clear, jargon-free (unless appropriate to the audience), personable, and genuinely reflective of the brand's voice (30:17).   Learn more about your ad choices. Visit megaphone.fm/adchoices

Does the thought of sales and selling make you squirm? You’re not the only one. Yet, selling a part and parcel of doing business, so how can you get over the ick? To help us reframe our thinking and banish that cringe factor for good  we're joined by Kate Toon. Kate is an ,award-winning business mentor, digital marketing coach,and author of the bestselling "Six Figures" series, including her latest, "Six Figures in Sales." We discuss what it really takes to sell without sleaze, why honesty trumps hype, how to price your services with confidence, and why building genuine rapport is your greatest sales asset—whether online, offline, or somewhere in between. If you’ve ever struggled with selling, this episode is packed with practical wisdom to help you find a sales style that actually feels good. Time stamped overview 00:00 Applying advertising skills to small business 03:56 Criticism of Meta advertising platforms 09:27 Setting freelance income goals 10:56 Discussing pricing strategies 15:28 Understanding Google's EEAT criteria 18:00 Challenges of running a bookshop 22:35 Importance of honesty in sales 23:38 The impact of brand connection 28:06 Improving your website's about page 30:17 The importance of strong writing skills 33:29 Focusing on emotional appeal Key topics 1. Mindset Shift in Selling ·     Selling  is not inherently "pushy," but simply about matching solutions to the people who need them and overcoming objections rather than convincing uninterested parties (05:12). ·     Highlighting that discomfort with selling often comes from a misconception—it becomes easier and less "cringe" when you know your audience genuinely wants or needs what you offer (05:35). ·      Moving away from "bro marketing" and push tactics, Kate Toon advocates for honesty, conversation, and real rapport with potential clients (00:48, 08:31). 2. Pricing and Value Perception ·     Accurate pricing starts with logical, unemotional calculation understanding minimum viable income, realistic billable hours, and tiered income goals (09:27). ·     Price is rarely the main objection in sales; most clients can afford the service or product but are concerned about value and outcome (14:10). ·     Transparent communication about what is feasible within a client's budget and honest conversations about the value provided are crucial for long-term trust (12:21, 13:38). 3. Building Trust and Reputation ·     The "EEAT" (Experience, Expertise, Authority, Trust) acronym from SEO as vital for any business's digital and real-world reputation (15:28). ·     Consistent branding and authentic rapport—both online and offline—help potential customers feel confident, acknowledged, and valued (19:11). ·     Testimonials, peer recommendations, and clear evidence of qualifications play a pivotal role in building the authority and trust that drive conversion (16:43, 28:24). 4. Human-Centric Digital Marketing (Beyond Ads) ·     Kate Toon advocates for organic methods over paid advertising, emphasizing SEO, content quality, and relationship-building (04:53, 27:01). ·      Businesses should build extensive and authentic about pages, accumulating third-party endorsements and trust signals to enhance their digital footprint (28:24). ·     Content—especially copywriting—should be clear, jargon-free (unless appropriate to the audience), personable, and genuinely reflective of the brand's voice (30:17).   Learn more about your ad choices. Visit megaphone.fm/adchoices

NOW PLAYING

From cringe to confidence: how to make selling feel good

0:00 36:29

No transcript for this episode yet

We transcribe on demand. Request one and we'll notify you when it's ready — usually under 10 minutes.

One Man Went To Row PepperDawesMedia Follow the journey, from training to finish line, of a man from Derby, UK who is going from having only ever rowed on a machine to rowing 3000 miles solo across the Atlantic...just after his 70th birthday! The Dennis Michael Lynch Show TeamDML M-F 10amET: Dennis Michael Lynch ("DML") is a popular conservative commentator who covers news, politics, culture, and society. His unfiltered approach in delivering hard-hitting commentary stems from DML's unique perspective as an award-winning entrepreneur, acclaimed filmmaker, respected cable news anchor, and dedicated family man. The show offers a collection of styles, including interviews, solo commentary, long form and short form, and is presented in both video and audio. VIDEO: The podcast airs Monday-Friday, LIVE on Facebook.com/DMLNewsApp, TeamDML.com. AUDIO: Available on The DML NEWS APP, TeamDML.com, and on all major podcast platforms. Tune in to listen to the most trusted man in news. Download the DML NEWS APP and never miss an episode. Alcatraz Radio2 "Fratello, la cosa assurda non è che sono un italiano nel braccio della morte di un carcere di massima sicurezza degli Stati Uniti. La cosa assurda è che tu stai fuori. Che tutti lì fuori siete liberi e state di schifo. Dov'è la tua libertà, tesoro? Nei lager dei quartieri di merda in cui vi hanno ficcato come bestiame, che cosa vi aspettate di diventare, onorevoli? Vi tengono in vita solo perché dovete comprare. Consigli per gli acquisti? Fanculo. Chi di noi due è nel braccio della morte? lo o te? Benvenuto ad Alcatraz, tesoro.” The Business Of Influence Karan White Being an influencer is no longer just a hobby or a side gig. It’s now a legitimate career and this has given rise to a new industry with its own set of challenges, but also so much opportunity. Despite the growth of the industry, there is a notable absence of established career paths and professional training available, which is why I’ve created this podcast. Each Tuesday, I’ll help you learn with confidence the tried and tested strategies that have generated millions in revenue for my clients across the globe. This podcast is dedicated to helping influencers navigate the business side of things, providing insights and guidance on everything from contracts and negotiations to branding and marketing. I believe that by sharing knowledge and experience, I can help you build a sustainable long-term career in the industry with secure and stable income streams.Stay tuned for solo episodes on all things brand partnerships, product development, media, and publishing, all through the len

Frequently Asked Questions

How long is this episode of Flying Solo?

This episode is 36 minutes long.

When was this Flying Solo episode published?

This episode was published on May 14, 2026.

What is this episode about?

Does the thought of sales and selling make you squirm? You’re not the only one. Yet, selling a part and parcel of doing business, so how can you get over the ick? To help us reframe our thinking and banish that cringe factor for good  we're joined...

Can I download this Flying Solo episode?

Yes, you can download this episode by clicking the download button on the episode player, or subscribe to the podcast in your preferred podcast app for automatic downloads.
URL copied to clipboard!