MSL 301 - Why selling feels so hard when you ARE the business (and the three hidden challenges no one talks about) episode artwork

EPISODE · Sep 15, 2025

MSL 301 - Why selling feels so hard when you ARE the business (and the three hidden challenges no one talks about)

from My Solopreneur Life · host Terry Pappy

Here’s the thing: nobody warns you how weird, and sometimes downright cringey, it feels when you try to sell your own services for the first time. If you’ve ever wondered why asking for business is so much harder when you’re the product, you’re not alone. In this episode, I open up about my own early sales stumbles, breakout moments, and the wild learning curve faced by solopreneurs who never planned on “selling themselves.”We dig into the three real reasons selling yourself feels so awkward: the “ick factor” (not wanting to sound salesy), the looming fear of rejection (because a “no” can feel oddly personal), and the chaos of having no actual process (hello, winging it). I share stories, hard-won lessons, and tactical prompts so you can start untangling your own story about sales and maybe start to enjoy it. Trust me: you can learn to sell without feeling gross, and the result is more confidence…and more clients you love working with. What’s your story about selling yourself and is it actually true? Maybe we should talk about it.

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MSL 301 - Why selling feels so hard when you ARE the business (and the three hidden challenges no one talks about)

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This episode was published on September 15, 2025.

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Here’s the thing: nobody warns you how weird, and sometimes downright cringey, it feels when you try to sell your own services for the first time. If you’ve ever wondered why asking for business is so much harder when you’re the product, you’re not...

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