MSL 301 - Why selling feels so hard when you ARE the business (and the three hidden challenges no one talks about)
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.”
In this episode, I 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.
Top three sales challenges for solopreneurs:
1. The "Ick Factor" and feeling salesy
They equate selling with being pushy, manipulative, or "gross"
Leads to underselling, undercharging, or avoiding sales conversations entirely
Often stems from bad experiences with pushy salespeople
Results in giving away too much value for free to avoid having "the money conversation"
2. Fear of rejection (“it feels personal”)
When someone says no to your service, it feels like they're rejecting YOU
Especially tough for solopreneurs because you ARE the product/service
Creates avoidance of follow-up, prospecting, or even pricing conversations
Leads to the "propose and pray" approach instead of confident selling
3. Lack of sales process or structure
Every sales conversation feels like starting from scratch
No clear path from initial conversation to signed contract
Inconsistent discovery process - sometimes they ask good questions, sometimes they don't
Results in inconsistent closing rates and exhausting sales experiences
The common thread: All three stem from treating sales as something that happens TO prospects rather than WITH them. Most solopreneurs haven't learned that great selling is really just great problem-solving with a clear process.
