Overcoming imposter syndrome

Overcoming imposter syndrome

Author: The Happy Startup School March 31, 2021 Duration: 57:19

On this episode of Waking up to Money we're joined by Sarah and Saskia.

They run different types of businesses but had similar challenges: how to be more confident about pricing.

Sarah runs a service based business and she was sending out proposals without first talking to her client about money.

Ben says that proposals never sell.

Proposals are there to reassure the customer they’re getting what they asked for.

Your job is to have money conversations upfront so that you can confidently put the right numbers in your proposal and your customer is in the right place to receive them.

The pressure isn’t on the proposal, the joy is in the conversation.

Saskia runs courses and an online community.

Because there’s so much free content on the Internet she gets a scary feeling when thinking about putting a price to her work.

It’s the same feeling she got when she first did abseiling and jumped off the edge.

Ben reminded her to think from her customers perspective and the solutions and good feelings they’re looking for.

There’s value in curating content so that people waste less time making progress.

There’s also value feeling part of a community when you’re trying to do things on your own.

Having conversations with potential customers and framing the value of what you do against something more expensive (i.e. 1 to 1 coaching) then helps them get more comfortable with the prices you offer.

You can find out more about these stories and hear all the feedback we gave Sarah and Saskia by listening to this episode.


For freelancers and founders who believe their work has genuine purpose, the conversation around money can feel like the most awkward part of the job. The Happy Pricing Podcast, from The Happy Startup School, steps directly into that discomfort. It operates from a simple, radical premise: pricing shouldn't be a silent calculation of fear or greed, but a clear, confident dialogue about shared value. This isn't about racing to the bottom to please clients or inflating rates to exploit them. Instead, each episode focuses on building the practical capability to have those necessary, often avoided, financial conversations. You'll hear real strategies for articulating your worth in a way that feels authentic, ensuring the exchange is equitable and that you are properly compensated for the impact you create. The discussions move beyond theory into the nuanced reality of running a purpose-driven business, exploring how to structure fees, negotiate with clarity, and ultimately create arrangements where both you and your clients feel good about the investment. Tuning into this podcast means re-framing pricing from a transactional headache into a core component of your professional integrity and happiness. It's for those ready to move past anxiety and into a practice where everyone truly shares in the value being delivered.
Author: Language: English Episodes: 75

The Happy Pricing Podcast
Podcast Episodes
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