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
How to price a retreat [not-audio_url] [/not-audio_url]

Duration: 47:43
In November Matthew Matheson is hosting a retreat to help people re-connect with their authentic selves.It's an idea that he developed during his time on the Vision 20/20 program.Carlos and Ben talk with Matthew about th…
How to help customers decide... to buy from you [not-audio_url] [/not-audio_url]

Duration: 24:38
Ben and Carlos try to interpret an email from Seth Godin to see how it relates to pricing and selling.How do we help our customers make a decision (to buy from us)? And how do we do that with integrity and not feel slimy…
Proposals and pricing [not-audio_url] [/not-audio_url]

Duration: 27:29
Proposal shouldn't contain any surprises – particularly not the price.The role of a proposal is to replay everything you've already spoken to your client about.In the previous episode, Carlos and Ben were joined by Hazel…
Pricing by value, not time [not-audio_url] [/not-audio_url]

Duration: 49:04
Beccie D'Cuhna is the founder of CourageLab and empowers leaders and teams to have courageous conversations, through mediation, training and coaching.She took part in our first Happy Pricing course and says her business…
More income, less effort [not-audio_url] [/not-audio_url]

Duration: 30:49
Jim Ralley helps with the design and strategy of learning experiences for NGOs, governments and corporate clients. Last year he tried to find the right balance between work, parenting and time for himself… and failed.Thi…
Personal brand and pricing [not-audio_url] [/not-audio_url]

Duration: 52:56
What’s the value of a personal brand? When building your reputation, what would this reputation do for you? What financial value does it have? What’s it worth to get on the radar of the people that you’d love to collabor…
"I'm nearly doubling my prices" [not-audio_url] [/not-audio_url]

Duration: 41:33
If you want to increase your prices, it has to start with an understanding of your value. Not just the mechanical tasks you perform, but the trust, familiarity, and unique value you bring to your clients. This can lead t…
The purpose of being polarising [not-audio_url] [/not-audio_url]

Duration: 24:05
Being polarising in your pricing and your offering is way more impactful than trying to appeal to the masses. But it means being clear about who you want to work with and focusing tightly on them.This not only helps attr…
Selling what you do differently [not-audio_url] [/not-audio_url]

Duration: 31:02
Changing the way you present your product can greatly affect how people see its value and price. When you’re faced with a sticky patch, lowering prices or costs might not be the right thing to do. So instead, what might…
How do you sell a book for €560? [not-audio_url] [/not-audio_url]

Duration: 38:03
Pricing expertise is not determined by traditional models. It’s about understanding the value and aligning incentives with the customer. By challenging conventional pricing logic and considering factors like value and sk…