The Nitty-Gritty:

  • How Hillary Rea, founder of Tell Me A Story, discovered her love of rich and nuanced storytelling
  • What she does to help new storytellers find more confidence in themselves and their ability to perform
  • What triggered a recent crisis of confidence and how its helping her move forward with growing her company
  • Why she’s channeling the confidence she feels in other aspects of life to provide the support she needs

I shared my own crisis of confidence a few months back on Instagram.

I wrote about how I felt at a loss with how to share our product with the people who needed it most. I’d spent 2 years trying to figure it out and I didn’t feel any closer to a solution.

I was feeling stuck and inadequate.

My friend Lou Blaser commented, “I had thought this was going to be a different post. Because Tara McMullin & ‘crisis of confidence’ didn’t compute in my brain!”

Just last week, someone else told me that they loved my interview with Claire Pelletreau from Get Paid because it can seem like people like me have it all figured out. And I share in that interview how much I do not have figured out yet.

The truth is that any entrepreneur can suffer from a crisis of confidence.

Any small business owner can find themselves riding high one minute and feeling lost the next.

Any smart and ambitious founder can have all the right answers… until the next question gets asked.

This month, we’re examining confidence. Specifically, we’re looking at how small business owners find the confidence to take a big step forward.

So let me say it again: any entrepreneur can suffer from a crisis of confidence…

…even an entrepreneur who is totally comfortable hopping on a stage in front of hundreds or thousands of people and sharing intimate personal stories.

My guest today is just one such entrepreneur. Her name is Hillary Rea and she’s the founder of Tell Me A Story, a company that trains entrepreneurs, start-up leaders, and those looking to leave a bigger footprint on the world, how to find their voice and share their unique story with honesty and passion.

She’s also the creator of a long-standing live storytelling show by the same name.

Right before we recorded this conversation, Hillary posted a vulnerable reflection on her blog looking back at her time producing this live show and how it’s matured.

In it, she shares her inner monologue about the doubt and even embarrassment she felt preparing for a big anniversary show. She wondered why the show hadn’t grown more. She wondered whether people took her seriously. She wondered if it was time to throw in the towel.

So while Hillary originally came on the show to talk about how she sources her confidence from showing up and being visible, we also talk about this very real crisis of confidence and how it’s impacting her business moving forward.

This candid conversation with Hillary is part of a whole series we’re doing here at What Works on confidence. We want to shed light on how small business owners continue to find confidence, long after they’ve taken the leap to get started.

Over the next month, you’ll hear about finding the confidence to raise your prices, come back after a major loss, experiment & iterate, stick with the plan, and land giant clients. When we’re not posting new conversations here on the podcast, we’re sharing personal essays and reflections from What Works Network members on how they find the confidence to take the next step.

To get the full series delivered to your inbox—and check out what we’ve already released—click here.

Now, let’s find out What Works for Hillary Rea!

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