54. Stop Just Knowing Your Enneagram Type & Start Using It: Ashton Ober-Whitmeyer on Self-Awareness, Business Pivots & Getting Comfortable with the Messy Middle episode artwork

EPISODE · Mar 20, 2026 · 36 MIN

54. Stop Just Knowing Your Enneagram Type & Start Using It: Ashton Ober-Whitmeyer on Self-Awareness, Business Pivots & Getting Comfortable with the Messy Middle

from Get Messy with Maddie · host Maddie McGuire

Have you taken the Enneagram test, had your entire personality confirmed in three paragraphs, and then... kept scrolling? Same. But according to my guest this week, that's exactly where most people go wrong.I'm sitting down with Ashton (aka Enneagram Ashton) — public speaker, author, and Enneagram coach who built a thriving business helping people go from "cool, I'm a 4" to actually using that information to grow.In this episode, I pick her brain on what it actually means to use the Enneagram (hint: it's not about finding your perfect match), the myths I know we've all believed about entrepreneurship, the sting of getting ghosted on a business deal, the rollercoaster of money and consistency, and how she recharges her creativity.Whether you're Enneagram-obsessed like me or totally Enneagram-curious, I think this one's going to stick with you.✨Connect with Ashton✨Follow @enneagramashton on InstagramCheck out her website: enneagramashton.com for The Support Squad membership & The Enneagram Advantage program✨Connect with Maddie✨Explore Maddie’s Website | @messywithmaddie

Have you taken the Enneagram test, had your entire personality confirmed in three paragraphs, and then... kept scrolling? Same. But according to my guest this week, that's exactly where most people go wrong.I'm sitting down with Ashton (aka Enneagram Ashton) — public speaker, author, and Enneagram coach who built a thriving business helping people go from "cool, I'm a 4" to actually using that information to grow.In this episode, I pick her brain on what it actually means to use the Enneagram (hint: it's not about finding your perfect match), the myths I know we've all believed about entrepreneurship, the sting of getting ghosted on a business deal, the rollercoaster of money and consistency, and how she recharges her creativity.Whether you're Enneagram-obsessed like me or totally Enneagram-curious, I think this one's going to stick with you.✨Connect with Ashton✨Follow @enneagramashton on InstagramCheck out her website: enneagramashton.com for The Support Squad membership & The Enneagram Advantage program✨Connect with Maddie✨Explore Maddie’s Website | @messywithmaddie

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54. Stop Just Knowing Your Enneagram Type & Start Using It: Ashton Ober-Whitmeyer on Self-Awareness, Business Pivots & Getting Comfortable with the Messy Middle

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This episode was published on March 20, 2026.

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Have you taken the Enneagram test, had your entire personality confirmed in three paragraphs, and then... kept scrolling? Same. But according to my guest this week, that's exactly where most people go wrong.I'm sitting down with Ashton (aka...

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