297 - What Happens When You Bet on Yourself Before You Feel Ready episode artwork

EPISODE · Apr 3, 2026 · 44 MIN

297 - What Happens When You Bet on Yourself Before You Feel Ready

from Become Your Own Boss: Tips for Starting and Growing Your Own Small Business · host Monica Allen

In this episode, Monica Allen sits down with Dr. Ashley Wood, a first-year entrepreneur navigating the real, unfiltered journey of building a business alone. From figuring out finances to learning industry language on the fly, Ashley shares what it actually feels like to be the CEO, marketer, and operator all at once. She opens up about mindset struggles, self-worth, and how trusting herself changed everything. This conversation pulls back the curtain on early entrepreneurship and reminds listeners that success isn’t about having it all figured out. It’s about growing through it.Episode Quote: If you don’t build your dream, someone else will hire you to help them build theirs. ~ Dhirubhai AmbaniWhat you will learn in this episodeHow to build confidence when you’re just starting outHow to navigate the financial uncertainty of entrepreneurshipHow to shift your mindset to support long-term successHow to make decisions without second-guessing yourselfHow to create a business that aligns with your lifestyleDr. Ashlee Wood:[email protected] Sponsor -  ⁠Zeus' Closet ⁠⁠Business Packages⁠Use BOSS20 to save 20% off business packagesHelpful Entrepreneurial Resources from Become Your Own BossSign Up for the⁠ ⁠Level Up Living Newsletter⁠⁠⁠⁠KICKSTART YOUR BUSINESS PROGRAM⁠⁠⁠⁠⁠Monica's FREE ebook⁠⁠⁠: 11 Essential Secrets for Small Business SuccessGet your⁠⁠ ⁠Become Your Own Boss Planner⁠⁠Ready to step into your next level? Tune in to this episode, subscribe to Become Your Own Boss, and leave a review to help more entrepreneurs like you grow with confidence.

In this episode, Monica Allen sits down with Dr. Ashley Wood, a first-year entrepreneur navigating the real, unfiltered journey of building a business alone. From figuring out finances to learning industry language on the fly, Ashley shares what it actually feels like to be the CEO, marketer, and operator all at once. She opens up about mindset struggles, self-worth, and how trusting herself changed everything. This conversation pulls back the curtain on early entrepreneurship and reminds listeners that success isn’t about having it all figured out. It’s about growing through it.Episode Quote: If you don’t build your dream, someone else will hire you to help them build theirs. ~ Dhirubhai AmbaniWhat you will learn in this episodeHow to build confidence when you’re just starting outHow to navigate the financial uncertainty of entrepreneurshipHow to shift your mindset to support long-term successHow to make decisions without second-guessing yourselfHow to create a business that aligns with your lifestyleDr. Ashlee Wood:[email protected] Sponsor -  ⁠Zeus' Closet ⁠⁠Business Packages⁠Use BOSS20 to save 20% off business packagesHelpful Entrepreneurial Resources from Become Your Own BossSign Up for the⁠ ⁠Level Up Living Newsletter⁠⁠⁠⁠KICKSTART YOUR BUSINESS PROGRAM⁠⁠⁠⁠⁠Monica's FREE ebook⁠⁠⁠: 11 Essential Secrets for Small Business SuccessGet your⁠⁠ ⁠Become Your Own Boss Planner⁠⁠Ready to step into your next level? Tune in to this episode, subscribe to Become Your Own Boss, and leave a review to help more entrepreneurs like you grow with confidence.

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297 - What Happens When You Bet on Yourself Before You Feel Ready

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This episode is 44 minutes long.

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This episode was published on April 3, 2026.

What is this episode about?

In this episode, Monica Allen sits down with Dr. Ashley Wood, a first-year entrepreneur navigating the real, unfiltered journey of building a business alone. From figuring out finances to learning industry language on the fly, Ashley shares what it...

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