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how to twenty-something

how to twenty-something

Ep. 148 The reality of being self-employed in your twenties

how to twenty-something · Apr 13, 2026 · 19:39

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Being self-employed isn’t as glamorous as social media makes it out to be. We’re talking numbers, emotions, expectations, timelines, doubts, and the grit that comes with this kind of decision. I walk you through my real income from my first job out of school through my first four years of being self-employed. I talk about the mental and emotional toll of entrepreneurship… the uncertainty, the self-discipline required, and why it’s not the “freedom” social media makes it seem. If you’re thinking about leaving your 9–5, this episode will help you decide whether you’re chasing the aesthetic… or you’re actually ready for the reality. 

Key Takeaways:



Helpful Resources: 


Let’s chat: https://calendly.com/coach_jessdiamond/success 


Email me: coach.jessdiamond@gmail.com


How to stop spiraling:https://jessdiamondcoaching.com/spiral/ 


Contribute to an episode: https://forms.gle/QwvBrZFbZXRdCjQv9 


Be a Guest: https://forms.gle/oiLVCbrydjzaK5pq5 


Music: Hide and Seek by Free Music https://soundcloud.com/fm_freemusic 

Music Promoted by https://www.free-stock-music.com

Creative Commons/Attribution 3.0 Unported License (CC BY 3.0) https://creativecommons.org/licenses/by/3.0/deed.en_US

Episodes: how to twenty-something

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