Episode
Ep. 148 The reality of being self-employed in your twenties
- Podcast
- how to twenty-something
- Published
- Apr 13, 2026
- Duration seconds
- 1179
- Processing state
not_requested- Canonical source
- https://jessdiamondcoaching.com/podcast/entrepreneurship
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Summary
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: Expect 3–5 years of hard work before your business feels stable or sustainable Set a clear timeline and savings goal, because dreams without deadlines stay dreams Know your backup plan before you dive in Your money will leave your account faster than it’ll go in Social media shows the aesthetic, not the years of survival mode underneath Helpful Resources: Let’s chat: https://calendly.com/coach_jessdiamond/success Email me: [email protected] 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