Should You Tell Your Boss About Your Side Hustle? (Big Career Mistake)
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Big Slick here 👊 Got a story or need advice? Text me now — might make it on Talk Ya Sh!t! 🎙️💯
Should you tell your boss about your side hustle—or keep it quiet? In this episode of Talk Ya Shit Daily, Big Slick breaks down the real risks of workplace transparency and why honesty can quietly cost you hours, trust, and promotions.
A listener writes in asking whether they should disclose a side hustle to a new job. We unpack how managers interpret “divided priorities,” why side gigs change perception even when performance is strong, and how one conversation can shift your schedule, evaluations, and future opportunities.
This episode lays out a smart, strategic approach to protecting your income and career. You’ll learn when disclosure is necessary, how to avoid conflicts of interest, and why privacy is often your strongest leverage. We cover contracts, HR optics, boundary-setting, and how to build your side hustle without sabotaging your main job.
If you’re working a 9–5 while building something bigger, this is required listening. Don’t let oversharing limit your growth.
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Write in to the “Let’s Talk About It Letter” at: Talkyashitdaily@gmail.com
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Disclaimer: The views and opinions expressed on Talk Ya Sh!t Podcast are those of the host and guests. This podcast is for entertainment and educational purposes only and should not be considered professional advice. Always seek guidance from a qualified professional regarding mental health, financial decisions, or personal issues. The host shares personal experiences and opinions — take what resonates and always do what’s best for you.