Should You Tell Your Boss About Your Side Hustle? (Big Career Mistake)

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.

📩 Got something on your mind?
Write in to the “Let’s Talk About It Letter” at: Talkyashitdaily@gmail.com

🎥 Watch Full Video on YouTube
https://www.youtube.com/@Talkyashit

👉 Hit that like, comment, and subscribe — and let’s talk our sh!t!

 New Episodes every Monday, Wednesday & Friday at 6AM! 

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.

Transcript

Reading The Listener’s Letter

The Case Against Disclosing Side Hustles

How Employers Perceive divided Priorities

Side Hustle To Main Hustle Path

Closing Thoughts And How To Write In

SPEAKER_00 0:04

You, you, and you. Oh, did I say you? Yeah, you too. Now let's talk about it. What up, what up, what up, what up? It's your boy Big Slick, and welcome to Talk Your Shit. Now check it out. We got another great show for you today. But first, I want to give a shout out to my audience. Whether you're at home, at work, in your car, all the truck drivers on the road, I appreciate you tuning in. Now let's get into it. I got a letter in. I'm gonna give you my raw, uncut, unfiltered, honest opinion about it because that's what the fuck I do, man. Let's check it out. Let's jump right into the letter. Should I tell my new job about my side hustle? Should I tell my new job about my side hustle? I had to say that shit twice. No, why the fuck would you do that? What's your new job got to do with your side hustle? I would definitely not do that. That's the that's some dumb shit. Don't do that. And I'm gonna tell you why a lot of people be like, oh no, that might not be dumb. You should tell them in a shut the fuck up, it's my show. No, you shouldn't tell them because this is what's gonna job is gonna look at it like, hold up, he's making money a different type of way, right? So now they're gonna feel in a way. First of all, they might not hire you because they're gonna think, like, all right, how you gonna prioritize this? Are you gonna put that side hustle before us? Is that gonna interfere with your work here? Right? So now they're looking at you funny. So, no, I wouldn't tell them about my side hustle. I will keep that side hustle exactly what it is for now. That side hustle on the side, the job has nothing to do with that, you know. I'm saying at all. You know, I mean, as long as you work in your scheduled hours, right? And you're doing your side hustle outside of your work hours. Why should your job know about that? It's none of their business. Do your job disclose everything with you? Nope, they do not disclose everything with your ass. You find out the day you come into work, you know what I'm saying? You find out your hours cut the day you look at the motherfucking schedule, you find out you gotta work Christmas when you look at Christmas, bro. It's like they don't give you no heads up. Why would you tell them about another way you're making money? I would not do that at all. You know what I'm saying? I I would definitely not do that at all. Keep that separate. Do not tell your job about no other money that you're making on the side. Because again, this is gonna happen. So let's say, for instance, you did tell a job about your side hustle, right? Okay, so you they know about your side hustle. Cool. You call out one day, or you gotta leave early one day, something like that, dealing with attendance. The first thing this job is gonna fucking expect it, suspect is that you are doing your side hustle. Anything with missing that job or coming late or have or have to leave early, they think you're gonna go make that money on the side. That's another reason why you shouldn't tell your job about a side hustle, and they're gonna handle you a different way. They might not act like they are, but they're gonna handle you a different way because you got another means to make money. So they're looking at it like, yo, he don't fully rely on us, right? So we can't fully rely on him. This is how jobs look at you, man. You you people don't look at it like that, man. At a job, you're nothing but a production piece. If they can't get full production out of you, then they treat you a certain way. And you coming to the to the to the you know, to them saying you you making money a different way, and you got a side hustle on a job, that's how they're gonna treat you. They're gonna treat they're gonna treat you just like that. So, nope, I wouldn't tell them nothing about a side hustle, you know what I'm saying? And eventually, a lot of times, a side hustle can turn into a main hustle, you know. I mean, and I hope your side hustle do turn into a main hustle where you're getting your money, you know, be an entrepreneur and get it on your own, you know what I mean? But a lot of side hustles turn into a main hustle because this is how people start off. You test it as a side hustle first. You might not want to jump all the way out the window, you want to test and see how much money you can make off this side hustle first. Once you start seeing that money coming in, and you can make more money if you have more time to do the side hustle, then you can transition into making that your full time and getting that money, you know what I'm saying? But until then, fuck telling a job about a side hustle, man. Keep that shit pushing, keep keep that side money on the side, you know. I mean, don't mix it with this over here. They don't need to know nothing about that, you know. I mean, and keep it moving just like that, bro. Keep on getting that bread. You already know what it is, it's big slick. This has been another easy one, man. Don't tell your motherfucking job everything, don't do it, it's not worth it. Listen, anybody that's listening out there, if you want to be a part of the show, just send an email in to talk your shit daily at gmail.com. That's talk your shit daily at gmail.com. You can send a letter in just like this. You know what I'm saying? It might make it on the show. You never know. And if that's too much for you, just put it down in the comments what you want me to discuss, whatever topic you got or whatever. Shoot it down there in the comments, and that might make it to the next show. You already know what it is, it's big slick and I'm out.