1794: Should You Tell Your Boss About Your Side Hustle by Nick Loper of Side Hustle Nation on Entrepreneurship
Optimal Work DailyAugust 29, 2025
1794
00:09:06

1794: Should You Tell Your Boss About Your Side Hustle by Nick Loper of Side Hustle Nation on Entrepreneurship

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Episode 1794:

Nick Loper explores the delicate decision of whether or not to disclose your side hustle at work, weighing the risks and benefits for both your career and entrepreneurial goals. He offers practical advice on navigating company policies, protecting your reputation, and ensuring your side project doesn’t jeopardize your main source of income.

Read along with the original article(s) here: https://www.sidehustlenation.com/should-you-tell-your-boss-about-your-side-hustle/

Quotes to ponder:

"If your side hustle is in a completely different industry and doesn’t compete with your employer, you’re probably in the clear."

"You don’t want to give your employer any reason to question your commitment to your job."

"The best thing you can do is to review your employment contract and understand what you’ve agreed to."

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[00:00:52] Keine Anlageberatung, die sich nicht mehr als Taboo verletzt. Keine Anlageberatung, wie HubSpot, auch immer aktiviert die Empowern zu starten, auf der Seite. Warum Menschen nicht zu sagen, dass ihre Boss über ihre Side Hustle ist? 1. Fear of Retribution Keine Anlage von Seite Hustlers fear, dass sie ihre Bossen würden eine Karriere Suicide werden. Sie werden zu denken, dass ihr Ihr Job zu denken. Sie kennen die Kulturelle, aber das war definitiv ein Ding in meinem alten Workplace, where people would start to get passed up for promotions

[00:01:22] if they were deemed less dedicated to the cause. Two, fear of judgment. Another common fear is having your boss pass judgment on your financial situation, especially if you're in a white-collar work environment. Are you so bad with money you need a side hustle? The questioning might go. And even if it's left unsaid, the perception might be there. That's unfortunately the conclusion that many employers will jump to, regardless of the fact that money is just one of many reasons why someone would start a side hustle.

[00:01:51] And three, fear of failure. If you share about your side hustle too early and it doesn't work out, will that make you look like a failure in front of your coworkers? All of these are valid concerns. Benefits of telling your workplace about your side hustle. While there are certainly some perceived risks of telling your boss about your side hustle, there may be some interesting benefits as well. One, leverage. The knowledge that your nine to five is no longer your only source of income

[00:02:21] gives you a bit more leverage when it comes to workplace negotiations. Does your boss really value your work? They might need to extend a higher salary or more flexible working hours to keep you motivated. Two, referrals. One surprising benefit of telling my boss about my side business was he started talking about it when we were out with customers. It was a little embarrassing because the website didn't look that great and didn't work amazingly well, but it became a topic of conversation. And if your side hustle is in a non-competitive industry,

[00:02:51] your boss is just one more potential referral source for new clients. For example, my wife does photography work on the side from her engineering day job. Over time, she's built up a reputation and has taken pictures for lots of her coworkers and their families. And three, respect. Finally, one benefit a lot of side hustlers experience is a newfound respect from their peers and managers. The percentage of people who want to start a business someday is much higher than the percentage of people who actually do.

[00:03:20] So there's a level of admiration for those who take the leap. You might start to hear comments like, good for you, or I had a business idea when I was your age, but never took action on it. On top of that, seeing the whole financial picture of a business from the CEO chair of your side hustle will probably make you a better employee at your day job. At least it did for me, until I quit. When you should come clean. One, if it's required. In certain industries,

[00:03:48] disclosing outside financial interests is a requirement. This is most common in defense, legal, and government jobs. Most agencies in the federal government will have an outside employment and activities page that spells out what you can and can't do outside of work. When in doubt, check with your HR department. Two, if your side hustle is public-facing. If there's a chance your boss will discover your side hustle on their own by Googling you or otherwise, I think it makes sense to be upfront about it. After all,

[00:04:16] you want to take ownership of the conversation instead of them making assumptions about what they find online. It could be as simple as, I've had a couple friends reach out for graphic design help, so I'm going to add that to my LinkedIn. And three, if there could be any perceived conflict of interest. Now, of course, you're not going to start a business in direct competition to your employer, but losing clients is a legitimate concern many bosses have. If your side hustle is in the same industry, make sure to explain how you're separating your business from your day job

[00:04:45] and honoring any non-compete contracts you may have signed, when you probably don't need to tell your boss. One, if your side hustle is in a completely different field. For example, I worked for a giant auto manufacturer and my side hustle was selling shoes online. There was no way the two roles could have been considered competitors. Two, if you're tapping into gig economy apps. With the rise of the gig economy and money-making apps, you probably don't need to tell work that you're moonlighting

[00:05:15] as an Instacart shopper or Airbnb host. Three, if your side hustle is super common. Your employer probably doesn't need to know if you're selling stuff on eBay or investing in real estate. Even though these side hustles do take time, they're not really a perceived threat because they're so commonplace. And four, if you're just getting started. I don't think there's much sense in telling your boss about every little side project. And frankly, they probably don't care until you start to see some traction. They don't need to know

[00:05:45] every detail of how you spend your off hours. Whether you were building a bird feeder for your backyard as a hobby or building a website for your new side hustle, it doesn't really matter. No employer owns you 24 hours a day. General rules for side hustling and workplace success. One, don't use company resources for your private gain. That means no using your workplace-issued laptop or phone for your side hustle. When I was traveling for work in my old job, I'd carry my work laptop and my personal laptop

[00:06:14] so I could work on my business when I got to the hotel. Two, don't use company time to build your business. Whether you're hourly or salaried, consider your work hours 100% dedicated to your employer. Hopefully, you're left with another 16 hours in the day and all day on the weekends to put toward your side hustle efforts. And three, don't steal clients. Your reputation is worth more than the potential legal ramifications here.

[00:06:45] You just listened to the post titled Should You Tell Your Boss About Your Side Hustle? by Nick Loper of SideHustleNation.com And thank you to Nick for letting us share his post today. Nick retired from corporate America at the age of 25 and is now a full-time entrepreneur involved in a variety of projects. He's also the host of the podcast The Side Hustle Show, which is for part-time entrepreneurs looking for actionable tips to start or improve their businesses. And it is a great podcast, I can tell you that, and usually in the top charts of business

[00:07:15] in Apple Podcasts, and definitely worth checking out. The blog is great too, of course, and you can come by SideHustleNation.com for a lot more and also to show your support because our contributing authors always appreciate it. But that's it for me today. That's all I've got for you. Hope you enjoyed the post and I will be back with you tomorrow where your optimal life awaits.