Day Job Secrets: Should You Tell Your Boss About Your Side Hustle? [LNIM141]

Day job secrets can be hard to keep. This week Mark looks at a real situation from listener Phil, whose side business is closely related to his day job and whose coworker has become a workplace troll about it. Mark offers a practical framework for navigating the tension between your employer and your entrepreneurial ambitions, plus unusual email marketing tips and the powerful concept of “bringing your own weather.”

What You'll Learn in This Episode

• Whether you should tell your boss about your side business and how to approach the conversation
• Why enlightened employers actually benefit when employees build side businesses
• The number one rule for keeping your day job and side hustle separate
• How to handle a coworker who tries to undermine your side business
• Why “bringing your own weather” is one of the most underrated business strategies
• Three email marketing tips that can improve your open and click-through rates

Episode Summary

Mark tackles a question that comes up constantly for part-time entrepreneurs: should you tell your boss about your side business? The answer, especially when your side business relates to your day job, is almost always yes. Transparency with people you trust at your company protects you and builds goodwill.

The episode uses Phil's real situation as a case study. Phil teaches engineering online, which is adjacent to his day job expertise. His boss knows and is fine with it, but a jealous coworker has been complaining to management. Mark's framework for handling this: do not feed the troll, check in with your boss proactively, and be prepared for any outcome. The worst scenario is being blindsided. Having the conversation early puts you in control.

Mark also covers the concept of “bringing your own weather,” inspired by Zig Ziglar, and shares email marketing insights about subject line length, front-loaded links, and why accuracy matters more than personalization.

Key Takeaways

• If your side business relates to your day job, tell the people you trust at your company
• Enlightened employers benefit when employees build industry credibility on the side
• Never work on your side business during your day job. Keep a bright, clear line between the two.
• When dealing with workplace trolls: thank them, extract any useful data, and move on
• Check in with your boss proactively to stay aligned and avoid surprises
• Attitude integrated over time determines success. Choose to bring your own weather.

What's Changed Since This Episode

The side hustle economy has gone mainstream since 2017. Over 40% of Americans now have some form of side income, and many companies have explicit policies about outside work. The creator economy has normalized monetizing professional expertise online. Phil's situation of teaching his field online would barely raise an eyebrow at most companies today. Mark's advice to be transparent and keep a clear separation between day job and side business remains the safest and smartest approach.

Resources Mentioned

• PaidInsights.com — Ross's podcast on paid search strategy
• 12 Email Marketing Fundamentals To Master (Marketing Land)
• Rate Late Night Internet Marketing on Apple Podcasts

Related Episodes

If you found this episode helpful, you might also enjoy:

• LNIM141 Transcript — Day Job Secrets Deep Dive
• LNIM140 — How To Get Started Online
• LNIM136 — Procrastination Tips: Overcoming Fear

Listen and Subscribe

Listen to Late Night Internet Marketing on Apple Podcasts or subscribe at latenightim.com/internet-marketing-podcast/. Have a question for Mark? Call the digital recorder at 214-444-8655 or drop a comment below.