Day Job Secrets: Managing Your Side Hustle, Handling Trolls, and Bringing Your Own Weather [LNIM141 Transcript]

Should you tell your boss about your side hustle? What do you do when a coworker tries to sabotage you? And how do you maintain a positive attitude when life gets messy? In this episode, Mark tackles the intersection of day jobs and side businesses, shares a powerful mindset principle called “bringing your own weather,” and offers practical email marketing tips that can improve your open rates immediately.

What You'll Learn in This Episode

• How to think about your entrepreneurial life in seasons and adapt accordingly
• Why transparency with your employer about your side business is usually the smartest move
• How to handle workplace trolls who try to undermine your side hustle
• What “bringing your own weather” means and why attitude is a business strategy
• Three email marketing tips that can improve open rates and click-through rates
• Why accuracy in email personalization matters more than using someone's first name

Episode Summary

Mark opens with a reflection on how entrepreneurial life moves in seasons. As a part-time entrepreneur with kids in elementary school and college, his available work time shifts throughout the year. Summer means fewer school duties and more early morning hours at Starbucks working on his business. The key insight is that your current constraints are temporary. Whatever season you are in now will change, and you can adjust your strategy when it does.

The “Bring Your Own Weather” segment highlights Mark's friend Brady, a pharmacist who started HelpfulPharmacist.com to help everyday people understand pharmacy topics. Brady's blog caught the attention of Pharmacy Times, a major industry publication, which invited him to contribute articles. Brady was savvy enough to negotiate live backlinks to his blog and social media profiles, turning the guest posting opportunity into real SEO value. The broader lesson is that you should always be looking for opportunities to write for larger publications in your niche and always ask for live backlinks when you do.

The attitude principle behind “bringing your own weather” comes from Zig Ziglar: instead of letting your circumstances dictate your mood, decide to bring your own sunshine everywhere you go. Mark has practiced this for 30 years and believes it is one of the most underrated business strategies available. Your attitude, integrated over time, can be the difference between success and failure.

Mark then covers three email marketing insights from a Marketing Land article on email fundamentals. First, subject line length matters more than most marketers realize. Research suggests that very short or longer-than-average subject lines outperform medium-length ones because they stand out visually in a crowded inbox. Second, front-loading a link in the first few words of your email's opening paragraph can significantly increase click-through rates because that is where the eye naturally lands. Third, accuracy trumps personalization in email. If your list contains bogus names, missing names, or misspellings, using a generic greeting like “Hey” is better than displaying incorrect personalization that erodes trust.

The main segment addresses a real situation from the Late Night Internet Marketing community. Phil, a listener, has a side business teaching engineering online that is closely related to his day job. His employer knows about it and supports it, but a jealous coworker has been complaining to management. Mark offers a framework for handling this situation that applies to anyone with a side hustle adjacent to their day job.

First, if your side business relates to your day job in any way, proactively tell the people you trust at your company. Enlightened employers will appreciate that you are building industry credibility that benefits the company. Second, never work on your side business during your day job. Do not even leave the impression that you are using company resources or time. Third, when dealing with a workplace troll, do not feed the troll. Thank them for their input, analyze whether there is any useful data buried in their criticism, and move on. Fourth, check in with your boss to make sure you are still on the same page. Acknowledge that the situation might be causing them inconvenience and ask how to resolve it together. Fifth, be prepared for any outcome, including the possibility that your boss asks you to choose. If that happens, it is better to know early so you can plan your next move on your timeline rather than being blindsided during a layoff.

Mark closes with a personal anecdote: a manager at his company called him for help writing a job posting headline, having heard Mark talk about copywriting on the podcast. Management was listening, and they were fine with it. The goal is to reach the point where your side business outgrows your day job entirely, like Scott Adams did with Dilbert while working at AT&T.

Key Takeaways

• Your entrepreneurial life moves in seasons. Optimize for the current season and plan for the next one.
• If your side business relates to your day job, be transparent with your employer. Most will support you.
• Never work on your side business during your day job. Keep a bright line between the two.
• When dealing with workplace trolls, do not engage. Extract any useful data from their criticism and discard the rest.
• Check in with your boss proactively to ensure you are still aligned
• Guest posting on larger publications in your niche is a proven SEO strategy. Always negotiate for live backlinks.
• Your attitude is a business strategy. Bringing your own weather means choosing positivity regardless of circumstances.
• Email subject line length, front-loaded links, and accurate personalization all impact email performance

What's Changed Since This Episode

Mark recorded this in June 2017, and the relationship between day jobs and side hustles has shifted dramatically since then.

The side hustle economy has become mainstream. In 2017, having a side business was still somewhat unusual and could raise eyebrows at work. By 2026, surveys consistently show that over 40% of Americans have some form of side income. Remote and hybrid work arrangements have blurred the boundaries further, making the separation Mark advocates even more important. Many companies now have explicit policies about outside work, so checking your employee handbook or employment agreement is an essential first step before having the conversation with your boss.

The “creator economy” has normalized online businesses. Platforms like YouTube, Substack, Teachable, and Gumroad have made it common for professionals to monetize their expertise online. Phil's situation of teaching engineering online would barely raise an eyebrow at most companies today. In fact, many employers now actively encourage employees to build personal brands because it reflects well on the organization.

Email marketing best practices have evolved. The subject line insights Mark shares still hold, but the landscape has changed. Apple's Mail Privacy Protection, introduced in 2021, made open rate tracking unreliable for a significant portion of email subscribers. Click-through rate and conversion rate are now the primary metrics to optimize. The advice about front-loading links and avoiding inaccurate personalization remains sound regardless of tracking changes.

Guest posting for SEO remains effective but requires more sophistication. Google has become better at identifying and devaluing low-quality guest post links. The kind of genuine, value-driven guest posting Brady did with Pharmacy Times is exactly what still works. The key is contributing to publications that are genuinely relevant to your expertise, not buying placements on random blogs for link juice.

Resources Mentioned

• HelpfulPharmacist.com — Brady's pharmacy blog
• PharmacyTimes.com — industry publication
• 12 Email Marketing Fundamentals to Master (Marketing Land)
• LNIM141 Show Notes — Day Job Secrets

Related Episodes

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

• LNIM141 — Day Job Secrets (companion show notes)
• LNIM136 — Procrastination Tips: Overcoming Fear
• LNIM140 — How To Get Started Online

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.