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You’ve made the decision: you want to explore overemployment. But there’s one big question left to answer: What kind of second job should you take on?

This isn’t about chasing any extra paycheck—it’s about finding the right fit that lets you earn more without burning out or blowing your cover.

Fit your second job around your current schedule

Ask yourself how much time flexibility you have in your current role. Does your first job give you unstructured or low-demand time during the day? Are your meetings and deliverables predictable—or constant? How much mental focus does your current role require?

Your second job should fit around the first, not compete with it. That usually means choosing roles that are asynchronous, results-driven, not time-tracked, low-meeting, and internal-facing.

Next, think about your skillset. Look for jobs that use the same strengths but require less energy. You already know how to do the work—now do it twice, more efficiently. For example, if you’re a software engineer, find a second dev role with minimal meetings or maintenance tasks. If you’re a marketer, take a contract or internal role focused on execution—not strategy. If you’re in ops or admin, find a backend support role that values structure and autonomy. Stick to what you already do well—but with less overhead.

Lower Visibility

Visibility is a dealbreaker. Your second job should be the one that has fewer live meetings, involves fewer cross-functional teams, has a longer leash on deadlines, and doesn’t require public-facing work like client calls or content tied to your name. Internal roles (like operations, engineering, QA, or analytics) are usually safer than client-facing or leadership positions.

Your second job should be one that:

• ✅ Doesn’t require public-facing work (like sales, client calls, or content tied to your name)
• ✅ Has fewer live meetings
• ✅ Involves fewer cross-functional teams
• ✅ Has a longer leash on deadlines

Finding the right job title

Job title matters greatly. Some roles are naturally more OE-friendly. Look for titles like:

• Product Specialist (Internal)
• Backend Developer
• Operations Associate / Manager
• Analyst
• Data Engineer
• Content Implementer / Copy Editor
• CRM Admin
• Automation Specialist

Avoid jobs that have:

• 🚫 Daily standups or excessive video calls
• 🚫 A constantly active Slack/Teams presence
• 🚫 Heavy collaboration or leadership responsibilities
• 🚫 Time tracking tools (Hubstaff, Time Doctor, etc.)
• 🚫 Any kind of personal branding or public contribution tied to your name
• 🚫 Titles like Lead, Senior Manager, Director, or anything that signals visibility, strategy, or decision-making.

Workstyles Compatibility

If your primary job is fully remote, you already have an edge from location independence, fewer interruptions, and more opportunity to manage your own hours. In contrast, if you’re hybrid or on-site, stacking a second job becomes trickier. You’ll need to find roles that are 100% remote, and flexible enough to work around your in-office days, and ensure you have a quiet space to work the second job in case you need to be in office for the first job. Ideally, both jobs should be remote—this gives you the breathing room and privacy that overemployment depends on. Hybrid plus hybrid? That’s high-risk. On-site plus remote? Possible, but only with strong time autonomy and zero visibility crossover. Read my Day In The Life: Remote + Hybrid Workstyle testimony to find out how I managed two jobs with these workstyles.

The best second job is the one you can do without being noticed, without extra stress, and without tipping off your first employer. You’re not here to climb—you’re here for the cash flow. So ask yourself: Does this job pay me… or expose me? Choose wisely.

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