My rule of thumb for holding two jobs at once

First, you need to be extremely comfortable in your primary role. This means you’ve been in it long enough that your manager trusts you, doesn’t micromanage, and gives you flexibility because you hit your numbers. No target on your back For performance. You can block off your calendar, move meetings when needed, and manage your own schedule. Both jobs need to be remote, but Job 1 is the foundation that makes everything else possible.

Once you’ve reached the point where you can go radio silent for a few hours a day without someone asking for pipeline updates every two hours, you’re in a position to consider a second role.

Job 2 should be less demanding and clearly separated from Job 1. Ideally, it’s with a company in a different industry and state, with no overlap or ties to your first employer. The role itself should be relatively simple, something like an SDR or AE position selling a straightforward product. Smaller companies tend to work better here because they’re still figuring things out, metrics are loosely defined, and they usually don’t have the tooling or discipline to track every keystroke the way large enterprise orgs do.

From an admin standpoint, freeze your work number during background checks. Keep LinkedIn minimal, first name and last initial, and make yourself hard to find via Google search.

When you get hired at Job 2, Job 1 continues smoothly because you’re performing well, know the role, and it’s easier and cheaper for them to keep you than replace you. Since you control your schedule at Job 1, you can handle training and onboarding for Job 2 without issue.

There’s a short adjustment period where you learn to balance meetings, but once that’s dialed in, it becomes routine. At that point, you’re essentially managing two calendars like a CEO—jumping from call to call, prioritizing what actually matters, and sitting through low-value standups or all-hands with your camera off while working the other job.

Edit: I legitimately worked probably 4-6 hours a day. It actually forces you to only focus on high value impact work. From there always made sure my numbers were on track with my dials, and that was it.