Who Really Needs to Know?

When you’re overemployed, one of the most important strategies isn’t found in a time management tool or clever automation trick. It’s found in silence and discretion amongst your friends & family.

Welcome to the Circle of Trust. Keeping it as small as possible (or even nonexistent) can make or break your overemployment success, not to mention reduce your paranoia about who might spread the word.

“Three may keep a secret, if two of them are dead.”

~ Benjamin Franklin

Why the Circle of Trust Matters

Overemployment is not illegal, but it is highly sensitive. The more people who know you’re working multiple full-time jobs, the higher the chances of it slipping, either by accident or intention.

Your “Circle of Trust” is the group of people who know about your dual work life. For most overemployed professionals, this circle is either tiny or nonexistent—and that’s by design.

Personally, I can count the number of people within my Circle of Trust over the years on one hand: my spouse, my parents, and my spouse’s parents. These are the people I trust inherently and know that they will never break. That’s right – I didn’t mention that my children are in on this secret too. My recommendation is don’t tell your children, as you never know if they will go to school one day and mention something in passing to their friend, who may tell their parents.

Who’s in—and Who Should Stay Out

✅ Who might belong in your Circle of Trust:

• Your partner/spouse – If they share financial or emotional bandwidth with you, transparency may be necessary (and healthy)
• A SUPER close friend – one that you trust with your darkest secrets, has a history of proven discretion, and is not connected to your professional world.
• A financial advisor, like tax professional or mortgage broker – Someone who helps you plan financials, secure loans, and protect your income legally.
• Other overemployed peers (anonymously) – Only in safe, anonymous communities where sharing strategies is common.

🚫 Who should absolutely not be in your Circle:

• Your children if they are younger & can’t discern facts from need-to-know facts, unless they are old enough (use discretion)
• Coworkers, managers, ANYONE from either job
• Industry peers or associates
• Most of your friends
• Anyone who can’t separate “interesting” from “dangerous”

The Risk of Oversharing

Even casual comments like “I’ve got a lot going on lately” or “I’m juggling more than I should” can invite questions. And once someone starts asking questions, it’s not long before they start connecting dots.

Trust isn’t just about loyalty; it’s about risk exposure.

One slip in a conversation, one screenshot sent to the wrong person, one LinkedIn post from a curious ex-coworker, and your whole second-income system could unravel.

If you have trouble deciding who should know or not, go by this one principle: If someone doesn’t need to know, they don’t.

This doesn’t mean living in fear—it means living with intention. You’ve built something powerful. Protect it.

You don’t owe anyone an explanation for how you manage your time, earn your income, or design your life—unless they’re directly impacted or essential to the operation. So ask yourself before sending your applications for that second job: who would be in your circle and are you sure they belong there?

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