The Two-Jobs Guy and Why Nobody Tells Their Manager Anything Anymore

Saw a thread on r/auscorp this morning that stopped me mid-scroll. Someone posted that their colleague is quietly working two full-time remote jobs, software engineering gigs, no overlap in required hours, both employers apparently fine with it (or at least not actively looking). The original poster wasn’t outraged. If anything they sounded a bit envious, which, fair enough.

What got me wasn’t the two-jobs part. People have moonlit forever; my old man used to do tax returns on the side every July while holding down a factory job. What got me was the reflexive, near-unanimous reaction in the comments: don’t tell anyone, especially not your manager. Dozens of people, in a thread about a colleague who’d apparently told the whole office, saying some version of “why would you ever disclose this, they’ll just say no.”

That’s the bit I keep turning over. Not the hustle. The trust, or the complete absence of it.

I’ve been doing hybrid IT work for a long time now, long enough to remember when “working from home” meant you’d rung in sick but weren’t quite sick enough to not answer emails. The deal used to be reasonably simple: you did the work, you turned up when asked, and in exchange there was some baseline assumption that your employer wasn’t actively trying to catch you out. That assumption has been eroding for years and remote work just put a floodlight on it. Now it’s keystroke loggers, “mouse jiggler” panic stories, RTO mandates justified by vibes rather than data, and a workplace culture where the default posture, on both sides, is suspicion. The two-jobs guy isn’t an aberration. He’s a symptom of a system where everyone’s quietly decided the social contract is optional and it’s every employee for themselves.

And I get why. I’ve sat in enough restructuring town halls dressed up as “exciting changes to our operating model” to know that loyalty, as a one-way street, is a mug’s game. If a company will make you redundant via a generic email on a Friday afternoon after you’ve given them a decade, I’m not going to pretend I blame anyone for keeping a second income stream quiet. There’s a tension here I’m not going to pretend to resolve: I think honesty at work matters, and I think the expectation of total disclosure from one side while the other side offers none in return is a bit rich.

What strikes me as properly Australian about this particular discussion, if I can even make that claim, is the pragmatism in the comments. Nobody moralised much. Nobody said “that’s fraud, dob him in.” Mostly it was logistics: check your contract, watch for exclusivity clauses, don’t flex it at the pub, and for god’s sake don’t tell your manager unless you fancy a very short conversation. It’s not cynicism exactly. It’s more a tired, accurate read of incentives. People aren’t lying because they enjoy it. They’re lying because the alternative is handing someone a reason to say no, and then you’re both worse off, except they’re not the one with a mortgage.

I don’t have a neat answer for this one. Working two jobs undisclosed probably is a breach of most standard contracts, and if it goes wrong it goes wrong fast and all at once. I also think an economy where people feel they need two full-time jobs just to get ahead, or just to feel secure, isn’t a healthy one, and the solution to that isn’t “work harder and keep quiet about it,” it’s wages that track inflation and housing that doesn’t eat half your pay before you’ve bought groceries. Both things can be true. The bloke running two jobs at once isn’t the problem. He’s just the most visible symptom of one.