Why Employees Get Away With Secretly Working Multiple Jobs

A growing number of employees – up to 5 percent of the tech workforce – are secretly working at two jobs, or three or more. Some of it is side hustle, sure, but an ever-increasing number of these folks are working two or more full-time jobs for two or more companies. 

And it’s becoming harder to keep it a secret.

I imagine their workday looks a lot like that cliche sitcom storyline when the protagonist accidentally schedules two dates with two different romantic interests on the same night at the same location. For what it’s worth, The Office did it the best in “Casino Night.”

It invites the question: How long can you keep that up? If television has taught us anything, it’s that this scheme always ends in sadness for everyone involved.

The thing is, CEOs and HR departments have sensed the overemployment trend for years, but they have a very hard time sniffing it out, even when it’s taking place right under their noses. I’ve witnessed it in my own companies, and I like to think I’m the kind of leader who is down with the kids and their K-Pop.

But in larger megacaps, where every employee is a number and their productivity is a tiny percentage notch in a chart, well, a lot of the time leadership doesn’t even know their names, let alone how many jobs they might be working. And middle management just wants to make sure those employees are getting more notches of productivity out of AI.

Well, they’re productive with AI all right. That’s actually part of the problem. In fact, the company might even be employing one of their AI agents. And that scares the holy hell out of them. 

“We didn’t figure out ‘Jared’ was an AI until we went to his desk and discovered that he was two pillows stuffed into an overcoat. We just thought he had a thing for floppy hats.”

Look, I’m not here to out anyone. I’m not here to judge. I’m not here to fix the glitch.

I’m just going to tell you the real reason why tech employees have multiple secret jobs.

It’s the Money. Or Is It?

The first and most obvious answer to any question like this is money. Always.

But like any obvious answer, it’s never that simple.

In this latest incarnation of the overemployment trend, the motivation might just be revenge. In fact, I believe it’s more like a pre-emptive strike against the treachery that lies ahead in a career in tech.

Now, this article from Fortune points to a Reddit community (shocker!) to which a lot of these folks come to get advice, talk leads, and discuss the tactical steps for getting away with working two or more jobs at once.  

And let’s not dive into clickbait. A lot of these jobs are being held down by legit independent contractors who are up-front about their free agency. But I’ll remind you that the concept of job is evolving, mostly because employers throttled loyalty to near zero, meaning pretty much all jobs can be considered contract jobs now.

A few years into the loyalty mess, we find the more ambitious among the tech talent making these pre-emptive strikes. Why put all your income eggs into one basket when your boss can light that basket on fire and replace you with a chatbot on a whim, then brag about their strategic productivity and efficiency gains to the board and in the press?

Nah, it’s not just the money. It’s about getting their bag while they can. And when that’s the endgame, the means aren’t always … shall we say, ethical? 

Use AI to Lie, Cheat, and Steal

My “favorite” line from the that Fortune article:

“Interviews should be gamified. Lie, cheat, and steal. Use AI. Tech interviews are 80 percent an opportunity for some blowhard at the company to impress their skill on you. With AI, the walls of tech are coming down.” 

The gall. The audacity. The sheer … bleeping … hubris. Where did these kids pick up this kind of behavior?

“From you, Dad, all right? I learned it by watching you!”

Yeah, I’ve used that joke before, but it works so well in this instance.

Leadership and management dropped ChatGPT on every desk and tacitly told employees to figure out how to use AI to work themselves out of a job. This went one of three ways:

1. The technically illiterate and fearful poked around fearfully until their productivity went to zero. Seeya!
2. The go-along-to-get-along crowd literally made shit up and performed AI productivity theater. Some got caught. Most didn’t. They’re still winning little fake AI productivity Oscars.
3. Some of the people who actually know tech started figuring out how to use AI to apply for, interview for, and even work additional jobs while also using AI to look hyper-productive for their current employer, who mandated they use AI. 

I mean, I’m an original AI platform inventor from 15 years ago, and when I got a hold of these new tools in the 2020s, the first thing I did was write scripts and hook them to chatbots to automate any stupid, mindless thing I had to do more than twice in a day.

How many stupid, mindless things does your average corporate employee do in a day?

I mean you put the candy right there in front of them and told them not to touch it.

So 95 percent of these workers were loyal and obedient, but 5 percent of them are working for someone else while they’re working for you, and filling their bags.

Here’s why that 5 percent is about to go way up.

We’re All Contractors Now

This is what happens when you tell workers they’re disposable.

First, they get mad about it. 

Then, they start acting like it.

Then they get good at it.

And that’s where we are right now: “How do I get my bag before they fire me?”

They will get fired. I mean, Michael Scott wound up alone at the end of the night (or did he?). Plus, it’s straight-up unethical. It’s a form of theft, according to every CEO it’s ever happened to. But that doesn’t bother the multi-jobbers. They’re expecting to be fired at some point. It’s the very reason why they’re setting up these little insurance policies in the first place.

There are, according to the Fortune article, 430,000 of them on Reddit and, also in that article, it’s clear that firing them doesn’t even stop them from doing it. They’re throwing around figures like $500K working three to five jobs at a time. Lose one. Get another.

If that last sentence didn’t trigger a little explosion in your brain – hey, maybe you should think about a second job, you know, just on the side or whatever – then you’re not human. And even if you have zero empathy, I’d ask you to at least consider human nature, and why this is all happening in the first place.

Join the rebel alliance of over 10K tech professionals on my email list. You keep living the dream, I’ll keep making the jokes.