Juggling Two Jobs: The Good, The Bad, and The How-To

Andrew Bush
ILLUMINATION
Published in
5 min readApr 26, 2024
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Imagine juggling two full-time jobs from your couch, in your pyjamas. Sounds wild, right? Well, welcome to the world of overemployment, where folks are doubling down on remote work to stack up the cash and bulletproof their careers against the unpredictable job market whirlwind. This trend is like the ultimate work-from-home level-up, especially popular among tech wizards, finance gurus, and product development ninjas.

Why Double the Trouble?

At first glance, the idea seems to scream “Show me the money!” with people aiming to supercharge their bank accounts. In the unpredictable saga of today’s job scene, especially in the high-tech playground, having two gigs is like holding a golden ticket to financial security land. But, oh boy, it’s not all rainbows and unicorns.

The Twist in the Plot

Imagine trying to spin two plates on sticks, one in each hand, while walking a tightrope. That’s what balancing two full-time jobs feels like. Burnout becomes your shadow, productivity might take a hit, and your job performance? It could be unstable, and there’s also the ethical issue. It becomes problematic if your jobs conflict or if you’re getting paid twice for the same time.

The Legal Labyrinth

Exploring the legal complexities of having multiple jobs is like trying to navigate a maze without being able to see. It’s all about the nitty-gritty of your job contract. Might want to check the fine print for anything about being exclusive, avoiding conflicts of interest, or promises of your undivided attention. Getting caught in a second job could spell drama, especially if it’s with a competing team in the same league. Yikes!

A Personal Adventure

Here’s a little story from my own adventure book. A couple of years back, I discovered one of my team members had a second full-time job. My first reaction? I felt surprised, somewhat annoyed, and perhaps a bit envious. We were paying him well, and apparently, so was his other gig.

Instead of showing him the door or dragging him to court, we kept him around. Why? He was nailing his job. If it ain’t broke, don’t fix it, right? But this saga opened my eyes. I was surprised to learn that our lead in automated testing, a key player in our squad, could ace two jobs and still outshine folks juggling just one.

I thought he was just a one-off wizard. Then, data engineers began confessing in interviews that they were on the hunt for a second full-time rodeo. My jaw dropped. “Wait, what? But our projects need you all in,” I’d say, thinking about the clashes with timing, calls, and meetings. “No biggie,” one quipped, “been there, done that, got the T-shirt… and a glowing reference from my other boss!”

If it works — don’t touch it

World, where are we heading? I took the contact, though, and after a chat with his former chief (yep, our competitor), I discovered their whole band was playing the over employment gig. And guess what? It was working.

That lightbulb moment got me thinking: If tech stars can manage this double-header and still be the top performers, they’re onto something. These folks must be super organized and mega efficient.e. We need more players like this on our team.

I’ve drawn several conclusions from hiring moonlighters and allowing my employees to moonlight.

Why this happens

Honestly, the term “full-time” isn’t always spot-on. The main problems usually come from how a company organizes its work or from some of us getting really good at looking busy — yep, I’ve been there too. And the idea of getting a second job instead of just scrolling through Facebook? Never really thought about it, maybe because I was too lazy.

The simple truth is that no job contract can stop someone from pretending to work more than they are or from keeping a second job secret. Without actually watching closely, managing two jobs can easily go unnoticed. This situation makes it clear why some people feel the need to look for more work.

Productivity considerations

Handling work that doesn’t spread out evenly can be tricky. In an ideal world, one job would give you a steady amount of work to balance out the surprises from the other job. But if both jobs are unpredictable, it’s tough for both the worker and their bosses, especially when busy times overlap, making everything more stressful and harder to manage.

Here’s another interesting point: starting a side job or project can actually make someone get more done, helping both their main job and the side one. This approach leads to new ideas and keeps your brain working on problems in the background, just like Daniel Kahneman talks about in “Thinking, Fast and Slow.” Usually, the side job ends up benefiting more, maybe because it’s new or because the person focuses more there.

Employer’s perspective

The chance of being tempted away by the side job is a real thing, showing bigger problems in how companies keep their employees happy rather than how loyal an employee is. The world of work changes fast, and if a company doesn’t keep up with what their employees need, they might lose them to someone else. Even though it’s a bit iffy, trying to lure employees away happens a lot in business.

For me, running a small IT agency, this whole experience has been quite eye-opening. It’s important to spot these multitasking people when we’re hiring and within our current team. They might not be upfront about juggling jobs at first. But when they see we’re cool with talking about and doing this, they usually open up. These employees are generally very organized — they have to be. Those who aren’t as organized often struggle and can really have a hard time. That’s exactly why it’s so beneficial to bring in people who can handle working more than one job.

Epilogue and Wisdom Nuggets

This journey through the overemployment galaxy taught me a few things. First off, not every “full-time” role demands your soul. Sometimes, it’s about smart management or, let’s face it, looking busy. And those job contract conditions? They might not be the shield you think they are against double-duty shenanigans.

My main takeaway? This whole over employment thing can work wonders, given the right stars align. It’s all about finding those superstars who can handle the heat, deliver the goods, and maybe, just maybe, redefine what it means to work full-tilt.

So, if you’re eyeing that over employment horizon or already surfing the twin-job wave, remember: it’s a wild ride, but with the right balance, the sky’s the limit. Just be sure to wear your ethical hat and keep an eye on that legal compass. Happy juggling!

Interested in diving deeper into the worlds of Data, Startups, work trends and my personal journey? Follow me for exclusive insights, stories, and lessons learned along the way — click here

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Andrew Bush
ILLUMINATION

Founder & CEO at A17 Technologies| 15+ years in Data & AI | Co-Founder at Mcookie | Occasional speaker and amateur cyclist