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Don’t Let Your Boss Become Your Side Hustle

by | Jul 4, 2022 | Entrepreneurs

A side hustle is a sexy idea.

(It can even cause me to wet my pants.)

Recently I had a revelation that knifed me in the head. A former colleague loves football and basketball.

What he loves about sport, bizarrely, is he’s obsessed with fairness. Making the world fair through sport is his passion. He gets to do it on the odd occasion when he umpires a football or basketball match.

He’d sell his left testicle to be closer to sports.

If you say his favorite football team’s name he can rattle off stat after stat. His face lights up. It goes tomato red. I hate football and yet, he makes me bloody excited about it too. Sport should be his side hustle. Yet it’s not.

I thought about why and then it hit me…

His boss is his side hustle.

When he plays back his weekend to me it sounds like this. “I finish doing spreadsheets and tracking user stories around 6–7 pm most nights. Then I sit down for a cold beer and get ready to study sports. Then the phone rings…”

That regular late-night phone call is what robs him of his dreams.

It’s his work boss aka his work wife. There’s always some surprise task that comes up — and only my former colleague can do it. Funny about that.

Instead of working on his side hustle after hours and on weekends, his boss has become his side hustle. His boss is his passion project, yet he doesn’t love his boss at all.

He’s a dry character that left his wife on the other side of the world after they got married. Every day he texts her, “I’ll be home soon honey.” He never goes home to her. Why? His dumb corporate job is his full-time side hustle.

His boss caught the job title virus early in his career and it obliterated parts of his marriage, his will to have kids, and all his spare time.

We’ve gotta carefully choose our side hustles. Not allow them to self-select us. Here’s how to ensure your boss doesn’t become your side hustle.

Create distance

Subtly hint to your boss about your views on work-life balance.

Make your side hustles known. Let them know when you currently work on them, and when you plan to work on new side hustles in the future. “I start around 6 pm each night. I love it. Shall I show you?”

A now less-confused boss will get the hint. Then they’ll pin their excess work on another donkey.

Leave on time

Warming an office chair in front of everybody else doesn’t make you more valuable to your employer.

That’s a myth. Quality output versus quality sitting will always get you further ahead at work.

Last year in my final corporate job (for this lifetime) I worked less hours than everybody else. Although I achieved higher sales results than everybody else in my department. Oh, and I worked 4 days a week so they had 20% more time to beat my results.

The time you leave the office creates a clear line in the sand. “This is when I work. This is when I don’t work and pursue my side hustles.”

Obviously there will be stuff that comes out of nowhere and has to happen at odd hours. That’s when you recalibrate. If I stayed back after work, I came in late the next day. Or worked from home aka slept in to start work later 🙂

Photo by Simon Humler on Unsplash

Don’t be on call (unless you’re a nurse)

On-call office jobs are a joke.

One evening at 11 pm I missed a phone call from my boss’s assistant. Because I go to bed at 10 pm. The next day my boss said “you missed an important meeting. Our IT systems went down.”

I asked the people who attended the meeting “what’d I miss champs?”

“Ahh nothing chief. We just jumped on a call and complained about IT for 2 hours. Hell, I tell ya.”

I don’t fix IT problems so knowing a system crashed at 11 pm was a useless exercise for me. I politely told my boss I couldn’t be on call like a nurse. I have family, a life, and need sleep.

Be prepared if you have a boss nanny, who wants you to be on call 24/7, to move on to another job. Most careers don’t need you to be on call. Bad bosses just like you to be because it strokes their fragile ego.

Me: “Nah mate. Not gonna happen your royal anus.”

Push back like a quiet badass

Bosses love to give us the motherload of all motherloads in terms of work.

The more work you do the smarter they look. So they get to collect more cash as a result of your potential lack of assertiveness.

I found a cool hack to protect my side hustle.

When they try to give you another mammoth task, politely say “could be difficult Chief with the current workload. Which task/project shall I deprioritize?”

Use family as a human shield

Bosses are suckers for family excuses. It’s all part of the politically correct, woke business culture we now all work in.

Use it to your advantage.

Take your sexy partner or those cute little kids and use them as human shields in the battle of workplace expectations. Let the work bullets hit their soft cheeks and don’t feel one bit guilty.

“Sorry good sir, you know I’d love to do that task for you but during these hours I’m tied up with the family. My wife would divorce me and hunt me down with an army knife and murder me while I sleep if I did that.”

“Think of the children” she’d say.

“You get it, right? Of course you do. That’s why you’re the best boss.”

If nothing works then do this

Okay, I realize for some of you that none of this may fly with your boss.

The bullet wounds are simply too deep. They’ve had you by the curly ones for too long, shackled to that cubicle life HR sold you as ‘the career dream of a lifetime.’

All you can do is try these suggestions and attempt to protect your side hustle time. After all, a side hustle is one of the most fulfilling things you can ever do. And for some, like me, your side hustle can replace your entire career forever.

But if none of these tips work, it’s time to get a divorce … from your job.

Go on LinkedIn. Hold up the white flag. Then start applying for jobs, chatting to recruiters, and networking your way to the next job.

The truth is most jobs will support your side hustles. And the employers who don’t are currently halfway through a slow death.

Protect your side hustle time. Don’t let your boss become your after hours and weekend side hustle.

If you let them, they’ll make you take your phone to bed.

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