How to Cheat on Your Boss as A Moonlighting Entrepreneur

Andy Gundel
Andy Gundel
11 September 2014 Business Insights, Tips and Tricks


Sometimes a common way to describe someone you’re attracted to is “cute”, “friendly” and “Sexy” and “I want you behind those doors!”. If that thing you pine over is your entrepreneurial dream, and you loathe your day job, then maybe a little nookie behind your boss’s back might be in order.

But how do you do it successfully without getting canned from your job like yesterday’s trash? Here are some smart side-hustle tips for your love affair without getting caught by your boss.

Use a virtual number as an “alias”

If you are still walking around with two cell phones in your pocket, you’re doing it wrong — unless you want people to think you have multiple rolls of pennies in your pockets, in which case, more power to you.

That said, when you have a new number that is routed by a virtual phone system to your cell phone, you’ll know if an unknown call is coming in for work, or for your own business, and respond as needed. It’s a great way to know when to “use the restroom” to take care of “business.”

Sound like a credible company

The last thing you want when you are at your day job is to hang up on customers calling your moonlighting business because you are at a meeting with your boss. To avoid that, set up a business phone system with a professional voice recording.

This makes you sound legit, rather than a fly-by-night gig, even though that’s what you really are!

Call in sick, strategically

Stay healthy, and use your sick days to run errands or go to events related to your own business or tend to your own customers.

Keep the love affair secret

After all, at work your side hustle is the love that thou shalt not speak its name! At least in the office. It’s important to not to communicate with your boss about this because generally he wouldn’t like the news that there is “another love” that being your entrepreneur hustle. Also it’s smart not to share it with co-workers too because sometimes they may get jealous which can lead to some serious, not-so-fun office politics working against you. Best to keep the secret between you and your side hustle love.

Dodge off your Boss at the office!

Like in a forbidden romantic relationship, it can be thrill to do things with the possibility of getting caught but getting caught by your boss is not the plan you need! Here are ways to avoiding disasters from happening if you are doing your business right at your office cubical as mentioned in LifeHacker’s How to Slack Off at Work (and Not Get Caught).

Make sure to have a handy mirror beside your desk to see your boss coming behind you. The mirror can give you heads up to minimize your browser. It also would help to minimize the brightness on your screen to ward off attention as you keep busy.

Of course you have to take caution and cover your tracks. As with all things, exercise discretion. If you get caught, maybe you need to read this post a little better!

In all seriousness, if you like your job or your boss, maybe you might want to try to nurture your moonlighting entrepreneurship in the evenings or weekends.

But if you hate your job, or your boss, the tips here might be just what the doctor ordered!

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