How to Get Your Boss to Believe You Are Sick When You Want to Go to Vegas

A lot of people have been asking, “How do I convince my boss I’m sick so I can take a long weekend?” Well, that is a tough one, but a few tips I’d give you are:

1. If you’re going to lie to your boss, lie with class.

You need to make up a convincingly believable lie about how you are sickā€”the more plausible your story, the better.

You don’t want to come across as a half-baked liar. Your boss will think you are a wuss and have ulterior motives for wanting to take the long weekend.

If you want to get creamed by your boss, make up a story like: “My mother got her hand trapped in the car door, and it’s swollen and greenish, and she has to be operated on tomorrow morning and has no one to babysit for her kids.”

2. The Rule of Persistence

Be persistent. If you want to go to Vegas, you have to be dead set on it. You have to be ready to be a real man here.

If your boss says no, then don’t back down. Be ready to be persistent.

Don’t say, “Oh, all right then. Can I have the long weekend off?” Don’t say that. If you do that, you are being a wimp.

You have to back up your story with persistence and resolve. If you want to go to Vegas, you have to be willing to stand up for what’s right.

The worst thing you can do is back down when your boss says no. Don’t be like: “Oh, OK…can I have the long weekend off then?” Don’t be wuss-like.

3. Don’t just ask him for a day off here and there. Schedule it ahead of time.

I don’t know about your boss, but I’m willing to bet that if you told him on a Friday you wanted to go to Vegas, he’d probably say “no.” So schedule it ahead of time. Early morning flight out on Friday have him thinking you’ll be missing work.

If you want to go to Vegas, you must implement the “I’m leaving” strategy. If you show your enthusiasm for this by booking flights and hotel rooms, it will be tough for him to say no.

4. Desperate times call for desperate measures.

If you want to go to Vegas, it’s going to be tough. You need a plan of attack. You need a strategy.

You have to go out there and make it happen. If you want to go to Vegas, you need to take the bull by the horns.

If someone says something like, “Why do you want to go to Vegas? It’s so hot there. It’s dry there. It’s dusty there. You’ll get a heatstroke.”

If you are going to make it happen, you have to go out there and rock the person.

I don’t know about your boss, but my boss is a tough man. He doesn’t understand the importance of a good weekend in Vegas.

He is a tough, hard man. If you managed to get a flight booked for today at 9:00 am, he’d probably say no. He’d dismiss it out of hand and say, “That’s ridiculous. You can’t go to Vegas on a Monday. Get back to work.”

But if you went in there with a hangar-sized plan, he’d have no choice but to say yes. You’d be like, “Sir. I’ve booked the flight. I’ve booked the hotel. I’m ready to go.” He wouldn’t have any choice but to say yes.

5. Practice your deception.

Get in the habit of lying to your boss. You have to lie for this strategy to work. It takes a lot of practice and skill.

I go out there and lie all the time, and I am pretty good at it. I’m careful to use the right words. I know how to spin a tale.

You have to be able to tell the story with conviction but at the same time not come across as too convincing.

If you want to go to Vegas, you have to be able to tell a convincing story that can convince your boss of your illness.


To sum it up, if you want to go to Vegas, you can do it. Your boss doesn’t have any power over you. You can show up at work on Monday with a game plan and an execution plan that will convince your boss that you are sick enough to take off.


I'm a human being. Usually hungry. I don't have lice.

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