How to ask for a day off (with 99% success rate)

Published on December 22, 2021
how to ask for a day off

Are you dying to take time off work to recharge your batteries? But you can't find the courage to ask your boss about it?

It’s best to request a day off work when you don’t have a lot of pressing duties and your company is not going through a tough or busy period. Also, it’s good to have a coworker who can handle some of your responsibilities while you are away.

You dream of going on a vacation with your best friend or your loved one. You want to give yourself a well-deserved 3-day weekend. Or quite simply to be able to finally get away from the big city and all of the noise.

But the fear of being frowned upon by your boss and coworkers is preventing you from asking about what you deserve and need so badly.

It would have been a lot easier to solve the problem if it was entirely on your end of things. But the game gets rough when you are meeting a lot of resistance from a pushy superior.

Here I will tell you the best tips and tricks I know to increase your chances of getting that precious day off work. Here is how to request time off.

How to ask your boss for a day off

how to ask for a day off

Asking your boss for a day off can be a mission impossible if they are a soulless corporate shark. Not to mention if you are experiencing social pressure and anxiety.

I will take a wild guess and say that if you need help asking your boss for a day off, then you are dealing with one of the following situations:

  1. You feel like an impostor who doesn’t deserve joy in their life.
  2. You are sure that your request will be denied because your boss is a spawn of Hell.

Or some miserable combination of the two, in which case you might as well give those concert tickets to your unemployed cousin Fred.

As you may know or not know, I have said many times before that time off work is very important because it helps us to unwind and it allows us to come back to work with a refreshed mindset.

So please don’t feel like an impostor and focus on all of the positives that come with taking a little personal time off.

Before I tell you how to ask your boss for a day off, I remind you that it is always a good idea to be aware of your company’s policy.

Also, keep in mind that employers are totally in their right to deny paid time off work in most states and countries.

But for now, leave aside the guilt and fear of repercussions that your request for time off work could bring.

Here are a few steps and tips that you can follow in order to request the time off work that you deserve:

1. Follow company procedures

Before rushing into your boss' office to make your arguments about why you deserve a few days for yourself, make sure to learn about your company’s procedure regarding time off.

Also, consider the order in which leave is granted within your team, and make sure to check the number of paid days off you have left until the end of the year.

And of course, take into account the workload of your colleagues and the consequences your absence may have on your team. Ask them if they are fine with you taking a day or two off work to recharge.

2. Make sure the timing is right

But, beyond the company technicalities, make sure the time is well chosen to take a break.

Are there any events, projects, or important deadlines planned during the time when you will be off? If so, can you postpone your projects without hesitation?

3. Test the waters first

Unless it is a definite event in time, like a wedding or the arrival of a friend who lives abroad, do not ask for specific dates.

Maybe tell your boss something like "I have ten days of vacation left, I would like to take some time off work in the next few weeks. Does this seem possible to you?"

This way you are giving them all the possible heads-ups to grant you some time off work.

Even if all the planets seem perfectly aligned, avoid claiming victory until you have first obtained the approval of your boss.

4. Plan your time off before or after a busy week at work

If you're looking for a longer break, like a vacation to another country, or spending a whole week watching Netflix shows, getting your approval will be much easier if you time it before or after a busy period for your company.

However, this can only be effective in a workplace where monthly activities are more or less scheduled and predictable.

For fast-paced jobs, you can tell your boss in advance that after completing a specific project, you are taking time off. By doing this, you are still prioritizing work, which is all a boss could ask for, and you will most likely get your time off.

5. Have a productive week

Bosses tend to ignore the little things but pick up on the bigger ones. I am talking about your achievements.

Your daily accomplishments may seem like they're not impressive enough but if you keep a list of them for an entire week, perhaps you will gain enough confidence and reasons to impress your boss.

Try to say something like:

“Hey, I’ve been working really hard recently and I accomplished X, Y, and Z. Would be it possible for me to take a day some time off work soon?”

6. Accept the verdict

Even if you have scrupulously followed all of the above advice, you should also be prepared to be refused. Always remember that no matter what decision your boss makes, you need to be accommodating in order to stay on good terms and make another request later on.

However, if it seems that your boss is never willing to give you even a day off, then this could be a sign that your workplace is actually quite toxic and exploitative.

How to ask your boss for a day off on a short notice

How to ask your boss for a day off on a short notice

Asking your boss for some time off work gets even trickier when it's done on short notice. Not to mention this might be in violation of company terms.

Regardless, here are a few tips and tricks you can try to increase your chances of getting what you want.

1. Ask your boss to talk privately

If possible, meet your supervisor privately and ask them in person. While this may seem counterintuitive, the idea is to be able to witness their initial reaction and diffuse any resistance.

Consider this, it would be a lot easier for them to deny your request in an email than to have to do it in person and witness your disappointment.

Most people will do whatever they can to avoid conflict and social pressure. But who knows, your boss might be a complete sociopath who doesn’t care the slightest how you feel and what you need.

That is why this next step is so important.

2. Don’t be discouraged if they deny you initially

Don’t give up just yet. Simply apologize and ask them nicely again. Use the words “please” and “sorry” a lot. Remind them just how much you need this or how important this is for you.

3. Use the most persuasive word

The most persuasive word in the English language is this.


And that’s simply because it is usually followed by a good reason. But make sure to use it regardless of whether or not you have a good reason for your request.

Even if you say something vague like “I need this day off because it is important to me.” you are still applying a powerful persuasion technique.

4. Promise that you will compensate

This is probably something that you should keep as a last resort.

When all else fails, pull out the “compensation” card.

Tell your boss that when you return, you will compensate for your absence by working extra hard.

This might mean staying an extra hour or two after the end of your shift. But it all comes down to how badly you want to get that day off in the first place.

5. Ask a coworker to work as your substitute

Finish all the important tasks that you are responsible for and ask a member of your team to take care of the rest of what you are leaving during your break. This way the work will continue even if you are not around.

In most companies, bosses focus only on getting tasks done, so they won't mind if you leave for a few days as long as the work progress isn't affected.

You can say something like:

"Hey boss, I don't have any urgent tasks to deal with right now, and I've already asked Simon to take over some of my duties if my vacation request is approved. So is it possible to take some time off? Perhaps next week?”

Just make sure to make it up to your coworker when you return!

6. Pull out the "You can still contact me by email or phone" card

If your work revolves around your computer, you can easily take it with you.

And this works perfectly because, even if you're not there, your boss won't be worried if something urgent comes up at work, or if you are suddenly needed for something that only you can provide the answer to.

It's actually that simple, there are no tricks behind this. You just have to think ahead of your boss’s concerns.

How to ask for a day off in an email

How to ask for a day off in an email

Asking for a day off in an email is not as personal and your superior on the other side has all the time they need to come up with a reason to deny you.

Of course, it all comes down to the reason for your request. Of course, you won’t be denied if something urgent came up in your life and you have to deal with it immediately.

However, I have a few tips and tricks up my sleeve that will be helpful if you simply want some vacation time. Here is what you can try.

1. Craft your subject line carefully

Unless company policy specifically requires such emails to be labeled, don't mention anything about days off in the subject line.

Instead, go for something like "Can I ask you something?" or "There is something I want to tell you".

These are very suspenseful phrases that will put your boss on edge. The created tension will be released when they realize this email is a simple vacation request. Their relaxed state will make them more agreeable and more likely to approve your request.

2. Start your email with a good reason

Here is a couple of how to ask for a day off example sentences:

“I would like to take two days off work to recharge my batteries because I have been working really hard recently on X, Y, and Z.”

“I have been working really hard recently on X, Y, and Z so I would like to take two days off work because I need to recharge my batteries.”

Even though both sentences consist of the same words, they have a different effect on the reader.

In the first example, the vacation request is the very first piece of information that the reader learns. "I want a vacation" becomes the frame of the entire sentence. This would have a negative effect if your superior is resistant to the idea.

In the second example, "I work very hard" is the frame of the sentence. This will have a more positive effect and it increases your chances of approval.

3. Mention how you are preparing

In your email, you can mention how you are preparing (and compensating) for your future absence from work. Mention if a coworker will take care of some of your responsibilities while you are away.

This is an important step because it shows your boss that you care about the progress of your work.

4. Mention they can always contact you

Of course, it would be quite unpleasant to receive a call while you are in the middle of something fun during your vacation.

But “hustle culture” has its own rules. If your company culture is this harsh, then this is just something that you will have to accept. So make sure to include your phone number.

5. Be polite and respectful in your writing

No matter what your work relationship is with your boss, always be polite, respectful, and professional in your emails.

Remember that these mails are considered official company documentation so don’t cross any boundaries.

How to ask for a day off when you just started

How to ask for a day off when you just started

Oh, this is uncomfortable. It’s only your second work week, you are still a trainy, and here you are asking for a couple of days off work because you want to go to this music thing or whatever.

That’s harsh.

My first advice would be to not do it if you really care about this job and you want to impress the people you work with.

But if you are going to do it anyway, then here are a few things that you should do.

1. Acknowledge the fact

Don’t ignore the elephant in the room. Instead, acknowledge the fact that you just started this job.

This will show your boss that you are not a self-absorbed person who is clueless about their surroundings.

Acknowledge that it is awkward and you feel bad for asking. This way you will look better and more reliable.

2. State that you will compensate for your absence

As mentioned above, this card is one of the few bargaining options that you have.

However, it is important to truly follow through with your promise. When you get back to work, make sure that you are giving it all you’ve got.

3. Apply the persuasion tactics I’ve taught you

You know I am big on persuasion and negotiation tactics. They are simple and subtle but they make all the difference.

So use the word "because" as much as possible, make promises, stay calm and respectful.

This way you will condition your boss to approve your time off work, even though you just started.

Key takeaways

  • Everyone deserves a break after working hard for a long time.
  • If you think you are burning out due to overwork, request time off and explain your circumstances to your boss.
  • Remember, being honest and polite at all times is very important.
  • If you are asking for time off because you just want to relax, travel with friends and family, just say so.
  • And of course, being in a good position at your company and doing great work is enough reason to have your vacation approved.
  • Here is how to tell your boss you won't be able to come to work in case something happened.
Written by:
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Alex Alexiev
co-founder / office worker
Alex has been an office worker for more than 10 years. He is dedicated to helping other office workers to achieve the perfect life-work balance through well-being, effective communication, and building productive habits.

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