I know. Your boss is the scariest person in the world, and asking for a raise and more time off is like asking the devil himself if he can spare you from hell. It is possible, however, to re-negotiate pay and time off, even after you are already established at a company or still pretty new to the job.
Recently, I had to go through this process at my own job. I wasn't getting enough time off, my family was planning a lot of summer activities without me, and I didn't want to miss out. That right there is a completely normal reason to ask for more time off. So I did. Along with that, I was either at on the clock doing absolutely nothing (which I am not morally alright with) or was overloaded with things to accomplish at one time. Comparing my skill level with my responsibilities, I felt I deserved a higher pay. So I asked for that as well.
Neither of these things was easy to do. I barely know my boss and we have not established a firm relationship, therefore I really did not know how she would react. I am also the youngest, least experienced person on the team and didn't feel I could ask these things of my boss. I have also been on this job for a few weeks and am already asking for things.
The secret about asking for a pay raise or time off at an early stage is this: You have the advantage of being new. Don't think of it as asking for things already. Instead, think of it as an adjustment to your original agreement, whatever that looked like.
As an established member of your job, you have the advantage of time. At this point, your boss should already know that you are diligent, a hard worker, and you bring good outcomes. This means that, if your boss has been noticing, they already see you deserve it, and chances are they are thinking the same thing. Being at a company longer also means you can use that as your leverage for re-negotiation of salary and time off. In my experience, I really had to just buckle down and do it because I am a big girl now and I wear big girl pants.
I did learn a few things while asking my boss for a pay raise and more time off.
1. They hired you, you didn't hire them.
You are not paying them to do this work. They saw something in you and therefore hired you because of it. They are probably not going to see something in you and go through an entire hiring process just to fire you for making a little noise. If they do, then be reassured that those are not people you want to work for. Also, most bosses do not want to lose employees, and not all bosses are out to make money by making other people suffer. Your boss is here to assist you, and this is one way they can do that.
2. You are not the first one to request these things.
Though you may have never seen anyone you know at this job ask for a pay raise or time off, that doesn't mean it has never been done. Chances are if your boss has been in their position for at least 2 years they have gone through this before. They are also (drum roll please) trained for this!! YAY! Find hope in knowing that your boss has a boss that is teaching and guiding them! They know how to doll out the money and shift things around so everyone gets what they want.
3. Rehearse before you talk, please.
When it comes to real talks with anyone, I have to rehearse. I have to practice what I am going to say, I have to go through several different scenarios. If I don't I usually say something stupid and something I don't want anyone else to know. I also add unnecessary information and just ramble. Having a mental checklist of what I am going to say calms my nerves and keeps me on track when the moment comes to talk to my boss. It also gives my boss a solid list of things that I am asking for, so there are fewer needs for clarification.
4. Stay professional.
Professionalism keeps me on the ball game and keeps me my job. Talking with my boss more professionally keeps the conversation on the right track and keeps it about the job. I remember several times where I have gotten off track and began discussing personal reasons for asking for a pay raise or time off and totally turned the conversation backward. Staying professional also goes hand in hand with rehearsing. Both will get me what I want. It also shows my boss that she/he can take me seriously and that I mean business. Most of the time it impresses my boss as well.
5. Mean What You Say.
You have thought about it, looked into the numbers and you know what you want. Great. Now go for it! Don't back down just because you are scared or in fear. If you have a boss worth working for, they will hear you out and consider your offer. Things might not change for you immediately, but expect those things to change. From an employer point of view, I want my employees to know their worth and how much their work is worth. If they think they deserve a raise because they can produce excellent work then I want to know about it. You can do this! You are bold, brilliant and amazing! Now go get you a raise!
You might be nervous, but don't let it stop you. You know what you want and what you deserve and your boss is going to work with you to achieve it! People ask for raises all the time, and plenty of people have re-negotiated time off. Life happens, and most people don't live at their jobs. So take a deep breath, rest in the fact that you are not alone in your wants and needs, and be confident when confronting your boss! You got this!