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Have you ever been too afraid to ask for a raise from your boss but you simply felt that the moment just felt right to ask for a raise?

This is my first post on this subreddit and one of my first post ever, I want to start by giving context to my little BIG issue; you see I started working in this small financial company on the rise a year ago, a lot has changed since my first day as a data entry clerk on quickbooks, and now we have evolved to become a big company, in this process of becoming bigger and bigger I was changed positions to become the IT manager even though I was not hired for such position.
Between the things I helped do to evolve the company are the following things:
Changed back office to improve workflow.
Started the process to transform our company into a online solution provider for our very wealthy costumers.
Added an mdm system for our company and made the company soc2 compliant (after discussing with other peers we came to the conclusion we don't really need more compliance but I am still open to some recommendations on this end).
Implemented a better licensing system for administration (I am in charge of administration all our licenses of every service we own).
I am currently implementing Salesforce and training to become the Salesforce guru (The implementation is completed and I am fairly knowledgeable on Salesforce.)
I am available 24/7 whenever they need me, I know is not a healthy practice but I keep a distance between my job and my personal life, but out of respect I normally try to resolve any issue even if it is outside of my working hours.
My salary is around 43k USD and honestly I want to be raised to the median over here which is around 65.5k USD, Yes I know asking for such a rise might be mad and inconceivable but in all honestly I've helped this company become what it is now, I was their first employee here in the US, and I am intrinsically connected to the development of this company, so more than a raise I think of this as an adjustment since I just want to be able to be near my peers.
I just want to know how should I go around this?
Is it just a stupid thing to do? why?
When do you think would be better to ask for such raise?
Should I just quit and go find a job in another place that pays more? If you're nervous about asking your boss/potential employer about raises/salary, don't think of them as authority figures you hope will be more generous, think of them as customers who are buying your time.
Money & Finance
EDIT: Wow, I did not expect this to make it to the front page.
From what I'm seeing in the comments, a lot of redditors have some pretty terrible employers. IMO, if your relationship with your employer is so adversarial that their response to you knowing what you're worth and asking to get paid as such, is for them to fire you out of spite, I wouldn't be hanging around at that job even if they did give me the raise I want.
Some employers are great and will happily give you what you're worth, a lot of employers are scumbags who who try to milk you for everything you're worth while paying you jack shit, but plenty of employers are simply businessmen trying to get the best value for their buck, but will pay a valuable employee what they're worth if it makes good business sense. Long story, been working IT for a company for about 2.5 years now. Currently working at the same rate they brought me in at. At the time, it was a very competitive salary for what I was doing, however, now with all the extra responsibility I've received, I think it's time that I make quite a bit more.
The reason I started thinking about this is because they brought in another IT guy (pretty different from what I do, think end user support vs. Asset management), but his pay was SIGNIFICANTLY higher than mine. Even weirder, I reported to this guy's BOSS, so technically I was higher level than him but still made the same amount as when I came in.
I've received good sized lump-bonuses every year while working here, but never received a permanent wage increase. I've recently moved around business lines, gotten a slight promotion with a hefty amount of responsibility, and have been doing pretty well at it for the better part of a year now. Now I think it's time to schedule a meeting with my boss and discuss a pay raise.
I'm getting a solid list of items together such as my new responsibilities, the competitive asset management salaries around the area, etc. Just looking for pointers such as:
- What else should I have prepared other than general reasons I think I should get a raise?
- Based on my time with the company and the recent promotion, how much % increase should I request?
- Any tips on the meeting with my boss? Any info would be incredibly appreciated. Really hoping to get a pay increase so I can afford a new place with my gf. Thanks so much for anything you guys can offer! How to get a raise, one way or another.
Tell them you need a raise. Don't tell them it's because X makes more than you. Tell them you want a raise because you think you deserve it. Articulate WHY you think you deserve it.
IF they don't give you the raise, start interviewing.
WHEN you get a new offer, tell them you're leaving and tell them why.
IF they try to match the pay, tell them you want $1 over because you'll have to break your word to the people who gave you the offer. (just an example, and you don't need to stick to this one if you like your current gig, take the match). EDIT: a lot of people commenting on this point. This only applies if you want to keep the gig. If you don't, don't even bother with a counter. Also, the dollar is an example for the young people who this post is meant to help, I understand that to some of you an extra 2k a year is nothing, but to some it's a better quality of life. It's entirely scalable for your industry/experience level/current pay.
If they don't match the offer, take it in stride, do your two weeks, and move on. If you don't get any other offers, grin and bear it until you do. If you never get any other offers, you're in the wrong place or you are the problem. Ladies who have asked for a pay rise, how did you ask and how did it go?
With my current job, I'm getting to the stage where I feel it's necessary to ask as the 'informal' start-up atmosphere means our annual reviews (and therefore chance to discuss raises properly) hasn't happened.
So I'm curious, how many of you guys have taken it in to your own hands and asked for a pay rise, and how did it go? Did you find it made things awkward? Did you just look for a different job to get that pay rise? I have been in my company for a little more than 1 year. I am 29 and have ~5 years+ experience in my field.
I feel like I have really step up my game, and during my yearly interview, I presented some key results from 2021 + the new responsibilities coming for me for 2022.
My manager told me they were planning for a raise next semester, but I asked for a +19% raise for this semester (early 2022). It matches what I found on glassdoor and some salaries I've been offered by recruiters (I didn't answer these job offers so they weren't actual "offers").
My manager was taken aback from my request. Like I was a bit too full of myself, asking that much of a raise after only 1 year in the company, etc (he didn't actually said that). He still wrote it and passed it up the hierarchy.
Could it backfire ?I really enjoy the working environment here and feel like I might have made a mistake. My boss is a small business owner and he's the cheapest person I've ever met. There aren't any scheduled raises here, i.e. you don't get a raise unless you demand one.
Any tips on how to broach this subject? I have no problems threatening to quit if necessary. But obviously I don't want to go there if I don't have to. But I'm barely making my rent right now.

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