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Context : I work in two companies, and I'm thinking about leaving the first one to have more time to focus on learning new technologies and a new language for the foreign country I'm planning to live in at the start of 2020.
I'm currently working 3 days per week in this first company since a year and a half, but I've been working here for 4+ years in total and never asked for a raise before (guess it was time to wake up).

If I was to leave the job about 2 months (maybe less) after asking for the raise, how appropriate would it be ?

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    Why do you want to ask for a raise now? – Dukeling Dec 13 '18 at 23:42
  • @Dukeling the point is that I may or may not leave soon after the raise. Maybe my second job gets lighter and I find enough time to learn my stuff without having to quit any company. So, why not ? It's been 4 years without any, and the salary is pretty below the market trends. – OddBrew Dec 13 '18 at 23:44
  • I don't think the matter here is if it is appropriate or not, as asking for raises or quitting is a professional decision... what matter is (like Dukeling said) the reasons why you want a raise... if getting a raise is condition of you staying then I think asking is a good idea (specially after 4 years) – DarkCygnus Dec 14 '18 at 0:02
  • @DarkCygnus getting a raise will not make me want to stay more, but not getting one might definitely push me to leave even earlier. – OddBrew Dec 14 '18 at 0:10
  • Under that light, I see no real point in asking if you are going to leave anyways... But as Joe said, it is hardly inappropriate to do – DarkCygnus Dec 14 '18 at 0:12
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I've been working here for 4+ years in total and never asked for a raise before (guess it was time to wake up).

If I was to leave the job about 2 months (maybe less) after asking for the raise, how appropriate would it be ?

It's perfectly appropriate. Asking for a raise and potentially leaving are two different things.

If you haven't had one in 4+ years, you are long overdue. Ask today.

If you later actually decide to leave - oh well, these things happen. If challenged, a reasonable reply is "I hadn't actually decided to leave at that point in time." or something along those lines.

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    yes, both are professional decisions, which are appropriate if done properly. – DarkCygnus Dec 14 '18 at 0:07
  • I understand what you're saying, but I want to keep good relations with them as much as I can. Wouldn't leaving this soon after arguing for a raise be considered a dick move ? – OddBrew Dec 14 '18 at 0:07
  • @JoeStrazzere To be honest I have no idea what a proper boss etiquette is about salaries. Is it considered a dick move to never give an employee a raise if he doesn't ask for it ? – OddBrew Dec 14 '18 at 0:14
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I think general advice that people give regarding "possibly leave job in X months":

Until you have signed contract or at least real offer, assume there is no "job in X months" and proceed accordingly.

That is not about ethics, but about your current situation. Reality right now is that

  • you feel like you deserve a raise, and
  • you have no other job offers

Maybe your other job will disappear, maybe company go bankrupt, maybe you'll have to stay with old gig for whatever reason, maybe you'll have to move and only your current job will be OK with remote work. If you want to make gods laugh, tell them about your plans.

  • While your points are valid, the chance that one of those events occur in the next year is so incredibly tiny that I'm willing to try my luck 100%. And I actually don't need an other job to replace the first one, the second one is totally enought to support me (that's why I would use the free time to learn). – OddBrew Dec 14 '18 at 1:08
  • All the more reason to ask for the raise. – David Thornley Dec 14 '18 at 16:04
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How appropriate is it...

There's nothing inappropriate about it, but, it could sour your relationship with the company in question possibly eliminating and chance of returning if you ever thought to.

Of course, if you've decided you can live with never, ever, returning to that company, sure, ask for a raise. It doesn't matter that you may leave. You should always be paid what you can negotiate.

One scenario I suppose you should consider is if their offer is good enough to actually make you stay, giving up company 2.

  • Good point. The work market in IT here is not clogged up enough to have me come back to them out of necessity, but I would still like to be welcome to pass by. Giving up the second company is not an option as I make here ~3 times the salary I get on the first company, working one day less. – OddBrew Dec 14 '18 at 1:05

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