Actually I always quit my jobs without having another lined up.

Imagine the Pope … Despite affirmations to the contrary he never meets with his boss!!!

I probably would not. I'm risk adverse to that situation. In my experience it's easier to find a job when you already have one. I have the impression that the unemployed job seeker can have a certain air of desperation about them,, like actors auditioning.. especially the longer you are on your job search. I absolutely applaud your desire to be respectful and I understand that the opportunity to have a face to face is in front of you.. but ask yourself.. if your boss was considering terminating you in the next month or so do you think he would mention it in your meeting? Save yourself the stress of no money coming in with payments piling up. Good Luck!!

Hustle and get your exit plan tight pre-seeing the boss. If you are going to adhere to a principle of doing it face to face, then make sure your exit plan is square prior. Otherwise, I'd go 21st century and exit via email or phone call.

Not unless you have a sick nest egg

Absolutely not. Never ever ever.

You are far too trusting, he will not hesitate in dropping you from the roster in a heartbeat. You should never give up a paying job without having your backup plan ready to go in it’s place. Your boss won’t want you in the company of other employees or customers as long as you are heading out the door.

i don't know whether or not it's a good idea, but i've done it more than once! some things are just that important.

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I did it a couple of times when I was in my twenties. I had no debt, didn't need much, and knew I could get a job waiting tables (side job since high school) if I needed the money. I never regretted it.
Now, no. Too many responsibilities, a mortgage, and a fairly comfortable lifestyle that I'd like to keep.

And don't sweat the 'gap' in employment. You were travelling OS, finding yourself, in prison, (maybe not that one) plenty of legit reasons why you were not working.

But in answer to your question. I have done it many times, but only when I had sufficient 'fuck you' money to carry me. <- thanks to Yanya for that gem. I work in an industry that has plenty of opportunity for moving elsewhere. Even around the world.

Only once in my working life have I had the perfect opportunity to tell a boss "Take this job and shove it (up your arse)" Woulda Shoulda Coulda. Well, I did quit to his face but I didn't use those exact words. Missed chances in life.....

I'm telling you from experience not to do it. It's much easier to find a job when you have one plus if for some reason it takes an extended period of time for you to find one you'll have to answer for that gap on your resume. You should be prepared for your boss to, assuming you're a good worker, offer you more money, say he'll change things, and you should be open to those things. Having lived through it and currently in it, you can always quit once you get a job, there's no reason to quit before you get the other job. No matter how bad it is. I was in a job for six and a half years and thought I'd get fired every day of that six and a half years so I saved money which has allowed me to live for four years without any income. If you can afford to do it then you can do it but I'm telling you that the hole in your resume will haunt you forever..

Do not quit or give your notice until you have the other job....

I would only quit if I had enough financial resources lined up to help me through the transition. That would be another job, enough money in the bank, or some other access to funds to tide me over. Otherwise, I'd save up and/or wait until I had that in place.

I have done it, a couple of times. Once the job I thought I had wrapped up was cut. And once I took a buyout that included a year's pay, but still didn't find a good job until after the money ran out. Sometimes the satisfaction of quitting a job you hate is worth it. But it never seems to affect your employer as much as you think it will.

I've done it before, but I don't recommend it. Unless you've saved enough to keep you afloat for a few months, you're putting yourself in a position to be homeless or borrowing from family/friends which indebtment comes at a cost sometimes too.

It's more irresponsible to quit without a plan. Just flat out is.

However you are in charge of your own life. Best of luck.

No way I would quit without having other income.

Would I? No. Should you? I can't answer that. I work freelance so I know all about the worries of figuring out how long you can pay for things/life until the money runs out. The hope is, obviously, that the next gig is right around the corner, but it might not be. If I were ever be in a position where I had a steady full-time, non-contract, permanent job and I were looking to move to something else, I'd rather have something lined up. But that's just me. Everybody is different.

I would not quite until you have something else lined up. A "promising conversation" is not an offer of employment. You are less important to your current employer than you think. Depending on what kind of industry you are in, you might not be able to give advance notice and instead be told to pack your desk immediately. Most companies will give you an an exit interview and you can lay out all your reasons for leaving there.

It’d be situational. Fuck it, just do it. You’ll have another lame job before long.

Well I'm self-employed but even when I work for other people I never worry about it I'm a Tradesman it basically means I have skills in all areas of construction so it's always been very easy for me to get work I never worry about it

From experience, I can tell you that you are taking a real risk. It could work out, or it could be a real disaster.

It could prove a bit risky in my opinion. You don’t say why you want to leave your current position, so it is hard to give advice without that information. Perhaps after your chat with the boss he will offer you better conditions or pay, if that is why you wish to leave, but you have to have that conversation with him. You are correct to say these things are better conducted face to face. As far as leaving without another position, my son did that a few years ago and it took him some time to get another suitable job. Promising conversations don’t always lead to positive outcomes unfortunately, so to quote the old proverb.....a bird in the hand etc.......!

Best time to get another job is while you still have one. Someone suggested having an honest rundown of you criticisms of the company with him but without pulling the trigger. That's a better plan.