Asking to work remotely - how to prepare, what to say, and what to expect?

Hi all,

Not the biggest fan of my job but I think I could manage my happiness better if I were somewhere that's not so stifling. My location is awful for a person like me. I've wanted to move for a while and I really need to start actually following through for the sake of my own mental health. I've been putting it off because I've been afraid of being unemployed and finding a worthwhile job in a place I don't live has proven to be impossible.

I am currently a DBA in the US (27 male on the east coast). I work the bog standard 40 hrs a week at a desk, and I can't see any reason that I can't work remotely apart from the convenience of being in the office in person. I do not have any certifications, though my employer has requested that I get a certificate through MS, which is frankly a rather large and expensive undertaking. Thankfully, they don't seem to stressed about it. My salary is rather low as a DBA, and I think it's low even considering the low CoL for my city and the fact I don't have a cert.

For a while, I was looking for a different job, couldn't find one, decided I'd just outright quit (w/ notice of course). Now I've decided that if I'm going to quit anyway, why not ask to work remotely first?

I've got some money saved ~12K USD, which isn't much I know, and an idea of where I want to go. At this point, I just need the courage to do it but more importantly, a plan of action. I don't really know what to say to my boss, nor have I ever actually worked remotely.

So, does reddit have any suggestions for:

*What to say to my boss and how to prepare for that conversation?

*How do I best present myself as someone who can do their job remotely and still be just as effective?

*What to expect if they say no? Look for another job/follow through with just outright quitting and move anyway?

*If they say yes, how do people work remotely without going stir crazy at home? Are there places that I can go/spaces to rent to work a full day on the regular?

Thanks all

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