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I'm a fifth year associate in a capital markets area and have been thinking more and more about leaving my biglaw firm. I am not sure exactly for what it is yet, whether it's taking some months off, going back to law school (I've often thought about doing a tax LLM and maybe pursuing that professionally) or going inhouse/into government. I just know hat I have been getting a bit burnt out and am more and more realizing that biglaw, at least in my current practice area, isn't what I want to do long term.

However, I am a bit afraid that I go to something, realize it isn't for me and that I then want to go back to another capital markets firm, as I would then figure that "hey, I won't like the job either way, best to get paid more for it." I guess this is market dependent, but does anyone have any insight on how hard it is to switch back to biglaw within a year or so if you're a mid-level associate who has left their biglaw firm?

The answer is "it depends." Whether you can go back will depend on how the hiring market is, what you are doing other than biglaw, and your market. I personally know several people who went back to biglaw after a few years in-house. The key was that they had in-demand specialties/sub specialties and several new firms had opened. But I wouldn't be too afraid of going the in-house route if you can find a good company.

If you were going to go get a tax LLM, you are likely going to have to go back to biglaw or Big 4 (which is like biglaw but with lower pay) and get paid as a first year. I'm not sure you'd necessarily find it better than what you are doing unless you've discovered a real passion for tax. It would make the most sense to try to transfer to a tax group (probably getting bumped down a few class years in the process) and do the LLM part time if you want to do tax. You could also do the LLM to go into government (IRS has a tough time attracting people), but you'll have to deal with low pay and a big workload.