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I'm a harvard law grad and I am applying for LL.M. (possibily leading to JSD) so as to re-enter the labor force (possibly, if I go then for the JSD, as a law professor).

Kind of just thought I would go for the LL.M. and then see what it leads to, but writing the personal statement is making me realize I am supposed to have planned what this is supposed to lead to.

I graduated middle+ in class, mid-90s, worked a lackluster year and a half at a top NY firm. Loved law school, never really engaged with law practice. Stopped working to raise my 2 kids, basically ignored the law for 15 years except probating some relatives' wills (in resume speak, "pursued a sole practice concentated in wills,trusts and probate litigation.")

So I need some ideas on what my well-designed plan might be (because "my kids are in school, no one will hire me as is and so I'm going for the LL.M. and see what comes up" is not going to cut it)

LLMs are predominantly for international students and tend to add little value. It might work for your purposes, but the posters on this website are unlikely to have much constructive to add since that would be a very unusual path.

JSDs also rarely produce domestic law professors. That's a pretty difficult goal to obtain after 10 years 'off', but if you are going to attain it, it will be much more about what you publish and much less about your terminal legal degree.

A tax LLM might be worth looking into, from Georgetown or NYU. Still no guarantees of employment coming out of it, but that's the one stand out LLM that many practitioners actually get / respect, so...

Yeah, a pretty unique situation. Not sure what to tell you or even really where to suggest for more info. Good luck!