Profs vs Bosses

[theD]

I've been out of UGrad for a few years now, finished grad school two years back.  I've been working as an intelligence analyst for over two years now.  I am planning on getting one letter from my thesis advisor from my MA program, for the other I am debating between another professor that I did research for in grad school or my boss.  I am hesitant to get a second letter from the professor because part of me is still considering ditching law school and doing a PhD (maybe applying next year).  I figure if I ask him for a law school letter, it may tarnish  my image in his eyes if I apply to his program next year.

Plus, my boss is obviously very familiar with my work over the last two years, which I think parallels with the type of work lawyers do with the written analyses of complex situations, etc. 

[Changed Name]

As, I'm sure you know, a general rule is that you want to have two academic letters of recommendation.  However, this general rule is often mitigated by many years of work experience and being far removed from the academic world.

There aren't any other professors you could ask for a letter?  If not, and you don't want to tarnish your reputation, as you put it, just use the boss's letter.

Don't spend too much time thinking about this.  Your letters aren't going to make you in any way.  They are merely a formality.  If you send them in, you're nothing special.  If you fail to provide letters, that will hurt you.

In rare circumstances, a recommender will say bad things.  That could hurt you.  But more than likely, this won't be you.

[theD]

I'm a splitter which is probably why I'm over thinking this.  I'm confident the professor I am determined to ask will give me a good letter, and I am especially confident that my boss will write me an outstanding letter, which I figure is better than a professor who may have forgotten about me because of his senility.