It sounds to me that you are already 1 (perhaps 3) steps ahead of the game. A graduate degree from Stanford will always "look good" on the resume, but I wonder

It sounds to me that you are already 1 (perhaps 3) steps ahead of the game. A graduate degree from Stanford will always "look good" on the resume, but I wonder what it will do toward further your freelancing goal. One thing to keep in mind, and all caveats apply, but in my experience I have found that many organizations/clients view higher level degrees as a "sign" (valid or not matters little IMO) that you are prime leadership material. This may be beneficial in winning contracts. At the same time it may make you appear over-qualified (less likely I would say). It's a delicate balance.