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You're the one that has to sell it and if you think that retail and service industries have lots of overlap, then absolutely you should talk about it. The more compellingly you can explain your case the better! It sounds like you really understand the limitations in your industry given your current degrees, and I would explicitly talk about how an MBA can skyrocket you into the positions you really are striving for. Your "insider knowledge" will give you a lot of credibility.

I can't say for sure that it will hurt you (for sure, it's impressive that you are working full-time AND getting a masters degree), but you just need to make sure to indicate how everything is working in concert to help you achieve your goals. It's just a matter of putting it all together.

I hope someone else weighs in because I like your story and think you have a great shot, but the flurry of Masters is a bit out there for my taste.

My question to you is this: what matters most to you and why?
I think that's the staple Stanford essay question, so being able to answer that would definitely help since you're aiming for that school anyway.

But the reason I ask is because although individual aspects of your profile are good on their own (good GPA, good ECs, good career trajectory thus far with that promotion), they don't build up to what I would personally consider a compelling story (I'm not an admissions officer, but hey you put this under Peer Review so I consider your profile fair game).

The biggest challenge, in my opinion, is that it's not easy for me to understand why you did what you've done. If you have a vision/goal, I'm not quite sure the decisions you've made so far all lead you closer to that goal. But that's saying a lot when you haven't even crafted your essays yet. Who knows, you just might be able to put an awesome spin to all the things you've accomplished!

Bottom line is: you've got a good background, and if you're able to tie it all together, you'll have a great story that will bring you to the best schools. Godspeed!