Did I choose the right path?

Can you articulate what you are unhappy with?

I suppose, if you can recoup most of the cost of the Grace and/or the 'phones, you could put the money into speakers. Something like a Squeezebox Touch has a decent enough DAC that many people use it without one. However, the Grace would be a nice base for some future system.

Samulcas091...I agree with all the comments above. A few questions though to try to pin down what you are unhappy with. When you just listen the to the Grace through your headphones, do you like the sound? If yes, your source is not the issue. If no, what type of files are you playing through thr Grace - MP3, lossless, etc? If you are playing MP3s, I would try lossless or full resolution files first to see if you hear the difference - you should? Finally, if you are happy with all aspects of your headphone playback system through the Grace, then the likely culprit is the amp-speaker interface. Your NAD integrated puts out 50wpc and B&W's in general can be a difficult load for partnering amps. Don't know the sensitivity or impedance characteristics of your speakers but the most likely upgrade should be to update the speaker (given its age and lack of suitability with your amp). I would get a more efficient book shelf speaker that should mate well with your NAD amp. Normally, I would tell you to build your system from your speaker backwards but in your case given speaker age and that you didn't specifically chose that speaker but rather it was a hand me down, I would say, find a speaker that you like that also mates well with the NAD. But as everyone has already adviced you above...no hurries on this front. Save up. Take your time. In fact, live with your current system for a while. Try to analyze what aspects of it you like and what aspects you don't like. And when you make any changes, make them one component at a time, so you can determine what that change has delivered in terms of sonic benefits/changes. Hope this helps.

There are kit assemble DYI speakers that are very good.
Madisound and Zalytron both have good products.

If you are into equipment then you may want to focus more on the music.

Equipment can ALWAYS be improved.

30 years ago I had a Harmon Kardan receiver, Boston Acoustic speakers, Dual TT, Teac tape deck.......now it is Goldmund and DCS. I bought SLOWLY and mostly **USED** and learned along the way. I have this system now. I still spend more per year on concerts than equipment!!

Find a quality audio store and give yourself time.

Enjoy the music. Listen to a clock radio if you must.
Enjoy

Yes, as the previous posters have indicated, don't consider audio a sprint to the "perfect" rig, but rather a marathon run over the course of life - a long rambling journey of many systems over time. There is no "perfect sound", so don't get the idea that if you had the right speakers you'd be close to the perfect sound. Nope. Not even close. The more years you are in this hobby the more you will see that there are thousands of sounds, hundreds upon hundreds of systems to potentially be built; having your shiny new speakers will not get you perfection, but only happiness for a little while.

Having said that, you are right, the sound is likely not as satisfying as you thought it might be. That means you are truly an audiophile; you want superior sound and the glorious experience of HiFi. Now you know it will become a hobby for you in life. I was never fully satisfied in audio until these past few years when I have been able to afford much better (and of course much more costly) equipment. Only you will be able to set your contentment level over time, but there is definitely something to the reality that the enjoyment increases substantially with finer gear.

I'd say you were smart to go for the free speakers. Now you have some electronics such that when you do finally get some means you can get decent speakers and some satisfaction. You made the decision to get the cans and headphone preamp, now you have to live with it. If you like that sound a lot then why be upset that you can't have both immediately? It's a lot less expensive to have cans at this stage of the game than a nicer set of speakers, so your choice was not foolish. I used a lot of econo gear for my system when I was in school. Don't get the idea you have to "compete" with anyone here. A sure way to discontent is to think that you should have a system like ones seen here at this point in life.

Keep your priorities straight; less school debt is far more important now than getting your ideal sound. You'll have plenty of time for that. You'll be unhappy as long as you think you deserve better sound now. Nope. You need to work for it for years, like I did.

You said, I am unhappy now. I have no money left for audio stuff..." Welcome to the club. There are thousands of audio addicts like ourselves who for one reason or another are not content with their rig and have a gnawing desire to upgrade but should not financially. It's all part of the game. ;)

You might find a buyer for the B&W's. Use that towards some newer efficient speakers like PSB's. You might be able to find Alpha B-1's for about $200(minus what you can sell the B&W's for).
This will be a much better match to your amp. Most importantly, have fun, and don't worry about making errors. We all make mistakes, and learn from them.

You learned.. that has value.. B&W.. hey you could have done alot WORSE. Take your time and rebuild slowly, hey you're still young! Don't go to too many loud concerts and fry your ears.. wear hearing protection...
keep at it, improve when you can.