Did I choose the right path?

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

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.

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.