“How does an individual know if he is doing Hashem’s will and following the right derech?”
The ONLY answer to this question is to have a Rov.
gavra, True, but a Rov or a Rabbi, whatever you want to call it, can also be Conservative. Or a Neturei Karta. One needs to be clear that the derech mehalach they are following is truly for an oivad Hashem.
P.S. The Chassidish (really Hungarian/Satmer) Mehalech (in general, Clearheaded!) is more Machmir regarding Tznius. This is NOT halacha Pesuka, but none the less should be applauded (within reason).
Tell me about it. Although I’m not Satmer, I know a lot about them. I look up to those who wear a shpitzel and the like, but would I grow up in that community, I would have a problem as I don’t think I could wear one. They are very machmir about tznius. Good for them, but of course, we are not talking here about what some feel are extreme chumros, rather chumros that are very reasonable and accepted by all over the world by frum communities, Chassidish, Yehsivish or otherwise.
The reason why need these chumros are because as the modes of change dress, the application of halacha changes. These are not chumros to make life harder, rather they are minhugim we adopt, as our nation has adopted throughout the centuries, to adapt our current lifestyle so that we can live according to halacha.
I’m not saying one needs to continuously look to be machmir. But the derech one a Yid needs to be on is a derech a derech of true avodas Hashem. One needs to fit in their current lifestyle into the parameters of halacha, not halacha needs to fit into their current lifestyle.