The onset of my glyco-mass spectrometry was a coincidental observation of mass spectral differences between positional isomers of phospholipids. I have been led for the last 26 years by fortunate sequences of events unfolding one after another, most times in the shape of structural determination of partially unknown samples. Struggling to rationalize fragmentation features, I have been elucidating sphingoid structures, positional isomers of sugar chains, linkage isomers of branched sugars, and finally trying to distinguish stereoisomers of sugars which is still only halfway through. With the most grateful appreciation for the award given by the Mass Spectrometry Society of Japan, my slow progress in isomer distinctions of sugars and conjugated lipids, in addition to some of the other projects I worked on along the way, are integrated in this paper.