Often their occupations were defined by their local area - generations would work the same pieces of land, either in their own freehold or working for wealthier land owners. Thus, families would often stay within the space of a few villages their entire lives - marrying into local families, raising children and in turn being buried in the local churchyard.
Others followed the previous generations into specific trades, 'like father, like son'. There is a several-generation 'tradition' of stonemasons in one of my family lines. This is not the basic 'stone-cutting' for building materials; it's more on a par with sculpture. A Master Mason would spend many years learning his craft, starting as an apprentice and learning much of their trade by helping with conservation of earlier constructions, following the age-old methods of hand-chiselling.
Grandad at work!
An eye for design and detail was essential and my Grandfather was a keen illustrator - a couple of pic's from one of his notebooks (whilst convalescing in an auxilliary hospital after WW1):
This is my Great Grandfather's headstone - it has some beautiful knot-work at the top (I need to go back up to Scotland and re-photograph it properly!) done by his own sons (my Grandfather and his brother).
Designing, producing and erecting headstones was the family's 'bread and butter' and a fair number of the stones in Carlisle Cemetery were done by the family 'firm':
The engraving and sculpting would all be done at the workshops, then the pieces would be assembled on site.
(My Grandfather's headstone being 'assembled' under the watchful eye of his nephew)