1888 for me...Hmm. Just shy of Dad's side of the family coming over from Naples (early 1890s is the best guess right now), and Mom's was scattered all over Ohio, Pennsylvania and the Midwest, but I'll give this a try from some different angles.
Assuming born in the same place and to the same parents, without family-specific careers: Maybe working in a Milwaukee factory or brewery; perhaps changing over to war production in 1917 and 1941 with the former, assuming it's a lifetime gig. Don't
think I'd be conscripted at 29 in WWI, but might volunteer; not sure where I'd end up in Europe, if so, or what my chances of coming back would be. Might end up doing union work, if the war and the "sewer socialism" of the city pushed me in that direction, not to mention the Depression.
Assuming same place and parents,
with family careers: With Dad being a college prof and Mom a French language major and technical writer (or an early 1900s equivalent of the latter), I'd be upper class, or higher part of the middle. Maybe go into academia as well, possibly mixed with politics given the Wisconsin Idea; might get involved in Progressivism or MKE "sewer socialism" and run for city, state, or even national office. This might also lead to me to speak out against the draft and the Espionage Act, which wouldn't go over too well...
Assuming just mother's side: Maybe farming or factory work in any of the three aforementioned regions, with perhaps eventual promotion to manager or some other office slot in the latter case. Might end up drinking like a fish, too, given the times, family lore, and the work, be it blue- or white-collar. God knows what the Depression would bring on for me in either type of job.
Assuming just father's side: Still in Naples until early 1890s, then Brooklyn or Queens after immigrating. Might work in and maybe inherit the family jewelry store (which my grandfather's father opened in real history), or work in a factory or some other heavy labor job. Probably would get a fair amount of crap thrown my way (figuratively AND literally) from a lot of quarters for being Italian and Catholic, most of it in the 1890s-1930s. It's a stereotype, but the Depression might force me to the organized crime way of life, or I might already "know some people" from an early age in the USA or back in the "old country", and thus find a niche in the Five Families, maybe even a leadership slot. Of course, that would bring me to Hoover's notice, and bring threats of potential hits from Family rivals....