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This brings up and interesting question: If more people enter the work force and pay taxes every year, how is SS (as im told) "drying up"? I don't doubt that it's dwindling, however, what happened?

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In 1945 there were 42 workers paying SS taxes for every retiree collecting benefits. For equal pay / retirement income after SS taxes, each worker only needs to provide 2.3%.

Today (actually since 2009) that ratio is three workers per retiree. Each worker has to provide 33%. By 2050 the ratio is projected to fall to two-to-one.

You can find the historical ratios here: https://www.ssa.gov/history/ratios.html

Did we get more people not working and paying taxes, or did we get more people consuming this resource? If it is the latter, how'd that happen?

Mostly people are living longer. When SS first started only 55% of males and 60% of females who made it to age 21 would have survived their working-age years to retire at age 65 in 1940. By 1990 that figure had risen to 72% and 83%, respectively. Life expectancy after retirement also increased, from 12.7 (M) or 14.7 (F) years in 1940 to 15.3 or 19.6 years in 1990. (https://www.ssa.gov/history/lifeexpect.html)

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