They say your first million is the hardest. But in reality, I think getting to $0 is the hardest - to go from college/credit card debts to $0 net worth - ramen, apartment in the ghetto, and no social life for 2 years. After that, $1,000, $5,000, $10,000, $25,000 (1st house), $50,000 (married), $100,000, $250,000 (kids). Working on $500,000 and getting close. One thing that I noticed - each milestone is easier than the last. It was actually easier to go from $100,000 to $250,000 than $1,000 to $5,000. Go figure.