Richard Bolles, job search guru and author of What Color Is Your Parachute? predicts that you can expect to search for work 1-2 months for every $10,000 you hope to earn. So, if youre looking for a $40,000 a year position, you may search for 4-8 months to land it. Back when the economy sizzled, that job search length would have seemed outrageous, but now, many people would be thrilled to only search for 4-8 months.