I was recently laid off from my $110k/year job. I have the option of accepting another job at similar pay in an industry I detest (same industry I was in before...) in an area of the country in which I have no interest in living. Alternatively, I can go the entrepreneurial route and try to live off my investment income while building a business. I've had a regular paycheck every two weeks for the past 18 years, and I'm having trouble with the concept of living without a paycheck. My investment income is a total of $40k / yr, $30k / yr from non-retirement accounts. I'm 43, so I'm a long way from having supplemental income from Social Security, modest pensions, etc. I can live quite well at around $22k / yr (no wife, children, or pets). I've come up with 26 reasons why the entrepreneurial route is a bad idea, and 20 reasons why it's a good idea. Damn - this is hard, hard, hard....