I'm 48, I've worked in a library for 23 years and can technically retire 2 years from now. The pension would only be around 30K. I have an index fund to supplement that, currently over 700K. I currently reinvest the dividends from it (VTSAX), but would use the extra 6-9K as retirement income and could withdraw 3% or less from the index fund. For medical insurance, I would probably get on my GF's insurance (we've lived together for about 20 years). I have a small amount of savings between 15 - 20K. My annual spending somehow only comes to about 35K a year in a HCOL area in NJ. If SS still exits in the future, I would be able to collect that around 10 years later after retiring at 52. If I understand correctly my pension amount would only go up about 1K per extra of year of working, so it doesn't seem terribly worth it to keep working. Hopefully I could always find some part-time work to make 4-5K a year for a vacation or something, if I wanted. Is this a risky plan?