Retirement planning has been shown to affect transition into retirement, and satisfaction with it. The current study was designed to investigate the effect that financial planning choices have on an individuals anticipated level of retirement satisfaction, their adjustment to retirement and their overall satisfaction with retirement. Retirement was defined as an exit from an organisation or career path of considerable duration, taken with intention of reduced psychological commitment to work thereafter (Feldman, 1994) therefore some retirees in the current study were working in retirement. To incorporate this into the current research, the relationship between working in retirement and planning was explored; looking at whether the previously discussed effects of financial planning (on anticipated retirement satisfaction, adjustment to retirement and overall retirement satisfaction) are affected by work in retirement. The Retirement Satisfaction Index (RSI; (Floyd et al., 1992)) was used to measure anticipated retirement satisfaction, adjustment to retirement and overall retirement satisfaction. Financial planning choices and demographic details were recorded from questionnaires. Participants were 98 retired persons living in New Zealand. Factor analysis was used to explore the factor structure of the RSI (Floyd et al., 1992) on a New Zealand sample, the factor struture was similar to structure repeorted by Floyd et.al (1992) and Fouqueraeu, Fenandez and Mullet (1999). Some changes were noted in the ‘retirement satisafaction’ factor. The implication of these are discussed. Individual financial planning had a positive effect on overall retirement. There were no significant effects found for anticipated satisfaction and adjustment to retirement. Further working in retirement had no significant effects on individual planning or the previously discussed effects of individual planning on the retirement experience.