Military personnel work in high stress situations and carry great responsibilites, leaving them little time to plan effectively for their retirement; typically, they tend to assume that their employer (the government) will do that planning for them. Focussing intensely on their jobs, retirement often finds them ill-prepared, and this in spite of the recent increase in discussion in society at large about retirement and how to deal with it. Government therefore needs to be more proactive in assisting these occupational groups in their exit from the workforce, especially because, as the baby-boomers age, the rate of retirements will increase dramatically. As well, whereas in the past, an average retirement extended for roughly a decade, today, a retirement could last as long as twenty-five to thirty years, with attendant cost pressures on retirement funds. This in turn will increase the burden on the rising generation, who will have to pay for those pensions. But while government has a role to play, retirees also have to be more active in planning for their retirement, and in particular, planning for second careers, rather than simple retirement. Government can assist here by developing programs to help military personel find a second career, thus reducing their reliance on pension funds, and reducing financial pressures too. As well, such planning would emphasize and enhance self-reliance, which can only be to the good of the larger society.