The decision to annuitize wealth in retirement planning has become increasingly complex due to rising longevity risk and changing retirement patterns, including increased labor force participation at older ages. While an extensive literature studies consumption, labor, and annuitization decisions, these elements are typically examined in isolation. This paper develops a unified stochastic control and optimal stopping framework in which habit formation and endogenous labor supply shape retirement and annuitization decisions under age-dependent mortality. We derive optimal consumption, labor, portfolio, and annuitization policies in a continuous-time lifecycle model. The solution is characterized via dynamic programming and a Hamilton-Jacobi-Bellman variational inequality. Our results reveal a rich sequence of retirement dynamics. When wealth is low relative to habit, labor is supplied defensively to protect consumption standards. As wealth increases, agents enter a work-to-retire phase in which labor is supplied at its maximum level to accelerate access to retirement. Human capital acts as a stabilizing asset, justifying a more aggressive pre-retirement investment portfolio, followed by abrupt de-risking upon annuitization. Subjective mortality beliefs are a key determinant in shaping retirement dynamics. Agents with pessimistic longevity beliefs rationally perceive annuities as unattractive, leading them to avoid or delay annuitization. This framework provides a behavior-based explanation for low annuity demand and offers guidance for retirement planning jointly linking labor supply, portfolio choice, and the timing of annuitization.