Aspects of the present disclosure are directed to techniques to simulate conditions while progressing towards a goal state using token conversions. Tokens can be assets associated with a defined goal and can be implemented to segment accounts for a defined purpose and to improve user planning. An account can be segmented by converting a portion of the user's account balance to tokens to progress towards the goal. In some implementations, a simulation can generate a target token conversion schedule that achieves a target number of tokens at a target date. However, user behavior can change the observed token amounts and cause deviations from the schedule. The simulations can alter the token conversion schedule and arrive at a new target date for the target number of tokens. In some implementations, automated agents and machine learning components can be used to implement the token tracking and simulations.