Goal insurance is provided as a purchasable option to users who wish to have a goal tracking system monitor and enforce their goals. The user may define the goal, a reward to be given upon successful completion of the goal and penalties to be applied if the goal is not met. To avoid penalties, the user may purchase goal insurance that may be used or apply under specified circumstances. Such circumstances may include death, illness, unemployment or the like. Goal information and progress may be monitored by the goal tracking system and may further be published to one or more sites. Other users may contribute to the user's reward or send encouraging remarks. If the user does not purchase goal insurance, the predefined penalties may be applied upon expiration of a goal time period if the user has not achieved their goal.