Stole stuff from grocery stores (candy and other childish shit) every day in school with my friends as a supplement to what we bought.
Move on to steal bikes and sell them with same friends.
Move on to steal from warehouses.
Get caught by friend's parents with crowbars etc. Risk reward wise stealing stuff from everyday stores or even small time heists are not worth it.
Still steal if there is little risk or a large enough reward to justify it.