A number writing development guide including a number guide sheet having sequential instruction indicia. The sequential instruction indicia includes discrete ordered steps that cue a user in proper writing strokes to write an associated number. At least one of the discrete ordered steps relates to a common childhood activity or experience to thereby form an association between the activity or experience and the sequential instruction indicia. The guide further includes a challenge sheet coupled to the number guide sheet and having number challenge indicia. The number challenge indicia cues the user to arrive at a numerical answer to the number challenge and write the numerical answer thereon.