The idea for an official holiday message from the Sovereign to the nation of the Principality of Woodlandia was first proposed by the "founding father", Sovereign Prince Shawn in 2019. Sovereign Prince Shawn had written his first Royal Holiday Message to the Principality of Woodlandia from his study at his private Canadian residence in Ontario, Canada on December 25th, 2019.

The following year, Prince Shawn had recorded his first Christmas message from the dining room of the same residence on December 25th, 2020. In 2019, the Prince was originally hesitant about issuing a video message, but by 2020 was reassured by the Prime Minister and agreed to carry out the concept and read the speech from a temporary studio set up his private residence.

On the day of the recording, the Prince was feeling ill. Later, upon watching the recorded footage, the Prince thought he looked visibly ill on camera and since the message was to be aired during the COVID-19 pandemic crisis, he therefore decided not to release the broadcast at Christmas, but issued a written message instead on December 31st, New Year's Eve. The unreleased holiday message video was archived by the Keeper of the Royal Archives.On December 31st, 2021, the Christmas tradition will continue with first video broadcast set to air on the internet.

The themes and direction of the speech are decided by the Prince and the text is largely written by the Prince himself. The topic of the message follows a general holiday greeting, reflections on the past and present and the direction of the coming new year.