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On November 30th, 2018, Redditor u/TheTopHatFish posted a photoshop to /r/TF2 showing the demonman squatting in a field of flowers with text reading, “you’re doin’ good, lad,” garnering over 900 upvotes in roughly two years (shown below).
On that day, Redditor u/Moronmaster commented under the thread with an Imgur link leading to a still version of the image from Spazmatic Banana’s YouTube video (shown below). This is the earliest known version of the image as a still.
The image was shared a number of times over the following years, notably by Instagram page @new.incognito.tab on January 28th, 2020, garnering over 4,000 likes in a year. On September 8th, Game Banana modder GenericEngineerMain posted a Spray mod that allows users to spraypaint the meme on walls during gameplay.
On January 22nd, 2021, Redditor u/DerangedLali posted an image of a sculpture of the “You’re Doing Good Lad” meme to /r/TF2, garnering over 11,000 upvotes in four months (shown below, left). On February 2nd, Redditor u/CartoonCrayon posted an original piece of fanart depicting the Demoflower titled, “You’re doin good lad. Have a bouquet of Demoflowers,” garnering over 8,000 upvotes in three months (shown below, right).
On February 15th, 2021, YouTuber wolt posted an original animation of a sunflower saying the phrase, garnering over 231,000 views in three months (shown below).
On February 25th, Redditor u/TheFlamethr0wer posted an animated image macro to /r/tf2 using the phrase, garnering over 10,000 upvotes in three months (shown below, left). On April 28th, Redditor u/TheSuspiciousSpider posted a screenshot from an Axe commercial with a number of faces on sunflowers, titled, “You’re doin’ good lad!,” garnering over 6,300 upvotes in two weeks (shown below, right).
Source: https://knowyourmeme.com/memes/youre-doin-good-lad