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Inspired by @kelly_gilbert's graphic and countless others' journeys here is a graphic of mine
My favorites: Find Ned! because the entire thread is one of those 'made me feel like a fly in the room' with the greatest minds from the inception of Alteryx creating one of the greatest threads.
The Locker Problem this one I will never forget because it is one of those few that can surprisingly be done with only a single tool. It was a great mathematical feat and truly fun to learn and investigate the solutions and theory behind them.
The challenges leading to the greatest lift at work have been the ones dealing with batch macros, a treasure trove of amazing functionality. Specifically, The Thousand File Challenge.
The challenges with everybody solving with a different tactic, those were my favorites too. Specifically, The Plinko Challenge comes to mind, where it didn't seem 'great minds think alike' and was more like 'great minds have different solutions and they're all incredible'. #NeverStopLearning