Good post, I hope to read more from you

This post really hits the nail on a recent situation I found myself, mentoring some of my Jr colleagues on game design and project management.

I have had trouble for more than a year trying to teach my approach to my Jr colleagues. I'll articulate them following your categories, as they helped me now to map better the problem:

1) [Complexity] A lot of situations while preparing a game design are based on the subject to design for. Theory teaches you some "design rules", but then you have to mix the "ideal game mechanic" with the kind of user target, the time at disposal for them, and foreseeing problems that could occour.

2) [Curse of Knowledge] This happens a lot because I have computer science skills, so I am able to quickly visualize "complexity" of what I am thinking, hence my design choices are driven also by this.

3) [Personal Context-Dependence] Last but not least, I am a very intuitive person, and lot of the knowledge I have and that I apply on the job is not even "formalized". The hard part on this is to try find how your "intuitive skills" are named and explained. If you even can isolate those intuitive skills.

To work on 1) and 3) I recently found that a possible solution was easier than expected: use the person you're trying to teach to, to observe you and "deconstruct" you. A person craving to learn from you this tacit knowledge will be very happy to "study you" and try to write down what you do and how you reason, finding a way to explain your tacit knowledge and map it.

This is a really good post and articulates a lot of the challenges well, and I like and can relate to the bakery example. 

From my POV the hard-to-transmit tacit skill of transmitting tacit knowledge benefits greatly from a couple of things:

1) For a given learner, first learn enough background to know some basic terminology and be able to ask basic questions to prepare yourself to dive deeper, then get direct, hands-on coaching and ongoing mentoring from multiple experienced practitioners. 

2) For a given teacher, develop enough broad understanding of fields outside your own, and enough understanding about how humans-in-general think and reason, to be able to efficiently figure out how a given audience thinks, what they know, and what avenues and metaphors and examples are likely to lead to learning. Listen mindfully, and be ready and willing to change course mid-conversation (or other live modality) as needed.

Good post, I hope to hear more of those London bakery recs !

"By now, I can take one glance at a bakery or cafe, in person or online, and be confident whether or not their baked goods will be to my taste before trying them." oh my god I am the same way! everyone says I am really shallow and judgemental about that but, like, I totally agree with your idea that people can just LOOK at things and know everything about their inner qualities!