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I almost feel like you're describing a job.

I'm always having to learn new practical skills for work, and getting into things I know nothing about and having to learn them to be successful.

The difference is that the skills you learn from playing games usually are not transferable to the rest of your life. There's some exceptions to this but most of the stuff you learn from complex games are completely fabricated for the game and have very little bearing on real life.... Though, am argument can be made in many cases, such as kerbal. I haven't played kerbal, but I understand there's some reasonably accurate orbital mechanics and rocket science involved. This is just one fairly obvious example that I know of. Not to be confused with a comprehensive list of games with practical educational value.

For me though, I usually don't want to learn anything useful while playing a game, since that's basically what I do for work. So any game, like our example of kerbal will, in all likelihood, feel like more work to me, which is decidedly not the objective I'm going for by playing a game.

I dunno. Different games for different folks or whatever.

I have some suggestions that fit this category with varying degrees so I will include some justifications so you can decide if you want to include them in your own playlists

• Her story/the stanley parable :: fit the category perfectly
• subnautica :: Survival game with heavy exploration. Unusually for this genre it has a story which you can only progress by finding some clues and piecing them together
• the witness :: This one has been mentioned already but I just wanted to reiterate that although it may seem like a simple puzzle game it's a good fit for this category. Here's an excellent analysis of it that you can watch after playing https://www.youtube.com/watch?v=KZokQov_aH0
• The talos principle :: the main part of this game is just a puzzle game so it seemingly doesn't fit very well. However, along with those there are some characters which ask you some philosophical questions which you unintentionally end up mulling over while solving the puzzles. By the end of the game you have understood some things that can make the ending very meaningful and emotional.
• antichamber/gorogoa/superliminal/baba is you :: Simple puzzle games but they are solved by lateral thinking where you're constantly pushing the boundaries and rules of the puzzle itself
• into the breach :: rougelike tactics game. Someone else mentioned how roguelikes in general fit this category and this is my honorable mention
• hacknet :: You are given some tools that can open some doors but you have to learn how to exploit those doors to open the remaining ones

Toki tori

OP's image is pretty good but some recommendations posted are really stretching it specially the RPGs.

Curiously Deep Rock Galactic is about practical knowhow. At least that differentiates greenbeards from greybeards.

• The oppressor is nearly immune to bullets but melee attacks are super effective
• The Driller will overheat digging about 12 meters (depending on the upgrades used) Digging ten clicks then pausing to cool will prevent overheat
• Cave leeches make a distinct yummy noise before attacking. You can escape by seeking cover again. Cave leech attacks are often facilitated by a distraction such as minerals or glyphid ambushes
• The Scout's grappling hook does not account for safe perch or landing. Scouting to a sheer cliff is a good way to just get hurt. Mind where you're going to land.
• On the other hand minerals embedded in a cliff face often protrude enough to get purchase. This can be facilitated with a flying pickax attack. Practice, practice!
• Likewise, dwarves can scamper up steep slopes like mountain goats with forward movement and spamming jump.
• Then again, gravity is the number one killer of dwarves, seconded by common Glyphid Grunts. Don't underestimate them.
• The Driller's Collette Wave Cooker can defuse unfuzed Exploders when it deals the killing damage (defuse = doesn't explode). The Driller's Cryo Cannon can defuse fuzing Exploders...sometimes.
• Overhanging cliff-sides are the nemesis to the Engineer's platforms. If you dont want to carve out headroom, extend them out a layer or two.
• The Engineer / Scout team (platforms and grappling hooks) can quickly exploit the high-positioned minerals in a cave.
• That said, platforms can make for great bridges. Do so at whimsy for starters and learn where it's useful.
• And yet, the engineer has the most trouble traversing sheer incline, especially in tight quarters. Make sure your Engie can get to the drop-pod safely.
• Speaking of extraction, Simple Mining missions are the most linear and require the most attention regarding preparing traversal back to the droppod. Escort is also linear but naturally comes with a big tunnel which makes it easy (when Dotty doesn't carve a vertical drop). Other missions feature a rounder, unlinear complex and a shorter exfiltration. Sometimes the pod will drop onto a crap place, with the ramp in mid air, or embedded in hard rock.
• Drillers should watch for adjacent chambers to connect by tunnel. Engineers should bridge chasms and seal holes. Engies can also create safe steps to traverse hot slag and slime. Both can level out arenas where fights are expected (say when prepping for a dreadnought or powering up a salvaged drop-pod)
• In escort the Engineer's grenades make short work of rocks and beamers. (The latter needs something that chips into rock, even a scout with a pickaxe power attack). The Gunner's hurricane rocket launcher manages both nicely.
• Dotty, Hack-C, Steeve, lootbugs, Hexawings, Breathers, Cave Vines can all be petted and should be. Bosco can be saluted. Using the laser pointer, other Dwarves can be talked to.

These are all off the top of my head. There are dozens of others one learns on the path to Greybeard enlightenment. Rock and Stone.

YYEEAAAAAAHHHH outer wilds!!! FUCK that game just absolutely slaps, top tier experience.

Trying frantically to remember some recs too but nothing that fits exactly comes to mind except those already mentioned. Probably Cultist Simulator? Though it has frustrating moments where you seem to exhaust all available options and hit the wall without noticing some seemingly random option you have to try. Maybe also Sorcery! series — the more branches you try, the more complete picture of the world you get.

Thanks for recommendations! Outer Wilds is phenomenal, and Obra Dinn was so-o satisfactory to complete.

Noita and Who's Lila? 🙏