How much skill is the right amount to gain? When to keep going, and when to quit?
Some thoughts based on a few quite good comments on "The 1 to 10 Scale vs. The 1 to 10,000 Scale" --
Random: "Knowing when to STOP developing a skill is vital if one's goal is to become a generalist. A decathlete can't afford working solely on his javelin throw all year long... he has 9 other sports to get good at! Of course, for the 1-sport performer, obsession is the name of the game."
Zach Obront: "Don't you think the returns [to continuing to develop skills] diminish at some point? Obviously it depends on the skill and how important it is to your goals, but I've often made the conscious decision to stop focusing on a particular skill so intensively at an 8/10 (even if that only represents a 500/10000) because the extra effort to make that jump from an 8 to 9 is about equal to the effort to build an entirely new skill up to an 8."
I think there's roughly four levels where you make big gains in an area, any one of which can be a natural point for stopping the amount of learning you do.
Conversational: You know enough of the terminology and general points to have an intelligent discussion on the topic. This means you can start to have interesting discussions with experts, and people in that particular field/skill will be able to have decent conversations with you. This level is surprisingly easy to get to in many skills, maybe 2-3 hours of talking with someone smart plus a half-afternoon of Google usage. I'm consistently shocked at how few people get to a level where they can at least talk about, EX, nutrition, medicine, pharmaceuticals, finance, accounting, programming, the various programming languages, history / historical eras of places they visit, etc, etc. It's really easy to do and there's huge gains to those first few hours.
Proficient: You can do the skill, slowly, to a passable result. This one is good, it means you can handle it in a pinch. This takes longer to do, but it's great to have someone onboard that can do them. Accounting and bookkeeping, writing basic contracts, being able to do basic conversion / split-testing work, being able to evaluate lifetime value, basic writing / communication skills, basic presentation skills, basic negotiation skills... this are key business skills that everyone entrepreneur ought to at least be proficient in. Proficiency will take you around a few dozen hours for most semi-complex skills. It can be sped up with great teachers or great hands-on immersion.
Mastery: This is where I'd make a divide between "very good" and "best in the world." I think it's possible and beneficial to get to a low to moderate level of mastery in maybe 2-4 "clusters of skills" that are next to each other. Just like how a German speaker can pick up a number of Northern European languages to fluency easily, there's a few skills that, when learned together, can all be brought up and reinforce each other. I think almost everyone should master at least one communication skill. Life changes dramatically as you get better at communication, and so much of the world opens up. At least one of speaking well, writing well, programming, communicating visually, connecting with people individually or in groups, hosting events, creating environments that people want to go, something... ought to be mastered. Mastery in different unrelated clusters is where most breakthroughs come in -- like how Apple took expertise from industrial design and mixed it with more traditional hardware-related and software-related skills.
Everyone -- everyone -- should pick up at least a low level of mastery of a few things. You're almost by definition chained to mediocrity if you don't. Length of time becomes less important to something like this, because it's got to be something you love anyways. So the way to gain mastery is to do something you love in, be immersed in it, but also be constantly pushing your limits and trying to do new things and innovate. The time is less important than the combination of love and immersion, plus constantly honing the skill consciously.
World Class Levels of Skill: I'm not there in anything, but I can't help but notice the world class experts get immense amounts of advantages far beyond simple levels of mastery. I had a client who were literally at the very pinnacle of his specialist medical field, and he was (1) constantly sought after for everything related to his field, (2) had a constant stream of other mastery-skilled people wanting to work for and with him, (3) earned immensely more money than anyone else in his field, and (4) had all the work he could handle. He was also a triathlete, regular traveler, and seemed to have a very interesting and vigorous life, which should put to bed the myth that you can't enjoy other parts of life if you pursue world-class skill.
There's no reason not to build mastery in a few levels of skill. The question that gets interesting is, are you better off pursuing world class levels of skill in a particular specialized field, or getting the advantages of combining moderate levels of mastery in different fields?
Amazing works come out of both, and both can be incredibly fulfilling paths. For my money, if you knew one particular skill/field called to you, and you were certain you'd never be bored with it, and you liked training in it constantly, and you didn't get bored with things in general, and you were highly persistent, and you knew you'd likely stay the same in all those ways -- then go the world class route, and constantly hone one particular skill/craft. Life seems to be particularly amazing for everyone who is the best at what they do.
If any of those weren't true, though, you might be better off diversifying somewhat to get the benefits of additional clear thinking, mental models, and synergies from different skills and disciplines. Interesting, important, meaningful, fun, impactful work seems like it emerges about equally from world class skill or combinations of masteries.
Your thoughts, dear reader? And your comments on how you've chosen to prioritize your own skill development?