It seems likely that any actually existing anarchy will involve a variety of economic practices, and that those practices will necessarily be different, and sometimes very different, as a result of the wide range of changes involved in transforming authoritarian relations. So, for example, on the question of planning production, it might well be that instead of having a pen factory, we would have more flexible sorts of productive apparatus. Maybe our pens will be made by 3D printers, using recycled plastic, at a facility that simply makes the next thing needed, rather than specializing. Or maybe our writing implements adapt to the overall changes in the community. Among those changes will undoubtedly be some changes in the way we think about appropriating raw materials, so all the changes in thoughts about "property" will also be factors. Lots of things that "make sense" under capitalist property and exchange conventions will look very different to us in anything like anarchy.
Money--or a circulating medium of some sort, since "money" is a very loaded term for lots of folks--is one of those things that we will undoubtedly have to rethink substantially. If some sort of explicit exchange remains part of the economic norms of a given locality, then some sort of marker will be required. Shared accounting systems are also a possibility, although currency may be easier to keep decentralized. In any case, the principle ought probably to be "the best tool for the job," without any very general assumptions about what "the job" of exchange is. After all, lots of local, daily exchange might be handled with an almost purely conventional circulating medium, while large-scale transactions probably demand a somewhat "harder" currency, particularly when those involved are not also involved in that network of routine, daily exchanges. So maybe you have wooden nickels and IOUs circulating alongside precious metals and secured credit currency. Hopefully, one of the first stages of reorganizing our economic life is breaking down the monolithic "economy," so that we can tackled questions with different stakes in different, individually appropriate ways. We tend to act as if we have to provide for general needs and individual preferences by the same system, probably because all of that has been captured under current circumstances by the same forces. But, moving forward, we should have the option of diversifying our practices to more naturally harmonize with our actual goals (rather than conforming to the demands of this or that system.) So, for example, we might be communists when it comes to supplying ourselves with a shared, stable basis for individual pursuits that might involve all sorts of supplementary competition, inequality, play, trial and error, and general tomfoolery. We could have boring, stable currencies where they were necessary, and fluctuating, fun currencies where the social costs of anyone's "failure in the market" aren't going to threaten to throw the whole network in some hierarchical or authoritarian direction. And people who are offended by distinctions between individuals wouldn't have to play.