In a chess game, the first moves are usually quite important. Players aim at taking some control of the center of the board and allow them to develop more freely their pieces. There are at least two important similarities between a chess game and a contemplative practice.
The first is that also in a contemplative practice one is playing a competitive game against an 'enemy'. This adversarial language might sound at odds with popular images of meditators sitting under blossoming trees with blissful expressions on their faces. But those images do not represent the initial stages of the game. Like in a chess game, when one starts a contemplative practice there are two players that fight each other: one is then bundle of intentional acts that somehow aims at supporting practice, while the other is the bundle of intentional acts that are based on other habitual patters and tries (if possible) to disrupt practice. Is one playing against oneself? It doesn't matter, since answering this question requires identifying with this or that bundle of intentionality, which ultimately is something to avoid. Nevertheless, the contemplative game is as competitive as the chess game, since the two bundles are at odds with one another, and they inevitably try to overpower the other for the sake of taking full control of the chess board (the field of experience).
The second similarity concerns more specifically opening strategies. In a contemplative practice, there are usually two dimensions that need to be developed: mental stillness and understanding. Both elements support each other, and they are both necessary. Without some stillness it is difficult to clearly understand what is going on and the game will become quickly fuzzy. Without understanding, it will become unclear what the game is about, what its purpose is, and how should one organize one's moves. The equivalent of opening strategies in contemplative practices are the different ways in which these two components (stillness and understanding) are developed, either sequentially or together, using any available and suitable method.
What would be the best opening strategy for a contemplative practice? Of course, much depends on conditions and circumstances and luckily multiple options are available in case one doesn't work out. However, assume that one is approaching contemplative practice from within a social and cultural context in which (i) this sort of game is not established by default (it's not something one learns since the beginning, and it must instead be 'discovered' somehow), and (ii) there is little external support and reinforcement (in terms of institutions, communities, peers), and (iii) there is plenty of stimulation that pushes intentionality in the direction opposite to that pursued by practice (urges for consuming goods, over-enjoyment of sensual pleasures, constant activation). In such a condition, strategies based on faith and tradition would not work, and a too sudden jump into the core insights that support understanding might simply be swallowed by the ocean of different views and opinions with which the ordinary view sustains and protects itself.
In this case, one of the most strategic openings might be the following:
(1) put the body first, as the overall context of anything else that happens. In contemplative practice, the body is not what we ordinarily refer to as 'my body'. Usually, the body is an avatar, a representation. We don't relate to the body as such, but to some idea or image of the body, what it should be, how it should look like, what it should mean for ourselves or for others. These are perceptions of the body, but they are not the body. In contemplative practice, the body is approached from within, intuitively, as a pure presence within space. It has no other quality, meaning, or aura than its being-there, as the overall context within which anything else is rooted. Putting the body first in this way allows one to uncover a context within which all the other intentions unfold, and thus creates room for disengaging from those intentions and come back to the general context.
(2) cultivate contentment, as a natural and default state. Intentions and actions aim at producing certain results, which to some extent are currently missing or absent, and in most cases this mechanism is predicated on some feeling of discomfort or uneasiness for what is currently present. Taking the body as a general background, one can begin to discern the intention of simply staying with the body from the whole array of other intentions. And then, one can discern how in this simple presence of the body there is nothing that is really lacking or missing. The sense of discomfort, uneasiness, and restlessness that characterizes most of the other intentional movements is absent here. By retreating into the body, one can thus discover a space in which a spontaneous sense of contentment and satisfaction is naturally present, without any need to do anything in particular. Of course, one needs to tune one's attention in order to discern this feeling of contentment, and then one needs to cultivate it in order to bring it more prominently to the foreground of experience. But in this very attempt, attention is also trained and refined, and stillness grows without effort.
(3) surrender, drop the sense of control, sink into the experience. Once the feeling of contentment is discernible and stable enough, it is time to sink into it, to abandon oneself to it completely, as if one would enter a warm bath or a pool of clear water, and would allow the body to go under the surface, towards the depth. This ability to let go of oneself (and letting go is always letting go of oneself) is what allows contentment to grow into something much deeper and more profound, a sense of enthusiasm and pleasure, a moment of rapture, which absorbs attention entirely and reveals a very important insight: there is no need to seek anything outside. There is an unfathomable reservoir of happiness and internal peace, just right here, within, free, always accessible, inexhaustible.
This does not make the external world disappear, but it takes a huge (unnecessary and unfair) burden out of it: the external world can remain simply that, a playground for experience, but it does no longer need to be seen as a provider for happiness. Freeing the world from the hard task of supplying happiness, one might eventually meet the world for what it is, instead of searching in it what it should provide 'to me'.
In terms of the ultimate goals of practice, this might not be the most fundamental insight. Nevertheless, in the perspective of opening strategies for practice (which is usually a fairly long game, which takes years, decades, if not whole life-times to unfold), this is perhaps the most strategic in the beginning. For one who gains some confidence on this point, it will be natural to protect one's own practice from external circumstances and conditions, cultivate continuity and commitment, invest the time that is needed, and gain a sense of confidence in what and why one is doing, which is necessary for all further insights to arise and take root.