The growing popularity of big data and Internet of Things (IoT) applications bring new challenges to the wireless communication community. Wireless transmission systems should more efficiently support the large amount of data traffics from diverse types of information sources. In this article, we introduce a novel data-oriented approach for the design and optimization of wireless transmission strategies. Specifically, we define new performance metrics for individual data transmission session and apply them to compare two popular channel-adaptive transmission strategies. We develop several interesting and somewhat counterintuitive observations on these transmission strategies, which would not be possible with conventional approach. We also present several interesting future research directions that are worth pursuing with the data-oriented approach.