How do SMEs company heads strategize? What are the strategic knowledge and skills associated with this process? How does it participate in shaping the strategy of the organization? To contribute to answer these questions, I present the preliminary findings of an ongoing exploratory empirical study. These preliminary findings suggest that company heads do learn different type of strategic knowledge when the play their strategist role through strategizing. Moreover, prerequisites for strategizing are identified: having perceived the need for strategizing and having made themselves available to strategize. As this process triggers changes in the company strategy, there is evidence that the knowledge and lessons learned are reuse in further strategizing and open to evolution depending on the emerging subsequent strategic issues. For strategist, learning to strategize could be a never-ending journey toward a form of practical wisdom.