The mid-1880s were a time of uncertainty and hesitancy in the affairs of the Mackinnon group. Although it was successfully consolidating its position as the dominant force in the coastal steamshipping of India and Australia, it was beginning to face a strong challenge to its position in Indonesia and its longdistance lines between Britain and India were in the grip of depression. Meanwhile, on the peripheries of its sphere of operations – in the Persian Gulf and eastern Africa – there was commercial stalemate. Trade was flat, profits were slack, and transport innovation had stalled. Overall, it was difficult to see where opportunities might lie for further expansion and diversification, once the upswing in the business cycle reappeared. Such uncertainties about the group's future strategic direction both mirrored and fed into the faltering efforts of William Mackinnon to define his own role within the social, political and business life of late Victorian Britain. His substantial efforts on behalf of Leopold II were failing to translate into concrete business opportunities for himself, his family and friends. He had finally abandoned his Glasgow firm and was no longer linked to the direction of any major British financial institution. He had no children for whose future he needed to make provision, and the deaths of so many old friends – above all Henry Bartle Frere – made him aware of his own mortality. For all these reasons he was casting around for some new sense of direction. Three episodes that took place between the summer of 1885 and the summer of 1887 illustrate his state of mind, and give pointers to the motives which eventually brought him to commit himself, with his family and some members of his business network, to his last great venture, in East Africa. The first was the general election of November 1885, in which he hazarded himself for the first time in the arena of British parliamentary politics; the second, a year later, was his launch of Stanley into ‘the heart of darkness’, in a mission to bring relief to one of General Gordon's loyal lieutenants; and the third was an invitation, which came almost out of the blue, to engage himself in a patriotic effort to open up the Persian Empire to British trade and political influence.