Though new goals for sustainable cities and transport systems have been developed, decisions and planning at a local level often fail to achieve these ambitions. The purpose of this article is to analyse the factors in local decision-making and planning practice that conduce to urban sprawl and increased car traffic. The article analyses how the conscious application of so-called “day-to-day decision-making and planning”, results in a diminution of planning's role as a strategic tool, in concealment of the environmental impact of increased traffic, in the deprioritization of environmental goals in favour of growth, and in the “tyranny of small decisions”, where the need to make many individual decisions distracts from the achievement of sustainable city and transport systems. Day-to-day decision-making and planning are analysed and described in a case study centring on retail trade on the outskirts of the Swedish town of Örebro.