The successful entrepreneur who is leading a closely held enterprise is more likely to be held in check by a sea anchor. This type of anchor is much smaller than the bottom anchor. It is cast overboard when a ship is at sea and the floor of the sea is many leagues below. The sea anchor moves with the tide and wind; however, this type of anchor always keeps the boat facing into the wind; furthermore, it slows down the movement of the boat resulting from either the tides or winds. Change in direction does occur with the sea anchor, but this shift occurs slowly and deliberately. The sea anchor allows for change, but doesn’t allow for precipitous shifting with the wind or for the endangering of the enterprise from a strategy that does not face into the wind (that is unrealistic or not aligned with the intentions of the enterprise). When a closely held enterprise is led by a reflective entrepreneur, then this enterprise is likely to be guided by a sea anchor rather than by a bottom anchor (or by no anchor at all). A skillful organizational psychologist can be of great value in helping an entrepreneurial leader discover and invent ways in which her closely held enterprise can be maximally responsive to the complex, unpredictable and turbulent conditions of our postmodern world, while also retaining its closely held mission, values and purposes.