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In this work, we develop a framework for analyzing an executive’s own- company stockholding and work effort preferences. The executive, character- ized by risk aversion and work effectiveness parameters, invests his personal wealth without constraint in the financial market, including the stock of his own company whose value he can directly influence with work effort. The executive’s utility-maximizing personal investment and work effort strategy is derived in closed form for logarithmic and power utility and for exponential utility for the case of zero interest rates. Additionally, a utility indifference rationale is applied to determine his fair compensation. Being unconstrained by performance contracting, the executive’s work effort strategy establishes a base case for theoretical or empirical assessment of the benefits or otherwise of constraining executives with performance contracting. Further, we consider a highly-qualified individual with respect to her choice between two distinct career paths. She can choose between a mid-level management position in a large company and an executive position within a smaller listed company with the possibility to directly affect the company’s share price. She invests in the financial market including the share of the smaller listed company. The utility maximizing strategy from consumption, investment, and work effort is derived in closed form for logarithmic utility and power utility. Conditions for the individual to pursue her career with the smaller listed company are obtained. The participation constraint is formulated in terms of the salary differential between the two positions. The smaller listed company can offer less salary. The salary shortfall is offset by the possibilityto benefit from her work effort by acquiring own-company shares. This givesinsight into aspects of optimal contract design. Our framework is applicable to the pharmaceutical and financial industry, as well as the IT sector.