In this dissertation, I try to advance our understanding of how managerial discretion and corporate financial flexibility affect various corporate outcomes such as failure, excessive (sub-optimal) continuation, firm growth and investment, in three novel ways. First, I show that the empirical effect of finance is not merely a misspecified real influence but rather that the financial structure of firms matter for firm growth and investment where the real effects of finance arise out of the imperfect substitutability between internal funding and external private credit. Second, using managerial mergers and acquisitions (M & A) investment decisions as an identification mechanism, I find that managerial discretion combined with corporate financial flexibility may lead to distortions in corporate investment and financing policies, and those distortions cost the various stakeholders of the firm dearly. Furthermore, using another sample of distressed firms worth more dead than alive, I, along with a co-author, show that most of these firms continue operations long after the optimal exit time. The failure to liquidate costs the typical sample firm over three years 8.7% of its assets in lost earnings relative to the industry median. Finally, I find that capital market does not fully internalize the costs associated with managerial sub-optimal behaviors in the short run. Although the market disciplines managerial sub-optimal behaviors in the long run, the market disciplinary mechanisms may not be swift enough to forestall falling values for the various stakeholders of the firm. Succinctly, the findings in this dissertation suggest that managerial discretion and corporate financial flexibility entail real consequences for various firm dynamics. The traditional line of argument, "Blame It on the Market," may not be well grounded, and firms need to carefully examine their investments and financing policies in good times to cushion against systematic shocks in bad times.