The new millennium has been characterized by rising digitalization, the proliferation of shadow banking, and significant advancements in machine learning and natural language processing. These trends present both challenges and opportunities, which my dissertation addresses. This cumulative dissertation investigates critical aspects of financial stability, monetary policy, and the transition towards cashless economies through three distinct but interrelated studies. The first paper examines the risk-taking channel of monetary policy transmission within the euro area, focusing on shadow banks. Through vector autoregressive models, it assesses the impact of conventional and unconventional monetary policy shocks on shadow banks' asset growth and risk asset ratios. The results indicate that lower interest rates lead to a portfolio reallocation towards riskier assets and a general expansion of assets in shadow banks. In the case of conventional monetary policy shocks, both effects last three times as long as in the case of unconventional monetary policy shocks. Country-specific as well as sector-specific estimations confirm these findings. This study bridges gaps in the existing literature, especially in the eurozone, by highlighting the significant role shadow banks play in monetary policy transmission, suggesting implications for financial regulation and stability. The second paper explores the influence of financial stability considerations on US monetary policy, particularly during the Great Recession. Utilizing natural language processing and machine learning techniques on congressional hearings, this study constructs indicators for financial stability sentiment expressed by the Federal Reserve Chairs. Empirical analysis is conducted using Taylor-rule models, revealing that negative financial stability sentiment is associated with a more accommodative monetary policy stance, even before the Great Recession. This work provides new insights into the integration of financial stability concerns into monetary policy frameworks, demonstrating the need for a balanced approach to economic stability. The article suggests that under a dual mandate, such as that of the Federal Reserve, financial stability can, to some extent, already be factored into monetary policy deliberations. The third paper sheds new light on ``cash paradox'' by uncovering the factors of the cashless transition that has not been entirely understood so far. Using a comprehensive dataset across 65 countries, the study employs panel data models to explain the paradox (increasing demand for central bank money despite soaring digitalization), especially among technologically advanced countries, e.g., Japan. Empirical evidence suggests that digitalization is not significantly associated with higher reliance on physical cash. It uncovers a unique non-linear relationship between trust and cash usage (``Arch of Trust'') which holds after addressing potential endogeneity issues using 2SLS estimation. Opposed to the widespread misinterpretations of Keynes' (1937) reasons for holding cash, the findings highlight that distrust is the key factor unlocking two distinct puzzles in economics, linking cash hoarding with ``missing'' funds on capital markets and slower shift toward digital payments in low-trust societies. A key insight is the role of trust as a (social) insurance, cushion or safety net, dampening the perception of risk and reducing precautionary and transactionary demand for physical cash, while encouraging a shift towards riskier alternatives. This, in turn, is connected to the third puzzle, the ``paradox of prudence.'' A shift from riskier investments to safer assets, cash, may be prudent at the individual level but risky for the overall economy, a concern for macroprudential policymakers. Additionally, the research highlights the critical role of culture in driving the global movement towards cashless economies. Moreover, cultures that are more self-expression-oriented (which is the main cultural dimension) and culturally closer to Sweden are associated with less cash-intensive economies. These insights are vital for macroprudential regulators as well as for policymakers designing payment systems and CBDC in culturally diverse regions like the Eurozone. Collectively, these papers contribute to a deeper understanding of monetary policy, financial stability, and the transition from cash-based to (nearly) cashless societies, offering significant theoretical and practical implications for academics, regulators and central bankers.