Three decades ago, inspired by a visit to Singapore, the vision of ‘Barbados: The Singapore of the Caribbean’ was born. Today, this vision is revisited not out of nostalgia but out of necessity. Post-COVID-19, Barbados’ socioeconomic engine is faltering, with sluggish growth compounded by domestic inefficiencies and global challenges. The question now is whether Barbados possesses the political will to pivot strategically for future prosperity while managing its current predicaments. Singapore’s transformation from a poor, overcrowded colonial outpost to a global economic powerhouse offers a masterclass in strategic nation-building. Under Lee Kuan Yew and the People’s Action Party, Singapore expanded its landmass, quadrupled its population through managed immigration, and skyrocketed its GDP per capita from US$500 to nearly US$93,000. In contrast, Barbados has seen modest growth, moving from US$367 in 1960 to around US$25,000 in 2024, yet remains stagnant relative to its potential. To transition from stagnation to sustainability, Barbados must unclog its economic engine by shifting skillsets, mindsets, and embracing cross-cultural communication. This involves learning from successful models, sharpening strategic vision, strengthening governance, eradicating corruption, investing in innovation, enhancing education and health, expanding the population base, modernizing infrastructure, reducing food import bills, and tackling the high cost of living. Singapore demonstrated that discipline and imagination can overcome limitations. Barbados, too, can rise if it steers with purpose. Establishing a Strategic Singapore Model Think Tank, staffed by experienced professionals to work alongside the government and recommend transformative actions, could be a pivotal step. It’s not too late to reignite the Singapore dream—if Barbados acts boldly, inclusively, and with disciplined intent.