As Payments Modernization initiatives emerge across the globe, Financial Institutions (FIs) will begin a journey of transformation to enable innovation. This paper analyzes the benefits and challenges of payments transformation for banks and customers, highlighting lessons learnt from key modernization initiatives across the globe and outlining 10 hard realities that Canadian FIs and payments service providers must overcome to benefit from the Canadian Payments modernization initiative. The recommendations in this research should help both large and small FIs who are either just starting their modernization journey or are well on their way.