“To be or not to be” is the famous opening phrase of Hamlet’s well-known soliloquy in Shakespeare’s play “Hamlet.” In the soliloquy, Hamlet questions the meaning of life, and whether or not it is worthwhile to stay alive when life contains so many risks and hardships. He concludes that the primary reason people stay alive is due to a fear of death and the uncertainty of what lies beyond. Now what does this passage in Hamlet have to do with future proofing a business or monetization? Many organizations grapple with unknowns as well. “Do I just focus on the now and not worry about the future? Change is scary; risk is even scarier, so I can’t be bothered thinking about the future.” For many, the future never comes as the decisions made in the present impact their ability to define their future. Instead their business is defined very precisely for them by what a billing system can deliver in the present. What seemed like a non-risk suddenly becomes life or death for the business.