In the 1980s there was an explosion in our ability to capture panoramic digital data from the sky and our ability to access cheap, powerful and flexible computers. We were awash in digital capabilities but held back by the lack of a similar explosive growth in square meters of glass and metal. This crisis changed the way ground based astronomy was done and led to astronomy leading the way in interoperability and scientific returns on digital assets. Now we may face another crisis as the cost of the data potential new telescopes can achieve, limits the science we can do. This will certainly change the way we preserve and value raw and science-ready data and the role of industry in advancing astronomy. I will review my journey in data intensive astronomy over the past 40 years and share some thoughts on future directions.