These are times when it is not the private enterprise investing in digital technologies, but the governments too are in the fray. When a country plans to go digital, it involves gigantic proportions of scale and investment.

What is the motivation? the driving factor for a nation to go digital? What are the anticipated challenges and roadblocks for a digital revolution? How is it different from an enterprise going digital?

Before discussing the how? We need to understand the why. Why should a country plan to go digital? The motives are different for each country.

For a country like the Maldives, where tourism is the most significant industry (about 40% of the GDP), enhancing tourist experience is a priority.  
But for a country like India, which faces multi-faceted issues, it is safe to assume that economic revival takes precedence. As per CMIE (Center for Monitoring Indian Economy), India's unemployment rate in May 2020 was 21.73% and in Jan 2021, it was 6.53%. 
During one of my visits to a central Asian country, I asked one of the officials the top 3 problems he would like to solve using technology. He took some deep breaths through his mouth with a cigarette burning bright. While blowing the smoke out, he said, "Corruption, Corruption and Corruption."
I told him that if this is the objective, then we are set up for failure. The resistance to change will be mammoth. It is similar to an enterprise that embarks on a digital mission to cut down on labor.

However, the world over the pandemic has changed the priorities. The objectives for going digital are now on healthcare, including the vaccination drive and online education.