I try to think of technology that will someday out match me. So far in life I have been able to adapt, but one day the technology will become useless to me or even worse I will be unable to use it. The technology gap is wide, but I've noticed it is wider between the newer generation and the middle aged then the new and the old old generations. This has been true for thousands of years, but I honestly expected it to change as soon as technology started to exponentially grow.
I've often joked that someday my grandchildren will spend their time moving their hands through empty space in complicated patterns that I cannot understand. Every once in a while, they will smile or snicker, and I won't have a clue. However, my hope is that adaptation might be a part of my generation and those younger than me. As you note, the baby-boomer generation seems to be on the other side of the gap. However, during their formative years, technological advance was relatively slow-paced. So perhaps they didn't adopt technological adaptation as a life-skill. That said, you might be right about the changing speed of advance. We might be more able to adapt to new technology than the boomers, but the rate of change might be something that we can't manage. Still, there has to be a human limit to the rate at which one can adapt, and therein lies the premise for singularity.