In this article, the author discusses the down side of a personal/professional makeover at any age, less to discourage risk-taking than to render it transparent, even plausible. He explores one aspect of the experience of redevelopment, what John Dewey called the "reconstruction of experience", with attention to the role of personality, ingrained habits, and judgement in that reconstruction. Even as new opportunities and horizons emerge, serious risks may also be incurred, personal limitations confronted, dreams deflated, enough to discourage anyone from starting over, particularly late in the game. But, as mentioned in this article, youth is no less liable to such risks and disappointments. Hubris, false leads, miseducation, egotism, even fashion, can thwart the best of plans. (Contains 17 notes.)