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Jerry Garcia had it right. As a kid growing up in New York City I never would have thought I’d end up taking the road that I did. Of course I credit Jacques Cousteau, but also have to thank Paul Rabinowitz, who hooked me on oceanography when I was an impressionable junior high school student. My professional career has been a completely unpredictable, but fascinating jaunt through science. In the name of science I’ve survived Crossing the Line, lived on four different submarines, flown through the eye of a hurricane, nearly gotten shot in Africa, eaten a cobra heart, busked in bars in Peru, and served every U.S. President since Ronald Reagan. If it hadn’t been for good luck, healthy scientific curiosity, a questionable degree of risk tolerance, and the good fortune of being connected to the right people in the right place at the right time, I might have been a lifelong academician as was typical of my generation of scientists. I will share a handful of tipping points in my career and how I’ve come to understand the value of transdisciplinarity, odds-weighing, and timing in developing what - for me - has been a fascinating, if not somewhat chaotic, life in science.