in general, no. E.g., a child with a high fever will dissipate more energy than a child without a fever over the same time period. who is more likely to survive?
We can even consider a specific type of dissipation that an organism uses to store memories (longer lifetime of memory = less reversible = requires more dissipation), there's no guarantee that the memories stored will be useful for survival. storing a memory that lasts 100 years costs dissipation that could be better spent elsewhere for an organism that typically lives 1 week...
but with appropriate restrictions on what is meant by dissipation, organism, ... the timescales involved, the driving ... then the reverse statement can be true "more likely evolutionary outcomes" <among all possible trajectories of configurations of 'organisms'> "are going to be the ones that absorbed and dissipated more energy from the environment’s external drives on the way to getting there.”
That is, can we control (not just predict) the outcome by manipulating dissipation patterns?
You take energy too literally here. You could say a spoiled child has evolved to be an efficient money dissipation system.
Ultimately (if this is true) - would it be possible to increase efficiency of a complex system (social, financial, computational - doesn't matter) by consciously shifting the radiation it emits to the lower end of the spectrum?