Judgment is affirmation with the intention to thereby affirm competently enough, and indeed aptly. That distinguishes judgments from mere guesses.

It is bad to want something that not even God could attain, especially when the impossibility becomes obvious.

One does not avoid incompetence if one makes an attempt whose likelihood of success is too low. This seems little more than analytic: when the performance is in a domain that imposes standards of risk, attempts may or may not meet such standards. And the relevant competence of agents then includes reliably enough meeting those standards.

Flourishing is properly the main human end, and flourishing is activity of soul that succeeds in accord with virtue.

The risk pertinent to a particular attempt (and to its evaluation as an attempt of its sort) is the risk that the agent will fail to attain the end constitutive of that attempt. This risk of failure is coordinate with how likely or unlikely it may be that the agent will then succeed.

Ultimately, my more significant agreement is with a virtue tradition that features Aristotle and Descartes.

Normal adults can doodle, amble, and drift with no need to assess risk, since there is normally no risk at all. Jazz improvisation seems less subject to standards of risk than surgery, and less than much formal athletic performance, as in a tennis match.