This essay discusses teaching transactional skills as part of traditional non-clinical, substantive law classes. It offers a very personal perspective gleaned from the author’s 40 years of combined experience as a San Francisco transactional law practitioner and law professor. Of necessity, due to length constraints, the author offers only a few selected opinions about what she thinks works in teaching transactional skills in substantive law classes. Despite this limited focus, the author weighs in, at least a bit, on a myriad of subjects, including the current push for law graduates to be more “practice ready,” the importance of skin-in-the-game type mentoring both pre- and post- law school graduation, the different challenges in training transactional lawyers versus litigators, the merits of multifaceted large drafting projects versus more discrete problems, course advising needs, the teacher as recruiter, balancing desires for breath versus depth of exposure, and using what the author calls factual “sidebars” as accommodation of traditional casebooks to the transactional perspective. The author hopes these offerings of her matured discernment from longevity in the field of transactional law skills training, in the various iterations she notes in the essay, provide some helpful insights to current teachers of transactional law skills, both clinical and non-clinical.