Peter Giovacchini (1986) once wrote – “The poorest understood and two most enigmatic words in psychoanalysis are working through.” And Patricia Coughlin (2022) recently wrote – “Like the middle game in chess, there is no playbook to guide us.” It took me 48 years to get here and a lot of encouragement from my students, but my presentation over the course of our two sessions will represent a rather bold effort on my part to conceptualize a broad strokes framework for this “middle game” in psychodynamic psychotherapy when deep and enduring characterological / structural change is the ultimate goal – in essence, a “how-to playbook” for how longstanding, deeply entrenched “defensive reactions” that impede growth can be progressively worked through and ultimately transformed into “adaptive responses” that promote growth. The process of advancing from rigid defense to more flexible adaptation is never a straight-line progression. Rather, evolving from psychological rigidity to psychological flexibility will involve the therapist’s strategic provision of not just “support” but an artfully conceived combination of “challenge” and “support” – namely, “optimal stress.” The ongoing therapeutic provision of this “optimal stress” will give rise to healing cycles of disruption (in reaction to the challenge) and repair (in response to the support) – and, eventually, progression from less-healthy defense to more-healthy adaptation. Over the course of the two sessions, I will be exploring the use of three specific groups of interventions – growth-promoting interventions that (always with compassion and never judgment) either (1) “support” the rigid defense (to demonstrate empathic attunement), (2) “challenge” and then “support” the rigid defense (to generate destabilizing stress and incentivizing dissonance), or (3) “support” the more flexible adaptation (to celebrate and reinforce the new normal). The strategic design of these “playbook interventions” is both an art (involving intuition) and a science (involving analytic finesse). Throughout both presentations, I will be sharing a number of vignettes that will demonstrate the application of these theoretical constructs to clinical practice.