Although not its original intention, Timberlawn prepared us well to practice psychiatry in a tumultuous time. We all agreed that if we had it to do over again, even knowing the residency program would burn, we would still train there. This realization not only speaks to Timberlawn’s training program, but also to the special bonds we developed with each other before and during Timberlawn’s demise. Where our PGY-3 cohort was in our professional development may have encouraged us to preserve our group, but this also clarified the importance of personality factors for selecting partners for subsequent practice relationships. This early opportunity to negotiate time-limited arrangements beneficial for multiple parties, with collective rather than individual efforts, prepared us to think creatively about “win-win” scenarios when facing other grim circumstances. Residents facing similar circumstances may benefit from adopting professional “adult” roles, allying with trustworthy others, collectively addressing needs of the institution and each resident, and remembering seemingly imposed “decisions” may only reflect initial oversimplified plans that are actually amenable to creative improvements and solutions.