Whilst detriment, retaliation or victimization after whistleblowing/speaking up is considered poor practice and unacceptable, they may also serve a wider more positive function. Speaking up in the workplace provides obvious benefits for the organization, yet many experience detriment for doing so. Why detriment is not addressed as well as it could be is explored and whether organizational resilience supports or is in conflict with the resilience of the whistleblower. This chapter considers what may be trying to emerge through the shadowlands of detriment—the hidden and suppressed. If skillfully and sensitively worked through, detriment may expose a greater compulsion that needs to be fulfilled and in doing so supports all parties to grow through the process. This chapter invites the reader to consider detriment is not always as it appears and the intersectionality of it can be complex. Working through the shadowlands may help create a more open transparent culture and compassionate society. The existential detriment to all parties including the perpetrators within the shadowlands needs to be acknowledged.