Episode #16
Thank God I Failed: Orlando Da Silva on Depression, Success, and Finding Hope
Host Tim Culbert welcomes Orlando Da Silva, lawyer, former President of the Ontario Bar Association, former senior Crown counsel, and author of Thank God I Failed , for a candid conversation about depression, mental health stigma, and the relationship between professional success and personal wellness. Orlando has lived with depression since childhood and speaks openly about his 2008 suicide attempt and recovery. He wrote his book to help others recognize they are not alone and find language for experiences that can be difficult to discuss. Despite an accomplished legal career, Orlando explains that professional achievement never cured his depression. He and Tim explore the disconnect between outward success and internal struggles, the importance of defining success for yourself, and Orlando’s decision to exchange the pursuit of happiness for the pursuit of meaning. Orlando also shares practical strategies he uses to manage his mental health, including a ten-point wellness scale, journaling, support from his family, and a letter to himself reminding him that depressive episodes can pass. Tim and Orlando also discuss stigma, disclosure, childhood trauma, family history, and Orlando’s concerns about medical assistance in dying in relation to mental illness. Orlando stresses that openness does not require sharing your struggles with everyone, but encourages those who are struggling to tell someone they trust and seek support. Ultimately, he hopes the legal profession can become more compassionate and recognize that experiencing mental health challenges is not a sign of weakness. About Orlando Da Silva, LSM Orlando Da Silva is a lawyer, public-sector executive, mental health advocate, and author of Thank God I Failed . Over a legal career spanning three decades in Ontario, Orlando has worked in private practice and public service, including serving as senior Crown counsel. He is a former President of the Ontario Bar Association and has been recognized by Canadian Lawyer magazine as one of Canada’s Top 25 Most Influential Lawyers. Orlando earned his J.D. from the University of Toronto and is also an alumnus of the University of Waterloo. He has spoken publicly about his experiences with depression and his recovery following a suicide attempt in 2008, using his story to challenge stigma surrounding mental illness within the legal profession and beyond. Today, Orlando serves as Chief Administrator of the Administrative Tribunals Support Service of Canada, which provides support services to federal administrative tribunals and boards. Through Thank God I Failed and his public advocacy, Orlando continues to encourage greater openness, compassion, and understanding around mental health. Key Moments: 00:01:48 Orlando explains why he wrote Thank God I Failed and his hope that sharing his experience can help others feel less alone. 00:06:12 Orlando describes the ten-point mental health scale he developed with professionals and how his family uses it to recognize when he needs additional support. 00:10:56 Tim and Orlando discuss medical assistance in dying and Orlando’s concerns about applying it to mental illness based on his own experience of severe depression. 00:15:53 Decades of journals reveal the cyclical nature of Orlando’s depression, leading him to write a letter to his future self as a reminder that depressive episodes can pass. 00:20:28 Orlando reflects on the response to Thank God I Failed and how messages from readers have helped him see the impact of sharing his story. 00:22:23 Orlando discusses mental health disclosure, stigma, and why his message is not necessarily to tell everyone—but to tell somebody. 00:25:32 Professional achievement and depression existed side by side throughout Orlando’s career, reinforcing for him that success itself does not cure depression. 00:29:12 Orlando reflects on childhood trauma, family history, and the possible combination of environmental and genetic influences on his mental health. 00:34:29 Orlando shares advice for law students and young lawyers about defining success for themselves rather than allowing the profession to define it for them. 00:38:08 Asked what he would change about the legal profession, Orlando calls for greater compassion, kindness, civility, and recognition that struggling with mental health does not make someone weak. Resources discussed in this episode: Thank God I Failed by Orlando Da Silva — Contact Tim Culbert: LinkedIn Culbert Law LinkedIn Instagram Facebook Contact Orlando Da Silva, LSM: Linkedin: Orlando Da Silva
