Jason Woolley is a Counsellor at The Counselling Place, working with individuals, couples, young adults, and families navigating transition, relational strain, emotional overwhelm, and identity change. He offers a calm, thoughtful, and collaborative space that supports insight, regulation, and meaningful change across the wider relational system.

After a 20-year career in senior leadership roles across global marketing, digital strategy, and organisational transformation, he transitioned into the helping professions. Jason holds a Master of Counselling from Flinders University, Australia, and studied the Marital & Family Therapy elective track to bring a systemic lens to his practice, recognising that whether the whole family is ‘in the room’ or not, individuals both impact and are affected by their wider personal and professional relationships. He has also completed Level 2 Training in Gottman Method Couples Therapy and uses Gottman Method Couple Therapy in his work. He is a certified Master Practitioner of Neurolinguistic Programming (NLP). He is a member of British Association for Counselling and Psychotherapy and Provisional Clinical Membership with Singapore Association for Counselling.

Jason has a particular interest in supporting boys, adolescents, young men, and families during developmental or environmental transitions such as school changes, relocation, puberty, parental separation or divorce, identity formation, and shifts in family roles, within both expatriate and local Singaporean communities. He works with families to better understand and respond to behavioural and emotional challenges in children and teenagers with clarity and compassion. Jason takes a collaborative approach, helping clients understand emotional and behavioural patterns through the lens of their family relationships. This often includes supporting mothers seeking ways to better understand and support their sons, as well as wives looking for greater insight into their husbands’ perspectives.

Jason is especially attuned to working with men who may feel uncertain about counselling or unfamiliar with emotional language. Clients value his grounded presence, clear thinking, and ability to hold difficult conversations with steadiness and respect. He commonly supports concerns including relationship conflict, communication breakdown, anger and emotional regulation, stress and anxiety, depression, addiction, self-worth and imposter patterns, career or identity transitions, and family or couple decision points.

Originally from the UK, Jason has travelled extensively across Asia, Europe, and North America, and been an expatriate in Singapore and HCMC, Vietnam. Having lived in Singapore since 2012, and experienced organisational volatility, retrenchment, and cross-cultural family life firsthand, he understands the pressures faced by individuals and families in fast-paced, high-expectation environments. This lived experience allows him to connect naturally without pathologising or oversimplifying complex situations.

Jason believes people are not broken, but shaped by the systems they live within. His work focuses on restoring connection, increasing clarity, and helping people and families move forward with greater confidence and compassion.