Jason Woolley

Jason Woolley is a counsellor who works with individuals, couples, young adults, and families navigating relationship difficulties, emotional stress, life transitions, and identity change. He offers a calm, thoughtful, and collaborative space where people can slow down, make sense of what is happening in their lives, and begin moving toward meaningful change across the wider relational system.

Before training as a counsellor, Jason spent more than 20 years in senior leadership roles across global marketing, digital strategy, and organisational transformation. These experiences continue to inform his understanding of the pressures many people carry - responsibility for work, family, and relationships, often while trying to hold everything together.

Jason holds a Master of Counselling from Flinders University in Australia and studied the Marital and Family Therapy elective track to bring a systemic lens to his practice. Whether the whole family is in the room or not, he recognises that individuals both influence and are influenced by their wider relational systems.

He has completed Level 2 training in Gottman Method Couples Therapy and integrates insights from both Gottman Method and Emotion-Focused Therapy when working with couples and relationships. Together these approaches help couples understand the emotional attachment patterns underlying conflict while also developing healthier communication and relational repair.

He is a member of the British Association for Counselling and Psychotherapy and holds Provisional Clinical Membership with the Singapore Association for Counselling.

Jason works from an integrative orientation, selecting approaches based on each client’s needs following assessment. His clinical practice draws from Person-Centred Therapy, Solution-Focused Brief Therapy, Narrative Therapy, Cognitive Behavioural Therapy, and Emotion-Focused approaches for individuals, couples, and relationships.

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. This often includes supporting mothers seeking ways to better understand and support their sons, as well as wives and partners 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. Many partners reach out seeking support for husbands or sons who may initially be hesitant about therapy. Clients value Jason’s grounded presence, clear thinking, and ability to hold difficult conversations with steadiness and respect. Men often find that sessions with Jason feel more like thoughtful conversation than formal therapy, making it easier to engage openly with difficult topics.

Many of the individuals Jason works with are thoughtful, capable people who are functioning well externally but sense that something deeper in their lives needs attention. This may appear as relationship conflict, communication breakdown, anger or emotional regulation challenges, stress and anxiety, depression, addiction, questions of identity or direction, self-worth and imposter patterns, or important couple and family decision points.

Originally from the United Kingdom, Jason has travelled extensively across Asia, Europe, and North America and has lived as an expatriate in both Singapore and Ho Chi Minh City, Vietnam. Having lived in Singapore since 2012, and having experienced organisational volatility, retrenchment, and cross-cultural family life firsthand, he understands the pressures faced by individuals and families living in fast-paced, high-expectation environments. This lived experience allows him to connect naturally with clients without pathologising or oversimplifying complex situations.

Jason also has more than 35 years of personal practice in contemplative and embodied disciplines including Tai Chi and meditation. While therapy sessions focus primarily on psychological work, these traditions inform his understanding of emotional regulation, awareness, and resilience. Jason also offers embodied development practices through the Elemental Wellness program at Counseling Perspective, where clients can explore Tai Chi, awareness training, and contemplative practices that support long-term emotional regulation and personal development.

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

Jason offers counselling for individuals, couples, young adults, and families and welcomes enquiries from those seeking a thoughtful, relational approach to change.

Jason also offers embodied development practices through the Elemental Wellness program at Counseling Perspective, where clients can explore Tai Chi, awareness training, and contemplative practices that support long-term emotional regulation and personal development.

Languages: English