Moira McCaskill

Personal Coaching

Moira McCaskill

About Moira


The story of my professional life turns on the Enneagram - pre and post discovering the Enneagram. That is why I am so dedicated to working with this body of wisdom and why I trust that what you need for your personal journey will show up - all you have to do is pay attention.

I first discovered the Enneagram when I was doing my Master’s degree in law, my LLM in Alternative Dispute Resolution, in 1999. The idea of personality type being a factor creating power imbalances in conflict resolution was the context in the course, but something resonated deeply with me when I saw the Enneagram symbol drawn on the board and discovered that my own type explained much of my life. Fascinated by the Enneagram I began to study with stellar teachers Don Riso and Russ Hudson of The Enneagram Institute, completing their extensive program over the next few years.

I next pursued my training and certification as a CCPC (Certified Co-active Professional Coach) through The Coaches Training Institute, a premiere coach training organization. I have been a coach since 2004.

Before I began this journey I was a lawyer. I practiced law for fifteen years, including being a partner in a large downtown Toronto law firm. Something never clicked for me with the practice of law although I was successful at it. Like many women I struggled with the high- powered, men's club atmosphere especially back in the mid seventies. I can remember going for department lunches at the National Club when everyone else (all men) had to go through a different door because I was with them. Boy did they let me know it too. Women then were trying to succeed by being virtual males, rushing back to work two weeks after giving birth - working from the hospital was considered a badge of honour. I knew I couldn't do this and although it was a time of struggle I eventually rejected the whole package and spent years at home being a full time mom. With so few women in law and the successful ones being prepared to hire day nannies and night nannies, there was no obvious way to have both career and family. There still isn't for many women lawyers who continue to exit the profession in droves.

This experience of being able but not willing was tough. I took it all personally and only now can I laugh at the ridiculousness, the systemic insanity of law firm culture. I am grateful my younger self had the courage to make necessary choices.

Going for my Masters in Alternative Dispute Resolution was a step towards what I care about- conflict resolution and healing. Enter the Enneagram and the exciting learning journey and fulfilling work that followed.

My work and my learning are one now and continuous. Recently I added another certification that was really a love affair for me with the Enneagram and coaching through the Deep Coaching Institute. I also study with Lucid Living, have completed a year long leadership program with CTI, added the Leadership Circle tools and others.

Looking back I see how my work and my world opened up through a series of both hard choices and amazing synchronicities - openings that appeared and all I had to do was pay attention and follow. I also see how much I struggled alone when I was young and how much support and guidance I have been blessed to receive since I began my inner journey. This is the message of my story- when you are ready doors will close, windows will open, help will show up if you pay attention.

My work supports the Canadian Non-profit, Rwanda Survivors Foundation.