Top-rated career coaches in The Annex
Here are the leading career coaches working with professionals in The Annex. Each has been assessed for expertise, clear communication, and a strong track record of client success.
Michelle Hillier
Self-discovery Coach
As a TEDx speaker, educator, and published author, I've spent over two decades helping people unlock their hidden potential through movement, creativity, and radical self-discovery. From captivating large crowds to intimate coaching sessions, I've helped millions reclaim their power and move beyond their limits. I'm all about creating safe, transformative spaces for people to reconnect with their inner flame.
Jillian Harris
Creative Industries Coach
Jillian is a coach and strategist who supports individuals through periods of personal and professional change. Drawing on psychology, systems thinking, creative practices and somatics she helps clients clarify direction, navigate the messy unknowns with grace, and design careers that feel aligned, resilient, and meaningful.
Dr John O'Dwyer
Leadership Coach
Leadership consultant, author, educator, and creator of the GettingItDone Toolkit. Known for blending practical wisdom, academic rigour, and humour, he helps teams and executives align vision, execution, and culture to deliver measurable results.
Working in The Annex
Employment Landscape
Professionals living or seeking work in The Annex will find a job market that is intimately tied to the University of Toronto and the concentration of professional, scientific and technical services in and around the neighbourhood. Local residents are heavily employed in education, law, social/community services, business and finance roles, reflecting the high educational attainment and proximity to campus and research institutions. Most businesses in the area are small boutiques, bookstores, cafes and creative service providers concentrated along Bloor Street West, not large employers, so opportunities typically arise through networking or part‑time and flexible roles tied to faculty, startups or cultural venues. Competition is real—renters and job seekers alike face pressure from both students looking for flexible gigs and long‑term professionals aiming for stable positions. The Annex does not offer big corporate hiring trucks, but it does involve localized, relationship‑driven employment opportunities rooted in education and cultural entrepreneurship.
Dominant Industries
Typical Roles
Hiring Patterns
Hiring in The Annex tends to be steady within educational services—contract and part‑time roles connected to the university remain available—but broader sectors such as hospitality and independent retail show signs of stabilization rather than growth. Professional services roles often appear through informal referrals and networking more than public postings.
"In The Annex, you do not wait for job postings—you meet someone at the bookstore, the café, or campus and your next opportunity begins there."
What is WORK-SELF?
Work Self is a career development system that helps people grow through coaching and daily habit support.
What Work Self provides
- One to one coaching for clarity and momentum
- Software that guides habits and simple next steps
- A structure that keeps progress moving between sessions
Why people choose it
- Builds confidence and better decision making
- Creates steady progress with small daily actions
- Makes career growth feel clear, guided, and achievable
How it works
- 1Meet with your coach to set goals and direction
- 2Follow daily guidance in the software
- 3Build habits that lead to long term improvement
A new way to grow your career
Innovative tools and coaching methods designed to transform how you develop professionally.
Career Audit Tool
Assess your professional path in The Annex with our comprehensive 360° audit.
Transition Blueprint
Map your move with structure and real momentum. Step-by-step guidance.
AI-Powered Coaching
Intelligent guidance available 24/7. Get instant answers to your career questions.
Rituals for Growth
Build clarity and confidence with intentional daily habits designed for you.
Personal Brand Builder
Tell your story clearly and powerfully to stand out in the local market.
Coaches available in The Annex
We select top coaches who understand the local market dynamics and global career trends.
Michelle Hillier
Self-discovery Coach
As a TEDx speaker, educator, and published author, I've spent over two decades helping people unlock their hidden potential through movement, creativity, and radical self-discovery. From captivating large crowds to intimate coaching sessions, I've helped millions reclaim their power and move beyond their limits. I'm all about creating safe, transformative spaces for people to reconnect with their inner flame.
Jillian Harris
Creative Industries Coach
Jillian is a coach and strategist who supports individuals through periods of personal and professional change. Drawing on psychology, systems thinking, creative practices and somatics she helps clients clarify direction, navigate the messy unknowns with grace, and design careers that feel aligned, resilient, and meaningful.
Dr John O'Dwyer
Leadership Coach
Leadership consultant, author, educator, and creator of the GettingItDone Toolkit. Known for blending practical wisdom, academic rigour, and humour, he helps teams and executives align vision, execution, and culture to deliver measurable results.
Simple, transparent pricing
Invest in your career clarity today.