Top-rated career coaches in Wynwood
Here are the leading career coaches working with professionals in Wynwood. 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 Wynwood
Employment Landscape
In Wynwood, creative and hospitality sectors shape much of the local job scene. Art studios, galleries and venues like Bakehouse Art Complex and MANA Wynwood continue to employ artists, curators and event staff, although some iconic venues such as Gramps and Wynwood Brewing have recently closed or relocated, reflecting rising rents and cultural shifts. Meanwhile, office development is advancing: new Class A office space including Wyncatcher’s coworking space and Highley House were delivered in late 2024, and major tenants such as Amazon and Live Nation Entertainment have committed to Wynwood Plaza, boosting demand for roles in tech, media and professional services. Retail is stabilizing even as vacancy crept higher in 2024, with luxury brands like Tiffany & Co. signing leases, suggesting selective strength in retail hiring. Job seekers in Wynwood face high competition, elevated operating costs and a dynamic mix of industries to navigate.
Dominant Industries
Typical Roles
Hiring Patterns
Hospitality and creative jobs remain common though competitive and impacted by closures of longtime venues. Office-based roles in tech, coworking, and professional services are growing, driven by new deliveries and major tenants leasing space. Retail hiring is selective, with luxury and boutique tenants adding some demand even as vacancies edged up.
"In Wynwood, building your career means balancing art and hustle in a neighborhood that rewards creativity but demands strategy."
Career developments in Wynwood
Recent news and trends shaping the job market in Wynwood. Stay informed about opportunities in your area.
Updated: January 7, 2026
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 Wynwood 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 Wynwood
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.