Top-rated career coaches in Chicago
Here are the leading career coaches working with professionals in Chicago. Each has been assessed for expertise, clear communication, and a strong track record of client success.
Wolf Magdelinic
Career Transition Specialist
I’m a certified career and leadership coach with 8+ years of experience helping ambitious professionals navigate pivots, burnout recovery, and identity alignment. My approach blends structured goal-setting with mindful rituals that fit seamlessly into daily life. I’ve worked with clients across tech, creative industries, and consulting to rediscover clarity, design resilient career paths, and step into leadership with confidence. My coaching style is equal parts pragmatic and supportive — I’ll challenge you to stretch while making sure you feel grounded and aligned. If you’re ready to move from uncertainty to momentum, I’d love to support your next chapter.
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.
Jordan Mae Antoinette
Mindfulness Coach
I'm a movement teacher, breath work coach, mindful meditation guide, retreat host, radio show host, and DJ. I also run an online movement studio. With years of experience in the wellness space, I help individuals achieve holistic well-being through the interconnectedness of movement, breath, and mindful awareness.
George Bent
Career Development Coach
George is a London-based career coach focused on tangible career outcomes and providing managerial-style support to his clients.
Working in Chicago
Employment Landscape
Chicago’s job market in early 2026 reflects considerable strain along with pockets of opportunity. Significant layoffs are underway in insurance, healthcare, cannabis, manufacturing, and nonprofit sectors, with companies such as GoHealth, CVS Health’s Oak Street Health unit, PharmaCann, and Printpack announcing hundreds of job cuts affecting Chicago‑area employees. Meanwhile, an immersive entertainment project, Universal Horror Unleashed, is slated to begin construction in early 2026 in a former printing facility, promising hundreds of new roles in hospitality, construction, and operations when it opens in 2027. Overall demand remains most robust in logistics, advanced manufacturing, life sciences, healthcare, finance, and tech, though competition for full‑time positions is real and the hiring pace remains cautious. Job seekers are likely to encounter a competitive, shifting environment where flexible and hybrid roles—especially in professional services and tech—may offer better access, while education and media sectors remain under pressure.
Dominant Industries
Typical Roles
Hiring Patterns
Hiring growth is modest and uneven. Healthcare, life sciences, logistics, and advanced manufacturing still show selective openings, while sectors like insurance, cannabis, and parts of nonprofit and education are contracting. Hybrid and remote tech and professional services roles are growing relative to traditional in‑office jobs.
"In Chicago’s current job landscape, finding a solid position often means choosing flexibility or emerging sectors over traditional stability"
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 Chicago 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 Chicago
We select top coaches who understand the local market dynamics and global career trends.
Wolf Magdelinic
Career Transition Specialist
I’m a certified career and leadership coach with 8+ years of experience helping ambitious professionals navigate pivots, burnout recovery, and identity alignment. My approach blends structured goal-setting with mindful rituals that fit seamlessly into daily life. I’ve worked with clients across tech, creative industries, and consulting to rediscover clarity, design resilient career paths, and step into leadership with confidence. My coaching style is equal parts pragmatic and supportive — I’ll challenge you to stretch while making sure you feel grounded and aligned. If you’re ready to move from uncertainty to momentum, I’d love to support your next chapter.
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.
Jordan Mae Antoinette
Mindfulness Coach
I'm a movement teacher, breath work coach, mindful meditation guide, retreat host, radio show host, and DJ. I also run an online movement studio. With years of experience in the wellness space, I help individuals achieve holistic well-being through the interconnectedness of movement, breath, and mindful awareness.
George Bent
Career Development Coach
George is a London-based career coach focused on tangible career outcomes and providing managerial-style support to his clients.
Simple, transparent pricing
Invest in your career clarity today.