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Flourish in the “Messy Middle”

Jory Stillman

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I work with thoughtful, capable people who find themselves in what I often call the messy middle — a season where work, relationships, family, and inner questions are all asking for attention at once. You may be carrying a lot, both visibly and behind the scenes, and want a steadier way to navigate what’s next without pushing or performing.

You know the value of steady, attuned support, and you’re ready to invest in more clarity, peace, purpose, and presence.


You may be in the Messy Middle if you find yourself:

  • Balancing a demanding career while nurturing a marriage or relationship — or considering a new one
  • Raising children or supporting adult children as they move toward independence
  • Carrying meaningful responsibilities within your community or broader world
  • Supporting aging parents and navigating the emotional and practical complexities that come with it

You may also be experiencing:

  • Burnout or overwhelm from carrying many responsibilities at once
  • Heightened stress from managing multiple roles and expectations
  • Worry or anxiety during uncertain or changing times
  • Resentment at home or work when balance feels hard to find
  • Difficulty setting healthy boundaries or managing your energy
  • A career transition — re-entering the workforce, changing direction, or questioning what’s next
  • Shifts in self-confidence or self-trust, often influenced by societal expectations or aging
  • Conflict at work or in close relationships, and a desire for clearer, more grounded communication
  • A pull toward personal or spiritual growth, with questions about values, meaning, and priorities
  • The experience of an empty nest, as children leave home and new questions about identity and purpose emerge

How does coaching with Jory work?

Our work together will be profound, thought-provoking, and intense.

  • We’ll meet three times per month for three months via Zoom.
  • You will have unlimited access to me, where I inquire, support, and challenge you in “real-time” through WhatsApp or another secure platform.
  • Everything is 100% confidential, and I commit to showing up for you as fully as possible. I always intend to respect, give my complete attention, and hold you in the highest possible regard. You are in the lead, but you can count on me to profoundly challenge you!
  • You will receive evidence-based, customized assignments, worksheets, and practices to complete between sessions.
  • You will be invited to practice mind-body practices that support emotional well-being, productivity, and peak performance
  • Various assessments such as the Values in Action (VIA) Characters Strength Survey, the Positive Intelligence Sabotueur Assessment

The Sessions

Our first session is about getting to know you quickly and beginning to support you right away. We’ll start where you are and work together to clarify what’s feeling most important in your life and work right now.

Each session is a chance to gently peel back the layers. We’ll move back and forth between your bigger-picture goals (which may shift over time — and that’s okay) and the day-to-day realities of your life. I trust your wholeness and will follow your lead, while also offering thoughtful challenge and bringing forward what I’m noticing.

Some clients like to begin sessions with a brief centering or grounding practice; others prefer to dive right in. We’ll work in the way that feels most supportive to you. Because we’re often in touch between sessions, we may already know what feels most alive or pressing to focus on.

I’ll ask questions, reflect what I’m hearing, offer observations, and invite you to go a little deeper — toward clarity, understanding, and meaningful action. At times, we may use simple exercises or assessments if they’re helpful.

You’ll always have agency in how you want to be accountable. This work is collaborative, responsive, and shaped around what supports you best.

Potential Outcomes:

At the end of the 12 weeks, if you prioritize coaching and the in-between session work, you will likely have made significant progress (and maybe met) your goals!

You may walk away with:

  • Greater clarity about what matters most right now  in your work and your life
  • A deeper understanding of your values, strengths, and recurring patterns
  • More grounded decision-making and follow-through, especially under pressure
  • Practical tools to work with stress, anxiety, and self-doubt when they arise
  • Clearer, more authentic communication at work and at home
  • Healthier boundaries and more sustainable energy
  • Increased self-trust and confidence in how you lead and live
  • Greater emotional steadiness and resilience during change or uncertainty
  • Simple grounding and breathing practices to support your nervous system

By committing to this work — both in our sessions and in the space between them — meaningful shifts tend to follow, often rippling across multiple areas of life.

My Approach:

My approach is whole-person, practical, and deeply personalized. We’ll work with what’s happening in your real life — your thoughts, emotions, body, and nervous system — so the insights we uncover translate into change you can actually live.

Depending on what’s most helpful, I draw from:

  • Cognitive Behavioral Coaching (CBC) and CBT-informed tools
  • Positive Psychology, including the SPIRE model (Spiritual, Physical, Intellectual, Relational, Emotional well-being)
  • Somatic and mind-body practices, such as breathwork, grounding, mindfulness, visualization, and simple regulation practices
  • Mental fitness tools, including select assessments from Positive Intelligence



Testimonials

Jory is an amazing coach. I was a client for 3 months and learned a lot about my own strengths and resilience. She helped me visualize and plan how to be a better leader, gain clarity about the synergy between my personal and professional life, and stretch my thinking. She honed in on activating skills and tools to better my self-awareness and growth! Her approach is always thoughtful and positive, even when discussing difficult topics. I really enjoyed our time together and highly recommend her services.

- Maya M, PHD, PMP Program Director | Director of Insights :: Public Health, Social Justice +Tech

I had the privilege of working with Jory as I was navigating a career transition. It is safe to say that there is no way I would have managed through the transition as effectively as I did without her and her exceptional coaching! Jory always asked extremely thoughtful questions, challenging me to think outside of the box in terms of how I was approaching the transition. She was willing to role play various scenarios with me so I felt confident going into meetings with leadership and felt prepared for the variety of questions that inevitably ended up coming my way. While Jory is a fantastic coach, more importantly, she is one of the kindest and most genuine people I have ever met. She cares deeply about her clients, and even when she is challenging you, you know she is coming from a place of care and a desire to see you reach your full potential personally and professionally. I will be forever grateful for my time with Jory, and I can genuinely say I am a better person because of her! I would highly recommend her as a coach, particularly if you are navigating a period of transition!

- Lauren N. PMP, Leadership Development | Program + Project Management | Career Development | Coaching + Mentoring | Public Speaking | Learning & Development | Health + Wellness

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Price

$3,000
OR
3 payments of $1,000 (monthly)
Book Now
This package includes
  • 9 x 50 min appointments over three months
  • You will have access to me, where I inquire, support, and challenge you in “real-time” through WhatsApp or another secure platform.
  • Everything is 100% confidential, and I commit to showing up for you as fully as possible. I always intend to respect, give my complete attention, and hold you in the highest possible regard. You are in the lead, but you can count on me to profoundly challenge you!
  • You will receive evidence-based, customized assignments, worksheets, and practices to complete between sessions.
  • You will be invited to practice mind-body practices that support emotional well-being, productivity, and peak performance
  • Various assessments such as the Values in Action (VIA) Characters Strength Survey, the Positive Intelligence Sabotueur Assessment