Life Transitions & Crossroads Coaching
Life Transitions & Crossroads Coaching
This work is part of my Whole Person Leadership Coaching practice and is for people at transitions or crossroads where life itself is asking for leadership.
I work with thoughtful people navigating seasons when things are not broken but not settled.
You may be carrying meaningful responsibility as you move through change, transition, or a quiet sense that something wants to shift. On the outside, life may look fine. On the inside, you know this season deserves care, attention, and clear thinking.
This work is not about fixing yourself or rushing toward answers. It is about slowing down enough to understand what is happening, clarify what matters, and choose a way forward that feels steady and aligned.
Life transitions ask for leadership, even when the change is personal rather than professional. This coaching is for people who want to meet these moments with honesty, discernment, and self-trust.
If this resonates, the next step is a conversation to explore fit.
“BETWEEN STIMULUS & RESPONSE THERE IS A SPACE. IN THAT SPACE IS THE POWER TO CHOOSE OUR RESPONSE. IN THAT RESPONSE LIES OUR GROWTH AND OUR FREEDOM.” - Viktor Frankl
This work may be a good fit if you want to:
Live with greater alignment between what matters to you and how you’re actually living.
Create more space to think, feel, and choose intentionally rather than staying in constant reaction mode.
Clarify your values, priorities, and direction during a season of change or reorientation.
Examine long-standing patterns or assumptions that no longer serve you, with support that is thoughtful and evidence-based.
Relate to stress, pressure, and responsibility with more steadiness and self-trust.
Reconnect with your body and inner signals as sources of information, not obstacles to overcome.
Build resilience and capacity in a way that feels humane and sustainable.
Bring greater coherence between your work, relationships, and inner life.
Life Transition & Crossroads Coaching
What’s included?
✓ One-on-one coaching sessions, typically two to three per month, held over Zoom or phone
✓ A multi-month engagement to support clarity, integration, and thoughtful decision making
✓ Between-session access for brief reflection or clarification when something arises
✓ When helpful, the thoughtful use of AI-supported reflection tools to surface patterns, deepen insight, and support integration between sessions. These tools do not replace our work together, but help extend reflection and learning in a grounded, intentional way
✓ Customized reflections, practices, or assessments when helpful
✓ Optional reflective or journal-based prompts for clients who find writing supportive
✓ Invitations to explore practices that support steadiness and nervous system regulation, when appropriate
Investment and Structure:
Coaching is offered through a multi-month relationship designed to support clarity, integration, and sound decision-making during complex seasons of life and leadership.
Most clients work with me for 3 to 6 months, meeting 2 to 3 times per month, depending on what this season is asking for. The pace and level of between-session support are decided together, so the work feels steady, responsive, and well-contained.
Investment typically ranges from $700 to $1400 per month, based on pacing and scope of support.
Rather than offering preset packages or pathways, I work with each client to shape a coaching relationship that fits their needs, responsibilities, and capacity at this moment in time.If this work resonates, the next step is a conversation to explore fit and determine what would be most supportive.
What is the “Messy Middle?”
You may recognize yourself here:
The messy middle often shows up when life is full, but not settled.
You may be:
holding meaningful responsibility at work while also tending to family, relationships, or community
navigating caregiving, parenting, or changing family roles
carrying a successful or stable outer life alongside an inner sense that something is shifting
facing questions about direction, priorities, or how you want to live the next chapter
At the same time, you may notice:
decisions taking more energy than they used to
tension between what’s expected of you and what feels sustainable
challenges around boundaries, communication, or balance
a desire to act with greater clarity and integrity in the midst of uncertainty
This work does not promise quick fixes or guaranteed outcomes. What it offers is a space to think clearly, stay oriented, and move forward with greater steadiness over time.
Learn more about how I work and the EXPANSIVE™ Framework that supports this approach.
-
Greater clarity about what matters most and how to act with integrity in the midst of complexity.
A steadier relationship with pressure, uncertainty, and responsibility allows for more thoughtful decision-making.
Increased self-trust and confidence in navigating conversations, boundaries, and choices at work and at home.
A deeper understanding of how internal patterns shape behavior, with more flexibility and choice in how you respond.
More grounded communication and presence, especially in moments that previously felt charged or overwhelming.
A sense of alignment between values and action, so leadership and life feel more coherent and sustainable.
This work does not promise quick fixes or guaranteed outcomes. What it offers is a space to think clearly, stay oriented, and move forward with greater steadiness over time.
Learn more about the approach and tools Jory uses in her coaching.
When you engage fully in this work, both in our sessions and in the space between them, meaningful progress often follows, with insights that ripple into many areas of your life.
“Working with Stillman has been groundbreaking in my success towards my personal goals. She is a calm place to discuss personal issues and is able to provide realistic tools and background on how to move forward in difficult times. Coach Jory challenges you to push yourself through the difficult times and is always there to celebrate your successes. She has set the path for me to continue growing to better understand myself and why I show up the way I do to work and other aspects of my life. I will miss working with her but am grateful our paths crossed as I continue my journey in self-discovery.”
- S. Maynard, Optimization Engineer at Chevron
Still curious?
If this work resonates, the next step is a conversation. I’d be glad to connect over a complimentary 30-minute coffee conversation to explore whether working together feels like a good fit.