Welcome to Highroads Coaching
Decision Coaching For Women
MAKE THE DECISION YOU CAN STAND BEHIND.
The Highroads Decision Process™ helps women clarify what matters, face reality, weigh the trade-offs, and choose their next step with confidence.
For Women, It’s Making the Decisions That Matter Most To Them.
At Highroads, we’re about high quality decision coaching for high-achieving women and organizations to build sustainable success.


“I deeply value her ability to help people feel seen. Annie doesn’t just offer support, she helps people reconnect with their own strength.”
Amanda Jacobson
Folsom, CA

“The “Higher Roads Better Days” coaching newsletter that comes in my email weekly is a great way to remind yourself to take a break and take a moment for yourself.”
Beatrice Rowan
San Jose, CA

“Annie continually guides me to utilize my best skills to attain confidence, while helping me achieve the best work-life balance with her kind and relatable qualities.”
Kathleen Brandon
Las Vegas, NV
26 Years Teaching. Two decades in public education taught me how burnout really happens—and what it takes to lead well without losing yourself.
1500+ Followers. Leaders, educators, and founders have used the Highroads Decision Process™ to make hard calls with more clarity and less burnout.

Annie Stephanos, M. Ed., NBC-HWC


Founder & Operator
Meet Annie.
Leadership and Decision Coach | Speaker | Creator of the Highroads Decision Process™
I’m Annie Stephanos, founder of Highroads Coaching.
After 26 years as a teacher, instructional coach, and leadership coach in public education, I came to understand something that changed the way I think about leadership.
Burnout rarely begins with one big decision.
It grows through hundreds of small ones—often made with the best intentions—that gradually pull us away from what matters most.
That realization became the foundation of the Highroads Decision Process™, a practical framework that helps leaders make values-based decisions with greater clarity, confidence, and sustainability.
Today I work with leaders, teams, and organizations who want to build success they can actually sustain.
My Approach
- Values before velocity.
- Practical, structured, and evidence-informed.
- Focused on better decisions—not just better coping.
- Designed for sustainable leadership.

THE HIGHROADS DECISION PROCESS™
01.
CLARIFY THE DECISION.
What am I actually deciding?
02.
IDENTIFY WHAT MATTERS MOST.
Which core values matters most to me?
03.
RECOGNIZE YOUR REALITY.
What circumstances and constraints must I consider?
04.
CONSIDER THE TRADE-OFFS.
What might I gain, preserve, or give up?
05.
TAKE ACTION. STAND BEHIND IT.
What is my next step?
“Annie has led several workshops for the Headspace Training Institute on the topics of Know Your Worth: Eliminate Burnout for Good and Step by Step – Building Your New Coaching Business, which were extremely successful. She brings a rare combination of deep expertise, clarity, and genuine care to her training. Annie creates an engaging, supportive environment while delivering practical, actionable insights you can immediately apply. Her ability to explain complex concepts in clear ways makes her workshops both engaging and empowering. If you’re looking for a knowledgeable, impactful facilitator who helps people move forward with confidence and purpose, Annie delivers this and more.”
Curious what a workshop like this could look like for your team? Let’s talk.

Shelby Garay
Program Director, Headspace Training Institute


Work with Annie
Whether you’re navigating a significant leadership decision, supporting your team’s growth, or looking for a keynote that sparks meaningful conversations, Highroads offers practical, values-based coaching and speaking designed for sustainable success.
Decision Coaching
One-on-one coaching for leaders navigating important decisions, transitions, and sustainable growth.
Speaking
Keynotes and presentations for conferences, organizations, and leadership teams.
Workshops
Interactive leadership workshops built around the Highroads Decision Process™.
Organizations
Partner with Highroads to strengthen leadership, decision-making, and culture.

Mary Alice Keator
Program Approval / Continuing Ed Manager, National Board for Health and Wellness Coaching

“Annie has a unique ability to meet people with compassion while still challenging them to grow. Her work is grounded in real-life experience and a genuine understanding of what it means to navigate burnout, rebuild balance, and create meaningful change. She doesn’t just teach concepts, she helps people integrate them in a way that feels sustainable and empowering. As reflected in her work, Annie is deeply committed to helping individuals reconnect with themselves, set boundaries, and build lives rooted in well-being and purpose.”
Ready to see what’s possible for you? Start a conversation.
Frequently asked questions
Answers to the questions I hear most from leaders considering coaching, speaking, or workshops with Highroads.

The Highroads Decision Process™ is a practical framework I developed to help people navigate difficult personal and professional decisions with greater clarity and confidence.
Rather than telling you what to do, the process guides you through five steps: clarifying the decision, identifying what matters most, recognizing your current reality, considering the trade-offs, and taking the next aligned step.
Whether you’re facing burnout, navigating a leadership challenge, or making a major life decision, the goal isn’t to find the “perfect” answer. It’s to make thoughtful decisions you can trust.
Absolutely. Highroads Coaching is designed to help you navigate complex decisions without losing sight of what matters most.
Using the Highroads Decision Process™, we’ll work together to clarify the decision you’re facing, explore your options, consider the realities and trade-offs, and determine your next aligned step.
My role isn’t to tell you what to do. My role is to guide you through a structured process so you can make decisions with greater clarity, confidence, and self-trust.
Not at all.
Many people come to Highroads Coaching because they’re feeling overwhelmed, exhausted, or burned out. Others come because they’re facing an important decision, feeling stuck, or noticing that the way they’ve always operated is no longer sustainable.
The Highroads Decision Process™ can help you navigate career transitions, leadership challenges, boundary-setting, workplace change, and other situations where competing priorities make it difficult to know what comes next.
Highroads Coaching is designed for thoughtful, high-achieving professionals who want to make decisions with greater clarity and confidence.
Many of my clients are women in leadership, founders, professionals, educators, and people navigating significant personal or professional transitions. They aren’t looking for someone to tell them what to do—they’re looking for a structured process that helps them evaluate their options and move forward in a way that aligns with what matters most.
Burnout doesn’t usually show up all at once. For many women, it builds slowly over time. You might feel constantly tired no matter how much you sleep, find yourself becoming more irritable, struggle to focus, or lose interest in things that used to bring you joy. Many high-achieving women assume they’re just stressed and keep pushing forward, but when exhaustion starts feeling like your normal state, it’s often a sign that something deeper needs attention.
Stress is a normal response to challenging situations and often improves with rest or changes in workload. Burnout develops over time and is characterized by ongoing emotional, mental, and physical exhaustion that doesn’t simply go away after a vacation or a good night’s sleep.
If you’re feeling depleted, disconnected from work you once enjoyed, questioning your effectiveness, or struggling to recover despite your best efforts, it may be time to look more closely at what’s driving those feelings.
Whether you’re experiencing stress, burnout, or simply feeling stuck, Highroads Coaching can help you gain clarity about your current situation and determine your next best step.
One of the biggest misconceptions about burnout is that the only solution is walking away from your career. While that may be the right choice for some people, many women recover without making a dramatic change. Recovery often starts by looking at how you’re working, what expectations you’re carrying, and where your energy is going. Small but meaningful shifts can create a surprisingly powerful impact over time.
Absolutely. In fact, many women seek coaching because they feel like work has slowly taken over everything else. Together, we look at the habits, expectations, and beliefs that keep you stuck in overdrive and create realistic strategies that help you reclaim your time, energy, and attention. The goal isn’t perfect balance. It’s creating a life that feels sustainable and aligned with what matters most to you.
Burnout and anxiety often travel together, especially for women who carry a lot of responsibility and put pressure on themselves to perform at a high level. While coaching isn’t a replacement for mental health treatment, it can help you identify the patterns contributing to overwhelm and create healthier ways of responding to stress. Many women find that as they strengthen boundaries and regain a sense of control, their anxiety begins to feel more manageable as well.
Clients choose Highroads Coaching because they’re looking for more than advice. They’re looking for a practical process that helps them navigate difficult decisions with clarity, confidence, and purpose.
My work is informed by more than 26 years supporting people in education, my own experience recovering from severe burnout, post-graduate training, professional coaching, and certification in health and wellness coaching. Together, those experiences led to the development of the Highroads Decision Process™.
Rather than telling you what to do, I guide you through a structured framework that helps you make decisions aligned with what matters most to you.
Therapy often focuses on healing, processing, and understanding experiences from your past, while coaching focuses on helping you create meaningful change in the present and future. Both can be incredibly valuable. Burnout coaching is typically more action-oriented, helping you develop practical strategies, stronger boundaries, and sustainable habits that support the life and career you’re trying to build.
Coaching is very client-centered and client-directed. Every person is different, and many women may begin seeing positive changes within the first few sessions as they put new insights into practice. The deeper changes, like stronger boundaries, healthier habits, and a more sustainable relationship with work, tend to develop over time as those new skills become part of your everyday life.
Coaching is an investment in your ability to navigate important decisions with greater clarity and confidence.
Many of my clients come to coaching because they feel stuck, overwhelmed, or uncertain about what comes next. Rather than offering advice or quick fixes, I guide them through a structured process that helps them understand their options, evaluate the trade-offs, and make decisions that align with what matters most.
The value of coaching isn’t simply solving today’s challenge—it’s developing a decision-making process you can continue using long after coaching ends.
Yes.
In addition to individual coaching, I partner with organizations to support employee well-being, leadership development, burnout prevention, and values-based decision-making.
My workshops and presentations provide practical tools that help individuals and teams navigate complex workplace challenges with greater clarity and confidence. Whether I’m speaking to a leadership team, an employee resource group, or an organization committed to creating healthier workplaces, my goal is to provide practical strategies that people can apply immediately.
Yes. Highroads Coaching is offered virtually, allowing me to work with clients throughout the United States and around the world.
Whether you’re navigating burnout, a leadership challenge, a career transition, or another important decision, coaching can be just as effective online as it is in person. Virtual sessions provide flexibility while creating a supportive space for thoughtful conversation and meaningful progress.
Getting started is simple. You can reach out through the Highroads Coaching website or email Annie directly at annie@highroadscoaching.com to schedule a 30-minute complimentary session. It’s an opportunity to talk about what’s been going on, ask questions, and explore whether coaching feels like the right next step for you. There’s no pressure, just a conversation about where you are and where you’d like to go.
Ready to Build What’s Sustainable?
Let’s talk about the leadership challenges you’re facing and how the Highroads Decision Process™ can help you move forward with clarity and confidence.
Begin where you are. Build what’s sustainable.
Hear Me on The Healthy Enterprise Podcast
Watch Me on Tube – Bold Moves with Mary Mehr
Coaching available online, worldwide

on her Weekly Podcast on
Apple or Spotify
