NORTH OF STUCK

Helping You Navigate What’s Next

No career fantasies—just practical, factual roadmaps to help you move forward.

Meet me:

I'm Jennifer Stillman, Founder of North of Stuck. For more than 30 years, I have helped people navigate important life transitions—from choosing a path after high school to changing careers, rediscovering purpose, or planning for retirement.

Along the way, I've served as a military officer, school counselor, and federal career counselor. Those experiences taught me that while every journey is different, the feeling of being stuck is something we all face at one time or another.

I created North of Stuck to help people gain clarity, explore their options, and confidently navigate what's next. I don't believe in career fantasies—just practical, fact-based roadmaps that help people move forward.

Together, we'll connect the dots between where you are today and where you want to be tomorrow by uncovering your strengths, identifying realistic opportunities, and creating a plan that aligns with your goals, values, and circumstances.

• Tired of your current role or feeling invisible at work?

• Unsure what to study in college, trade school, or a certification program?

• Nervous about the job market or how AI may affect your future career?

• Worried that your military experience won't translate into civilian opportunities?

• Struggling to help a teenager, young adult, or family member gain traction?

If you answered "yes" to any of these questions, you don't have to figure it out alone. Together, we'll create a practical plan that helps you move forward with confidence.

I would be honored to be part of your journey.

Why Trust Me With Your Next Chapter?

My work approach is built on a unique blend of military leadership, career counseling, and executive strategy:

• US Naval Academy Graduate and Former Marine Corps Officer As a U.S. Naval Academy graduate (’96) and former U.S. Marine Corps Aviation Intelligence Officer, I know what it takes to transition from uniform to civilian life. My career began by developing future Navy and Marine Corps leaders and later expanded to mentoring exchange students, high school students, families, and professionals.

• Certified School Counselor Armed with a Master’s in Educational Counseling from National University (’04), I spent seven years as a Professional School Counselor in California and Maine helping students navigate the high-stakes decisions of preparing them for post-secondary life.

• 30+ Years Helping People Navigate Major Life and Career Decisions  For 17 years I served as an Educational Services Specialist (ESS) where I managed and advised future career and educational pathways for nearly one hundred thousand students in 175 high schools and career programs in the states of Maine and New Hampshire.

• Strategic Leadership Experience I hold an MBA in Leadership from Saint Joseph’s College of Maine (’18) and, while serving as an ESS, I was also a Program Manager responsible for training educators and government employees, as well as coordinating services and asset allocation between school administrators, students, families and the Department of Defense.

I look forward to putting that experience to work for you!

What You’ll Receive:

Together we’ll identify your strengths, clarify your goals, and create a practical plan for what’s next. Most clients achieve meaningful clarity in 1-3 sessions. When we finish our work together, you will get a Personalized Guidebook with an actionable roadmap for your future reference including:

• A summary of our sessions with key insights, themes and discoveries.

• The results and interpretation of your career, personality, and strengths assessments.

• A customized action plan with prioritized next steps.

• A curated list of resources, tools, and opportunities aligned with your goals.

You’ll leave with clarity, confidence, and a practical roadmap you can begin using immediately so you can maintain your forward momentum!

Services:

Career Direction Session

Gain clarity and leave with a practical roadmap:

For anyone feeling stuck, weighing options, or seeking greater clarity and direction.

Young Adult Launch Session

For students and young adults navigating what’s next:

College, trade school, gap years, career exploration, first jobs, and independence.

Mid-Career Reset Session

For professionals considering a new direction:

Career changes, burnout, layoffs, retirement transitions and reinvention.

Ready to Get Unstuck?

"To live is to choose. But to choose well, you must know who you are and what you stand for, where you want to go and why you want to get there." - Kofi Annan, Secretary-General of the United Nations 1997-2006

“The average American holds 10 to 15 jobs over the course of their working lifetime, typically staying with each employer for about 4 years...(also) workers generally go through about 3 to 7 distinct career changes during that same timeframe.” - World Economic Forum 2023