Career Mapping Session
Helping mission-driven leaders answer the question, “Where do I go from here?”
Thank you for your interest in coaching! The Penney Leadership practice is full and individual coaching spots open infrequently. When spots do open, we’ll announce it via our newsletter, The Strategic Leader’s Toolbox.
Gain clarity on your skills &
your vision for what’s next
Build confidence in your decision-
making and professional goals
Create a custom career path, instead of
what you think you should or have to do
We all get to a place in our careers where we could use a sounding board.
As a mission-driven leader, your head and your heart are in your work, and with that can come some complex and lonely questions. Questions like…
“I feel like my professional path is just happening to me — how can I get in control?”
“The job economy is so uncertain — how do I move forward when I don’t feel like I can make a plan?”
“How do I change course in my career after investing so much here? Do I have to start all over?”
“How can I figure out a big decision when there’s so much on my mind to sort through?”
“How do I articulate my transferable skills?”
When spinning in your own thoughts isn’t getting you anywhere, you need support to help you get unstuck and in gear.
Let’s locate where you are and map out where you’re going.
If you don’t know where you’re headed, you can waste precious time and energy feeling stalled out or driving in circles. It’s time to reorient and map the way forward that’s right for you.
Career Mapping Session
Your opportunity to pause, reorient, and refuel.
A Career Mapping Session is your private sounding-board to help you outline clear steps that answer your nagging question: “where do I go from here?”
If you’re feeling stuck, off-track, or overwhelmed, you can begin to find your way with clarity and renewed energy.
If you’re feeling pressure about a big decision, you can sort through your considerations and evaluate thoughtfully.
If you’re ready to grow beyond where you are, you can start to figure out how to identify and maximize opportunities.
If you’re just starting to open your eyes to possibilities, you can create structure for your exploration.
Just one session can help you map your mindset, your skills, your career path, or a decision.
work towards goals like:
Creating a pitch for a new role in your current company
Making a decision thoughtfully and confidently, instead of from a place of fear
Finding the connections in your career path so you can authentically articulate your professional story in interviews and while networking
Sorting out why you feel stuck at this career crossroads and planning next steps to move forward
Establishing new mindsets to change the way you think about yourself, your current situation, and what’s possible
No two Career Mapping Sessions are alike — we’ll go wherever you need to go in order to get the perspective and jump start that you need.
Your session, your goals.
Here’s how it works:
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Step 1
Your pre-session questionnaire helps you pour out everything that's in your head and your heart. You have complete permission to be messy or unsure - we'll make sense of it together.
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Step 2
In our session, your coach will ask questions, pick up on themes, and reflect insights back to you. Together we organize your thoughts, make meaning, and plan strategic steps forward.
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Step 3
By getting to the root of the problem, you walk away with deep insight and a practical action plan. You have clear next steps - and the fresh perspective and renewed energy to follow through on them.
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"It was invaluable to have the chance to talk through strategies around the shifts I'm wanting to make, and I've already started building out the opportunity filter you suggested. That's a fantastic tool! I so appreciate your compassionate, insightful approach."
— Elizabeth B.
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"I can't tell you how refreshing it was to talk with someone who just gets what I am debating internally and seeking out in my career. You created such a warm and safe environment for me to lean into the experience and reflect on my strengths."
— Leigh H.
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"Speaking with you really helped me organize my thoughts. I feel like I have such a better grasp of my skills and what I'm looking for in my next role."
— Sam B.
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"It was so great to finally find the thread that connected all the interests and ideas that were bopping around in my head, and to feel validated. I'm really feeling a lot more inspired to do the things I truly want to do."
— Christina E.
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"I feel more empowered to take control of my career decisions, rather than letting external expectations dictate the moves I do or do not make. And I feel reinvigorated about the potential career options I have in front of me!"
— Lisa M.
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“Thank you so much for our session! My head has been swirling with ideas as I mull over everything we discussed. I felt pretty lonely with these mixed up feelings of what to do next, so it's so reassuring to know that it's normal.”
— Jenn W.
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"I really appreciated Carole-Ann's ability to sum up my dilemmas quickly and concisely, the organized approach to different ways of thinking about my career path, and how we outlined different paths forward."
— Tracy L.
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"I especially enjoyed the free writing through the discovery prompts. A few answers actually suprised me as I typed, and I came away with a broadened perspective on potential options for the next steps in my career."
— Becky M.
Your Career Mapping Session includes:
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A comprehensive pre-assignment so you can finally get everything out of your head where we can start making sense of it
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A 75-minute coaching session via Zoom with questions, exercises, and tools customized to help you get unstuck (finally, a meeting you don't have to plan and run!)
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Post-session notes that help capture your new insights
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Tailored resources curated for you (like podcast episodes, book recommendations, and quality articles) so you can continue exploring beyond your session
Investment: $325
We offer a limited amount of sessions each quarter, so if your career path needs some TLC, don’t hesitate to book!
If you’re considering trying out coaching over a longer term, getting started with a Career Mapping Session is also a great way to begin.
If we’re a good match and you’d like to continue working together, the 1:1 Career Navigation Coaching program would be our next step.
Purposeful, practical coaching for your professional self-care.
Meet Your Coach
(Or in other words, your career path Siri)
Carole-Ann Penney, CPC
Strategic Career & Leadership Coach
As a certified professional coach, I've guided over 175 mission-driven leaders just like you through career path challenges and transitions. Through deep listening and powerful questions that get you thinking differently, I'll help you get unstuck and intentionally connect with The Great Work you’re meant to be doing.
Building meaningful career paths is my favorite thing to think about. Where you may see frustration or dead ends, I help you see opportunity and possibility. When your path feels jumbled, I help you find the connections. And when your internal compass is spinning, I help you reconnect with the wisdom that’s already inside of you.
I bring energy, compassion, and real-world resources to our conversation, and we get you moving forward, together.
Individual Coaching Application
Thank you for your interest in coaching! The Penney Leadership practice is full and individual coaching spots open infrequently. When spots do open, we’ll announce it via our newsletter, The Strategic Leader’s Toolbox.