1:1 Career Navigation Coaching

Where mission-driven professionals design an aligned career path

These days our careers demand more and more of us.

It’s easy to get consumed by the demands of your work…only to look up one day with the sinking feeling that you’re not sure where you’re headed or what you’re meant to be doing. 

Deep down, you know that this right here isn’t quite it. 

  • You’re the type who needs meaning in your work, not just a paycheck or a rung on a ladder.

  • You want to find and follow your purpose instead of making career decisions from fear or uncertainty.

  • You’d love to be able to clearly articulate your skills and own your professional identity… but your career feels more like a random series of events than a purposeful path that you’ve created.

Stress, self-doubt, and spinning your wheels can drain your work, your energy, and even your well-being. But how do you start getting unstuck?

Your gifts, skills, and purpose are too important to hold back.

It’s time to break free from the rules, leave behind the “shoulds,” and create your own path. 

You were made for more than feeling stuck in a toxic job, trapped on a career ladder that no longer fits, or directionless in your work. Although your questions and doubts about your career can feel overwhelming, they’re so normal, and they mean that you’re paying attention.

Tackling your big questions opens up a more affirming future, one where you get to:

  • Navigate an exciting career landscape with purpose and resilience, instead of dread or uncertainty

  • Connect the dots in your career path and position yourself for opportunities that feel right - even ones that are a pivot from what you've done before

  • Own who you are - including your professional skill set! - with confidence

  • Feel the deep relief of finally gaining momentum and clarity on how you want to grow

And the best part? The answers to your questions are already within you. You just need the space and guidance to uncover them.

The world of work has changed—are you ready?

Nobody’s taught you how to navigate this career landscape… until now. 

Today’s career path no longer resembles a ladder. In fact, it’s no longer even linear. 

Now, we create our own custom career paths and changing industries isn’t the exception—it’s common. The average professional now switches jobs about every 4 years and holds about 12-15 jobs throughout their career. 

This new landscape gives you the opportunity to evolve and develop your interests, but it also requires you to get good at managing change. 

If the thought of having to navigate these transitions over and over fills you with dread, you’re not alone. Doubting yourself and starting from scratch each time is exhausting when you’re not clear on your vision, your skills, or how to articulate what you bring to the table.

But you don’t have to stumble through your career one blind move at a time. Career coaching can help you find not just the next step but the right path, and I’m here to show you how. 

Career Navigation Coaching for mission-driven professionals

Clarify your vision, navigate what’s next, and craft a career path that’s meaningful to you. 

1:1 Career Navigation Coaching is your personal 10-week coaching program to help you get clear on your career vision and confident in your next steps. It’s a proven, supportive process to help you swap feeling stuck in a career path that’s happening to you for one that you intentionally design. 

It’s time to leave behind the linear, forward-and-up career concept and trade it in for something truer to you—a career path that gives you the freedom to follow your curiosity, own your professional identity, and do work that’s meaningful to you.

It’s completely possible to feel grounded, impactful, and fulfilled in your work—and you deserve the guidance to help you get there.

Now you can realign your career with intention—and without starting over. 

Clarify your career path in just 10 weeks.

You’ll walk away from 1:1 coaching with:

  • Your personal roadmap to developing a career path that’s meaningful to you—so you can own your professional identity and make decisions free from stress and “shoulds”

  • A toolbox of resources, exercises, and practical know-how, preparing you to navigate the ins and outs of the career landscape in alignment with who you are

  • Clarity on your specific skills, vision, and value, helping you to secure your next job, promotion, or professional goal with confidence

  • The support you need to move forward and keep up your momentum, freeing you up to release stress, pursue new possibilities, and feel like yourself again

How does Career Navigation Coaching Work?

Here’s how you’ll discover your direction:

  • Step 1: Map Your Background

    We begin with discovery assignments that help you define your greatest professional challenges and potential. You’ll immediately feel lighter with all of your thoughts finally out of your head where we can start making progress.

  • Step 2: Create Your Compass

    In weekly sessions, we’ll explore and develop a career path that feels meaningful to you, whether you’re preparing for a pivot or looking to grow right where you are. Assignments and unlimited support between sessions will keep you moving and feeling energized.

  • Step 3: Chart Your Path

    In just 10 weeks, you’ll walk away with your complete, personal Strategic Career Compass and the clarity and confidence you need to guide your way forward.

I’ve coached hundreds of leaders just like you along their career journeys.

  • Libby

    Talent Developer / Education Advocate

    “I can now confidently articulate what I bring to the table and what I'm looking for, which has made this job search overall more successful than in the past. I've been invited to a final interview from every place that I had a phone interview, and just negotiated and accepted a position that is aligned with my professional values.”

  • Jay

    Strategic Leader, Systems Builder & Talent Developer

    “When you've been in the same sector for your entire career, there is some fear around change and the voice of doubt begins to creep in. I wanted a coach who was able to have hard conversations, call me out, and help me see the possibilities. I definitely got that!”

  • Angelica

    Grants & Data Manager

    “Working with Carole Ann has been absolutely liberating - I was able to wipe away many societal standards and measures of success that are untrue to who I am, making clear my path forward and the things I hold most dear.”

  • Betsy

    Project Manager & Museum Exhibit Developer

    “The homework exercises were incredibly valuable. They really helped me take a breath, free-associate, brainstorm, and then focus my thoughts. Plus, they were fun!”

  • Cindy

    Communications Director

    “The Strategic Career Plan I developed with Carole Ann freed me from expectations and opened me up to possibilities. I feel so adaptable and excited about whatever life brings.”

  • Corinne Gregory

    Entrepreneur

    “She asked the right questions, expertly guided the work, and shared tools that helped me along the way.”

  • Jane

    Graphic Designer

    “Carole Ann managed to pull all of the thoughts, dreams, and aspirations that I've been harboring behind closed doors, out into the brilliant, clear light where they are now undeniable.”

  • Katherine

    Adult Learning Specialist / Lifelong Learning Facilitator

    “I've been able to really own my mission that we crafted together, and it's working: I have gotten a call back for everything I have applied for since I started working with you!”

  • Lorraine

    Geological Administrator

    “Our coaching helped me to see my career search—and myself—in a whole different light.”

  • Pascale

    Education Policy Leader

    “My career-hunting perspective has changed from attempting to prove that I am good enough to the more liberating approach of deciding whether the role meets MY standards.”

  • Rachel

    Collections Manager

    “In a time of so much uncertainty, the Strategic Career Compass we created feels so grounding, and I feel ready to move forward in so many different ways.”

  • Riahl

    Trainer, Facilitator, Education Director and Consultant

    “Coaching with Carole Ann was a very fruitful experience at a critical time. It helped me to reach inside and find answers that I didn’t know were there.”

  • Leigh

    Social Finance Manager

    “I'm grateful for the space you created for me to explore my future goals, celebrate my wins, and just be fully and transparently myself.”

  • Amanda

    Artist / Writer / Curator

    “When I came to coaching, I was at a real pivot point in my career and life. I felt unsatisfied with how I'd settled into priorities that didn't feel true to me. This process helped me truly get back to who I am as a person, and helped me make a big decision, develop goals, and set concrete steps to move forward with my plan.

    I loved the balance between a sort of open-ended, client-driven process and the structure of the different assignments and tools that Carole Ann has developed. There's plenty of room to customize your own process but also plenty of concrete directions to go in if you need more scaffolding.”

  • Alonso

    Conversation AI Designer, Artist, Technologist and Design Educator

    “I was feeling stuck and wasn’t seeing the career progress I wanted. Carole Ann helped me organize my thoughts to more clearly envision my future and gave me the tools to figure out my career ethical principles. I also appreciate that I’ll be able to continue this learning process on my own thanks to her expert guidance.”

Your 1:1 Career Navigation Coaching Investment

Helping you come alive on a career path that finally aligns.

Your personalized coaching package includes...

  • 10 weekly 1-hour coaching sessions via phone or video — finally, consistent and actionable support from your new personal thought partner

  • Opening discovery and mapping exercises that will define your greatest professional challenges and potential — and help you make progress from week one

  • Weekly customized assignments and supportive accountability, so spinning your wheels isn't even an option anymore

  • Penney leadership's extensive, curated library of tools and resources that will help you develop your professional skills, self-knowledge, and confidence (no more Googling that creates more doubts than answers!)

  • Unlimited email support between sessions to ask questions, try out what you're discovering, and celebrate your successes

  • Your complete, customized Strategic Career Compass — the roadmap not just to your next step but to an aligned, fulfilling professional future

  • An additional coaching session dedicated to resume, cover letter, or interview prep with our go-to expert, Wendy Wallace (once you discover what you want to say, finding how to say it gets so much easier)

  • One month membership to The Compass Club alumni community following our 1:1 work so you have the support and accountability to implement what you've discovered and keep growing

Investment: $3300

(split into 1, 2, or 4 no-fee installments)

I support a limited number of 1:1 clients each quarter, so if you’re interested in working together, don’t wait to reach out! 

Not certain that you’re ready to jump in? Let’s schedule an informational call to talk through your questions. Fill out the application and I’ll be in touch to set it up!

Meet Your Coach for Career Clarity

(In other words, your professional Siri, career path therapist, and wise work bff.)

Carole Ann Penney, CPC

Strategic Career & Leadership Coach

As your coach, I’m here to help you navigate your career with purpose and resilience. For over 10 years, I’ve coached mission-driven professionals like you on their path to design a meaningful career that aligns with who they are. 

If you’re feeling uncertain, discouraged, or like something within you is calling out for more, I’m here to be your thought partner and guide. It’s my mission (and my passion!) to help you explore your big questions, get clear on who you are, and close the gaps between where you are and where you want to be.

As a Certified Professional Coach (iPEC), I offer you all the resources and tools you need to become the confident leader of your own life and career. And as a formerly burned-out but “successful” leader who had to dive deep and design her own path, I understand.

Nobody has taught you how to navigate this modern world of work — until now. Let me help guide you out of the doubts, away from the “shoulds,” and onto a path that’s uniquely yours. Are you in?

You don’t need more advice.

Leave the outside opinions behind and find the answer within. 

"If only I could hear or read the right career advice, everything would finally make sense and fall into place." Right? Not quite. 

If you’ve spent months or even years stuck in the same circular thoughts—or having the same old conversations that get you nowhere—it’s time to give yourself permission to try a new way. 

Don’t lose who you are in the noise of everyone’s expectations, generic career self-help, or anxious thinking about an extra “just in case” degree. Taking personality tests, venting to your partner, or tweaking your resume won’t get you anywhere until you get clear on what’s actually meaningful to you. 

Coaching is an objective, nonjudgmental setting where you can tune out the distractions and go within, uncovering the wisdom that’s already inside of you. We help you to bring that insight out into the light and to turn it into real action—that’s how you move forward.

These leaders traded proving themselves for pursuing their purpose. Are you ready to join them?

  • Rakib

    Biotech Strategic Operations Leader & Entrepreneur

    "This process was transformational. There were a lot of Aha! moments that gave me different perspectives on my strengths and weaknesses, and I walked away with deeper insights about my leadership style. Without a doubt it boosted my self confidence and added value to my personal brand.”

  • Heather

    Business Developer & Leader

    “Asking for help can feel like a weakness, but working with Carole Ann has made me stronger in a way that I could not have achieved on my own. I was able to restructure my role at my company, enhance my compensation, and feel reenergized and excited for what comes next.”

  • Amy

    Lawyer, Advocate, and Storyteller

    “Choosing to work with Carole Ann was one of the greatest investments in myself that I have ever made. She taught me how to clear out the old blockages, obstacles, and narratives to step into myself and my power.”

Count Me In!

Is Career Navigation Coaching right for you?

Here’s how to know if you’re a perfect fit. 

Whether you’re in the midst of a job search, on the verge of a complete career change, or looking to grow right where you are, Career Navigation Coaching can help clarify your path. 

You’re in the right place if...

  • you're a mid-level or established professional in need of a new perspective on your professional identity and career path 

  • you feel called to make a meaningful impact through your work—and do work that’s meaningful to you

  • you’re curious and thoughtful about your big-picture career questions

  • you’re ready to dedicate consistent, weekly time and energy for focused career development 

You’ll walk away from coaching as the leader of your own life and career, ready to make confident decisions that align with your purpose and skills.

Your big questions, answered.

Here’s what others have asked before working with us.
Click on a question to get the full scoop.

  • In short — yes! Being mission-driven is about doing work that’s meaningful to you. It’s about feeling called to make a positive impact that matters to you — and this can be true in any role, in any sector.

    I’ve helped clients from industries including international service, museums and libraries, data science, arts and design, healthcare, manufacturing, education, social work, law, entertainment, finance, marketing, and so many more.

  • Most of my clients don’t come to me already sure of themselves as leaders, and that’s okay! We’re taught to think of leaders as someone with a certain job title or set of responsibilities, but leadership is actually a practice, not a destination.

    We’re all leaders and have been practicing leadership throughout our whole lives. We can lead formally or informally at work, by managing people or influencing what’s happening around us, and we can also practice self-leadership by being intentional about our careers and choices. After our time together, you’ll walk away as the leader of your own career path and with a clearer sense of what leadership means to you.

  • In supportive and comfortable coaching sessions, we explore your thoughts, questions, and goals, we try out new ideas, and we even have some fun.

    I’ll give you a personal space to feel heard and supported, to share what’s on your mind without being judged, and to gradually untangle the jumble. Instead of telling you what to do, I offer fresh tools and perspectives you may not have considered before. As we work together, you’ll discover and practice new mindsets that can serve you for a lifetime, increasing your confidence in your career and throughout your life.

  • Nope. Unlike your friends, family, or colleagues, I’m objective and completely non-judgmental. While those people can be supportive and well-meaning, they have their own hopes and expectations for what you should do in your career. I’m here to help you figure out what YOU want, free from those influences.

    And unlike career advice articles, personality tests, or type surveys, I won’t try to tell you who you are or what choice to make next. You are the expert on you. I bring the tools and questions to help you access the wise part of yourself that is always there, ready to offer you advice and guidance from within.

  • If you’re a new professional: I’d recommend waiting on coaching until you have more experiential “data.” Your job right now is to go out there and try things out — see what you like and don't like, discover your skills, and notice what lights you up.

    If you’re looking for someone to give you advice and answers: I can’t tell you what career is right for you or what decision you should make when. Coaching is a partnership where you dump out everything that’s in your head and your heart, and we help you organize it, make meaning from it, and thoughtfully act on it.

    If you don’t have the time or the energy to commit right now: coaching will be a better investment for you at a moment when you can fully dive in. To make the most of coaching, you need to be in a place where you’re open to new possibilities, determined (even if you’re nervous!) to get unstuck, and ready to give your full attention to our sessions and your action steps in between.

  • Just about anyone can call themselves a coach, but it’s important to us to bring the highest level of skill and service to our work together. I’m a Certified Professional Coach through the Institute for Professional Excellence in Coaching (iPEC), a program that’s accredited by the International Coaching Federation (ICF). I’ve each been coaching for over a decade and have helped hundreds of clients get unstuck and find their paths.

  • Once we work together, you can always consider Penney Leadership your go-to for coaching and support. To stay connected beyond this package, you get an exclusive invite to the Compass Club, an online community of practice for alumni of Penney Leadership programs. In that group, you can ask questions, brainstorm, request feedback, share resources and job opportunities, and celebrate progress. Plus, you get access to additional coaching sessions at a special rate.

  • It can be intimidating to personally invest in your career. But over the years I’ve seen how much staying stuck can cost, from lost opportunities and unfulfilling work to the health and relationship impacts of stress. Think of coaching as “professional self-care” that helps get your career and yourself back into alignment, so you can move forward feeling more focused and free.

    Practically speaking, many of my clients go on to negotiate and land a promotion or new role after working together, so you may also find that coaching helps you increase your compensation. Several clients have also been successful having their employers sponsor some of the cost of coaching — I can walk you through how to ask!

It’s time to give yourself permission to break free and move forward. 

Discover the fulfillment of creating your custom career path. 

It’s not your fault that you’re feeling stuck, but only you can decide to get moving. And we promise—finally taking action is a relief. 

Let’s get you into the driver’s seat as the leader of your own life so you can navigate your world with purpose and resilience. 

In just 10 weeks, you can craft a career path that aligns with who you are, what you stand for, and what you bring to the table.

Are you ready to set yourself up for a future where you thrive and make an impact?

Individual Coaching Application

In order to provide you with in-depth partnership & coaching support, I work with a limited number of clients at a time. 

Right now, individual Career Navigation Coaching spots are full, but I have availability for the Define Your Direction Coaching Program and Career Mapping Sessions!