Define Your Direction Career Coaching

Get clear on where you’re going with purpose, heart, and renewed energy.

Are you spinning your wheels in your career?

Whether you’re job searching, looking to grow right where you are, or still trying to figure out your options, you’ll get clearer on your next steps here. 

You’ve got big questions about who you are and where you’re headed, and they’re not getting easier as time goes by. 

  • “My job looks good on paper… so why doesn’t it feel good in practice?”

  • “How come I feel so lost when everyone else seems to have this career thing figured out?”

  • “I know I need to make a change…but where do I even start finding my way out?”

It’s draining and isolating when you can only see everything you don’t know about what to do next in your career. Without a dedicated space to tune out everyone’s expectations, weigh your options, and sort through the overwhelm, you’re left going through the motions instead of making decisions and taking concrete action. 

It’s no wonder that you feel trapped or lost — the modern career landscape is vastly different from the one traveled by the generations who came before us, and yet we’ve been taught all of the same rules and expectations for how we “should” climb the ladder and navigate our work.

It’s time to throw out those rules and create a new roadmap for your career.

Trade the forward-and-up ladder for limitless possibilities. 

It all starts with defining your direction.

Your career isn’t something that happens to you—you can actively shape its direction, and choose the stops along the way, by getting into the driver’s seat of your own professional life. 

In Define Your Direction, we’ll work together to break free of outdated expectations and embrace the new rules of the career road. 

It’s all about exploring key mindsets and practical tools to help you define your own direction and recharge your momentum in the modern world of work. And after just a few weeks, you’ll be able to confidently move forward with intention and adaptability.

By the end of this coaching program, you will:

  • Let go of old guidance about what your career should look like

  • Define what drives you

  • Map out your career vision

  • Get clear on your personal measures of success 

  • Open up greater possibilities for creating your own meaningful career path

  • Create an action plan to put what you’ve learned into practice so that you can make intentional, informed decisions about your next steps.

With some reflection, practice, and accountability, you’ll turn your overwhelm into relief, then clarity, and then momentum.

Here’s how you’ll refocus and get moving. 

Define Your Direction’s coaching framework is designed to help mission-driven professionals get out of analysis paralysis and into clear, confident action.

You’ll try on new mindsets, work through reflective exercises that help you apply those concepts to your specific career path, and have my support as your coach to work through your questions and next steps.

  • Kickoff

    In a 45-minute coaching call, we start by getting the lay of the land. We take stock of where you’ve been, get oriented, and set goals for our work together moving forward, whether you’re curious about a career change or wanting to grow where you are.

  • Content

    Over the next 4 weeks, you’ll learn key career navigation concepts and begin implementing them in your own life. Through 4 self-paced modules of short videos + accompanying digital workbooks, you’ll learn, reflect, and capture your takeaways.

  • Coaching

    Now it’s time to explore and unpack everything you’ve learned! In a personalized 75-minute career coaching session, we’ll talk through your insights, get clarity on your questions, and solidify your progress on what’s most important to you.

Create a custom, fulfilling career you can be proud of.

Here’s everything waiting for you inside Define Your Direction.

Your coaching experience includes:

  • A discovery assignment + 45-minute kickoff call

    This is where you’ll start getting all of your thoughts out of your head and onto the page, helping to clarify your goals for moving forward. Then in our first call, we’ll unpack where you’ve been in your career, where you are now, and where you’re curious about exploring next.

  • 4 modules of insightful + practical video content

    You’ll transform the way you approach your career and create new mindsets to guide you for life through 22 short, digestible videos. (That’s a total of 2.5 hours to dig into over four weeks.)

  • 4 digital workbooks for self-discovery, learnings, and reflections

    Here’s your dedicated space to shake things up, discover new possibilities for your career, connect deeply with who you are, and craft your own definition of success.

  • Ongoing email support

    While you’re diving into all of the content, I’m always just an email away! You’re able to reach out anytime with questions and get personalized support to keep you moving.

  • 75-minute 1:1 career coaching session

    Once you’ve completed the videos and workbooks, we’ll have a 1:1 career coaching session, customized to focus on what’s most helpful to you. You’ll shift from learning into action!

  • Invitation to join the carefully-crafted Penney Leadership community

    After we wrap up, you’ll be invited to join the Compass Club. In this supportive space where it actually feels good to network, you can apply what you’ve learned and continue to grow with solidarity, motivation, and new perspectives.

Investment: $750 USD

(or two no-fee payments of $375)

It all adds up to newfound clarity on your professional identity and the criteria you use to make decisions moving forward. And unlike one-off career advice, these new tools and insights are evergreen — you can come back to them again and again as you design and navigate your custom career.

All of the Content Inside Define Your Direction

  • The program starts with a 45-minute 1:1 coaching call, where we’ll unpack where you’ve been in your career, where you are now, and where you’re curious about exploring next.

    • Video: Introduction - 2:15

    • Video: Making the most of this program - 6:16

    • Video: About your facilitator - 3:53

    • Week 1 Workbook: Exercise 1: Map Your Career Map; Exercise 2: Reflect & Look Ahead; Notes

    • Video: Map your career - 3:07

    • Video: The outdated beliefs about the “right way” to navigate your career - 12:53

    • Video: The new rules of the career road - 8:56

    • Video: Rethink your trajectory - 4:38

    • Week 2 Workbook: Exercise 1: Values Assessment; Exercise 2: Reflect; Notes

    • Video: Your job title does not define you - 4:44

    • Video: Explore and define the core values that guide you - 10:32

    • Video: Navigate your career with your core values as your compass - 16:53

    • Week 3 Workbook: Exercise 1: Personal Success Statement, Exercise 2: Vision; Notes

    • Video: Break free of the one-size fits all version of success - 18:23

    • Video: Articulate your career vision - 12:14

    • Video: Your career path is not about where you’ve been—it’s about where you’re going - 10:12

    • Week 4 Workbook: Exercise 1: Capture Your Career Unknowns; Exercise 2: Build Your Personal Board of Directors; Exercise 3: Set Intentional Goals; Notes

    • PDF Resource: Informational Interview Guide

    • Video: Manage the unknowns that hold you back - 10:15

    • Video: Rally your resources - 12:37

    • Video: Set intentional next steps that put what you’ve learned into practice - 10:10

  • Once you complete the video modules and workbooks, you’re ready to schedule your 75-minute 1:1 Coaching Session.

Meet Your Coach

You don’t have to navigate your career on your own.

I’m Carole Ann Penney, and I’m here to help you navigate your career with purpose and resilience. For over 10 years, I’ve coached mission-driven professionals from all industries and sectors on their path to design a meaningful career that aligns with who they are. 

If you’re feeling lost, trapped on a trajectory that doesn’t fit, or like something within you is calling out for more, I can help you redirect onto a path that you choose. I’m all about debunking the old rules about career expectations and freeing you up to pursue your own version of success.

As a Certified Professional Coach (iPEC) and experienced group facilitator, 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 on a limited career ladder, I understand. 

Nobody has taught you how to freely navigate this modern career landscape — until now. Let me help guide you past your doubts, out of the detours, and towards a direction that’s uniquely yours. 

Here’s what past participants had to say:

  • "I was feeling lost and unsure how to move forward to a new career without falling back into what was familiar and wasn't working for me. This program gave me a sense of hope and direction I was looking for. I have a better sense of what I want and now I just need to go out and get it."

    - Kathryn

  • "The program was wonderful in helping me develop fresh perspectives and see new possibilities. I know myself better, and feel like I have more agency to shape my role. I'm feeling more clear on my identity as a leader, and how I want to show up for my team and myself." 

    - Clarissa, Museum Professional

  • "Carole Ann's words and tools helped me find direction and purpose, both professionally and personally. The confidence she instilled in me about who I truly am helped distinguish me from other candidates in a recent job search because I can speak about my mission, vision and “why"— and it led to my dream position. The best part about this program is that it doesn't stop here. The tools that we acquire can be taken with us forever."

    — Anjali

  • "I had never really invested in my own career development before. It felt like a leap, and it definitely was...but it was 100% worth it. I gained so much more than my investment in terms of insight and confidence. It was invaluable to have a neutral, encouraging space to work through messy career-related thoughts and issues. After completing the program, I was able to renegotiate my role to better suit my interests and skills, earned a raise and a promotion, and even flexed my newfound leadership skills to start my own business."

    — Theresa

  • "My biggest takeaway was a clear vision of my values and how they connect to and drive my career. Moving forward, I feel ready to define my next career goals."

    - Kate

  • "Moving forward, I feel ready to use the tools from the program along with my own reflections to make more confident career decisions that are aligned with who I am. I feel ready to be the driver of my career path. "

    - Erin

Is Define Your Direction right for you?

The program is for you if you’re:

  • Ready to make space for 1-2 hours per week of course videos, reflection, and assignments to help you get unstuck

  • Excited about getting the best of both worlds—recorded program content you’ll work through on your own time, bookended by 1:1 career coaching sessions to transform your insights into action

  • Self-motivated and willing to shake up your ideas about your career, putting what you’re learning into practice

Whether you’re job searching, looking to grow right where you are, or still trying to figure out your options, you’ll get clearer on your next steps here. 

Questions about your career path are normal – and here are some questions you might have about Define Your Direction!

  • In short — yes! Both the content and coaching aren’t industry-specific and are designed to be applicable to professionals in a variety of roles and levels.

    After all, 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 developed this coaching program with my best insights from over 10 years working with clients in 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.

  • When we first enter the workforce, beyond advice about resumes and interviews, it’s rare to have been taught anything about how to actually navigate our careers with intention. If you’re a new professional, Define Your Direction can help you get clearer on your career vision and next steps with a little less “winging it” along the way!

    If you’re a more established professional, all of the experiential “data” you’ve gathered along your career path is right at home here. You’ll be able to assess what you like and don’t like, what lights you up, and what pivots or changes you might like to try out.

  • I understand that it can be intimidating to personally invest in your career. (Or that it might be a completely new concept altogether!)

    But over the years, I’ve seen how much staying stuck can cost my clients, from lost opportunities and unfulfilling work to the health and relationship impacts of stress. It might help to think of this program as “professional self-care” that helps get your career and yourself back into alignment, so you can move forward feeling more focused and free.

  • I’ve designed the program with enough breathing room to offer flexibility and enough accountability to keep you on track. You’ll have access to the course materials for 8 weeks: we recommend that you work through the 4 modules week-by-week for a month, but you’ll have a second month of access just in case.

  • I’m excited to get to work with you 1:1! To be able to get the most out of that coaching session, you’ll need to complete the modules and the workbooks first. That way, our time together can be less about learning concepts and more about your personal goals and putting it all into practice. You’ll receive a link to schedule your session once you’ve completed the content!

  • Due to the digital nature of the program content as well as the personalized nature of coaching, I can’t offer refunds after you purchase. I’m happy to answer any questions in advance, though! After you apply, you’ll have an opportunity to book a call where we can talk through anything else you’re wondering about.

This is your chance to go from lost to leader of your own career.

If you need…

  • new perspectives on where you are and where you’re headed…

  • to reconnect with the feeling that work can be meaningful and fulfilling…

  • clarity on how to move forward...

  • and the structure and accountability to make it happen…

This is the career coaching experience for you.

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. To begin, please fill out the application below. If we’re a fit, we’ll get back to you within 2-3 business days to share next steps. Thank you for inviting Penney Leadership alongside you in your career journey!