You Never Know.

Late last summer, I received one of the most lovely emails I've ever gotten—and it was from someone I didn't even know.

Jessica's email landed in my inbox in the middle of a busy day, but her heartfelt message immediately drew me in. She was writing to express gratitude for the impact that these issues of the Strategic Leader's Toolbox had for her, and to share that she recently made a big decision to make a brave career change.

She didn't expect a reply. But she wrote so wholeheartedly that I knew I needed to meet her.

Now, I'm so proud and excited to introduce you to her as the newest member of the Penney Leadership team. That's right—Penney Leadership is shifting from a "me" to a "we"—a coaching practice with two Certified Professional Coaches.

Jessica's story goes to show—you never know what will happen when you bravely reach out to someone whose work you admire.

Here's how she tells it:


Carole Ann's guiding word for 2021 was frequency.

It’s no coincidence that in 2021, two years after starting to follow her work, I felt magnetically drawn to her more than ever. She inspired me in ways that I needed at exactly the right moments. This frequency is what compelled me to reach out in August 2021 to thank her for her powerful Quit Week.

Two months prior, I had been contemplating quitting my own job as Director of Human Resources at a mid-sized museum. With my background in career coaching, the Penney Leadership newsletters had always resonated deeply with me. No matter what the topic was, it always felt as if her messages were intended just for me (even though I knew it was hitting so many other people in their own very personal and meaningful ways). I often found myself forwarding issues of the Strategic Leader's Toolbox to my friends, family members, and colleagues because I knew they would benefit in their own lives, and also gain a deeper understanding of what I was going through professionally.

Like so many others in the “Great Resignation,” I faced a fork in my own career path. After finally making the very painful but simultaneously relieving decision to quit my job, I reached out to Carole Ann to let her know how much she had impacted me during this very difficult time. I almost didn’t email her, because I knew how many messages she must get, and I didn’t want to add to her inevitably already full plate.

Then it occurred to me that by NOT letting her know what a profound difference she made in my life, it would be like keeping an invaluable gift to myself. So often, we’re positively impacted by others, and those people have no idea exactly just how wide their ripple effect spans. Here’s a snippet of the email I sent to Carole Ann last summer–I know many of you will relate to the feeling I had about the power of Penney Leadership:

I will never forget the moment when I read your email about how the best career move you ever made was to take a similar leap of faith. Tears were streaming down my face as I read about your experience because it not only felt like a sign that I was making the right choice, but for the first time, I also felt validated that I wasn't completely crazy for letting go of the career direction that I've worked so hard to achieve. Since then, your emails continue to resonate with me (and clearly SO many others). I've been wanting to reach out to you to thank you for the wonderful, and impactful work that you do.

I quit my job two weeks ago--although it's my dream job on paper, it was ultimately not serving me in creating the life I want to live. As a career coach, I find it's ironically so difficult to follow the advice I give to others, but once I made this difficult decision and followed through with it, I felt an overwhelming sense of relief…

I want to thank you for being such an inspiration in so many ways. You have helped me navigate this scary next step in my journey with more courage and grace than I thought I had in me. I know many people reach out to you, and just imagine how many countless other people are out there who you don't even know you've had such a profound impact on.

Fast forward to the Fall. Carole Ann and I connected over Zoom to discuss our many shared interests and backgrounds, including the discovery that we’re both mothers of daughters, and we both received our coach training through the same certification program, iPEC! Carole Ann is not kidding when she talks about the joy she gets out of building the synergistic connections between promoting clients’ unique talents and growing Penney Leadership’s impact at the same time!

It turns out, the rate at which Penney Leadership was growing was not sustainable for Carole Ann to be the sole coach working 1:1 with clients and still honor her own evolving goals, priorities, and mission. I wasn’t interested in building my own coaching practice from the ground up, in part because being connected to a bigger team is one of my core values, and integral to my professional vision. Our shared background, interests, coaching philosophy and approach, and our commitment to integrating diversity, equity, inclusion, and belonging into all that we do helped us to quickly realize that this collaboration was a true win-win-win: not only for each of us, but also for all of the current and future members of the Penney Leadership community.

When we first started talking, little did we know that we are also united by an unexpected, small world connection: I asked Carole Ann about her Vermont cell number, only to discover that we grew up in neighboring small towns in southern VT! We never knew each other as kids, but we learned we know many of the same people–like my next door neighbor who was also Carole Ann’s good childhood friend. We danced at the same dance studio, training under the same instructor and were even in the same performance of The Nutcracker. In elementary school, Carole Ann performed in The Apple Blossom Cotillion, an annual fundraiser where a group of elementary students perform alongside a group of high school seniors. My senior year, I performed in The Apple Blossom (with my now husband)! That year I also attended prom in Carole Ann’s hometown. Our paths came SO close to connecting so many times growing up, but I’m so grateful that they eventually intersected right when they did–at the very moment when we both needed it in our career journeys.

In our high-speed world with so many competing demands, it’s easy to move from one email, and one task to another without pausing to communicate to others the impact they’ve made on us. But you truly never know what can happen when you take the time to reach out.

Connect with those who make a difference in your life even if they have no idea who you are–because that connection could just turn out to be the biggest win-win of your life.

There are times when my dreams have been spurred forward by someone I met at the right place when I decided to be bold in my words. - Luvvie Ajayi Jones


👋🏼 Carole Ann again here: What Jessica didn't know when she reached out was that I was wrestling with my desire to help everyone with the limits of the reality of my capacity as a solopreneur and mom of two small kids. I didn't know I needed her, but once I met her it felt like she was an answer to a prayer.

She is the perfect person to join me as a coach in the Penney Leadership coaching practice, because her mission, values, and skills align perfect with what we're here to do: Empower mission-driven leaders to transform meaningful insight into intentional action, and bring their sense of purpose to life.

You can learn more about Jessica here, and sign up to work with her in a Career Mapping Session here! You're going to love her as much as I do.

Carole-Ann Penney, Founder

As a Career Strategist and Founder of Penney Leadership, I help mission-driven leaders navigate their work and lives with purpose and resilience.

http://www.penneyleadership.com
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