Letter 117: Accepting Transformation
When we find our confidence
Happy Mid-March!
I’d never had a career or leadership coach before, but last year, I came to a place needing outside advice on work. I did a good bit of research and eventually found Dr. Jessica Wilen. And truly, finding her was one of the best things I’ve ever done for myself professionally. After working with Jessica for several months and learning to align my career goals to my core values, I knew I had to share her magic with The Learning Curve readers as soon as possible.
Today, Jessica not only shares a beautiful letter about working motherhood and her own journey, but I’ve also included an insightful Q&A with Jessica. Jessica also writes an incredible Substack, A Cup of Ambition, which covers a wide range of topics—the gender pay gap, saying “yes” when you want to say “no” and one of my favorites: chasing values, not goals. I treasure her wisdom and depth of knowledge and I’m eternally grateful for her kind heart and steady advice. I hope you enjoy her message today.—Molly
The summer after my second miscarriage, I seemed to see butterflies everywhere. They were remarkable not only because of their sheer quantity but also because they were always in pairs. Though I’m not a particularly spiritual person, I took great comfort in these butterfly dyads. I imagined that they were manifestations of the babies I had lost.
As mothers, we tend to think of our children first and ourselves second. In retrospect, I wonder if those butterflies were signaling something else—something specifically about me. Butterflies typically signify growth, change, and new beginnings. And though all I could feel at the time was sadness, stagnation, and abundant loss, I’m now able to see that I was in the midst of my own metamorphosis.
But I’m getting ahead of myself…
Let’s rewind to early 2015 when I was 8 months pregnant with my son. It was my first pregnancy, and I knew—with complete certainty—that I was going to continue working after finishing my maternity leave. I had spent years in graduate school and then worked my way up the proverbial ladder and finally felt that I was on the brink of something bigger.
Though I was bored in my current role, I had spent several months conceptualizing a new program focused on helping students of concern. The Vice-Chancellor had just reviewed the project proposal, and I was sitting in her office, waiting to learn whether she was going to give it the green light. She was pleased with my work and agreed that I was the obvious choice to lead the new program. “But,” she noted, “you may not want it.”
My jaw dropped, and I must have looked at her like she had three heads—of course I wanted it! It was a major promotion that played to my strengths, and I had spent months designing the program model myself. This was the professional opportunity I was looking for! She smiled kindly and, with genuine concern, said, “Once the baby comes, you may find that you’re less interested in work. You might find that you’re less… ambitious.”
I assured her that I very much wanted the role, and she said it was mine. I called my husband—he was thrilled that the big promotion was finalized and wanted to celebrate.
As I sat at our favorite restaurant later that night, I couldn’t help but feel there was a dark cloud over the festivity. Lose my ambition? What kind of sexist bullshit was that? Ambition was in my blood. I’d show anyone who doubted me.
And I did. I built a well-respected program that made a real difference in students’ lives. I also settled nicely into motherhood. After a difficult pregnancy, I was one of those rare individuals who loved the newborn phase, finding sleep deprivation superior to near-constant vomiting. I had reliable childcare, a decently flexible schedule, and a sense of purpose.
I hit my stride… and then I stumbled.
The wheels started falling off after a devastating and medically complex miscarriage; followed, a few months later, by another miscarriage. Shortly after, things started crumbling at work, too. My boss, who had been a mentor to me for over a decade, was arrested on federal charges. I felt betrayed by him but also lost confidence in myself and my ability to read people—a trait I’d always prided myself on. When senior leadership made a series of decisions that didn’t align with my values, I was overwhelmed with feelings of betrayal and burn out. It was a dark time, and the dissatisfaction at work and devastation in my personal life were mutually reinforcing.
After several rounds of fertility treatments, I was finally pregnant with my daughter. I was also on the job market. My husband was applying for a new job, and we were in the midst of a national dual-career search.
Interviewers asked me, “If you could design any role for yourself, what would it be?” I didn’t have a good answer. Part of me wanted to continue up the academic leadership ladder and part wanted to step back into a part-time gig that would allow me to spend more time with my kids. My ambition had turned, unsettlingly, into ambivalence.
It took time and serious introspection to regain my sense of professional identity. In retrospect, I see that I spent those years in my own chrysalis. Though we often consider cocoons dormant places of rest, the caterpillar is hard at work during her transition. And so was I. I was doing the kind of work I guide many of my coaching clients through—clarifying my values, reframing unhelpful thoughts and beliefs, and gaining confidence in my priorities.
* * *
This summer, I was on the back patio with my kids when two butterflies landed on the table in front of us.
“I wonder if it hurts the caterpillars when they turn into butterflies,” my son mused.
“I think any sort of transformation is uncomfortable and even painful,” I told him. “But look at how beautiful they are now.”
A Deeper Dive into Leadership Coaching
[Editor’s note: I believe when you find something valuable, you share it with others. This is why I wanted to include a brief Q&A with Jessica about her coaching work. Quite simply: She’s incredible. I hope the information below helps illuminate more about the path Jessica walks with her clients in coaching. —Molly]
Molly: When is a good time for someone to work with a leadership coach?
Jessica: Truly, when someone is ready to learn and grow, they're ready for coaching. It's not necessarily determined by a certain title, level, or years of experience.
Molly: What age clients do you work with?
Jessica: I work with people of all ages--and I work with non-parents, too!
Molly: How would you describe the type of coaching you do?
Jessica: I always say that my style of coaching is transformational, as opposed to transactional. For example, if a client wants to get better at having difficult conversations at work (which, by the way, is hard for most people). Some coaches might provide some readings and then help a client role play the tough conversation. That’s fine, but it’s a bit of a band-aid solution.
I would start by asking the client to dig in a little further and identify why she’s uncomfortable with the conversation. What thoughts, beliefs or values are creating tension? I sometimes find that clients can get stuck when they have mental models that are oversimplified, too rigid, or incomplete (we all hold mental models that fall into these categories—it’s not a judgement or a weakness, it’s just reality). By unearthing these underlying beliefs, we can begin to change them. The reason this is so powerful is because we’re fundamentally reframing the tension, so that—in this case—difficult conversations can become more tolerable. This shift then applies not just to the difficult conversation she’s having this week, but is transferable to future situations, too.
Molly: What are some of the main themes you hear from your coaching clients?
Jessica: Of course the specifics are unique to each client, but two major things client seek are:
Wanting to infuse intentionality into their career. Clients sometimes express feeling like their career just happening to them, and this lack of intentionality concerns them. They don’t want to stay in a job just because it's easy to stay, or they start to wonder if they’re just climbing the ladder because that's what they think they “should” do. These clients want to feel more empowered in their decision-making and intentionally build a career and a meaningful life.
Looking to define who they are as a leader. Sometimes this is triggered by a job change or promotion, but not always. These clients want to move away from constantly reacting and putting out fires, to living their leadership more authentically. Part of this is building leadership skills, but it’s also about consciously crafting a leadership vision.
Jessica’s 5 Favorite Things
I'm a huge reader, and my favorite book from 2024 (so far!) is Crying in H Mart. It's a beautiful and heartbreaking memoir by Michelle Zauner about family, identity, and her mother's death from cancer. I'll also give honorable mentions to The Wonder of Small Things (best poetry) and A Planned Occasion (best short story)
I can't function without two cups of green tea daily, and Harney & Sons has the best loose-leaf teas.
One of my favorite interviews I've done was with sociology professor Caitlyn Collins, who conducted a series of interviews with working moms in both Europe and the US for her recent book. If you're interested in understanding the unique madness of American motherhood, I would encourage you to check it out.
OK, this one's kind of random, but I've been struggling with neck pain and this heating pad is ah-mazing. It fits around your neck & shoulders, and the best description I can give you is that it's like a big, warm hug.
I'm turning 40 this year, and my husband and I just booked a trip to Portugal to celebrate. I've been following @wonderlust_portugal for amazing photos and travel inspiration.
In gratitude,
Jessica Wilen
P.S. Like Jessica, April shares her bravery here and Lainey shares about the beginnings of her career journey.
