WMW #21: Jessica Wilen, executive coach for working parents and mum of 2
"Many of the competencies that make a great parent also make a great leader."
Hi there,
I hope you had a nice Spring break, and found some calm in the chaos of having the kids home for 2 weeks. Am I the only one who feels like our kids are always on holiday?
I’ve been lucky to have my mother-in-law and sister-in-law visiting. It’s been so great to have them around, and its been an absolute treat (literally :) for the kids.
I have shorter hours at work due to Ramadan, yet I feel like I’ve been running against the clock. Why is that!? Is it just me?
A small achievement from my end this week has been being able to this silk thing. Far from perfect, and I needed 45 minutes of conditioning before I could do it, but hey! My teacher calls me the ‘woman with determination’ lol.
On to this week’s interview
I came across Jessica Wilen’s newsletter on Substack and was immediately drawn to it as it is for mothers who care about building a meaningful career and being an involved parent - very much the reason of my own newsletter.
As an executive coach, Jessica has also spent the last 15 years working with leaders to maximize their potential and organisations to help them be more human-centred.
Meet Jessica Wilen, executive coach, writer, consultant, advocate, and assistant professor at Yale University; mum of 2.
Q. Tell us a little bit about yourself
I’m the founder of Jessica Wilen Coaching, a boutique executive coaching and organizational consulting firm focused on supporting the unique needs of working parent professionals.
I also write the popular Substack newsletter, A Cup of Ambition, for mothers who care about building a meaningful career and being an involved parent. I live in an adorable little shoreline town in southern Connecticut about halfway between New York City and Boston with my husband and two kids, ages 7 and 4.
I’m also a terrible cook, an ice cream aficionado, a fiercely competitive Trivial Pursuit player, a beach-lover, and avid bookworm.
Q. What inspired the launch of your coaching business?
Despite being trained in both developmental and organizational psychology it wasn’t until I became a mom that I fully appreciated how much these two fields have in common.
At its heart, leadership is about influencing people towards a common goal, which means that working parents are constantly leading! Many of the same competencies that make a great parent also make a great leader.
I believe that cultivating these transferable behaviors and skills makes us better in both domains.
I was also motivated by personal experience. Back in 2017, I was asked to apply for a Dean-level job. I was deeply ambivalent about the opportunity. I didn’t feel ready—or interested in—that kind of responsibility. More importantly, my son was a toddler and I was about to start IVF treatments after suffering repeated miscarriages. I worried about the toll that having such a time-intensive job would have on my family. And yet, I was terrified that I was giving up the professional opportunity of a lifetime.
To help me sort through my confusion, I met with a coach. He completely misjudged the situation. He told me I needed to get over my “imposter syndrome” and work on my confidence.
He totally missed the bigger picture: now that I was a mom, there was more to my life than solely climbing the professional ladder. Yes, I wanted to achieve great things in my job, but I also wanted to be an involved parent.
I really could have used someone who understood that complexity—who understood all that was at stake for me—and who was willing to question some of the assumptions I was making, expand my thinking, and lead me to greater clarity. And that’s what I offer my clients—an understanding of their complete lives, and the willingness to partner with them to ensure we’re meeting all of their goals.
Q. How do you help working parents on their professional and personal journey?
I think many working parents, and particularly working moms, feel like they are so busy and overwhelmed, that they don’t have time to be as intentional as they would like.
I offer a reflective space for clients to clarify their core values (so that they can make decisions that align with them), increase their self-awareness, and explore underlying beliefs that might be getting in their way. After we dig below the surface to explore these deeper issues, we can focus on developing necessary skills.
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.
Q. What is your best advice to working mums looking to achieve their full potential as professionals as well as mums?
First identify your core values and then align your actions accordingly.
You will be presented with many tough situations at work and in parenting, but you will never regret making decisions that feel authentic to who you are and who you want to be.
Q. What are the challenges you face yourself as a mum and professional? What do you do to overcome them?
I love owning my own business, but it can be all-consuming. I’m constantly thinking about it—which is exciting and energizing—but it also means it’s hard for me to “turn off”. I’m still working on how to deal with this. I used to un-synch my work email from my phone when I went on vacations and I need to start doing that again.
Speaking of phones, like so many people, I’m in a constant battle with mine. When I start to feel the urge to check it, I try to pause and identify the underlying need—am I bored? In need of connection? Looking for a distraction? But listen, sometimes that’s easier said than done and I can certainly waste a half hour scrolling Instagram. Sometimes physically putting the phone in another room is the best solution for me.
Q. How do you manage your time?
I thrive on reliability and discipline. Now that I’m solely in charge of my schedule, I have had to create my own structure for the week. Generally speaking, Mondays are reserved for writing and administrative catch-up, Tuesdays-Thursdays are devoted to coaching, and Fridays are a combination of coaching, working on longer-term projects, and networking. I also try to intentionally build in time every week to connect with others. Since I no longer have “colleagues”, I joined a few different accountability groups that keep me inspired, motivated, and connected.
Q. What is your ultimate goal as a working mum?
To raise well-adjusted and thoughtful adults who care about other people and their world, while maintaining a thriving professional life rooted in helping others.
Oh, and attempting to get eight hours of sleep each night ;-)
Q. Where do you get your inspiration?
Lots of places. Of course, my kids, my husband, and my own experience of working motherhood. But also conversations with friends, and—maybe most of all—my coaching clients. I get to work with the most incredible women and men, and I draw a lot of inspiration and energy from our conversations.
Q. What is your best productivity hack?
At the beginning of each week, I map my to-do list onto my calendar—each task gets an assigned time. It helps keeps me focused and accountable.
Q. What is your best parenting hack?
When everyone is melting down (including me!), I throw the kids in the tub. Seriously, my kids can spend a solid 45 minutes mixing “potions” in the shower.
Buy a set of plastic beakers and graduated cylinders on Amazon, pick up cheap shampoo and shaving cream at the grocery store, and let them mix away to their heart’s content.
When all else fails, turn up the music and dance. It’s hard to stay angry when you’re listening to fun music and moving your body.
Q. What do you do in your 'me-time' and how does it help you?
I am—and have always been—a big reader. My undergraduate major was in English, and I always say that my ability to empathize and understand others was born out of my experience discovering characters through literature. If I have free time, I often spend it curled up by the fireplace with a book. Also, I try to go for a run a few times a week. I do my best thinking when I’m out on the jogging path, listening to music, and alone with my thoughts.
Q. Favourite tool that makes your life / business easier?
I am obsessed with my Remarkable tablet. I love taking hand-written notes but hate the clutter of tons of loose paper. This device is the perfect solution.
Q. Favourite quote
I always tell my kids “Be kind to yourself and others”.
Q. Best thing you have read or watched lately
I recently read a great book by Caitlyn Collins, a professor at Washington University in St. Louis, called “Making Motherhood Work”. She interviewed moms in Sweden, Germany, Italy and the US to learn how they navigated work and family within different political and cultural contexts. Fascinating.
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I’m so happy to have connected with Jessica and am adding her book recommendation to my (very long) list of books to read.
You can read her newsletter A Cup of Ambition, here.
Should you want to chat with her about anything she could help you with, you can schedule a complimentary call with her, here.
You can also leave a comment for her here, and I will make sure she gets it.
If you like what you read today, please share it with someone who can benefit from it!
Have a good rest of the week.
My next newsletter will be from the shores of Mauritius!
Love,
Abha x