Meet a Mom: Meet Julia Hudson of Pennyworth Projects! | Chicago North Shore Moms

Hello friendly faces! It’s that time of the week! We’re back with a new CNSM Meet a Mom spotlight brought to you in part by Mary Gifford of Gifford Law. This week’s Meet a Mom interview is with Lake Forest mom of three wee ones, survivor of a near death snorkeling incident, your new best friend and owner of Pennyworth Projects, a boutique support and placement consulting agency, Julia Hudson!

Originally from Rhode Island, Julia has wasted no time getting to know the amazing places to hang on the North Shore with her family – get her list below! When she’s not managing her own family, she’s running a booming support and placement consulting agency as a “matchmaker.” Julia matches high caliber executive assistants and house managers to CEOs, founders, managing partners, investors, high-profile individuals – or just incredibly busy families! Welcome, Julia!

Photo credits: Carole McCulley

Hi Julia Hudson! ​​Please introduce yourself. Where do you live?

I am originally from Rhode Island, but my husband and I lived in the Bay Area for over a decade before moving to Lake Forest. My husband, Matt, is from Libertyville so we were drawn here by family. We are lucky to have grandparents, aunts and uncles, and cousins locally here on the North Shore!


Tell us about your adorable kids!

We have three amazing kids – Wesley (6), Conrad (4.5), and Penelope (almost 3!). They are all sweet, hardworking, loving, energetic, and adventurous in their own special ways – keeping us laughing and on our toes at all times! There is never a quiet moment in our house with three under the age of six!



What are one or two interesting facts to know about you?

It’s a small world. Moving to Illinois was a big deal, I really didn’t know anyone except for my husband’s family. We moved into a great house in East Lake Forest and on the first day our new neighbor across the street came over to welcome us with a bottle of champagne. We chatted briefly and realized he grew up in Rhode Island too – though a generation or so older than me. Turns out – that wasn’t even the ‘small world’ part – my father (a general contractor) built his family’s childhood home in Rhode Island some 35 years ago!

I was once lost at sea – like in the movie “Open Water” – off the coast of Mexico with about 8 other snorkelers when our boat lost us in a sudden and severe tropical storm. We were finally found floating together on a life ring by a scuba diving boat that had lost all of its scuba divers in the storm. It was the only near-death experience I have ever had, and I’d like that to be it!


Wow – I’d love to know more about that story another time!

What are a few favorite North Shore places to hang with or without the kids? 

We love the Chicago Botanical Gardens and The Morton Arboretum. When we first moved here, I took our kids there all the time for outdoor exploration. We had just left California where much of our life was spent outside so I was craving that and found an outlet at these two places! We are so lucky to also get to enjoy the Winter Club in Lake Forest as one of the most special places in our neighborhood and our lives – with so much community connection and memory-building as a family! We have also hit the beach and every playground in the area we can! The most popular in my house right now is the ‘Spaceship’ playground in Highland Park. Our favorite pizza place is Silos, of course.



What gets you through a tough day?

Coffee. Lots of coffee. I think as a parent, sometimes it’s just one foot in front of the other. When I am having a rough moment and I am around my kids, I try to refocus and state out loud something I am grateful for. Although my children think I am doing this exercise for them, many times it is really an exercise for me to recenter and take a beat. Getting through a difficult day is a combination of self-reflection and support from family and friends. It could be as small as taking a few minutes to participate in a hilarious text thread with a girlfriend, or scheduling some time for me to have a moment to myself during the upcoming weekend.


Please introduce the business you founded, Pennyworth Projects

Pennyworth Projects is a boutique support and placement consulting agency. We work with clients to help find and onboard the perfect support they need – Executive Assistants, Personal Assistants, House Managers, and everything in between. We also support some clients on an ongoing basis for administrative and project management and special projects. Our clients are CEOs, Founders, Managing Partners, Investors, high-profile individuals – or just incredibly busy families! We are there to help them thrive day-to-day. We focus on productivity, efficiency, and effectiveness through personalized support at a very high level.



Tell us about your business partner, Lisa Casson.

My business partner, Lisa Casson, and I have known each other for over eight years and both have a shared passion for the work we do and the people we serve both on the client side and the candidate side. I couldn’t ask for a better partner in this business – we are aligned in our sense of purpose, common philosophy, determination, and integrity when it comes to our work. Not only that, she has a great sense of humor and an unmatched ability to just understand what I am thinking before I even think it! The reason for our success is not based on our business model; we are unique because of our partnership, experiences, and natural strengths. I am grateful for that every day.



What’s the most difficult aspect about owning and running your own small business?

It can be difficult to ‘turn off’. I want to be the best I possibly can be for our clients, for my business partner, and for our candidates. I find our work exciting, challenging, and fulfilling – and sometimes it can be hard to step away. Otherwise, I truly love running a business I believe in from the core values to the end mission.


Describe something you’re most proud of as it relates to Pennyworth Projects.

We have recently been able to work with quite a few female Executives that have been exceptionally impressive and inspiring! Although we also work with remarkable clients all around – our recent experience with some fantastic female leaders has brought me a lot of joy. It is really energizing to help them find the right support so they can keep succeeding in both their professional and personal life. I have felt like it was a true partnership of helping each other climb higher.


What did you do before starting up Pennyworth Projects? What was the impetus behind starting this new business?

Prior to Pennyworth, I was an Executive Assistant in Silicon Valley, working with CEOs, Founders, and other leadership from big tech companies to small start-ups. Lisa and I met at Yahoo where we worked in the Office of the CEO and supported the company’s Board of Directors. Starting Pennyworth Projects was very organic – we were already ingrained in the world of support at the highest level, and our network and roles required us to help successfully connect great people to each other. Pennyworth’s origin story was very natural and genuine for us in that way, we understand both the client and the support side through our years of experience.


When clients come to you what quality of service can they expect?

Owning a boutique company allows us to be thoughtful and intentional about everything we do. Every client relationship is entirely personalized – each search is curated to the specific client – their needs, personality, expectations, communication style, and lifestyle. We carry a different approach and perspective that is mutually beneficial for both our clients and ourselves.


What’s on the horizon for Pennyworth Projects?

It’s an exciting time for Pennyworth! Being a smaller firm allows us to be extremely personal with our approach. We’re able to be nimble, engaged, and accessible. We are currently working with candidates for support roles at new companies, and with clients who need support beyond EA responsibilities. Due to recent layoffs, there are many clients who need extra hands for planning offsite, company meetings, specialty projects, marketing efforts, and more. This has allowed us to introduce exciting opportunities for part-time or contract positions as well as our full-time opportunities with clients.


Is there anything else you’d like us to know?

Pennyworth is always looking to connect with great people – from new clients looking for support to candidates interested in new opportunities. We’re committed to learning more about people – what drives them, what they need, their aspirations, and experiences. Every client and candidate we work with is unique and we love this about our everyday work. We value our relationships with new people and being a resource to them. We look forward to making those connections and hope sharing more about Pennyworth opens that door to continued and new conversations in the Chicagoland area.


How should our readers get in touch with you?

We’d love to help you gain back more time in your life! Visit us at and email me directly at [email protected].

About Our Meet a Mom Sponsor

A very heartfelt thank you to CNSMoms’ Meet a Mom sponsor, Lake Forest mom of three and owner of Gifford Law, a solo Estate Planning Firm (wills and trusts). Mary, we appreciate your support of local moms in our North Shore communities! Learn more about Mary by visiting her Meet a Mom spotlight here! Contact Mary directly here: [email protected].

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