Productivity + Time Management

How to Buy Back Time with Pennyworth Founders Julia Hudson and Lisa Casson

January 16, 2024

I’m Cherylanne.
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Today’s conversation is really an extraordinary lesson in one of the limiting beliefs that we often hold as contemporary women. And that is the belief that we have to do every single thing ourselves in order for it to count. My guests today, Julia Hudson and Lisa Casson, are co-founders of Pennyworth and have more than 13 years of experience as the right hand to company leaders at top Silicon Valley companies, and they know a thing or two about the value of having a radically talented support team around you. 

I had the opportunity to sit down with Julia and Lisa and dig into the limiting beliefs that keep us from pursuing this idea, even when we know we need support. They help unpack what a process can look like to decide if it would be valuable to bring in some additional support either for your work life or your home life, or a blend of both. And they tell you exactly what the process looks like if you want to use a company like theirs to help you through that process. 

I hope you learn something from this conversation that will give you permission to explore the idea of bringing some additional support into your life if you think that is something that will help you unlock the next level for you, whatever it’s that, that may look like. The summary of our conversation is below, but if you want to listen to the full podcast interview with Lisa and Julia, you can do that here.

Cherylanne Skolnicki: Welcome to the brilliant Balance show. Julia and Lisa, I’m so happy to have you both here.

Julia Hudson: Thank you for having us. We’re thrilled to be here.

Lisa Casson: Thank you, Cherylanne.

CS: Tell us a little bit about what you had on your calendar today. What have you been up to?

LC: Wednesdays are truly my favorite day of the week in that it is my midweek mindful prioritization. In the mornings I take a look at my calendar, my analog calendar. Julia jokes that I’m an analog head <laughs> I have a paper calendar that I absolutely abide by. So Wednesday is the day that I look back on the first two days of the work week and then look forward to the next two days to see where we’re at and to really prioritize. And then it was getting my two-and-a-half year old son off to school and really preparing a bit for chatting with you today.

JH: Wednesdays are my longest day of the week, and I am actually the opposite of Lisa. I have 12 calendars. When I pull them all up on my phone they are all different color codes. But I have three kids at three different schools. I have a business, and I see my husband’s calendar at work and my work calendar and personal. So this time of life, this season of the year is the most complicated. I try to jam pack Wednesdays because I take my kids to swim lessons in the evenings. So bedtime is always pushed back and I try to get as much work in in the mornings as possible. Everybody’s off to school by 8:30 AM and I’m at my desk with a coffee.

CS: I wanna talk a little bit about the origin of this incredible business that the two of you run together today. So as the co-founders of Pennyworth, I’d love for one of you to share what Pennyworth is really all about in your words. What’s the origin story of this business?

JH: We are an executive support and placement agency. We’re a boutique agency. We’re small on purpose, we’re intentional, we’re thoughtful with everything we do. So we’re not a big agency that you call for tons of staffing needs that place tons of roles. That’s just not us. We do high level executive support. So we’re supporting folks in their personal life or their professional life with structural roles: an executive assistant, a personal assistant house manager, a chief of staff, a family assistant, anybody who’s helping our clients thrive. Our clients might be an individual, a business person, or a busy family. 

We also do things for our clients that are more short term. We might help with a special event or a certain chapter of their life where there’s a lot of projects – outsourcing trips and things that are happening in their business or personal life, or it might be just a lighter lift. Maybe they don’t need something full-time, but they need to outsource some things in their life. So we intentionally chose projects because we can sort of fill a lot of gaps and help in a lot of ways. This all came to fruition very organically because Lisa and I both worked in executive support and we supported the former CEO of Yahoo [Melissa Mayer]. We were in Silicon Valley together for years, and we saw from the inside out what having the right support can do for people. And it’s not something we take lightly, right? It’s transformative. It is so impactful to people’s ability to thrive and to flourish and to have connection with their friends and their family and take care of their health and grow their careers and learn and connect. And we know from the inside out that it’s not the same thing over and over. It’s not the same person, it’s not the same solution, it’s not the same setup. We can see what is needed because we’ve been there and done that. So that’s sort of where we’re coming from to begin with and why we started what we started because we know how impactful it is and how meaningful it is not only for the clients, but also for the candidates who are on their own parallel journey.

CS: You just listed all ways that you could support your clients, and there were a couple that really jumped out at me, particularly the idea of when you were in a season where you need a lot of extra support. That might be an inflection point where somebody’s saying, wait, I’ve never thought about this before. Or maybe I’ve never let myself think about it before, but based on what’s happening in my life right now, I’m drowning and I really could use help in a number of different areas in my life. 

LC: Someone might come to us and say, I need some support. I don’t need something full-time. I’m not looking for an executive assistant or house manager and know very specifically what those people do and, and what those roles are. But to your point, I’m just drowning and I have a lot going on, and this is a busy chapter. We kind of walk through what that looks like because it isn’t copy and paste. We’re really trying to figure out what their picture looks like and what their investment and expectations around that could be like or would be like, and it might be bringing in, we work with a few contractors who are part of Pennyworth and it might be bringing in someone in their lives who’s part of our company who says, I’m going work with you 15 hours a week and take things off your plate.

And it doesn’t matter that those things week to week aren’t the same, but just alleviating the pressure. So I’m going to plan that family reunion for you. I’m going to organize all the gift giving for this big event. I am going to set up all the doctor’s appointments for the kids and I’m going to help organize the move. And maybe it’s just six months or a year. There’s a lot of life that is not just one thing consistently. And we are able to fill those gaps in different ways.

CS: When I crossed paths with the two of you, that was what really struck me. I work with a lot of entrepreneurs and when they reach a point where they need help, one of the first things they’ll be coached to do or told to do is hire a Virtual Assistant. And then it’s an executive assistant and it’s somebody that you can have on site and in a permanent role. I know you offer these permanent placements and in many cases its the perfect solution. However, for me, this notion of seasons of support is so compelling, and that it crosses both personal and professional, I think is so unique.

So who comes to Pennyworth for support – can you paint a picture of your typical client? What kinds of jobs do they have, and where do they live? 

JH: People really do see personal help as a luxury. The truth is, having support is on a spectrum. And you might not have an estate manager that flies around the world and manages multiple properties, but that is the 1%. And there is a whole slew of other people, everybody else who’s just putting the pieces of the puzzle together in their life and really need the help.

And if you think about it, we were all raised in an era where you were encouraged to go to school and have a career and have aspirations and have big jobs and big dreams, but also to raise your kids and be fit and volunteer at school and raise a, you know, cook dinner and, and raise this whole family and, and run a busy household. And the truth is that women cannot have it all, not all at once, not all together at the same time, all by themselves. It’s just not possible. So we don’t look at it as a luxury. We do look at it as a practical solution. We do look at it as an investment, and it’s an investment in someone’s time and in their energy and in their attention. And when you’re buying back your time, you get to commit that to other things.

You might be able to grow your career, you might be able to spend more quality time with your family and, and be more present with your relationships and with yourself and self-care, which is all on an upward trajectory to sort of doing better overall and thriving overall. The biggest misconception about time is that we all have the same amount. We do not all have the same amount. We work with high level executives and high profile families who buy more time and outsource things and they’re investing in their time and they’re growing these networks and their careers and these big personas and lives. And they’re doing that because they get to delegate all of these non-core tasks that they don’t need to be doing and involved in and have their attention focused on. And we think of that as some sort of luxury, but it really is an investment. 

So if you’re feeling constrained, and I know that so many women who listen to the show are feeling constrained in their day-to-day life, the number one thing that women would say to me if we’re in a one-on-one conversation or exploratory call is CS: There’s too much to do and not enough time to do it. Sometimes that’s because we’re really ambitious and we have really big dreams and plans that we’re going after. Sometimes it’s because a lot is falling on our shoulders, right? Either we’re a single parent or we don’t have a particularly engaged partner, or we have really complex family lives, like we’re involved in elder care or we’re involved in support within our neighborhoods and communities. And that can feel like there is just not enough of me to go around. This is an avenue for essentially being a force multiplier on your time, that your time is more highly leveraged because you’re taking tasks that you are not uniquely qualified to do. Someone else could in fact do them. 

LC: It’s our honor and it’s our privilege to be able to serve the same community that we care so deeply about. We welcome that call and we will absolutely help you identify what that solution might be.

JH: We want to meet people where they are and also offer them a little bit of clarity because sometimes we see things that they don’t. Simply gaining the insight to what their life is helps us define what solutions might be. When we see the job description or the tasks that they want to delegate, we know what kinds of people with what kinds of backgrounds fit really well.

CS: So it’s important to break things down and identify the work that is needed. What are the things that are dragging you down in your life at home? Is it returning the library books and going to the grocery store and you know, planning for, like you said, all of the gift giving of this season and getting the cards organized and is it putting up the decorations? And then at work, what are the things that you’re saying, why am I still the one doing this? How would someone get started in conversation with you?

JH: We can be found very [email protected]. You can also reach out to us at [email protected]. And those emails go right to Lisa and I so you already know our voices. Hopefully we’ll be familiar and comfortable in that way. Listeners who reach out to us from Brilliant balance in general will receive a discount on their contracts if they do decide to move forward. But our conversations are really a no risk casual, brief introductory conversation that anybody can have at any time. 

CS: If you think about the women who might be contemplating this idea really for the very first time, whether they choose to pursue an engagement with Pennyworth or not, what words of advice or encouragement would you give them as they think about the value of bringing support into their lives? 

LC: Show up. I know it sounds so simple and so basic, but it’s the foundation of respect, and sometimes we can show up to the events for people in our lives, but we don’t show up for ourselves.

JH: Prioritize yourself. When we talk to our clients, a lot of the conversation is about them setting boundaries and giving themselves permission to delegate and to put themselves first and put things down or away or to, you know, navigate their time and energy and effort differently than what they think is expected of them and being able to focus on what matters and that their journey is not going to look like everybody else’s and they don’t have to fit other people’s expectations and that they are capable and they really deserve to thrive also.

CS: Thank you both for being here and sharing this message. 

JH: Thank you so much for having us. It was a pleasure.

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