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The Coffee Chat (#47)
My conversation with Catherine, Director of Community & Marketing at Kahilla and Jason, Operating Partner at Level Up who together are also parents to a toddler!
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Hi there 👋🏽
It is funny how in my day job I always advice clients and teams to not get sucked into the allure of vanity metrics - those shiny objects that on the surface look great but fail to tell the real story on what is really happening! In the context of a newsletter a vanity metric would be total subscribers - feels good to look at the number but the real insight comes from tracking things like open rate, click through rate of links, unsubscribe rate, forwarding rate etc.
But alas, I am human therefore I am flawed.
I sat late Friday evening to write this and noticed I am 6 subscribers away from 1K!
So here is a request I have of you, help me get this dopamine hit. If this newsletter is something that you enjoy reading, tell a family member, friend or a co-worker about it. I will really appreciate it, and it will make this a very HAPPY Thanksgiving weekend* for me!
*That's right! Canadian Thanksgiving happens a full month and a half before American Thanksgiving, on the second Monday in October
☕ Now, on to today’s coffee chat…
Meet Catherine is the Director of Community & Marketing at Kahilla, a digital platform that scales leadership development to retain and advance diverse talent in the corporate world.
Jason LOVES being a dad. On the professional side, Jason has teamed up with Ethan Evans (retired Amazon VP now executive coach) to build Level Up, candid career advice that includes a free newsletter, live course, on-demand courses, and more. Jason also serves as a First Round Capital and Techstars mentor. Prior to Level Up Jason worked at Amazon.
I had an absolutely wonderful time chatting with Catherine and Jason and getting a peek into how they think about work, life and raising a little mini human together…
Please tell us a little bit about yourself and your family
I am Catherine (C) and I work at Kahilla, a startup that scales leadership development for women in the corporate world. I feel very inspired by and aligned with our mission.
And I am Jason (J) and am currently building a content business called Level up with Ethan Evans, Ethan’s a retired Amazon VP who I met during my stint at Amazon. The business is candid career advice, so we have newsletters, online courses, executive coaching, etc. Prior to this, I was at a startup founding team, about a 12 person startup we raised a 8 million seed, gave it our best shot but after a year and a half and I knew there was not much for me there. Together, we are parents to a 1.5 year old baby girl!
What has parenthood been like?
J: My experience of being a parent if I had to sum it up is I love being a dad! I would do it full time, if I could. What is interesting is I've always been on a path to achieve FIRE but the motivation on why I want to do that has changed - before it was simply to retire on an island, sit on a beach and be with nature. But now I want it because it would allow me to spend all the time I want with my daughter and maybe future kids. I didn't think I would love being a dad this much. And being a dad has really changed how I look at my career. Before fatherhood I was willing to work 110% all hours of the day. I wanted to constantly climb the corporate ladder as fast as possible. Now it is I want to live a in the moment and have a fulfilling life with my family, which does include having impact and doing interesting work but it is not all unidimensional!
C: Parenthood helps you learn so much about yourself. So I taught kindergarten for a couple of years and I've always loved kids, I've nannied I've babysat…. I just adore kids. And so I thought parenting would also come very naturally. Jason infact, doesn't like to hold other people's kids and doesn't feel comfortable around other people's babies. And so I really thought that I would just be so natural at it, and it would take him to start bonding with our baby … I was SO wrong, it truly was the other way!
I struggled a lot the full first year really and only now feel like I am really starting to bond with my child. She's a year and a half now and now that her personality is emerging, our relationship is really blossoming. In that first year I also realized how much I actually love work and how much I value having a place to go and getting to just be an adult and I started valuing my career at lot more!
I get that, as the birthing parent you do go through an entire roll coaster of emotions and so much physical change…
C: And in our case that was prolonged….I always imagined that once I wanted to have a kid you know it would just happen and that was not our story! We started trying in 2019 and it took us three years to conceive. Eventually I did IUI and then IVF . After 3 rounds of IVF we finally our daughter! My own journey of personal development really started in 2019 - I did so much reflection and felt I grew as a human.
In a way I also feel like it sort of robbed some of the joy of pregnancy ..once we were pregnant, I thought well at any moment this could get taken away, just because we're pregnant doesn't mean that we get a health happy baby. Even into my eighth month of pregnancy on calls when people would tell Jason or me congrats and we would still say fingers crossed.
Given that we spent three years just trying to have the baby I think I lost sight of the goal - I was so focused on getting pregnant and ensure we had the baby that once she was here I was not really sure what to feel. It was also hard because she didn't sleep very well for the first 10 months - It was really difficult, we weren't sure if she had colic, we weren't sure if she had a breathing issue. …at one point I was getting up like 14 times a night. And what's amazing though, as a woman, I still had ample energy to show up at work. Be present in meetings and get all of my work done. In a way my work saved me because I would otherwise have lost myself. You know they say nothing really prepares you for motherhood. That was me in the first year. This also sort of became worse because I felt guilty given we had so much support from day one. My parents moved in with us, and they have been watching her full time since she was born. And even then it was really difficult. So I always wonder how do people do it without support? You had yours during the pandemic….that must have been pretty wild.
Oh it was pretty wild. Looking back I smile now, but I don’t think I was smiling as much in 2020! Thank you for sharing your pregnancy journey. This level of transparency is so important. I know a lot of women who have gone through or are undergoing IVF and it is just rough. I am curious to hear Jason your perspective, as the man, watching your wife go through this…
J: If I had to summarize it in one word then it would be helplessness - 99.99% of the work was being done by Kathy, physically and mentally. So the best I could do was support her as much as I could. I felt so helpless. I also didn't realize what the process entail, and how much it required, including the daily shots. I don't know if I could handle that. That's pretty tough.
Jason, from what I have learned about you so far it does look like you're someone who balances pros and cons, has plans laid out and likes things to be a certain way. Given that and the added pressure of being a new dad, how did you decide that this was the best time in your life to do something entrepreneurial?
J: It was quite the seismic shift. I grew up in an environment where the majority of the people do see the male in the family unit strive for professional success and is ambitious and that usually entails running after either financial success, or titles and accomplishments. In the previous generations, there were male members in the family who worked a lot and didn’t have the close family bonds and ties. But now there is enough research out there which says as you get older and you look back at your life and introspect on what you could have done differently, usually having more time to build relationships with family is at top.
So I've taken a big step back, done a lot of reading and introspection to understand what is really important in life - ruthlessly prioritize what I want for my 80 year old self. I just worked backwards from that, using the regret minimization framework. And that helped me pivot my focus was.
A business has a lot of pros and cons. The biggest pro is the flexibility - in terms of what I spend my time on, who I spend my time with and where we choose to build our life. For example, we have moved from Seattle and have basically moved in with Kathy’s parents in Ohio as they are both retired and offered to help us with child care in these initial few years.
Catherine, how did you react to the move when Jason said, I am doing this…
C: You you nailed it when you said Jason you seem like someone who would think about all the different possible scenarios. I know Jason always thinks through things with a lot of rigor so when Jason came to me and said he had decided to make this shift in his career, I was fully on board and very supportive. I think it's a great opportunity. He did remind me that Kathy, remember you are the one now who is going to be offering health insurance and things like that. I'm very happy to support whatever he does, and I know together we're just going to figure it out. There is so much talent in him that I don't worry about the downsides.
J: I know one should not just jump off a ledge without a parachute. I am cautiously optimistic and take cues from FIRE - we are frugal and we have built a safety net…
So you have brought up the FIRE movement a couple of times. I know a lot of folks who think about the FIRE movement, but it looks like you've obviously thought about it more than just as an intellectual exercise and you are practicing it. What can you share from this movement that will maybe help a few parents get rid of their golden handcuffs?
J: I like to look at it from two perspectives. The first perspective is keeping costs under control. To do that, I personally allocate 50% of my household income towards investments or a safety net, which means living on 50% or less. Some other cost-saving strategies include avoiding eating out and prioritizing cooking at home and buying groceries, which is not only critical for financial reasons but also for health. When it comes to children, you don't have to buy everything new, especially clothes, as they outgrow them quickly. I learned this from my parents-in-law, who recommend consignment stores or thrift shops for kids' clothing. It's important not to succumb to the pressure of keeping up with the Joneses…
Now, moving on to the second perspective, which is equally critical. It's about smart investing. Personally, I prefer individual stocks, cryptocurrencies, and real estate. Regardless of your choice, it's essential to commit and go all-in on what interests you. One thing I've changed my mind about is diversification, especially when you're young. If your goal is to maximize your return on investment, I believe a concentrated portfolio with fewer, larger bets is better. So, fewer stocks but with more significant investments.
C: The other hack I always share is traveling with credit card points. We try to not increase our spending, but if we're going to spend money on our credit cards, we might as well maximize the return. For example, we put our IVF on a credit card and used the points we earned to fund a luxurious trip, like a 10-star Bora Bora vacation all essentially free except for taxes. We did the same for New York City, staying at the St. Regis. We love to travel and get the most out of our spending. We're not spending more, but we're spending smart. For instance, with the Amex Gold card, you get 4x points at the grocery store, so we buy gift cards for services like Spotify, earning 4x points on our monthly subscriptions.
The other big money saver for us is childcare. We're fortunate because both grandparents are retired, so they help with childcare. I have a strict work schedule from 9am to 5pm, and after 5, I'm fully involved with the baby. We do not feel the need to pay for childcare right now but at some point in the future we might enroll her in daycare for social interaction. With a child your costs will increase but we've also realized that kids don't need every toy. Thrift stores and trading toys with friends' has been a great solution. With kids it is all about newness for them, does not matter if 4 families have used it before yours!
These are all great tips, in my case though the first thing I probably need to do is cut down on my bubble tea consumption. I want to pivot our conversation back into the professional side of things. Katherine, you work in the space of leadership development and you work with a lot of women, what is your perspective around this idea of working moms in the corporate world hitting a glass ceiling?
C: It is still such a significant issue. We recently had a conversation with a mid career female leader at a large software company, and she shared her experience of returning from maternity leave only to be passed over for a promotion. The feedback she received was that she had just come back from maternity leave, and they didn't think she was fully committed. At the same time, she said her husband was being praised for being so involved and an active dad. This highlights the motherhood penalty, which we see occurring at all levels, even in top leadership positions.
Funny, or rather not-so-funny, stories abound. For instance, when we interviewed senior tech correspondent from CNBC, she mentioned that when she was pregnant, men would often come up to her and make comments about her weight or question her commitment to her job now that she had a family. This issue is consistently part of our discussions.
Interestingly, one thing that COVID-19 did was to open up our homes to each other, breaking down formalities. We've become accustomed to seeing kids in the background, imperfect rooms, toys scattered on the floor, and children coming and going during meetings. It's become more normalized, which has been a positive aspect of the pandemic.
We often emphasize the importance of having frank conversations with your manager. Many of our members find that their work ethic and the time they dedicate to their jobs don't decrease; they simply become more efficient in managing their time. Jason also applies this approach in his work. Being intentional during the day allows them to log off and spend quality time with their families.
As leaders and managers, women need to normalize and initiate these conversations within their teams. Leading by example is crucial because it sets the tone and makes it acceptable for others. Boundaries are a key topic of discussion. It starts with understanding your own boundaries and needs, as many women may not be clear on these aspects. Once you are clear, the next step is to communicate and negotiate these boundaries with your teams and managers. Of course some days you have to be flexible - if there is a senior leadership team call at 6 pm or 8 am you have to make it work but if this is a daily affair that makes it hard and unsustainable.
I think what you are trying to do here helps - There are resources for women for mothers out there, but I really love that you incorporated the male voices as well and you have opened up the conversation on what it's like to be a working parent, not just a working mother. I love getting perspectives of dads, and I think that really helps change the conversation because as women we cannot just do it all by ourselves. The truth is we are only half the equation and when the men become fully committed fathers that is when the true shift in culture will happen - where parenthood will be celebrated and the skills you acquire will be valued.
Quick-fire questions:
What’s the best thing you have watched recently?
Catherine: Season 2 of Suits #DonnaKnowsBest
Jason: Ace of the Diamond (makes me want to play baseball and run 100 miles).
(2) Best thing you have read recently?
Catherine: "Lessons in Chemistry" by Bonnie Garmus — loved it and can't wait for the series on Apple TV+.
Jason: This was a fun collaboration The Magic Loop: A framework for rapid career growth
(3) Best thing you have heard recently?
Catherine: Borrow from your future self. When I'm feeling stuck or having trouble seeing beyond the trees, I think about what Future Me has accomplished, and what she knows that I don't yet. What is she doing that I need to start? What has she stopped that I'm still doing?
Jason: The Magic Window of Parenting. There is a 10-year period of time when YOU are your kid's favorite person in the world. Ages 0-10. I plan to maximize this magic window and extend it.
🤓 Open tabs…
(I have modeled this section after those “open tabs” that we all have with a few (okay 30-40) interesting links that we promise we will eventually get to one day. These are the links that I had open for sometime that I finally got to …)
⭐Why Are Women Freezing Their Eggs? Look to the Men.
The struggling American man is one of the few objects of bipartisan concern. Both conservatives and liberals bemoan men’s underrepresentation in higher education, their greater likelihood to die a “death of despair,” and the growing share of them who are not working or looking for work. But the chorus of concern rarely touches on how male decline shapes the lives of the people most likely to date or marry them—that is to say, women.
⭐What You Should Chase Instead of a Dream Job
My institution didn’t expect me to work 70+ hours a week, but I did. I didn’t know how to work any other way. …Underperforming was not an option and so I went above and beyond. To onlookers, and even sometimes to myself, I appeared to be thriving. But residing within me, was a deeper confusion (why wasn’t I genuinely happy?) and embarrassment (how could I be so ungrateful to have a prestigious job?)
⭐ The Highly Sensitive Parent
The surprising, opposite-of-a-horror-story tale of a highly sensitive parent… everyone these days is opening up about the difficulties of parenting, and that’s great, but we’ve swung so far in that direction that all you hear today are the horror stories!
📖 My private thoughts from my very public diary…
(My Twitter use has drastically gone down, I am now more active on Threads)
I would love to hear from you, feedback is always welcome!
And if you happen to know an inspiring working parent who should be featured in a future edition (or if you yourself are one) - please do get in touch
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Disclaimer: All views expressed are my own and do not necessarily reflect the views of my employer