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C-Suite Moms: “It’s okay to have others help”, With Olivia Brooks Allan

By Landmark Venture

As a part of my series about “C-Suite Moms” I had the pleasure to interview Olivia Brooks Allan. Olivia is the Practice Head of the industry-leading strategic events business at Landmark Ventures, facilitating relationship building among technology-focused dealmakers through prestigious summits and philanthropic events. She is responsible for the success of all aspects of Landmark’s events business including leading an experienced group of event directors and production staff, thereby shaping the vision for all elements of year-round events including partnerships, production, marketing, communications, programming, operations, logistics, growth, and ongoing innovations. Previously, Olivia has been a successful leader within corporations with recognizable brands including American Express, Gartner, Four Seasons, The Peninsula, and Taj Hotels, and more recently with Mastercard. Throughout the past 19 years, she has focused on business development, management, marketing, and public relations. As an independent consultant to the events industry, Olivia developed and executed high-end event projects for corporations and individuals. Olivia is recognized as a leader who creates long-term and mutually beneficial relationships between clients and service providers. Her signature management style is delivering impactful results by energetically guiding her team in an environment where they flourish professionally. Olivia was the recipient of The President’s Club Award of Achievement twice during her tenure at American Express. Olivia graduated from the University of California at Davis with a degree in Rhetoric and Communication. A native of Northern California, she remains passionate for the outdoors continuing to enjoy running, hiking, and swimming. Her other personal interests include yoga, travel, and healthy cooking. Olivia resides in Connecticut with her husband and young daughter.
Thank you so much for joining us Olivia! Can you tell us the “backstory” behind what brought you to this point in your career?

I’ve always had a passion for human interaction. Bringing people together, building connections, communities, and creating beautiful experiences, but also most critically, how to drive positive and profitable business outcomes from those interactions. A common thread throughout my career has been working in companies that value the customer’s voice and thoughtfully integrating it into the evolution of their products, services, and solutions. From my tenure within the luxury hotel industry to financial services to technology-focused companies, the common thread with all of my professional experiences is a maniacal focus on the needs of the customer to empower the direction and values of the company.

Can you share with us how many children you have?
I have one daughter who is 4 ½ years old.

Where were you in your career when your child was born/became part of your family?
I had my daughter in my late 30s and was well established as an executive. I was in my seventh year of tenure at American Express, working from the world headquarters in downtown Manhattan. Having grown up in Northern California and being married to an Australian, neither of us could compute raising a child in Manhattan — although, in retrospect, it would have been amazing, and we often dream of moving back! We opted for a slightly slower pace in Connecticut and were in the process of buying our home during my pregnancy. We had the perfect plan to move in approximately one month before the baby was to arrive. Throughout my pregnancy, I had been active by swimming, spinning, running, and traveling for work. At week 28 of my pregnancy, my husband and I landed at JFK after a combined work + family trip, dropped our bags at our apartment, and went straight to a pre-planned dinner with friends visiting NYC. I wasn’t feeling great, but I attributed it to the travel and not to my pregnancy. I kept my routine the next morning, heading straight to a 6:00 a.m. spinning class, shower, smoothie, and straight to the office by 7:30.

A few hours later, when I started seeing black spots and felt faint, I called my OBGYN who instructed me to rush to the emergency room. I thought it was a bit extreme, but I followed his instructions. I was hooked up to the cardiotocography machine and, after a few minutes, the resident looked at me and asked, “Don’t you feel that you’re having major contractions?” The next three days were some of the scariest of my life. I was prepped for an emergency c-section 24 hours after being admitted to the hospital. I remember being in tears and absolute panic, thinking that our baby just couldn’t come this early. My husband was amazing as he pushed back on my OBGYN (quite aggressively, I might add, for a laid- back Australian) and instructed him that I needed more time. My doctor said, “My team is scrubbing in and this baby is coming today; otherwise, we are putting your wife at significant risk.” I was diagnosed with Placenta Previa, which can be quite dangerous in the most extreme circumstances. Still, it is also hard to see the severity until delivery, so it is often treated very seriously due to the risk for both baby and mother. I will always credit my laid-back and spiritual California roots for what happened next. I went to a place both mentally and physically where I was able to get the contractions to slow down enough to buy me an extra hour. An hour became two, then three hours, and within 48 hours I was moved into a non-delivery ward for high-risk strict bed-rest pregnant women where I would stay indefinitely.

So, there we were, straddled across living in two states and a hospital room. Our daughter thankfully arrived one month later and only one month earlier than my due date. Little did I know at the time I would never return to my job at AMEX as after a lot of thoughtful deliberation, and a tiny baby, my husband and I decided it was best to be home with her for an undetermined period of time. I was 100% focused on our daughter, and admittedly she rarely left my arms! I worked with our lawyer to start an LLC about four months after my daughter was born and started doing some independent work for the next two years. I will forever be grateful for my time at home to nest, nurture, and bond with my daughter. As my husband likes to say about our mother-daughter bond, “We are thick as thieves,” and I believe it’s in part because I was able to be home with her for two straight years. I know that those two years will forever be one of my life’s greatest gifts of time. All of this is to say that I was well established in my career, had a plan I was executing on to continue to progress my career with American Express, and life took over and changed my professional trajectory in ways I couldn’t have anticipated.

Did you always want to be a mother? Can you explain?
I always knew that I wanted to be a person who provided love, nurturing, and support for others, but I was open to that being through my child or my nieces and nephews. Now that I am a mother, it is truly a gift that I feel incredibly fortunate to have; our daughter is my greatest joy, and I have this unbelievable sense of responsibility for how she is integrating herself into this world. Motherhood is one of the most impactful, spiritual, and emotional experiences of my life. It truly is a gift having the opportunity to watch a human life immerse themselves into the world as they explore, observe, mimic, question, and cherish the world.

Did motherhood happen when you thought it would or did it take longer? If it took longer, what advice would you have for another woman in your shoes?
It took longer. My life trajectory changed from what I had planned in my early 30s, which allowed me a beautiful moment to pause and be open to the possibility of being a mother in a non-traditional sense to my nieces and nephews and focus on my career — which I loved! I was comfortable and confident in the fact that I may never have my biological child but regardless could make an impact on the lives of others. When I met my husband, we were open to the possibility of simply being the “cool” aunt and uncle. Then something shifted for us both and we quickly became excited and committed to having a child together. While I lose focus from time to time, health and wellness have been a consistent concentration throughout my life. This, coupled with great genetics, gave me the confidence that I could and would get pregnant whenever I wanted.

I was totally taken back when I couldn’t get pregnant. Infertility for our generation of women is so common that I, like many others, went straight to IVF. After failed attempts I was fed up with being told by the IVF Clinic that I “just had to keep trying, and these things take time.” I Googled, ‘The Best reproductive doctors in the world,’ and found a phenomenal Female Reproductive Specialist at Weil Cornell Medical Hospital in NYC who backed up my process. He took the time to diagnose the problem appropriately, and he didn’t put it all on me. I remember sitting in his office during our first meeting. He was so thorough with all that he was going to do for me, then he paused, looked at my husband and said, “I don’t treat you; you’re making an appointment with this doctor today.” I was in awe as up until that point the treatment plan had been rather one-sided. We both had surgeries during the summer of 2014, and I was pregnant by the Fall — it was an unbelievable journey that taught me a lot of lessons.

A common thread throughout my career has been working in companies that value the customer’s voice and thoughtfully integrating it into the evolution of their products, services, and solutions.

Can you tell us a bit about what your day-to-day schedule looks like?
My schedule is dynamic day-to-day because of travel and work commitments, but my week generally includes all or part of the following:
· School Drop-Off and Pick-Up: I commute into NYC rather early from our home in Connecticut so it isn’t possible to drop-off or pick-up my daughter every day, but I try to prioritize my weekly schedule to make sure it happens a few days each week. The car rides with my daughter to and from school and her activities are amazing — we listen to music, sing, talk about the week, remind each other of things to come, or reflect on memories. It is a cherished time in my weekly routine. I’m incredibly fortunate to work for an amazing company that allows me the opportunity to prioritize family and manage my schedule to allow me to find this balance.

· Health/Wellness: My mind really doesn’t work properly without exercise. It has always been my go-to for a mental reset. I do hot core power yoga 1–2 times each week and sweat it all out, as well as make sure to walk as many places as possible or go for a run — even if just running a few sprints! Fitting in exercise can be tricky and sometimes requires a VERY early wake-up call, but I know I’m a better mother, wife, daughter, professional, and friend when I’m also taking care of myself. I also take my wellness routine seriously with tons of water, vitamins, sleep, minimal dairy, and it doesn’t matter how exhausted, jet-lagged, or completely out of it, I ALWAYS thoroughly wash my face and slather on my face oil and moisturizers. Even on the cloudiest of days I’m always covered in SPF 50, no sun for my skin anymore! My weakness is a glass of wind-down wine with my hubby at the end of the long day, nobody’s perfect, right?

· Team/Leadership: I have weekly standing meetings with members of my team, but I also try to do random, walking, ad-hoc catch-ups as much possible. I love leadership and gain just as much from their insights as I hope they gain from mine! Making time to really listen and lead has been important in my career. Seeing my team thrive, grow, and deliver results has been one of the most gratifying elements of my career. I often say that I’m my team’s personal public relations agent! Seeing and promoting their successes, and having them trust me enough to coach them through their opportunities, is a real privilege in my career. I struggle with deadlines, competing priorities, filtering through hundreds of daily emails, and a packed calendar just like every other executive, but do my best to make time to lead from a place of honesty, kindness, empathy, and genuine excitement for their growth and development!

· Gratitude: My mother was amazing about always reminding my sister and me to practice gratitude. It was required that we send a hand-written thank you note when someone did something for us, whether it be a gift or just random kindness, and that’s stuck with me. I try to pop at least one hand-written personal note of gratitude in the mail per week. In the amazing digital and fast-paced world we live in today, I receive lovely feedback from people who are so appreciative, and a little surprised, to receive my hand-written note!

Has being a parent changed your career path? Can you explain?
I finally know what I’m working for and toward. I have a tremendous sense of pride in the home that my husband and I have built, the community in which we live, and it is comforting on weekends to be home and feeling like, ‘Ah-ha, this is what you’ve been working so hard for all week!’ A little girl giggling and running in the backyard with our puppy, long walks, cooking together, celebrating with friends. Compared to my 20s, the life I lead today feels so distant from where I was, and I’m incredibly grateful for the journey that has led me to this place.

Has being a mother made you better at your job? How so?
I’m a really tough critic of myself so I’m not sure I would ever be so bold to say I’m better at my job, but I’ve found this lovely layering of who I am as I’ve continued to journey through my career. I’m grateful that I’m in the workforce and never had to take a step back in my career trajectory because I took time off. I think a lot about the incredible talent who were once in the workforce in the traditional sense and are now taking the important time away to be home with their children and aging parents. I wish there was a less challenging path for re-entering the workforce once you’ve done the most important job in the world — caring for others. Companies like Mastercard, PwC, and Goldman Sachs are making some real headway with this and it’s wonderful to see!

What are the biggest challenges you face being a working mom?
There are weeks when I feel completely suffocated because I want to be with my daughter more or the logistics of our home just don’t seem to be working. I heard a senior executive woman speak many years ago, long before I was married and have all the home responsibility I have today, and she shared with a large group of us that she learned early on that she didn’t have to be the one doing everything. That asking for help from family, friends, and having professional help to keep the home working was okay.

My mother was a professor when I was growing up and since retiring she has dedicated her retirement life to helping my sister and me care for our children, and I’m so grateful — I hope to do the same for our daughter! I also have a great home team from a handyman, to housekeeping, and our wonderful nanny who cares for all of us with meal prep, errands, and looking after our puppy. There have been moments when my home team has been out of sync and it’s incredibly disruptive to my ability to be focused and deliver to my highest potential at work. Getting the home team right is equally as important as having a strong team at work.

Are there any stories you remember from the early days of parenthood that you want to share?
I had the lovely opportunity to be home with my daughter for the first two years of her life while also doing some consulting. It was amazing, but I do remember having a sinking fear of missing out. I would keep up with stories on LinkedIn and have catch-up calls with former colleagues, but I felt really distant from my professional identity. I missed it in many ways and was terrified I wouldn’t be able to re-enter the workforce.

Are there any meaningful activities or traditions you’ve made up or implemented that have enhanced your time with your family? Can you share a story or example?
I’m a big believer in the ‘food is love’ concept. I love being in the kitchen and I’m always hacking a recipe to see if I can make it just a little healthier while not sacrificing taste. My daughter is fabulous in the kitchen for a 4-year-old.

From the moment she was born I’ve been holding her while preparing food, letting the food, smells, textures, and my happiness in cooking awaken her senses. Now she will rinse, chop, add seasonings, go to the garden for fresh herbs, and always have an opinion about what the missing ‘secret’ ingredient is for a recipe (it’s usually maple syrup). I suppose I carry through my work in creating experiences for clients/partners into my home life. We always sit down and eat together at the dinner table. Sadly, we don’t live close to biological family, but have created some beautiful traditions with our friends that are like family including things like ‘Sunday Supper’ that rotates from home to home, or we all meet at the beach with to-go pizzas as the kids splash around while the parents drink wine and catch-up — we sincerely support one another. My family is known for making a tradition out of about everything so we have a lot — most of ours seem to revolve around food!
We all live in a world with many deadlines and incessant demands for our time and attention. That inevitably makes us feel rushed and we may feel that we can’t spare the time to be “fully present” with our children. Can you share with our readers 3–5 strategies about how we can create more space in our lives in order to give our children more quality attention?

I’m not perfect and my husband would share that he’s witnessed me in a lot of freaked-out moments where I just can’t imagine how it’s all going to get done, but these would be my suggestions:
1.) It’s okay to have others help: I love to nest and tend to my home. I really struggled when I went back to work that there were things that I just wouldn’t have the time to do on a daily basis anymore like cooking, or cutting some fresh flowers from our garden for the bedrooms. I learned that I needed a support system that understood how I like things to be done and let them attend to them on my behalf while I was at work.

2.) It’s okay to say yes: Children, including my daughter, are so scheduled these days. It’s the way of our society so I’m not suggesting a negative opinion, just stating the reality. When I was a 4-year-old kid I had so much more freedom to just to be, without scheduling. When my daughter wants to do something unexpected, I like to be able to say “yes” occasionally — there is so much structure today, which whether we like to admit it or not, implies ‘no’ all day long so I try to find easy ways to say yes without spoiling.

3.) Take care of yourself: The weekends that I haven’t taken time to fit in a yoga class or go for a run are the weekends where the house seems to feel more frazzled. I’ve learned that being a good Mom is about being there; for me exercise clears my mind, makes me more present and happier. Bringing that energy home is more important than being in the room physically but somewhere else mentally.

How do you inspire your child to “dream big”? Can you give an example or story?
There are a few things that I hope are driving our daughter to dream big!
The first is through experiences. We’ve been fortunate enough to travel a lot with our daughter, and she has been on over 40 flights already in her short life. We have family spread all over the map, including Sydney, San Francisco, Santa Cruz, Brussels, London, Hong Kong, Birmingham, and Auckland. Our travels, as well as our visitors, have unlocked incredible new experiences and thinking for her. We love arriving at our destination, but the journey itself has taught her independence, bravery, and confidence. We spend months talking about the trips before they happen, and to this day, she will blow my mind by referencing an experience we had while traveling that I was sure she would have forgotten.
Secondly, I also work to inspire her by being aware of my own bias. I grew up in a small town in Northern California, and now having lived in Chicago, Boston, San Francisco, New York City, and Greenwich I’m acutely aware that my experiences have created my own biases. Being aware of my bias is something I work on every day, so I don’t unintentionally judge her decisions and shape her mindset by wanting her mindset to be like mine. This is a tricky one that I know will only get more difficult as she gets older.

Lastly, I don’t mask the challenges of the world for her. At appropriate levels we have real and honest conversations. We talk about the environment and how much it needs her help, what it means to be a leader, what it means to care for others selflessly, and the things she sees and hears in the news.

What are your favorite books, podcasts, or resources that inspire you to be a better parent? Can you explain why you like them?

Podcasts are fantastic for working moms! I learn so much and can listen during my commute, in airport lines, and between school drop-off. I’m always looking for new ones, but my go-to the last few years have been: Talks at Goldman Sachs, NYT Daily, Stanford ETL (Entrepreneurial Thought Leaders), The GOOP Podcast, HBR Women at Work, WSJ Secrets of Wealthy Women, and NPR Up First. There are also some great podcasts for kids, my daughter and I are enjoying Journey with Story right now, she asks for it all the time!
Can you please give us your favorite “Life Lesson Quote” that you share or plan to share with your kids?

My college sorority had a saying we used to recite, which was, “If not now, then when, if not you, then who?” When I don’t feel like doing something, I generally say this to myself, and it kicks me into gear!

If you could sit down with every new parent and offer life hacks, must-have products or simple advice, what would be on your list?

Soak it in, the stages all pass so quickly and I’ve been incredibly present and focused on my daughter’s development from the moment I found out I was pregnant. I say all the time that I wish she was back in my belly where I knew what she was eating, that she was safe, warm, wasn’t going to get a bug bite or fall and skin her knee, or have another child be mean to her … but that will never be again. I miss her with my entire heart and soul while away working, but I also have been so present for every stage of her life when I am home. My advice is to recognize that everything that feels unsurmountable today, such as teething, sleepless nights, temper tantrums, picky eating, will be gone soon and there will be a new stage of delightful opportunities to enjoy and conquer.

My Must Have Products:
· Daily Kids Probiotic: Mix up the brands and therefore strands

· ChildLife, Essentials Echinacea: A few drops on airplane rides or whenever sickness is lurking

· Living Libations Seabuckthorn Best Skin Ever: I use for my face every morning/night and it’s so gentle/natural I can easily slather on my daughter too

· Cancer Council of AU Kids Sunscreen My mother-in-law got it for me and it’s the best!

· Coconut Oil: We use for everything from post-bath moisturizer to rashes / bug bites

Thank you so much for these insights! We really appreciate your time.

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