Why Timing Isn’t Everything

My unexpected path from pregnant college student to Founder and CEO of Care.com.

Me with (from left) my younger son Adam, my husband Ron, and my older son Ryan.

Timing is everything, they say, and how my husband Ron and I started our family had little to do with timing things perfectly.

I was born in the Philippines with a very structured and organized life plan. It was determined early that my siblings and I would each have a dedicated career path: one was to be the doctor, one the dentist, one an accountant, and so on. I was going to be the lawyer. I was well on my way to that plan, enrolled as an undergrad at Mount Holyoke, when the plan didn’t just go out the window — it left the stratosphere altogether.

I discovered I was pregnant my sophomore year. Twenty years old and terrified, a million thoughts raced through my brain — finishing school, starting my career, telling my parents — but all I could focus on was, “Now what?” Ron, a junior at Yale, had the radical idea: “We’re going to get married.” And so we did. He graduated and moved to Massachusetts while I finished school, carrying my infant son, Ryan, in a carrier to class and seeing the looks exchanged by my fellow students.

Becoming a mother at such a young age has a way of putting your priorities into sudden sharp focus. There’s not a lot of room for the freedom, frivolity and fun many twenty-somethings enjoy. You put what’s important first, and those once-grand life plans become an afterthought. I had to finish my education, get a job, and support my family. There was no time to waste. After graduation, I deferred my acceptance to Harvard Law School (that original plan from my parents), and instead went into litigation consulting.

If my first challenge as a working mom was letting go of that very orderly, organized life plan, then my next showed itself during my job interview with the first firm I joined. I was convinced that if they knew I was a mother with a baby at home, I wouldn’t get the job because they’d think I couldn’t put in the hours. And if I did get the job, they wouldn’t give me the plum assignments, thinking I’d be less committed or distracted by my family. So I didn’t tell them I was a mom. I was so worried about what others would think that I wasn’t what I call my “authentic self.” I moved on within a year and joined a telecom strategy consulting firm, and I made a promise to myself that I’d never make that mistake — never sell myself short like that — ever again.


Our son, Ryan, was six years old when Harvard Law School came calling. If I wanted to matriculate, they said, I couldn’t defer again. By then I knew I wanted to pursue a career in business, so I applied to Harvard Business School and the joint JD/MBA program — and I encouraged my husband to apply to HBS, too. So off we went, all three of us. There must be something in the water at university campuses, because our family’s second surprise was having me walk to get my Harvard diplomas seven months pregnant with our now younger son, Adam.

So there I was, 29 and a mother of two before my career had the chance to really get off the ground. Not exactly what my traditional parents had planned for their daughter, who was supposed to be the lawyer, when she left the Philippines to attend an all-girls college. It wasn’t the path I’d seen for myself, either.

It’s not easy to start your career when you’re already a mom of two small children. There are times when it feels like the deck is stacked against you, when you feel like there’s a certain image you have to live up to. And there are going to be countless sacrifices you — and your family — have to make along the way. It would have been easy to give up on my career aspirations when I was bouncing Ryan on my knee while cramming for exams. It would have been easy to give up when I was begging my parents to move from the Philippines to help with childcare. Or when my father, who was 54 at the time, had a heart attack and fell down the stairs holding Adam, our baby.

Those who know me know that taking the easy way out or giving up is not who I am. Yes, I was a working mom at 29 and as soon as my dad fell down those stairs, I was also a member of the Sandwich Generation. There were people counting on me… people I loved. So we found a way to make it work. My career path wasn’t going to look like other young professionals’, but I was starting to understand that every step of it would lead me to where I am today.

Being a working caregiver forces you to have the kind of uncomfortable conversations you might try to avoid if your career has taken off before you start a family. Ron and I juggled childcare during school and as we started our careers. As we grew together, we made choices together, for our family. Traditional roles didn’t define us—since our youngest was in 2nd grade, Ron did most of the afternoon pickups and coaching teams. I was still responsible for after-school coordination of the schedules, finding caregivers to assist us and help out with homework, but we decided we were going to split things at home very early on. Ron has been an exceptional partner in raising our two boys. And eventually, at a point in my career where it demanded more hours at work for me to continue balancing the juggle, I became the breadwinner, and he opted to be the primary caregiver. I had to move beyond my own expectations of what a mom should be, but it made it easier to know these were decisions Ron and I made together.

Even as I discovered my true calling in the world of entrepreneurship and startups, Ron and I were having heart-to-heart talks about what we both wanted, and what our expectations were for ourselves and one another. I had similar conversations with managers and bosses along the way.


Quick story: Years ago, I took a job in New York. The plan was that if I loved the job, after a year I would move my family to Manhattan from Boston. The job was wonderful, we were about to put a bid in on a house in Tribeca, and I was visiting a school our younger son would have attended. On the sidewalk outside of that school, I buckled. Just waterworks. I thought, “I can’t do this to my family. I love this job, but my family loves Weston, Massachusetts. They’re happy there. What am I doing?” So I gave my notice. It was a tremendous opportunity, and it wasn’t easy to leave behind. And no, I didn’t have another job waiting for me. I didn’t even have a plan.

It might have seemed like a bold move at the time, but if I was being honest with myself — being my authentic self — there was never really a choice. And it was there, crying on the sidewalk, that I decided the two scariest moments of my life up to that point — getting pregnant in college and my father’s heart attack — would lead me to the third: Starting a company. I got through the first two, and it gave me the courage to tackle this third one.

After I left my job in New York, I thought back to that girl I was that sophomore year, how she could have used a service like Care.com. I thought back to how, when Ron and I were working at tech startups the only options to find care for our sons and my dad were the Yellow Pages or word-of-mouth. I thought about how many other mothers, fathers, sons, and daughters find themselves in the same position Ron and I were in, looking for solutions to real pain points in life. At the same time, I was being recruited to join a hot new online entertainment company and it was tempting. Unsure which path to choose, I met with a trusted advisor who asked me a simple but life-altering question: Did I want to be in the pleasure business or the pain business? My authentic self knew the answer. I wanted to help people solve the challenges and pain points in their lives.

So it’s no coincidence that the company I founded, Care.com, helps families find caregivers and caregivers find meaningful work. Finding care for their loved ones is the biggest challenge most American families face.


Today, 25 years after becoming a pregnant college student, 15 years after becoming a member of the Sandwich Generation, and nine years after becoming the founder and CEO of Care.com, I think about how we are helping families with all the unexpected changes of plans in their lives — an aging parent who breaks a hip; twins; the birth of a special needs child; or just the everyday twisting plot lines of their lives. And I’m grateful for my own twisty path.

The timing, in my view, couldn’t have been more perfect.


Medium is convening a conversation about work, parenthood, and how the two mesh — or don’t — in our lives. To get involved, please follow the Working Parents publication and the tag, and help us expand the dialogue by writing a post or a response.

This contribution arose in collaboration with New America’s Breadwinning & Caregiving Program, which focuses on gender equality and changing the national conversation about work, family, and excellence.