My Year of Saying Yes

Cathy Pearl
4 min readAug 14, 2018
At the KNIME User Group Meeting in Berlin (2015)

I’ve always been a person of “what ifs”. What if the cat gets sick right before we leave on our big trip? What if I get on the wrong bus? What if I sign up to do something but I don’t know how to do it?

In 2014, I decided to try something a little different, ignoring the doubts and saying “yes” to as many things as I could.

The lead-up to this period of saying yes had started years before. Before having my son, it had taken me almost three years to get pregnant, and at the end of that time, I quit my job to focus on fertility treatments.

After he was born, I decided to spend a year as a stay-at-home mom, which would have surprised the heck out of younger me — I’ve never been a baby person. I warned my husband I might go stir crazy and go back to work before the year was up, but in the end I did it. And then another year passed. And another.

I was getting restless, but I wasn’t sure what I wanted to do next. I didn’t want to work on designing IVRs — phone trees — any more. But I didn’t know what else to do. In 2011, a former colleague called me up and asked me to join his start up. I said “Does it involve speech recognition?” He said “Yes” and I said “No thank you!” But he persuaded me to come see his demo, and I was intrigued.

I spent the next couple of years working part-time on some cool interactive technology, but alas, after a two-and-half-years the company, like so many startups, folded.

It was 2014 and I was adrift. I was 41 years old, and one night, standing in my sister’s kitchen, I told her:

“My career is over. I’m too old. I haven’t worked full-time in seven years. No one will ever hire me again.”

I remember her looking at me incredulously, but I was convinced.

With some encouragement from a friend, I decided to see a career counselor, and slowly, over time, it became the year of saying yes. I had no idea what I wanted to do in this next phase of my life, but the career counselor suggested focusing on something I was really interested in, regardless of its career possibilities. In the end, I chose to spend time thinking about relationships: I’ve always been fascinated by how people choose their romantic partner. I started a blog called Love Data and wrote about things like sweaty t-shirt parties, and interviewed experts in the field.

I still had no idea how to turn this into an actual job, but opportunities started to pop up. I was invited to a conference in Berlin to speak about work I’d done analyzing Tweets about online dating. When the organizer asked me to come, I told her:

“I can’t… it’s a data science conference, and I’m not a data scientist!”

She gently but firmly encouraged me, saying, “Of course you can.” So I set aside my hesitation and went. Did I get lost wandering the streets of Berlin in the February cold, because of my legendary inability to read maps? Yes I did. But I had a great time exploring, and speaking at the conference.

I said yes to consulting for more startups, including one that makes a smart grill, even though I don’t like to cook. I said yes to volunteering for Girls Who Code, even though I found the idea of standing up in front of a bunch of teenage girls terrifying. I said yes to writing a book, after hemming and hawing about how much work it would be and whether I had the skills and the experience to do such a thing. I said yes to a taiko drumming class, something I’d always wanted to do, even though I was the only beginner and the only thing the instructor ever said to me was that I was holding the sticks incorrectly.

I sent out a lot of resumes and got a lot of rejections and even more of those silences that make you wonder if your email is broken and the Send button puts things straight into a trash folder. I signed up with recruiters and got nowhere. I interviewed for jobs I didn’t get.

In 2015, after consulting for a health tech startup part-time, I joined as their Director of User Experience. I spent three years wearing a lot of hats and learning a ton about virtual avatars, the healthcare system, and writing SQL queries.

In April this year, I made the move to Google as the Head of Conversation Design Outreach. I now get to spend time doing something I was already doing on the side for fun: speaking to people about how to build great conversations.

I feel so grateful to the people in my life: my family and friends for being so supportive, and my colleagues for encouraging me when I doubted myself and for sending leads my way. I want to give back. I want to encourage and support people the way they’ve done for me.

There’s a quote out there about how saying yes to everything means never getting anything done, and I get that. Everyone is in a different time and place in their lives. Sometimes you don’t have the luxury or the time or the energy or the option to say yes. Sometimes saying no is the right move.

Lately I’ve been thinking back to four years ago, when I felt so lost, and so convinced that I’d never have a career ever again. Today, I feel so fortunate, to have had the opportunities I’ve had. They didn’t all lead to successes, but in the end, I’m glad I had my year of yes.



Cathy Pearl

UX Lead on Google Gemini. Author of "Designing Voice User Interfaces" from O'Reilly (More at