This is a rough transcript of a lightning talk I gave at a Microsoft event in June 2017.
It was 2011, and I walked into a small office. The 8.5 x 11 inch sheet of paper on the door said The Obvious Corporation. I entered a small conference room and sat down across the table from Ev Williams. He looked at the paper in his hands with my name on top, and then he looked at me. He said, “So your background seems pretty straightforward and impressive, but one thing stands out. You only spent 1.5 years at Google right out of school, and then you quit. And it looks like you didn’t have anything lined up. Tell me more about that. Is that typical for you?”
I thought about it for a few seconds, and said, “Well I guess maybe, yes. Every once in awhile, I really love this feeling of being thrown in the deep end. I just have no idea what’s going to happen, except that I’m going to learn a lot from the opportunity, and that’s super exciting.”
I got the job.
Four years and two kids later, my reality could not have been more different. The days of uncertainty and jumping in the deep end and taking big risks seemed like the past.
Every morning I woke up to two small children, made them breakfast, dropped one off at preschool and the other off at daycare, and took BART in to work. Most of the time, I had 6–8 hours of meetings, often back-to-back, and then I took BART home, and my husband and I fed the kids and put them to bed. Then we had an hour or two to do all the house chores before going to sleep and doing it all over again.
On Fridays, I looked forward to the weekend, and on Sundays, I was grateful to have survived the weekend, and looked forward to work. For those of you with small children, you probably understand what that’s like.
It was one of these evenings, after we put the kids to sleep, when I was scrolling through Twitter in bed, when a tweet grabbed my attention. It read, “The 100 day project starts tomorrow.” I had followed along with Elle Luna’s 100 days of self portraits and Susan Lin’s 100 days of watercolor trees, and it always seemed like something other people did — creative people. They had time to do that, I didn’t have time to do that. But, in a moment of weakness — or maybe strength — I opened up the Medium editor, and jotted down this post:
“Last year, I set a goal to publish 52 posts. I didn’t publish 52 posts, but I published far more than I would have had I not set that aggressive number. Which is a funny thing I’ve noticed about myself. Sometimes I’m not quite sure if I’m working too hard or not hard enough. Do I really not have time to write (which is what I tell myself, especially with the two kids), or is it that I have time to write every day if I commit to it, I just haven’t committed to it?
Anyways, I saw that The 100 Day Project is kicking off tomorrow, so why not?”
101 days later, I published my 100th post for the project. When I reflected back on the past 3 months of my life, I realized that, if I had known, really known, how much work it would have been, there’s no way I would have committed to it. But I was very proud of what I had done.
So I thought of myself as someone with no time because I work and have these two kids, but I also somehow bypassed this worrying inhibiting part of myself — that usually says “that seems like a lot of work, don’t even try it” — by signing up for something when I didn’t really know what it entailed.
I was curious if I could do this again. As an engineer by training, I decided to see if these results were reproducible.
About a month later, I saw an ad for the Berkeley Half Marathon, which also include a 5k and 10k, and it goes right in front of our house. I didn’t consider myself a runner, especially after having two kids. I’d done a 5k before, so I knew I was physically capable of it. But the 10k seemed very out-of-reach. So I signed up. I was also motivated by my daughter Alina, who was three at the time — one day she was standing on the sidewalk when a runner ran by, and she looked at the runner and then she looked at me. And she said, “I wish I could be a runner...I’m just a walker.”
After three months of training, I completed the 10k in the rain and ran past the exact same spot in front of our house, waving to her. She wore a light blue raincoat, and was holding her little polka dot umbrella as she cheered me on.
Ok so my little life hack works, at least those two times. Right around that time, I started contemplating leaving Medium after 5 years. I was talking to a good friend, and I said, “You know, there’s two things I’m considering. The first is sort of a logical next step. I’ve been managing teams of up to 15 engineers, so I think I could interview for head of engineering positions at some smaller startups and build out a team. But there’s this other thing I’ve been thinking about, and I don’t really know what it is, but what if I could coach engineering managers at a bunch of companies, and help them be better managers? Imagine the positive impact I could have on their lives and the lives of their teams…”
And when I thought about starting my own business, it wasn’t the coaching that scared me, but the selling and marketing my services that honestly terrified me, and I wasn’t sure I could do it. But I realized it was the same feeling of uncertainty as when I realized that 100 days is a lot of days. And it was the same feeling as when I realized that 10k is still 10k even if it does go in front of our house. But I also remembered the thrill and the sense of pride I felt when I did it.
When I joined Medium, it felt like I had kind of stumbled and then fallen into a pool, and I realized it was the deep end and learned to swim. But when I left five and a half years later, it felt like I stood right at the edge of the pool, looked down into the water, and chose to jump.
