Interview with Caroline Fleetwood
On Making Big Life Decisions
This week you all have the treat of hearing from my dear and delightful friend Caroline Fleetwood, Assistant General Counsel and Practice Group Leader in Healthcare Law at Genentech, on how she’s made big life decisions. I took so many nuggets of wisdom from this conversation—like shedding notions of ideal timing and getting “on the train when it comes,” erring on the side of decisions that open doors, and how to think beyond buzzword well-being to pragmatic well-being. And, of course, we talk creativity and how Caroline thinks about it as a “hyperrational” decision-maker—and future pottery class participant.
Q. Tell me about the career transitions in your life and how you’ve gone about making them?
It’s interesting because I feel like I’ve had less of them than some of our contemporaries. I was lucky enough to get put on this career path completely accidentally and incredibly early. And given how well it has turned out, I feel like it was a tremendous gift.
At 21, I went to college career fair thinking I might want to look at paralegal jobs. I met with a paralegal who shouldn’t have been there, but talked her way into tagging along. I told her I was majoring in politics. She was a healthcare paralegal at Sidley Austin, and she told me she’d be leaving soon, and I should come and take over for her. Despite having no healthcare background, she convinced me that it would appeal to my interest in policy and politics. She turned out to be right. I liked the work, and I saw that it gave attorneys viable in-house options. So I finished my two years as a paralegal, went to law school, and became a healthcare attorney.
My first big career choice came about three-and-a-half years into practicing as an associate at Sidley Austin LLP, when a colleague seconded at Genentech asked if I would be interested in an in-house role there in the Bay Area. It was a big surprise to have this opportunity present itself so early—I assumed I would be in big law for at least six years. But my colleague said it was a great culture, and I had close friends in Bay Area and my partner Isaac’s family. At the end of the day, it was a hell yes. I was scared to make a leap away from the safe, lucrative choice of a law firm. But I also didn’t want to be working until 8 pm each night. It ended up being an excellent choice for all the reasons we anticipated.
Q. Did you have moments of doubt when you were making that decision?
I had real doubt about moving far away from my parents. My parents were older, and I am very close with them, and there weren’t other siblings nearby. But at the end of the day, all the other boxes were checked. It was a solid company, a role with growth opportunities, my partner was enthusiastic, his family and our dear friends were nearby. It was all seeming to line up. For better or worse, I grew up with the idea that you don’t make life choices based on someone else. My parents both moved away from where they grew up, and I really couldn’t see myself making a different decision given the circumstances.
Q. You’ve also made a big transition within Genentech into management. How has that gone?
Yes, so the next big choice for me came after being at Genentech for six years. I was on maternity leave and a management role in my group became available. That was a much harder, fraught decision. I didn’t know if I would like management—and this was very much middle management. I was really struggling with the part of myself that was an overachiever, asking if I just wanted the next shiny object or if this was actually what I wanted to do every day. I talked to mentors, my mom, my friends. I had to decide kind of quickly. I was legitimately curious about whether I would like management. I just didn’t know.
Backing up a bit, we haven’t gotten into how having children impacts all of this. When we moved to California and I went in-house, I wasn’t immediately looking to have a baby, but I knew we would be setting ourselves up for that. Genentech has fantastic maternity leave policies and a great day care. I had very supportive family nearby. The attitude of my boss was like, have all the babies! So when we did have our first son, it was a pretty ideal experience. That brings me back to the management decision—I would be deciding to take a leap right as I was coming back from leave, which most working mothers would tell you is less than ideal. You don’t know how you will feel physically or mentally or how difficult that transition would be, and I would be making it much harder by having to figure out a new role and establish myself as a new and relatively young leader. I was really worried that I wouldn’t be setting myself up for success.
I think I ultimately ended up making this decision in the same way as the others: My parents always told me opportunities happen when they happen. If it is something you want, and it is just a question of timing, then you need to go for it. You have to get on the train when it comes. That’s how it felt moving to California, and that’s how it felt with this. So I just jumped in and did it. And I’m happy I did. I’m growing into this role.
Q. Not to bring everything back to creativity, but you know I love to talk about creativity. Would you say the creative part of you has played a role in making these transitions?
Sometimes I wonder how in touch I am with my creative mind. I know it’s in there, but I think that I made these decisions heavily with the rational part of my mind. When you meet your husband when you are only 18, you grow together, and Isaac is hyperrational. So I’ve become pretty hyperrational about decision-making. A lot of listing pros and cons, and if pros outweigh the cons, you do the thing. But I will say that so far when faced with choices to hang tight or go for it, I’ve tended to go for it. I don’t think you always do that. There are times in life when you simply don’t have the capacity to take on more. But so far, I have been able to seize the opportunities that presented themselves, and I feel very lucky that it has worked out.
Q. Would you say you are more creative in your job now than you were in your first job?
I think this role has tapped into my EQ creativity. I have to learn how other people think about things, how they see themselves and their development. I have to think about my approach to help them get somewhere. This is difficult to do, and it does involve being kind of creative. There was no creativity in my role at the law firm. I had to write well, but I had to write the way they wanted me to write. The way that going in-house feels more creative to me is really related to leadership and problem solving. I have license to look for how things could be better and raise those with people.
It’s not creative like art is creative, though. I feel like that is an underutilized part of my brain at this phrase in life. As I think of the next half of my life, I hope there is more of that. But I think I feed that part of my brain by taking risks in leading and trying to solve problems I see. I’ve never thought about it this way until this now, but I think that’s maybe why I don’t feel the lack of creativity so much in my life right now.
Q. It’s a privilege to have a job where you can show up in that way.
It really is—being empowered to take action in your role is intellectually stimulating and personally fulfilling. I do think a lot of people aren’t particularly stimulated in their job. That may mean you need another job, or it may just mean you need to get what you need elsewhere. Not everyone has the luxury of leaving their job or of being able to fulfill every need at every time. I actually think “wellness” culture can be a little toxic to the extent that it makes us feel that we should all be able to fulfill our every mental, physical, spiritual, creative needs at any given time. That just isn’t realistic.
I think a big part of well-being—not as a buzzword, but to the extent it has real meaning—is being aware enough to know what you need that you aren't currently getting. If you can’t make the change now—maybe you have family or work obligations etc., that is okay, as long as you are aware of it. Then, when you have time and capacity to change it, you do. Where it’s a problem is where you don’t even allow yourself the time and space to reflect, identify those needs, and spot your opportunities to fill them when the moment arises. One day, when my kids are more self-sufficient and my job feels less hectic, I hope I have the wherewithal to say wait, I have capacity again, I need to join a freaking pottery class!
Q. So in second half of your life, where you said you’d like creativity to feature more, how do you see that happening?
Hopefully it doesn’t have to wait until retirement! I have loved painting and music and pottery at different points in my life. I would love to find a way to tap into one or more of those again.
Q. There’s something different about doing a creative project entirely for you—not for your kids or for work.
Exactly. There’s a freedom in that that unlocks something in your brain. I do miss that very acutely, but I am also okay with the fact that it’s not something I can add in right now.
I have realized that I need a lot of time and space for things. The fact that you could write a novel and hold down a job and have a baby is totally amazing to me [NOTE TO READER: This all took me a loooooong time, and the baby came after most of the novel doings!]. I need a fair amount of down time to transition between things (work, caretaking, work out, house stuff etc.). Sometimes I feel like I should have more capacity, but I am really working on self-acceptance. Comparison truly is the thief of joy.
That’s one thing that’s really hard about the choice to have more kids, and grappling with motherhood generally, is that it really does take over for a period of time. So that is part of the choice—how much capacity do I have? How long do I want to be foregoing certain things that are important to me because I simply cannot fit them in. How can you possibly weigh mothering a child against vague but important notions of your own growth and wellbeing?
Q. When you were deciding to have both kids, did you have that tradeoff in mind, or is it something you’ve come to think about later?
Oh I did. I’m keenly aware of my capacities. I think I always knew that having kids was going to take up most of my bandwidth. And even now that I’m not on the brink, teetering, I sometimes think, what about a third kid, and then I’m like, oh my god are you insane? It’s an amazing, tremendous experience, but there are tradeoffs.
Q. What wisdom do you want to pass down to your kids about making these big life decisions?
I always come back to this thing that my mom used to tell me: You should always be assessing decisions by whether they will open doors or close them. Especially in the early part of life, I think it’s important to make decisions to open more doors than they close. You will come to moments in life where either your desires are so clear or your capacity is so limited that it will make sense to make decisions that will ultimately close doors. But, hopefully, when you do that it is out of self-knowledge and not out of fear. Thinking about things in those terms has never steered me wrong.
Q. I’ve been in this conversation with myself recently about what decisions will matter to me when I’m 80. Do you find that kind of thinking helpful?
Oh, it’s so difficult to weigh the preferences of my future self. Future me would have four kids! Isaac too. But how I am functioning day-to-day matters too. No one will ever say they regret the life of a human that they love. But how do you build a life that you can maximally enjoy and learn from and grow? How do you sort out the bullshit, I don’t want to get fatter reasoning for not having another kid from the real, I want to feel like a whole person and paint one day and have moments to reflect on how beautiful my life is type of reasoning?
My mom first picked up a paintbrush in her retirement, and it’s been an incredibly powerful thing for her. I look back and see how stretched she was, raising us. And when she wasn’t stretched, what wonderful parts of her emerged! Kids want a wonderful mother, but they also want to see an example of life well lived.
Q. So very true. Are there other things that come to mind on these topics that we haven’t talked about?
So much of this is just luck. And I recognize that it’s a privilege to have this kind of conversation. Capacity is so determined by finances, partner support, family support. I recognize that most people don’t get to make these kinds of decisions with the options I’ve had. It’s important to feel the gratitude.
Q. It really is.
It helps in those moments when I am trying to figure out whether I am acting out of fear or whether my hesitation is about real desires or questions of capacity. It’s like “oh man, I am lucky enough to have these opportunities, I better have a damn good reason not to take them.”
Dear Reader: You matter! If you’d like to share what you found meaningful or interesting in this interview, please drop me a line at hello@logansteiner.com. I’ll pass any kind words along to Caroline. Also, please reach out by email if you have an interest in being interviewed on a decision related to creativity or becoming a parent and how you are sorting through it.