The big shiny life with Rae Katz

"Until now, I never felt like what I was doing was good."

This Q&A is part of a series of conversations with people who are forging meaningful lives in a time of chaos and unpredictability. They take time and skill to produce, but I keep them available to all subscribers rather than paywalling them. If you value the themes explored in these conversations, consider upgrading to a paid subscription here. You can find links to past interviews here. (If you’re already a paid subscriber, thanks.🙏)

If you’re looking for a CV that features all the premiere brand names of American excellence, look no further than the resume of Rae Katz. The self-described “chronically ill ex-startup CEO” graduated from an Ivy League, did a Fulbright scholarship in China, worked for McKinsey, and co-founded a Y-Combinator-backed Silicon Valley startup, which she sold in 2020.

But as you might’ve guessed, that’s not why I wanted to interview her for this newsletter. I discovered Rae’s writing recently, with an essay about her time on the Silicon Valley grind. As a reader, I was delighted to hear the excesses of the startup world dissected with such lucidity and female rage. As a writer — I’ll be honest here — her writing made me insanely jealous.

Rae describes herself as “terrified of the internet” and found her way to writing on Substack reluctantly. She says her newsletter

Inner Workings

is about “my health journey, my work journey, and how they relate,” but I think it’s also about something much larger than that.

Rae is a person who has achieved everything we are supposed to want and realized that, actually, the big shiny life is not for her. Her writing is a balm for anyone looking for permission to pursue a softer, gentler, smaller life — and who has a hunch they may be much better off for it. I’d go a bit farther and say the world might be slightly better off for it, too.

In this interview we talk about the fundamental untruth at the root of both startups and business journalism, holistic versus conventional healthcare, why we continue our pursuit of big shiny lives even when they make us sick, and what might actually make the world a better place. (Hint: It’s not a startup.)

Image: Getty / Khanh Bui

Rosie: I’ve talked in the newsletter before about this idea of the double life. On the one hand we’re performing capitalism on the outside – in your case, very convincingly with all the right brand names — and then we have this deep unease on the inside, this sense that life is not working. Maybe we’re ignoring a lot of things that really upset us, or make us sick, or don’t align with our values. I wonder if that framing resonates with you?

Rae Katz: I think it went through a few phases. Early on when I graduated from college and was applying to jobs, my story to myself was: “This isn’t me, I want to do good in the world, but McKinsey is a great place to get the skills. So I’ll do this for a couple years and then go out and save the world.”

Once you go there, you’re getting flown first class, you’re getting put up in hotels, you’re being told you’re the best over and over. I think that during that time I was having this big internal struggle: I hated the place I was in but I also really wanted to succeed at it because everyone around me thought it was the best. The whole setup of the place made me want to succeed there even though it wasn’t really a good fit for me as a job.

R: Right, this is true of so many people that go into management consulting or finance. The jobs that are seen as “safe bets” out of university. 

RK: I eventually quit. I had lost my creativity and relationships and wanted to reclaim those. I moved home to live with my parents. But I wasn’t done with my ambition. I had this really great friend and he wanted to start a company with me and it seemed like a great opportunity. I lived in SF. That's what everyone did. 

The turning point — the time when I really started to see the difference between my values and the value system around me — was when I looked around at Y Combinator and realized, “Wow the only value here is to make as much money as possible.” I didn’t see any conversation about how much money was enough. I realized, I don't want to be here, I don't like these people, I don't value the same things as them. That was 2016, but I kept doing the startup for four more years after that. It was literally killing me, but I kept going. The only reason I ended up stopping was that we sold the company in 2020. 

R: But you weren’t just saying no to startup or Silicon Valley life. You were saying no to a whole existence of professional and successful milestones that other people could immediately recognize. You were opting out of more than just a company or a job.

RK: Yeah I think at the ground level my stress level was so high, that was truly the main thing I was opting out of. I didn’t really have a vision for what would come next. But I did know that the thing so many entrepreneurs and businesspeople around me were working for, no matter what they said, was to make as much money as possible. And that goal did not resonate with me, even if the person trying to make as much money as possible is me. 

R: Even the question “what is enough,” in those circles, in that way of thinking — it doesn’t exist. I used to cover earnings calls as a journalist and it would be an out of body experience every time. The underlying assumption of the whole thing was that growth is good no matter what, no matter what the externalities were. And I was always sitting there thinking: this just isn’t true. But for some reason it was taken as the bottom line when you step into this world. I always found it so jarring, and then I’d have to write 800 words with that assumption underlying it, never questioning it even though I was a journalist.  

RK: That experience you described of feeling out of body was super common for me. I’d be in these rooms where there’d be some underlying assumption like that – that growth is good no matter what – and I’d be like: “Does anyone else see that this doesn’t make any sense?” But it’s so deeply ingrained. 

R: My other thought was I’d be so terrified of getting something wrong in the story I was writing, and getting found out for being someone that didn’t really know what I was doing writing financial journalism. It would be like these two parallel scripts of: “this is dumb” and “omg wait how do I figure out net profit again?” 

RK: That’s so familiar to me. I now feel that my whole character was very antithetical to this path and that’s super interesting because that’s just luck. I’m not sure if you’re familiar with the concept of a highly sensitive person, which are people who have more nervous system sensitivity to external inputs, like heat and cold, or other people’s emotions.

It’s pretty clearly genetic, and when I read about that in my thirties, I thought no wonder those intense business environments were especially difficult for me. But even though I knew that, I wasn’t like “I should go do something else.” I was like, “This is the thing that you’re good at if you’re a successful person.” So I pushed forward for a really long time. 

R: You talk in your writing about some of your health struggles and about your interest in alternative medicine. In my experience, outside of a distinctly liberal California-esq lifestyle, it’s still viewed as pretty out there or woo woo to suggest that your emotional or inner life may be expressed outwardly in physical symptoms. It’s also somewhat of a slippery idea, that your physical symptoms or illnesses or diseases are your fault. I wonder what you think about that. 

RK: I do fundamentally believe that working like I did had an impact on my health. How it did exactly is anyone’s guess. I’ll tell you when I was in that state, I would get a really bad cold every three weeks, I had crazy rashes on my body, and I had chronic diarrhea. It was obviously related. 

I’ve had a few different health conditions. One was chronic foot pain, which was my first introduction into big life-changing health stuff. And then infertility and this autoimmune disease called Hashimoto’s. And through all those I’ve experienced a lot of different types of healthcare that I’ve sought out. So I think there is a lot of value across the whole spectrum of care from the holistic/alternative to the conventional. But I agree it’s a very dangerous line of thinking to start blaming yourself for your ailments. That also has a really long history in women's health of doctors blaming women’s health problems on women’s mental state. Hysteria is the classic example. 

These narratives of how mind and body interact and affect each other have long histories. All the stories that sound novel right now have been around for a long time in different forms. It’s not new-age to say your mental state affects your cancer, that whole line of thinking dates back to the 1800’s. That’s all very interesting because it suggests that these stories we tell are more about our cultural understanding of our mind and body than our scientific understanding. 

R: I think the physical symptoms we experience — whether it’s the common ones like insomnia, back pain, migraines, digestive stress, or more serious, chronic stuff — can be viewed as signals that we can listen to or at least be curious about if we’re trying to get out of this double life. And I wonder if that happened for you. If all of those symptoms you described did end up being the catalyst for change in your life. 

RK: I said I was going to quit my startup in 2019 and then never did. I was just sick all the time. The thing with my story that makes it complex is that there is no moment when I was like “I'm out, I’m gonna make this big sacrifice.” I got this crazy lucky thing where I was able to sell my company before some unknown rock bottom that would have finally prompted action. Therefore I never had to make that choice. After we sold the company, I knew I was not going to try to get the next name brand achievement – that ship had sailed by then. But I didn’t have to make the hard choice of giving up. And so I understand why people don’t.

R: Your candor about that is really refreshing because it’s not a tidy narrative. You’re on the other side of it, but not because you had the grand epiphany. 

RK: Or I did have the grand epiphany, but then I didn't act on it [laughs], so that’s even worse. 

For the record, I definitely believe that the stress I was under and my current chronic health conditions are at least related. For Hashimoto’s, it’s definitely genetically predisposed and then turned on by certain lifestyle factors. But I also know I can easily go too far down the path of blaming myself for being sick.

One way I like to mitigate the idea that all my health issues are caused by my own actions, is this idea that the definition of stress is much broader. There is work stress, then there is also the stress put on your body by pollution, chemicals, the things you eat, social issues like racism and poverty, and the stress within the body caused  by things that are already a little off like imbalanced hormones. There are lots of different stressors, and your body can manage a bunch, but it makes sense to me if you blow past that manageable level of stress for a long enough time, it’s gonna result in all kinds of physiological stuff.

R: Yeah, and it’s not a faucet. You can’t just turn it off and go back to normal.

RK: No it’s very much systemic balance and dysfunction that takes a lot of time to address.

R: Obviously these conditions you’ve experienced have caused a fair bit of suffering in your life. I wonder if the experience has given you anything as well. 

RK: It’s especially relevant since I’m a writer. Because I like thinking about turning over questions over and over — this definitely provides a lot of material. I don't wish these things had happened, but I do agree these types of experiences create you in a lot of ways. The people I know who went through experiences like this earlier in life do tend to have a certain depth and ability to understand other people’s experiences, even if they’re not the same ones. And then those people that haven’t gone through any big so-called “life quakes” before, are usually a little less able to understand. I do pride myself on that aspect of myself. I wouldn’t have wished for it but I do think there’s something to be gained. 

R: Smart people seem really hesitant to connect these concepts of self help and personal development with things like climate and social justice. But they feel really linked to me. There is a set of values that arise from responding to the deep unease of the double life, and those values have positive ripple effects, I think. So I wonder if on your journey you feel that connection to the collective at all? 

RK: I think because of my time in Silicon Valley I am loath to overstate any impact of anything because of how much of that happens around here. I’ve come to a perspective that basically you never know if a company or idea is going to have a positive or negative impact. Hearing over and over this huge story about how Airbnb is the ultimate connector of human beings — it gets you really jaded about anything like that. 

But what I will say is that until now, I never felt like what I was doing was good. Which is a really sad thing to say. But doing what I’m doing right now, I do feel like it’s good, and that sense comes from a bodily feeling rather than a logical one. The way I evaluate goodness is what I see in the reactions of people immediately around me. I’m much more drawn to community work than, say, international aid. I can’t say that community work is better than international aid. But that is what I feel personally when I do it: I know this is good. I don't really know about the rest of the world. 

R: Right, and perhaps we weren’t even designed to know or think on that scale. 

RK: I respect the efforts to do that, but I can't weigh in on them. I'm not prepared to say one is better than the other. But as a thought experiment: What if everyone only worked 20 hours a week at their paid job (in an economy where that was feasible) then spent the rest of the time doing things for themselves and their community. I think that world would look better than if everyone tried to save the world with their startup. 

R: Absolutely. 

RK: That’s the way I think about these questions. Whether my writing is going to help with climate change in some way, I'd love to think that it will, but I don’t know. 

R: But your honesty about the shortcomings of the life that you were pursuing might precipitate other people examining that life. And those people may realize: “Hey, maybe this quiet, smaller life where I actually have time, energy, and inclination to work on things in my neighborhood or even just know who my neighbors are is worthwhile.” We need models for that. I am convinced these changes start at the local level, as cliche as that sounds. 

RK: The thing that I’ve done in my life that I'm the most proud of is that in 2019 my husband and I and some friends bought a piece of forest property in the Santa Cruz mountains. It was raw land and we’ve been improving it together ever since. I have a hard time talking about it because it takes certain resources — but not as much as you think with nine people involved. Doing that is so much better than my startup. It’s not even comparable. It’s not even on the same level of goodness. 

 R: But it’s the same human spirit that drove you to do that. The same as the startup.

RK: Yes, it’s starting something. And then the question is what are you going to start? Around here it’s a VC-backed company, but also, you could start a shared property. And it’s crazy how many people in our generation have a dream along those lines. 

R: Where are you finding the most meaning these days? 

RK: I'm finding so much meaning in the comments section of my Substack, which is so crazy to me because I’m so not an internet commenter. I didn’t realize how genuine the interactions can be there. How getting that feedback as a writer is an absolute dream. I really really hope it can be maintained, because this comes back to our original conversation: Substack is a Y Combinator company. They have a mandate to grow. I really really hope we can see this grow and maintain what it is. I wish they could grow slower.

Me too. I’ve been on Substack since 2019, and recently have been finding it all a bit much. I keep thinking: This was working, just do less.

RK: “This is working, do less” is a good motto for life. 

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