Why success is never linear with Claire Hughes Johnson

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2:49One of the hardest things about work is that when it feels hard, we assume we're doing it wrong. And yet, when we look back at the work we're proudest of, it almost always felt hard in ways we didn't expect. It's only later that we can make sense of that struggle. I was talking to a friend recently who was in that low place, full of self-doubt. At one point, she said to me, honestly, it kind of feels like everything I've ever done has been a failure. This is not someone you would look at on paper and think, failure. But I nodded and said, I actually feel that way about my own career all the time, like everything I've ever done is a failure too.

3:33And that's true. If you're even a little self-aware or a little self-critical, it's remarkably easy to tell the story of your career from a place of failure instead of success. You can look at the exact same facts and come to very different conclusions. Since then, I've thought a lot about how easy it is to look at other people's careers from the outside and think they look smooth and intentional, while yours feels messy and full of near misses, like everyone else's success was inevitable and yours was accidental. The same is true of companies. The truth is that building something, even something wildly successful, feels like a mess most of the time.

4:20So what do you do when you find yourself there, deep in the mess with no clear path forward? How do you decide on the next step? How do you know if you should even keep going?

4:34I'm Molly Graham, and this is Work Life, a show where we untangle the messy human side of work.

4:43Today, I'm talking to someone whose career is often held up as an example of obvious success, the kind that from the outside can feel inevitable. But I know that underneath that story, there was a lot of uncertainty, a lot of moments when things didn't feel obvious at all, and a lot of struggle that never showed up in the headline version. Claire Hughes Johnson is the former COO of Stripe. Even if you've never heard of Stripe, you've almost certainly used it. If you've ever bought something online, paid for software, or signed up for a subscription on a website, there's a good chance that Stripe was quietly powering that transaction in the background.

5:23During Claire's time there, Stripe grew from a tiny startup into a piece of core internet infrastructure used by millions of businesses all over the world. But in those early days, Claire was there, wading through years of uncertainty, when the outcome wasn't clear and the work was anything but tidy. Today we're going to talk about those experiences and learn from Claire how she navigated those confusing, doubtful moments, and how we can too.

5:53Claire, welcome to Work Life. Thank you. This is so exciting. Yeah, well, you're one of my favorite people to learn from. So when I thought of guests, I was like, got to get Claire. Right back at you. Okay. So speaking of which, you and I were having a conversation a couple of months ago, and I asked you what was most surprising about your journey at Stray. And you said something really interesting. Do you remember what it was? I do. I do. And it was, I had come out of a dinner with a friend of mine who's a professor, and she has questions for me sometimes about, you know, this whole Stripe thing.

6:31Did you know it was going to be like a big deal? I'm like, yeah, not really. I mean, I hoped. I had some good indicators. But then she said to me, you know, what surprised you? And I said, I guess that we just kept going. Like some really hard stuff happens when you're trying to build a company. And I hadn't been in the inner circle of all of that stuff before. And you kind of just get really punched in the face a lot more than people realize by any manner of things. Like it can be person quitting, person acting badly, major customer churning, major partner saying, we're going to stop working with you, a regulator who sends you a terrifying notice, not getting anything done because your whole day gets exploded by some crisis, right?

7:25And you sort of just go to bed and can't stop thinking about all this stuff going on. And you just dust yourself off somehow and wake up the next day and are like, we'll figure it out. We're going to figure it out. Even if you have no idea how you're going to figure it out, you got to have some really resilient DNA. So much to unpack here. But first of all, I want to like make this real for people because I think that it's so easy to look at stories like yours or companies like Stripe and think, oh, that was so like a walk in the park. They figured it out and then it just went up and to the right.

8:01Yeah, it was ordained. It was ordained from on high. So I'm curious, like, will you tell me a story or a couple of, like, memorable moments when you were like, oh, this feels existential or this feels really scary? I'll tell you one that I think could have ended up existential if you work in tech. You would relate to this. But I had – so I joined in October 2014 and pretty quickly took on all go-to-market. So all the country leads then started reporting to me, let's say within a few months. And we started a practice of having them all fly into town and have a couple of days of like, let's call them quarterly off sites.

8:44So now we're in 2015. 2015. So I've got the heads of not just sales, but sort of think of it as account management, customer success kind of function, and sales all with me in San Francisco. And I decide, oh, I'm really bad, Molly, at organizing team building social time. I'm all about work, right? So I took a little feedback. I said, we're going to go and like make pizzas together, whatever. So we go to some restaurant that puts us at the table. We're making pizzas together, Bonding, right, having social time. All of a sudden, all our phones blow up. Stripe had gone down. So when you're processing people's payments and you have a reliability, stability kind of issue, it's really serious if you're like an API that they're integrated with that is doing this work for them and that work is collecting money for them and you have downtime, it's really, really, really very, very bad.

9:43Does that literally mean like if somebody went to go hit pay that it would like error out on somebody else's website? There were different kinds of things happening. That was, you know, some errors, some did not go through, some thinking the payment went through, but then the payment didn't go through. Like it was all manner of disaster. faster. And all of a sudden, you know, of course, the support team's getting inundated, the account managers, the country leads are getting directly because they are helping to sell the biggest startup at the kind of like biggest startups in Europe are like moving on to Stripe.

10:21And we basically stayed up all night. We're like, we need to understand this. We need to come up with messaging. We need to fall on our swords. We need to, how do we make this right? how do we um and it wasn't the only it happened happened a couple times in sort of a month two month period it felt pretty scary i'm very proud to say by the way now stripe process over a trillion dollars a year in payments and has like nine five nines of uptime so we also learned as a company guess what you know this is critical infrastructure know-how and go down you can't go down you can't go down. Because you're literally, I mean, you're literally selling trust us with your, the way you make money to other companies.

11:09Yeah. Trust us to collect your money for you and make sure you have it, you know? So that was a lot of different lessons. And for me, I was like, I mean, I think this happens, this happened to my team and to me, which is we are one, ourselves, customer facing. Two, our teams are getting inundated and need support and their morale is dropping like a rock, right? Three, for me, I'm also an executive and leader in the company. And I'm like, how do we never have this happen? But you can see in that moment, you know, will the center hold? You know, people could sort of get their guns out internally and blame each other.

11:48Or people come together and are forgiving and solution-oriented. it. I think we did culturally do pretty well in not collapsing under our own stress. Yeah. Walk me through this a little bit because I think it's so important for people to understand how these moments feel. Because now it's like, oh, and now we have however many nines. Oh, now we have all these great things, right? You have so many nines of uptime. You never go down. And Stripe has obviously grown and become very successful and very well known. But in that moment, you've made your decision to go to Stripe. You've got your career on this place.

12:24True. I was not even a year in the job. I'm curious, like, just, like, what did all of that feel like for you? I think this is what I mean by just keep them going. I never – it's funny you bring it up because you're right. I had left a very stable, steady, highly lucrative role at Google. And, like, Google, as you can imagine, is pretty strong technically. Less downtime. No kinds of issues like this. Like this is a young company issue. I didn't for a minute think, what am I doing? I think if you start to think that way, you're really going to end up in a bad place. Like sort of woulda, coulda, shoulda.

13:08I'm not sort of someone who looks back and is like, what was I thinking when I came here? I'm someone who I guess maybe over rotates on this, but I try to have a lot of agency. Like this was my decision. I own this. I'm going to make it work. I think what's hard in a moment where you're in a company and things are kind of going wrong, and they go wrong. I mean, you know, things go horribly wrong sometimes. You sometimes have it in your control that you can go and address it. But most of the time, it's other people, other people's responsibility. It might be external factors. So you're sort of like, how do I keep going when I'm not the one who can actually fix this, but I sort of just have to believe and try to add value and try not to complain.

13:52And, you know, I'm just drafting customer communications. I'm communicating with customers. I'm propping up morale. I'm trying to help redirect resources to help, but I'm not able to like do the work to fix it. That, that, I don't love that feeling, but I never doubted I should be there. I just kept going. Well, I'm curious because you actually just mentioned something that I think is very real in these moments when you're a leader, which is like there's your own psychology and managing whatever's going on for you. But then there's also showing up for the team and showing up for the business. So I'm curious if you can like talk a little bit about like – it sounds like you were just like we're just going to get through this, you know.

14:35But then you have to bring the team with you. Yeah. And this is also, I used to have this boss a million years ago where I'd come in with like, oh my God, there's this crisis. And he would say, huh, has no one ever experienced this before? And, you know, ding, ding, ding, go do some homework, figure out how you solve things like this. But, you know, I also, I had a belief that it could be addressed. So I was able to maintain perspective and not, I'm not panic. But I do think the psychology is multi-layered. And I think one of the things that I say to managers is, I think you can teach a lot of good management practices.

15:20The thing you can't teach is you do have to care because humans are animals. Like we can smell it. Like we can feel it if someone is just sitting in a one-on-one, oh, that's really too bad. that that happened to you. Anyway, you kind of actually have to care about the person and their development. But I think that's true about even moments like this. If I had gone into a dark place and been questioning, oh my God, should I be at Stripe? Is Stripe going to make it? So much of what you transmit to other people is body language, tone, energy fields. We don't know. There's stuff. There's quantum stuff out there.

16:06And I think you can start to not exude confidence, but exude fear. And your team will feel it even if you don't say the words, I'm afraid. It's going to show up in your voice and in your behavior. And so part of the other thing is, I mean, people accuse founders of reality distortion. And I'm not such a reality distortion person. But there is an amount of belief. relief like we're going to get through this and I think if you don't believe that people can sense it and you're not only going to undermine yourself but you could undermine your whole team.

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19:50So there are these moments, and I can think of like a bunch in my career where, you know, like layoffs or honestly just like real moments at Facebook where I was genuinely like, this thing is going off the rails or we might screw this whole thing up. But moments when I had to choose a path forward, either staying and believing in the dream or, you know, cutting ties with the company, choosing to jump ship. One of those is, you know, about buying in or rebuying into the company and the story. And the other is about saying, you know what, this just isn't right for me anymore. In those moments, like, how do you decide?

20:30How do you know what's right for you? Oh, yeah, yeah. No, I think that's real. I find myself career counseling people either who are thinking of taking a new job or they're in a job and they're thinking, and they start to list out for me like circumstances of the company, the product, the organization, the people. And I look, this happened to me like not even a week ago with someone who used to work for me at Stripe, who's, I'm not going to get too many specifics, but I listened, I wrote some notes and I said, I'm just going to read back to you what you just told me about the circumstances. Because this is a situation where there's a macro issue, there's a leadership issue, there's a company traction issue.

21:18And I said, I'm just going to play back to you what I heard. What do you think I'm going to say to you? You got to get the hell out of there. What is happening? I mean, I love this particular individual is a very loyal person. Someone who makes a commitment. And once they make a commitment, they work their butt off and they would hate to leave anybody in a bad situation, right? But this is not a good situation. It's like even when all the signs are pointing to, maybe this isn't it. Yeah. Yeah. I mean, I really worry and I've seen some people make some really horrible decisions because, oh, well, my friend started this company or I heard it's going to be great.

22:00Or, you know, I'm like, I don't care what you heard or who you know. Have you looked at the numbers? Have you met the founder? Do you know who the investors are? Have you used the product? Have you talked to some customers? I mean, this is like making an investment, but it's an even bigger investment than your money. It's your time. Yeah. Well, so first of all, I love what you just said because I'm a huge believer in that, that you need to think of your time as the most important investment you have. It's the most precious resource you have. But I am curious because part of what I hear you saying in those stories is that part of the reason why you could just muscle through what felt like an existential event at Stripe and sort of keep going is because you had these underlying fundamentals of the business that were just made it clear that there was something so powerful going on that it was going to take a lot to screw it up.

22:55Is that? I think so. I think it was a belief system in what we had and what was working in the founders and the leadership, including myself. I mean, maybe that's how you just keep going is you maintain a certain amount of perspective. I know right in front of me, I'm like sort of picturing a chessboard or like if you can stand back far enough from a crisis and be like, I see the whole board. you are either going to say, all right, we got a lot going for us. This is overcomable. This is going to hurt like hell. And it did. It was not a fun period for anyone at the company. But in the big picture, we're still winning the game.

23:36We're going to get there. I think where people get lost is they get too myopic about their part of the board and they're either getting too down on it or too positive on it. And they're not seeing the whole picture, which happens when we're in our day-to-day grind. But yeah, that's the thing you need is like the zoom in, zoom out power. Even if you're not able to get all the way out, just get far enough that you can calibrate. Is this, because you said existential crisis, like existential to me is a word you don't want to, like, there aren't that many existential things, especially if you have a good product, right?

24:16And you have like a customer base and it's growing and your revenue is growing. There's not that many. And so being really aware of what they could be. And then when you take a big punch in the face, gut check, is this existential? Could that have become existential? Sure. If we'd had persistent reliability issues, yeah. We would have had a reputational issue that we might have struggled to overcome. We might have lost our traction because we were small then. It's much smaller. But you had to believe. You see the board and you say, can we overcome this? Yes. Will we redirect resources and get experts and fix this?

24:59Yes. Yeah. It's so funny. There's this really famous story at Facebook that predates me, but I told over and over again because it was really important to the DNA of the company that when Mark launched News Feed, because Facebook was originally just profiles and there was nothing interconnecting the profiles. And when the company launched News Feed, the users just freaked out for any number of reasons that were both to do with just it was new and to do with the way the company launched it. There were literal physical protests outside the Facebook office with people hoisting cameras up to try to make their news stories about Facebook.

25:33But on the other side, people were using the site more. Like the data actually went way up. And so it's one of those stories that you have to have conviction. You have to have conviction and there has to be, well, hopefully, and I think this is your point, there has to be a reason for the conviction. Right. Right. And ideally some data-driven reason. And also belief like, hey, we have this mission and this fits with what we're trying to build and we're going to get through it. Right. Yeah. But I do want to zoom out just because like, I think it's like what we said at the beginning. Like, it's so easy to look at stories like Stripe, like the career of Claire Hughes Johnson and just think like, it just must have been so easy.

26:16And, you know, I think, or at least it's so obvious, right, Claire? But like, I think, you know, and I've certainly experienced that often the internal experience is the opposite. I mean, there's this definition, which is luck is when opportunity meets preparation. And I liked that one because I think I had some opportunities and I got lucky with some people who noticed me who had networks who used, you know, I mean, we both know Sheryl Sandberg and she definitely told people, oh, there's this talented woman and here's her name, you know, and somehow I'm getting contacted by, because I was too busy working.

26:59I was like not looking for jobs, you know, but I think that I had a combination of preparation and some opportunities and I'm, that's where I get uncomfortable. I'm like, you know, I, I didn't create all those opportunities, but I do think in retrospect, I managed my career because I really care a lot about, am I learning? Am I motivated? Am I in the right job? Is this the right impact? Is this what I want to be doing? And sort of some of my restlessness created more active career management in some ways that then became a loop that I think some people look to and they're like, oh, you charted this course of success.

27:46I was like, no, I'm more just was kind of unsatisfied and just kept trying to find the thing, which I think might be my life's work. I'm not like, I'm just not very satisfied. Wait, say that again. What is your life's work? So I would sort of talk to my mom about this and she'd say, oh, well, you have until you're 30 to figure out what you're going to do with your life. And then we had a joke where I was like, I think I need until I'm 40. And she's like, all right, fine. You get another 10 years. But I don't feel like I will figure out what my life's work is. It will end up being the work that I did.

28:29And that's, some people just get really attached to a mission that they can articulate quite succinctly and they can just make decisions against like, this is what I'm put on this planet to do. It's this thing. And for some people, and I think I'm one of them, it's a little more organic, a little more iterative. And part of how it feels is I am not satisfied. Like I'm like, oh, not doing all the things I should or could be doing with my time to have maximum impact because I'm not exactly sure what my definition of that is. Right. But as a result of that restlessness and that lack of satisfaction and that seeking, seeking, I ended up managing myself into a pretty interesting career.

29:14Totally. This is great because I want to talk to you about the individual level of this. And when you're describing how you make decisions, you sound like a very intuitive decision maker. You're like, this feels right or this feels like the right next thing for me to do or this feels wrong. So I am curious, like, have there been times in your career when it was really hard and you thought about quitting or you hit a wall or – and what did those situations feel like given the intuitive decision making? When I'm making a decision, I go from being super intuitive to actually being quite analytical.

29:51I don't just trust my intuition. Let's just say that. I will do a lot of extra homework and work, which is, I think, you know, how you end up choosing, oh, like, yeah, Google seems like a good place to work. And this Stripe company seems pretty good. Like, I don't think that was all an accident of my network. It was also me thinking really quite deeply about them and their position and their technology and the people involved, et cetera. But I would say there are jobs that I ended up in where I felt, oh, this is not good. This is not it. And I, earlier in my career, had a lower tolerance for that feeling.

30:37And I got myself out of those pretty quickly. like for at one point at Google, I was getting recruited externally to be head of sales or a CRO. And I was like, what? I'm not, that's, I mean, I could do it, but I was like, that's not like my next step. I'm not going to be a head of ad sales somewhere. But if you actually looked at what I've been up to at Google for the couple of years, that's what I looked like. Really good ad sales person. And I had to just do like a real gut check on, uh-oh, I'm writing a story that I don't like the ending, but I have 2000 people reporting to me and like a quota.

31:19And I can't just be like, I don't really want to be ahead of bad sales anymore. So then you have to navigate, how do I get from here to there honorably? And I think some people just don't even pick up their head. They just all of a sudden are the CFO of some company. They're like, I hate finance. And then they call me. I'm like, Ooh, we get a problem, you know, because that's what you're doing all day.

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34:54I heard you say a couple of things that you tend to go to when you hit these moments. One of them was actually consulting people outside. Like your friend who said, are you the first person who's ever had this problem and you're like, oh, no, go talk to people that have had this problem before and calling people outside to give you some outside perspective. That sounds like a really helpful tool when you're sort of in the muck and you can't see which way is up or you can't see the right path forward. Yeah, when you feel stuck, you're not going to probably unstick yourself. So one of your tools is other people might have some good ideas or perspective or have done this before, but if you don't go ask them, they're not going to just notice that you're in trouble.

35:36You need to actually ask for help and advice. And that, I think, early in my career, I would have gotten a little stubborn or embarrassed or just quiet because I tend to get quiet. Well, I think it can feel really scary. Oh, isolated and lonely. Yeah. Totally. Yeah. Totally. Because you're like – sometimes it feels like you're the only person in the world that's ever gone through this. Or you feel like everyone's going to think I'm a failure if I ask for help, you know. I think that's one. Another is sometimes you feel stuck and you think there's no move I can make. And that actually just starting to make moves is powerful because you realize I can do something.

36:18And then you get your confidence back a little bit from being stuck. Yeah, totally. It's a classic case of sometimes the only way out is through. So, you know, one of the things you're really confirming for me, which is sort of like one of my beliefs. Actually, I'd say two things. The first is that there is no success without mess, right? Like anybody's story that you would hear if they were to really tell it to you, it would be like, and then I failed and then I fell flat on my face and then I picked myself up and dusted myself off and kept going. Yeah. And I think those two things live like much closer than we think.

36:52Yeah. And the second thing I was thinking is that just because it's hard doesn't mean it's wrong. So I am curious as someone that people would look up to and someone that people would think like, gosh, Claire's career is so linear and perfect. What would you tell someone that's in a struggle or that like looks at your career and thinks, gosh, I want that? I mean, I think that you touched on this, which is how do you know this difference between sort of this is a struggle that's worth it, that's going to maybe shape me. And then this is the struggle that I should get out of or like doesn't feel right.

37:29Right. And a lot of my sort of personal philosophy, a lot of what I wrote in my book is about self-awareness and being able to sort of pretty objectively look at a situation and know, okay, this is the role I'm playing. This is what I'm doing well. This is what I'm not doing well. But also being aware of like, again, go back to the chessboard or like I can see the pieces. I see the pieces and I'm not, and trying to be unemotional about, you know, some of those elements that are controlling your environment and ask yourself, am I comfortable with this? Is this the right place to be? And a lot of my value system is about learning and impact.

38:14So just choose what yours are. You know, someone else, it might be about joy and competition. You know, I don't know, but mine are about learning and impact. And so you pick your head up and you say, am I learning? Like, am I really still learning here? And am I having an impact? And if I'm answering yes to those, I usually think I should keep going. Unless there's forces that are pushing against me learning or having a positive impact. And I'm thinking, what's going on here? Like, why are these forces overcomable? And that's where you got to be really self-aware and really honest about the situation you're in.

38:54But let's say the answer is yes, and you see a path where you have some agency. Then you probably should keep going and maybe even through some really rough stuff. But if the answer to one or both of those is no, that's super gut check time. But most of the time when I made a change, it was because I was stopped. I'd stopped learning. And I started to realize, we got to get self-aware. Maybe I wasn't having such a positive impact as much anymore. And sometimes that's someone else that's like being done to me, but it was sometimes also myself and my own path, right? But I do agree with you, Molly, which is things look much easier on paper.

39:38Just like a plan is easy to say, oh, a great plan we have, you know, and then reality punches you in the face or whatever the quote patent, right? Anyway, so I think that it looks cleaner. It was really, it's messy. You have doubt, you have disasters, you have failures, but you sort of keep trying to make the very best choices that you can make. Sometimes you just got to put one foot in front of the other. You got to keep going. This is the, you got to keep going and you got to go at it hard and commit to it. Claire Hughes-Johnson, thank you so much for coming on WorkLife. My pleasure.

40:31When my friend that I talked about at the beginning of this episode said it felt like everything she'd ever done was a failure. Nothing about her career had actually changed. What had changed was her perspective and how close she was to the pain of that moment. Listening to Claire made me realize how often we confuse that feeling with the truth. So when work feels hard, the question isn't always, should I quit or push through? Sometimes the better question is, who do I need to talk to so that I can see this more clearly? Ask for help. Borrow someone else's perspective. Get out of the echo chamber of your own head because this dark moment isn't the end of your story.

41:16It's just the part where it's hardest to see the way forward. Thanks for listening to Work Life.

41:28Work Life is a production of Ted and Pushkin Industries. This episode was produced by Isaac Carter. Banban Cheng is our story editor. Ted's executive producer is Daniela Balarezo. Constanza Gallardo is the executive producer for Pushkin. Special thanks to Roxanne High Lash, Valentina Bohanini, Lainey Lott, Tansika Sungmanivong, and Ashley Murphy. If you like the show and want more, come join the discussion on my substack, Lessons. I'm Molly Graham. Thanks for listening.

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