Why success is never linear with Claire Hughes Johnson

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They handle capturing invoices, routing approvals, and syncing with your accounting software so that your team can focus on growth instead of paperwork. Bill is so reliable, according to Bill, 98 of the top 100 accounting firms in the U.S. trust it to simplify and secure their bill payment processes. Bill's handled over a trillion dollars in secure payments and is ranked number one overall on G2's 2025 list of best accounting and finance products. So stop the guesswork and start scaling with the proven choice. Go with the company whose financial infrastructure is trusted by nearly half a million customers. Ready to talk with an expert? Visit Bill.com slash proven and get a $150 gift card as a thank you. That's Bill.com slash proven. Terms and conditions apply. See offer page for details. This episode is brought to you by Walmart Business. Here's something I've seen over and over in high-growth organizations. The leaders who actually transform how their teams operate aren't the ones with the biggest visions. They're the ones who ruthlessly protect their team's time and attention. And yet so many of us are still losing hours to the basics, like procurement, ordering supplies, chasing down purchases that should just happen. That's where Walmart Business comes in. It's built to simplify your operations, a huge assortment of business products, everyday low prices, and fast, reliable shipping and fulfillment. You can manage all of it on your schedule, online, in-store, or right from the Walmart Business app. It's Walmart, built for your business. Get your team focused on what actually moves the needle. Sign up for a free Walmart Business account today at business.walmart.com. One 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. And 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. So 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? I'm Molly Graham, and this is WorkLife, a show where we untangle the messy human side of work. Today, 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. During 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. Claire, welcome to WorkLife. 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 Stripe. 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, did you know it was going to be like a big deal? I'm like, 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, like, terrifying notice, not getting anything done because your whole day gets exploded by some crisis, right? And you sort of just go to bed and can't stop thinking about all the 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, well, that was so like a walk in the park. They figured it out and then it just went up into the right. Yeah, it was ordained. It was preordained 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, 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, I'll go to market. So all the country leads then start 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 offsites. So now we're in 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 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. Does 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. And all of a sudden, you know, of course, the support team is 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. And 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? And it wasn't the only, it happened, happened a couple of times in Great. 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, like, belief, like, we're gonna 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. This episode is brought to you by Walmart Business. Here's something I've seen over and over in high-growth organizations. The leaders who actually transform how their teams operate aren't the ones with the biggest visions. They're the ones who ruthlessly protect their team's time and attention. And yet so many of us are still losing hours to the basics, like procurement, ordering supplies, chasing down purchases that should just happen. That's where Walmart Business comes in. It's built to simplify your operations, a huge assortment of business products, everyday low prices, and fast, reliable shipping and fulfillment. You can manage all of it on your schedule, online, in-store, or right from the Walmart Business app. It's Walmart, built for your business. Get your team focused on what actually moves the needle. Sign up for a free Walmart Business account today at business.walmart.com. This episode is powered by AT&T Business. If you're running your own business, you know that the Sunday scaries are real. You're thinking about the invoices, the client calls, the inventory, the list that never actually ends. And honestly, we usually don't think about our internet or our phone service until it isn't working. Sometimes a simple glitch can feel like a total catastrophe. That feeling of powerlessness when your tech fails you is the worst. It's a reminder that our connectivity isn't just a bill we pay. It's the backbone of everything we do. AT&T Business gets that. They know that for a small business owner, good enough isn't good enough. You need reliability that stays in the background so you can stay in the lead. If you're tired of the friction points and just want a provider that understands the stakes, check out AT&T Business. Powered by AT&T Business. Built to work. Get AT&T Business at business.att.com. This episode is brought to you by LinkedIn. Running a small business means every hire matters. A bad hire can cost you time, money, and momentum. A good hire? They can change everything. But finding great talent isn't easy, especially when you don't have the time or resources to sift through piles of resumes and find the right fit. That's why LinkedIn built Hiring Pro, your new hiring partner that screens candidates for you so instead of sorting through applications, you can spend your time talking to candidates and finding your next great hire. With Hiring Pro, you can hire with confidence, knowing you're getting the best talent for your business. In fact, LinkedIn found that its users are 24% less likely to need to reopen a role within 12 months compared to the leading competitor. Join the 2.7 million small businesses using LinkedIn to hire. Get started by posting your job for free at linkedin.com slash worklife. Terms and conditions apply. So 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? How 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 looked, 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. And 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. Or, 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. Is 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'm now right in front of me, I'm like sort of picturing a chess board or like if you can see, 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. Like we'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? And 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. That would have, we would have had a reputational issue that we might've struggled to overcome. We might've lost our traction because we were small then. It's much smaller. But you, you have to believe, like you see the board and you say, can we overcome this? Yes. Will we redirect resources and get experts and fix this? Yes. Yeah. It's so funny. There's this really famous story at Facebook that was predates me, but I told over and over again because it was really important to the DNA of the company that when Mark launched Newsfeed, because Facebook was originally just profiles and there was nothing interconnecting the profiles. And when the company launched Newsfeed, the users just freaked out for any, any number of reasons that were, you know, 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, you know, hoisting cameras up to like try to make their news stories about the Facebook. But 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 a 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. And, you know, I, I think, Accessories and even wheel options, the ways to personalize your Range Rover Sport are nearly unlimited. When your time to lead arrives, you need a vehicle that rises to meet it. The Range Rover Sport. Exclusive offers available now. Explore further at RangeRover.com. This episode is brought to you by LinkedIn. Running a small business means every hire matters. A bad hire can cost you time, money, and momentum. A good hire, they can change everything. But finding great talent isn't easy, especially when you don't have the time or resources to sift through piles of resumes and find the right fit. That's why LinkedIn built Hiring Pro, your new hiring partner that screens candidates for you. So instead of sorting through applications, you can spend your time talking to candidates and finding your next great hire. With Hiring Pro, you can hire with confidence, knowing you're getting the best talent for your business. In fact, LinkedIn found that its users are 24% less likely to need to reopen a role within 12 months compared to the leading competitor. Join the 2.7 million small businesses using LinkedIn to hire. Get started by posting your job for free at linkedin.com slash worklife. Terms and conditions apply. This episode is brought to you by National Business Furniture. You can find them at nbf.com. What your workspace looks like says a lot about the way you work and can make a big difference when it comes to productivity. The truth is, our surroundings can impact how we think, how we feel, and who we become while we're in them. Your workspace can affect engagement, productivity, and maybe even retention. That's why getting your workspace right matters. It's proof that you value your team. National Business Furniture believes that every business deserves furniture that lasts, service that cares, and a partner that gets it, all on a budget that works. That's National Business Furniture's commitment to you. Find the right furniture for you and your team at nbf.com and use the promo code POD10 to save 10%. That's NBF.com and experience the better way to buy office furniture. I 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, like, 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 gonna 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 gonna just notice that you're in trouble. You 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 and lonely. Yeah, totally, 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 gonna 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 and 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. And I think those two things live, like much closer than we think. 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, right? 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, I'm 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. So 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, are these forces overcomeable? And that's where you gotta be really self-aware and really honest about the situation you're in. But 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're 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 you, things look much easier on paper, just like a plan. It's easy to say, oh, this is a great plan we have, you know, and then reality punches you in the face or whatever the quote. Patton, 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. When 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. It's just the part where it's hardest to see the way forward. Thanks for listening to WorkLife. WorkLife is a production of TED and Pushkin Industries. This episode was produced by Isaac Carter. Banban Chang is our story editor. TED's executive producer is Daniela Ballereso. Constanza Gallardo is the executive producer for Pushkin. Special thanks to Roxanne Highlash, Valentina Bojonini, Lanie Lott, Tonsica 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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