Keep Going

John Biggs

When you're going through Hell, keep going." This is a podcast about failure and how it breeds success. Every week, we will talk to amazing people who have done amazing things yet, at some point, experienced failure. By exploring their experiences, we can learn how to build, succeed, and stay humble. It is hosted by author and former New York Times journalist John Biggs. Our theme music is by Policy, AKA Mark Buchwald. (https://freemusicarchive.org/music/policy/) www.keepgoingpod.com

  1. Keep Going: How this comedian survived a career in comedy

    4D AGO

    Keep Going: How this comedian survived a career in comedy

    I sat down with comedian DC Pearson and what struck me wasn’t the success. It was the patchwork. From the outside, it looks clean. Comedy group, Sundance film, books, writing for TV. A straight line. But it isn’t. “Our life is composed of days,” he told me. “And this is one of them.” That’s the job. Not the career. The day. Because most of the time, it’s not the dream. It’s the gap between dreams. DC spent the last year working in social media advertising. Not because he wanted to pivot. Because the work slowed down. Because strikes happened. Because the industry does what it always does, it dries up and then floods again. “It was challenging to my identity as a creative person,” he said. “But then it was also cool… and I was grateful for it because it’s a job and it allows you to be alive.” That’s the truth nobody puts in the highlight reel. You don’t “make it.” You stitch it together. You jump from one thing to the next. You write jokes for someone else all day, then try to find enough energy at night to write something for yourself. You take the corporate gig, then try not to let it eat the part of you that wanted this life in the first place. And most of the time, it almost does. The only thing that saved him was simple. Another person. Someone else in the same situation. Same background. Same problem. “We would kind of be accountability partners… I’d say I’m gonna write this thing this weekend… and then I’d come back and say, I did it.” Not a system. Not a course. Not a master plan. Just two people refusing to let the work die. That theme came up again when we talked about how he started. It wasn’t strategy. It was proximity. Five people. One group. Each doing a different thing well enough to make something real. “We had… the ability… to go and make sketches that looked better than a lot of stuff that was out there at the time.” Not because they were perfect. Because they were there. This is the part people miss now. Especially with AI sitting there, ready to do everything faster. You can generate the thing. You can fake the output. You can make something that looks right. But you lose the reason you started. “I would rather come up with ten dumb toilet puns… that nobody’s ever going to notice… and be like, I did every single one of those.” It’s the quiet satisfaction that you made the thing yourself, even if no one sees it. We talked about AI, and he didn’t panic. He didn’t celebrate it either. He just called it what it is. “Plausible.” It looks right. It feels right. It passes at a glance. But it doesn’t hold up. And more importantly, it doesn’t carry the weight of a real life behind it. “A server farm can’t do that,” he said, talking about the weird, difficult experiences people put into their work. That’s the bet now. Not that AI disappears. It won’t. But that the connection between a person and the thing they made still matters. Even if it gets harder to make money. Even if the pipeline gets worse. Even if everything gets noisier. Because the alternative is easy. Too easy. And easy work rarely means anything. At the end, I asked him where this is all going. Where media goes. Where attention goes. He didn’t pretend to know. But he said something I keep thinking about. “There are things fomenting that we don’t even know what they are… it’s probably already happening, and the algorithm is not picking up on it.” That’s where the next thing is. Not in the feed. Not in the obvious place. Somewhere small. Somewhere ignored. Somewhere real. And if you’re paying attention, you’ll find it. Or better, you’ll build it. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.keepgoingpod.com/subscribe

    29 min
  2. APR 13

    Keep Going: Follow the fun, even when it costs you everything

    I talked to Ela Thier this week on Keep Going, and she said something early on that told me exactly where the conversation was headed. Filmmakers, she said, know a lot about failure. That sounded like a joke, but not really. It was more like a basic fact of the trade. Thier is a writer, director, and the founding director of the Independent Film School, which now has something like 65,000 members. The strange part is how it began. She could not get a job. She applied for a dog-walking job and did not get that either. So she did what a lot of people do when the normal routes close up. She made her own opening. She announced that she was starting a screenwriting class. Two people signed up. One of them wanted a discount. So she made the first class free, twenty people showed up, eight stayed for the full course, and the thing took on a life of its own. That story sounds neat when you tell it fast, but what I liked about her version is that she does not pretend she had some polished strategy from the start. She was trying things. She was paying attention. She was making changes. Now people would call it a lead magnet and act like it was all part of a system, but back then it was just common sense. Let people see what you can do. Let them decide if they want more. There is a lesson in that which has nothing to do with film school and everything to do with work. A lot of people wait for permission, or for the market to confirm them before they begin. Thier did the opposite. She put something in the world, saw what happened, and kept moving. That is a better way to build almost anything. The phrase she kept coming back to was “follow the fun,” which could sound soft if it came from somebody less serious. From her it did not. She meant it as a discipline. She meant that when the work stops feeling alive, you should pay attention, even if the safer move is to keep grinding in the same format. She said she has changed things at the school in ways that cost her students and forced her to rebuild. The biggest break came when she moved from in-person teaching to online teaching. Most of the old students vanished. She had to start over. But the move let the school grow in a way it never could have otherwise. That is the hard part of following what feels alive. It is not comfort. It is risk. Adults forget that. Kids do not need to be taught how to enjoy making things. They do it by default. Then school, work, status, and all the usual junk come in and flatten that instinct into a set of measurements. Thier’s point was that the chase for success and fear of failure can pull you away from the work that actually matters to you. For artists that is deadly. It is probably bad for everyone else too. She was also blunt about money, which I appreciated. When I asked how an artist makes enough to survive, she did not romanticize it. She said you get a job. That was her answer. Being an artist, in her telling, is a labor of love, not a reliable business model. If some money comes from the art, good. But counting on that is like building your life around a winning lottery ticket. Better to separate the two goals. One is keeping the lights on. The other is making the work you need to make. Once you jam those together, you often fail at both. That answer matters because too much advice around creativity is built on fantasy. We tell people to monetize their passion, build their brand, scale their gifts, and all the rest of it. Most of the time that just means turning the thing you love into another machine for stress. Thier has a more useful view. Protect the work first. Protect your ability to do it. Get honest about the economics. Then keep going. At the same time, she does not draw a hard line between art and business. She said that when she moved the school online and had to learn marketing, course-building, team management, and sales, she found that process deeply creative too. She treated it like making something, not like taking a day job away from her real work. That is probably why she got through it. She was not just doing admin. She was building a structure that could hold the rest of her life up. Still, there was a cost. For a few years, she had to put filmmaking aside and put her energy into the school. That tradeoff was not theoretical. It took real time away from the work she most wanted to do. But the payoff came later. The school made it possible for her to direct another film, one starring J.K. Simmons, which she is releasing this year. That is the kind of delayed return most people hate because it takes too long and gives you no guarantee. It is also, very often, the only kind that counts. One of the strongest parts of the conversation came when she talked about her film Tomorrow Ever After. By her account it did everything an independent filmmaker could ask once audiences actually saw it. It got standing ovations. It won awards. It had a perfect Rotten Tomatoes score during its run. And yet it still could not get proper distribution. She told me about meeting with an executive at Sony Pictures Classics who said they loved the film and could not buy it. It was not at Sundance. It had no known actors. They could not sell it. That, she said, was when she became a grownup. It is a hard line, but an honest one. She realized that if you want to beat the game, sometimes you have to pretend to play it. So the next films got built with financeable actors attached. That was not the death of her principles. It was an adjustment to reality. There is a difference. Artists hate that distinction because it feels like compromise, and sometimes it is. But there is also a point where refusing the rules just means nobody sees the work. That can become its own kind of vanity. I asked her why she stays in New York when it is expensive and hard and increasingly absurd in all the normal ways. Her answer had nothing to do with career. It was about people. Family in Brooklyn. Her nephew. The relationships that make a life feel real. She said those are the safest investment we have. I think she is right. A lot of people make decisions about where to live or what to build based on some abstract idea of winning. Thier’s view is more grounded than that. Stay near the people who make you yourself. By the end of the interview it was clear that her school is not some side project that got out of hand. It is part of the same body of work. She cares about her students. She would like to coach all of them herself, but the thing is too large now, so she coaches the coaches and keeps the system going that way. She also argues, correctly I think, that her students are better served when she keeps making films. If she stopped doing the work, her advice would go stale. She has a book coming out in May called How to Fail as an Artist: My Best Tips, which is the exact kind of title I like because it does not pretend the road is clean. She described it as a memoir, but also as a pep talk for artists who have given up, or are about to, which probably means most artists at one point or another. That is what this whole conversation was really about. Not failure as branding. Not failure as a cute origin story. Failure as the weather you work in if you care about making something real. Thier’s answer is not to deny that. It is to build a life sturdy enough to keep working anyway, keep teaching anyway, keep making films anyway, and keep some part of the whole thing joyful enough that you do not turn into a dead machine while doing it. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.keepgoingpod.com/subscribe

    21 min
  3. APR 10

    If a job asks you to paste a terminal command, walk away

    I ran into a strange hack this week. It looks simple at first, but it is not. It targets job seekers. I think I recall submitting a resume for a job at a company called Runeapes, which, at least on the surface, looks like a real website. You get a message saying you missed an appointment. It points you to a booking page. The name looks normal, the flow looks normal. You click through, pick a time, go through the usual steps. Nothing stands out. Then it asks you to get ready for the meeting. There is a download for Windows, which is expected. Then there is a “download” for macOS. That is where things change. Instead of a file, you get a terminal command. A curl command. It tells you to paste it into your terminal. If you’re not technical, this step can inject so much malware into your system that you’ll probably be hacked for life. That should stop you right there. The command points to a domain that looks real at a glance but is not. The domain was created recently. Same with the app domain tied to the booking flow. Both showed up within the past month or so. I started poking around. The site has all the usual pages: Pricing, About, Blog, Careers, Contact. Every single one is dead. Links go nowhere. Social links are junk. It is a full layout with no substance behind it. I tried to pull the file without running it, just to see what it was doing. Even that failed. The endpoint is already gone. Whatever was there has been taken down or moved. So what is the point? The point is to get you to run a command you do not understand. If you paste that into your terminal and hit enter, you are giving it permission to do whatever it wants on your machine. Download code, run it, install something, pull data, anything. Most people are not used to seeing terminal commands in a normal workflow, but the setup here is convincing enough that someone might go along with it. It looks like a meeting tool. It feels like onboarding. You are already halfway committed by the time you see the command. That is the trick. If you take one thing from this, it is simple: Do not paste random commands into your terminal. Ever. It does not matter how official the site looks or how normal the flow feels. If you do not know exactly what a command does, do not run it. Also, we know that hackers are targeting the desperate. There are endless crypto scams out there, and this one targets job seekers who are already probably exhausted. Please be careful any time someone asks you to use anything outside of Zoom, Calendly, or Google Meet. Also, make sure you never, ever download weird apps to connect to any kind of video meeting. This one is already dead, but there will be more. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.keepgoingpod.com/subscribe

    4 min
  4. Keep Going: Entrepreneur Bobby Mascia on leaving the family business and building something of his own

    APR 6

    Keep Going: Entrepreneur Bobby Mascia on leaving the family business and building something of his own

    I talked to Bobby Mascia this week on Keep Going, and what struck me was how different his story is from the usual startup script. A lot of founders like to talk about building from nothing, but Bobby’s problem was almost the reverse. He had something waiting for him, a family business, a clear role, a life that had already been sketched out by other people, and he still had to figure out whether staying in that world was loyalty or surrender. Mascia came out of Wall Street and landed in the one place he never wanted to be, his family’s Dunkin’ Donuts and Baskin-Robbins business in New Jersey. After 9/11 and a series of health problems in his family, he stepped in because his parents needed help and because, in his words, family came first. Over nine years they grew the business from 20 locations to 40, which sounds like success until you look at the cost. He was underpaid, frustrated, and stuck inside a structure that ran on old rules, unclear expectations, and the kind of family tension that never stays in the office. That is really the center of his story. Family businesses are rarely just businesses. They are full of old slights, private assumptions, and power struggles that started long before anyone talked about margins or strategy. Mascia said the biggest failures in his own experience were communication and transparency. Everybody had expectations, but nobody actually said them out loud. He assumed he would eventually take over. His father assumed he would hand over more responsibility when the time felt right. Other relatives had their own ideas. None of that added up to a plan. What I liked about Bobby’s take is that he does not dress this up as some clean business lesson. He talks about resentment, confusion, and the weird emotional math of trying to be a son, an operator, and a future owner at the same time. He gave a good example during the interview about how family members in business often switch roles in the middle of an argument without even noticing it. One minute you are talking as CEO and CMO, then suddenly you are talking as siblings, then as equal owners, then as two people reliving something from twenty years ago. Once that happens, the actual issue is gone. You are no longer solving a business problem. You are fighting over identity. That part felt useful well beyond family business. A lot of people build companies with friends, spouses, or long-time collaborators, and the same confusion creeps in. If you do not know what role each person is playing in a given conversation, then every disagreement becomes personal. Mascia’s answer is simple enough to sound obvious, but most people never do it. Name the role. Name the conversation. Stay inside it. If you need to have a different conversation, have it later. The other part of his story that stayed with me was what happened when he finally left. He started over in finance, built Green Ridge Wealth Planning from scratch, and spent a year barely speaking to his father. That split sounds brutal, and it was, but it also gave him the space to figure out who he was without the family machine around him. He did not leave with a pile of money. He left with a wife who told him he looked miserable and needed to do something that felt like his own life. That may have been the smartest advice in the whole interview. There is a common lie in family business, and probably in life in general, that staying is always the noble move. Sometimes staying is just fear with a respectable face. Sometimes leaving is the only honest act left. That does not mean leaving is clean or painless, and it certainly does not mean everyone will thank you for it. In Mascia’s case, success only changed the conversation later, once his father could see that walking away was not a tantrum or a mistake. It was a real choice. We also talked about AI, which could have turned into the usual stale debate about which jobs are doomed, but Mascia had a more grounded answer than most. He thinks people who hide from AI are making a mistake, but he also thinks the businesses that will hold up best are the ones where human judgment still matters and where people still need to sit across from another person and work through hard decisions. In his world, wealth management is not just portfolio construction. It is helping people through conflict, grief, risk, inheritance, and fear. Those are not spreadsheet problems. Those are human problems. That led into one of the better lines of the conversation, which was not really a line so much as a theme. Hard skills still matter because you need to know when the machine is wrong, but soft skills are going to matter more than people expect. Communication matters. Presence matters. Being able to understand what someone means when they are scared matters. If you cannot do that, then all the automation in the world is just faster confusion. Mascia wrote a book called Unchained, and unlike a lot of business books, it came out of something real. He said he had no interest in writing the same recycled advice everybody has already heard a hundred times. What pushed him to write was not some urge to build a personal brand. It was the sense that his story might actually help somebody who was stuck in the same kind of trap, caught between loyalty and ambition, between what the family wants and what a life requires. That is the part that makes this episode worth hearing. It is not really about succession planning, although that is in there. It is not just about entrepreneurship, either. It is about what happens when the thing you are supposed to inherit is also the thing that is holding you in place. It is about the cost of not saying what you want. It is about how many people spend years trying to be good sons or daughters when they should be trying to become themselves. For all the talk about hustle and grit, this was a conversation about boundaries, and that feels a lot more useful right now. Not every good opportunity is your opportunity. Not every family duty has to become your whole identity. Sometimes the best thing you can do for the people you love is stop pretending you can live the life they picked for you. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.keepgoingpod.com/subscribe

    26 min
  5. MAR 30

    Keep Going: Stop numbing yourself and start paying attention

    I sat down with Anne Karber and what struck me right away was not the résumé. Entrepreneur, author, podcast host, all of that is fine, but it is not the story. The story is what happens when you build a life that works on paper and still feels wrong when you wake up in it. She came up in construction, which is not a forgiving place. Long hours, constant pressure, and a culture that rewards output above everything else. She learned to operate in that mode early. Work harder than everyone else. Push through anything. Do not stop to think about how you feel because that slows you down. That approach got her success in the way most people define it. Money, stability, control. But it also trained her to ignore anything that did not fit into that system. Then her sister died, suddenly and without warning, and that kind of loss does not fit into a system built on control. It breaks it. What followed was not some dramatic collapse. It was something more common and more dangerous. She kept going, but she started numbing herself to get through it. Work during the day, drinking at night, and repeating that cycle until it became normal. Not chaos, just a steady flattening of everything that mattered. She described it in a way that is hard to ignore. You are not living your life at that point, you are anesthetizing it. You remove the parts that hurt, but you also remove the parts that make anything feel real. The problem is that it works, at least for a while. That is why people stay there. What changed for her was not some sudden moment of clarity. It was exhaustion with the pattern. She got to a place where she could not look at herself and feel any sense of pride. That is a low bar, but it is a real one. When you cross that line, something has to give. She went to rehab. She doubled down on therapy. She started doing things that sound simple and are anything but simple when you are used to avoiding yourself. Writing things down. Sitting without distractions. Paying attention to where her time and energy were actually going. Not where she thought they were going, but where they really went when she looked at it honestly. One of the sharper points she made is that energy is the only resource that really matters. Everyone talks about time, but time is not the issue. Energy is. You can spend hours doing something and feel fine, or you can spend twenty minutes on something that drains you completely. Most people never track that. They just move from one habit to another and assume it is all the same. She started treating energy like something that had to be accounted for. What gives it back. What takes it away. What is neutral. Once you see that clearly, you start to realize how much of your life is built around habits that do nothing for you. Endless scrolling. Drinking. Overworking. All of it framed as necessary, but none of it actually helping. There is a hard part here that she did not soften. You have to be honest about what you are doing. Not in a vague way, but in a direct way. If you spend three hours a day on your phone, you write that down. If you drink every night, you admit what that is doing, not what you tell yourself it is doing. Most people avoid that step because it is uncomfortable, but without it nothing changes. She also pushed back on the idea that people do not have time to fix any of this. That excuse falls apart the second you look at how your day is actually spent. There is time, it is just not being used well. That is not a moral judgment, it is just a fact. What I found interesting is that she did not replace one extreme with another. She still works. She still builds things. The difference is that it is not coming from the same place. Before, work was part of the numbing. Now it is something she chooses with intent. That sounds small, but it changes everything. There is also a broader point here about how people define success. She followed the standard path for decades. The house, the cars, the outward signs that you have made it. When she got there, it did not deliver what it promised. That is not a new story, but it is one that people keep ignoring because the alternative requires more thought and more responsibility. The question she kept coming back to is simple and uncomfortable. What are you using to avoid your own life. Not what are you doing to relax, not what are you doing to unwind, but what are you using to not feel what is actually going on. If you answer that honestly, you start to see the structure you are living in. Most people sense that something is off at some point. They have that moment where they think there has to be more than this. The usual move is to ignore it and keep going. What Anne did was stop and follow that thought instead of pushing it away. There is nothing clean or easy about that process. It is slow and it forces you to deal with things you have been avoiding for years. But the alternative is to stay in a loop that never changes. The takeaway is not some neat system or set of rules. It is more basic than that. Pay attention to what you are doing. Be honest about why you are doing it. Then start making changes, even small ones, based on what you see. Most people never get past the first step. She did, and that is the whole difference. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.keepgoingpod.com/subscribe

    44 min
  6. Keep Going: Building a System That Supports Mothers

    MAR 23

    Keep Going: Building a System That Supports Mothers

    The American healthcare system is full of software. It is not always full of care. That was one of the clearest lessons from my conversation with Melissa Hanna, the co-founder and CEO of Mahmee, a company that provides prenatal and postpartum support through doulas, lactation consultants, nurses, mental health providers, and nutritionists. The services are bundled together and, in many cases, covered by insurance. The support begins during pregnancy and continues through a child’s first year. At first glance, Mahmee sounds like a healthcare startup built around coordination. In one sense it is. But Hanna’s story is really about something harder. She started with the belief, common in startups, that a broken system could be fixed by better software. Over time she found that software mattered, but it was not the thing standing in the way. The original problem that pulled her in was simple and disturbing. The United States has some of the worst maternal and infant health outcomes in the developed world. For Black women, the numbers are far worse. Hanna said Black women face maternal mortality rates three to four times higher than peers with similar clinical and economic profiles who are not Black. Native American and Indigenous women also face sharply elevated risks. These are not small gaps at the margins. They are structural failures. Hanna began by treating the issue as a data and communications problem. Why were patients falling through the cracks. Why were providers not sharing information. Why were systems not talking to one another. Those are reasonable questions, especially in American healthcare, where fragmentation is a defining feature. Patients move between doctors’ offices, hospitals, insurers, specialists, and community providers, often with little continuity between them. So Mahmee’s first life was as a software company. For roughly five years, the company built tools to connect providers and surface information that was not being captured elsewhere. Hanna and her team focused on the providers who often sit outside the formal medical stack, doulas, lactation consultants, nutritionists, nurses, and mental health professionals working in communities, private practices, or local nonprofits. Those providers often knew a great deal about what was happening with a patient. A doula might hear details a patient never shares with an OB-GYN. A lactation consultant might see warning signs that never make it into a medical record. A mental health provider might understand a patient’s risk in ways that do not show up in a standard clinical workflow. But much of that information was effectively invisible to the larger system. Mahmee built software to change that. The company created electronic health record tools, care management systems, communications features, and scheduling and billing software aimed at these community based providers. In doing so, it found real demand. Thousands of providers signed up across 44 states. The footprint was broad. The product was useful. But scale did not follow. That was the hard part. Each provider might only serve dozens, or perhaps a hundred, clients a year. The software worked, but the market around it was too small and too fragmented to produce the kind of reach Hanna believed was necessary. She used an analogy from The Founder, the film about Ray Kroc and McDonald’s. You can have a very good milkshake machine, but if the burger stands are too small to use it at scale, the machine alone does not solve the problem. That was the pivot. Hanna realized the real barrier was not simply that community based maternal health providers lacked software. It was that they lacked a place inside the formal healthcare economy. Insurance often did not cover their services. Payment models were broken. The people who were often best positioned to support mothers before, during, and after birth were sitting outside the system that paid for care. At that point Mahmee stopped being a pure software company. It became a tech-enabled healthcare services provider. Instead of just selling tools to doulas and lactation consultants, the company employed them and built a coordinated care organization around them. The software remained important, but it became infrastructure for a services model rather than the product itself. This is a more interesting kind of startup story because it runs against a habit in tech. Founders often want the clean answer. There is a messy industry, and software will organize it. Hanna found that the mess was deeper than that. The system was fragmented not just technically, but financially and institutionally. Data could not solve a funding problem. A dashboard could not make insurers reimburse the people who were doing essential work. That matters because maternal care is not a niche. Hanna put maternal and infant healthcare in the United States at roughly a $200 billion market. Yet for something that large and consequential, the experience is often poor, costly, and isolating. Many women move through pregnancy and birth without enough support, without clear information, and without much sense of agency over what is happening to them. One of the strongest parts of our conversation came when Hanna described a patient story that made this concrete. The woman was in her early twenties, already had one child, and lived in a rural area with limited hospital and doctor access. During her first pregnancy, she felt judged throughout the process. She was young, a woman of color, and she came away from the experience feeling that she had no control. Labor was difficult. The care felt harsh. She was in pain, asked for help, and felt talked down to rather than supported. When she became pregnant again, she was afraid. She wanted the baby, but did not want to relive the first experience. Through Mahmee, she learned something basic that had been missing the first time. She had choices. She could ask questions. She could slow a conversation down. She could say no. She could ask about pain management options beyond the narrow set that had been presented to her before. She could participate in the process rather than just endure it. That may not sound radical, but in practice it often is. The modern medical system moves quickly, especially in high stress environments like labor and delivery. If a patient is not informed and supported, decisions get made around her rather than with her. Hanna’s point was not that doctors and nurses do not matter. Quite the opposite. In high risk pregnancies, they matter enormously. Her point was that support, education, and continuity of care change the experience and often the outcome. This is also where her critique of the system is most useful. She does not reduce everything to one cause. Systemic racism and bias, she said, are real and they amplify disparities. But she also pointed to two other drivers, fragmentation and the chronic underfunding of preventive care. If support is only available at moments of crisis, then people will continue to arrive at those moments without the preparation, context, and trust they need. Hanna also spoke frankly about the difficulty of funding a company in this area. Building in healthcare is hard. Building in women’s healthcare is harder. Raising venture money for maternal health can mean explaining the problem to investors who have never had to think about it in concrete terms. Part of the job, she said, was reframing the opportunity so people could understand it as both a human problem and a business one. Another part was finding investors for whom the issue already felt personal, because they or someone close to them had been through a birth experience that was worse than it should have been. What stayed with me most was the shape of the lesson. The original thesis was not wrong. Technology does matter. Mahmee still builds software. It still uses connected tools and remote monitoring. It is now looking at how AI might fit into care delivery. But the mature version of the thesis is more grounded. Better care does not come from software alone. It comes from software plus people, software plus payment systems, software plus trust, software plus someone who is actually there when a patient needs help. That is not as neat as a pure software story. It is more true. There is a tendency in startups to assume that every broken institution is waiting for the right app. Sometimes what is actually missing is a workforce, a reimbursement model, and a way to bring overlooked people into the center of the system. Mahmee’s story is about discovering that the missing layer in maternal care was not just information. It was support that had been treated as optional, informal, or outside the reimbursable core of medicine. Hanna’s company now tries to make that support part of the default package rather than a luxury add-on. The goal is not only to improve outcomes, though that is clearly part of it. It is also to change what pregnancy and postpartum care feel like for the person going through it. That may be the real measure here. Not whether a startup found product-market fit in the usual sense, but whether it found a way to make a system less cold, less fragmented, and less likely to fail people at a moment when failure carries enormous cost. — Transcript John Biggs (00:00.161) Welcome back to Keep Going, podcast about success and failure. I’m John Biggs. Today on the show, we Melissa Hanna. She’s the CEO and co-founder of Mahmee M-A-H-M-E-E, which is a fascinating startup. You guys work with doulas and you work with care during birth, right? So why don’t you tell me about that? Welcome. Melissa Hanna (00:30.561) Thanks, yes. Well, Mahmee provides wrap-around prenatal and postpartum support. We do that with a team of doulas, lactation consultants, registered nurses, mental health providers, and nutritionists. And it’s all included in one bundle. that’s actually covered by insurance. In most cases,

    26 min
  7. Keep Going: Why Work Dread Is Taking Over Our Lives

    MAR 16

    Keep Going: Why Work Dread Is Taking Over Our Lives

    Work is eating our lives. That much feels obvious. What is less obvious is why we let it happen. I spoke with psychologist and author Guy Winch about his new book Mind Over Grind, which looks at a familiar but poorly understood problem: the slow psychological takeover that happens when work becomes the dominant force in a person’s life. Many of us think we are simply tired or busy. Winch argues that something more corrosive is happening, a kind of sustained dread that alters how we think, how we behave at home, and how we relate to the people around us. The timing is not accidental. The workplace is changing in ways that make people uneasy. The pandemic briefly pushed companies to talk about emotional health and work life balance, but the underlying pressure never really went away. Burnout continued to rise. Now a new layer of uncertainty has appeared in the form of AI, automation, and the constant sense that entire professions may shift under our feet. That uncertainty produces a specific emotional state. Winch calls it dread. It is not simple stress or boredom. It is the heavy anticipation of something bad that may happen but cannot be clearly defined. Psychologists have studied this kind of anticipation in laboratory settings. In one set of experiments people were given a choice between receiving a mild electrical shock later or a stronger one immediately. Many participants chose the stronger shock simply to avoid waiting for the mild one. The anticipation itself was so unpleasant that people preferred to get the pain over with. Work can produce the same effect. When people wake up already dreading the day ahead, the stress does not remain confined to office hours. It bleeds into everything else. A common pattern looks like this. Someone finishes work but cannot mentally leave it behind. They replay conversations with colleagues, worry about tomorrow’s meetings, and anticipate problems that have not yet happened. These thoughts arrive uninvited. They intrude during dinner, while watching television, while trying to fall asleep. The result is hours of unpaid emotional overtime. The damage compounds quickly. Poor sleep makes people more reactive the next day. Emotional withdrawal leads to tension with partners and family members. Hobbies, friendships, and personal interests slowly fall away because the person feels too drained to engage with them. Over time the individual begins to lose parts of themselves that once had nothing to do with work. Winch has seen this pattern repeatedly. He also admits that he has experienced it himself. That admission is important, because the problem is not limited to employees trapped inside rigid corporate structures. It often appears even more strongly among founders, freelancers, and people who run their own businesses. Self employed workers do not have a boss setting limits on how much they can push themselves. If you are ambitious and motivated, there is always more to do. A new client to chase. Another product to ship. Another email to send. The boundary between effort and obsession can disappear without anyone noticing. Technology complicates the picture further. AI systems can now perform many of the small tasks that once filled the workday. Drafting emails, organizing schedules, producing summaries, even generating reports can be handled automatically. In theory this should reduce pressure. In practice it often does the opposite. People rarely use saved time to step away from work. Instead they fill the space with more tasks. At the same time the presence of automation introduces a deeper anxiety. If a machine can handle part of your job today, it may handle the rest tomorrow. Entire professions now operate under that shadow. Even psychologists are not immune. Winch mentioned that some of his clients already consult large language models when he is unavailable. Others bring AI generated advice into therapy sessions and ask whether it matches his recommendations. The implication is obvious. If a machine can simulate the voice of expertise, what happens to the human expert? These questions are still unfolding. Researchers have only begun to examine the psychological consequences of widespread AI interaction. One emerging concern involves emotional attachment to digital agents. Some people now describe their AI assistants as companions or collaborators. Winch views that development cautiously. Emotional attachment to software may signal that other relationships have weakened. When work dominates a person’s attention and energy, connections with family, friends, and communities can erode. In that context it is not surprising that people begin forming attachments in strange places. None of this means that work itself is the enemy. Winch argues that work occupies a central place in human life for understandable reasons. Most people spend more waking hours working than doing anything else. Work provides income, which satisfies basic needs like shelter and food. It also offers social structure, status, identity, and a sense of accomplishment. Much of Maslow’s hierarchy of needs, from security to self esteem, flows through employment. Because of that, threats to work feel existential. Losing a job does not only mean losing income. It can mean losing status, routine, social networks, and a sense of purpose. The unconscious mind interprets those risks as serious dangers, which helps explain why dread becomes such a powerful emotion. The real question is how to prevent work from overwhelming everything else. Winch’s approach is pragmatic rather than philosophical. He focuses on specific behaviors that interrupt the cycle of rumination and anxiety. One of the most common traps involves replaying workplace conflicts or uncertainties long after the workday ends. The brain returns to the same problem repeatedly because it has not identified a resolution. The solution is to convert the worry into a concrete plan. If you are stewing about an argument with a colleague, the task becomes identifying what outcome you want and how you might achieve it. Do you need a conversation to clear the air. Do you need to set boundaries. Do you need to escalate the issue or simply move on. Spending fifteen minutes outlining a response can quiet the brain because the uncertainty has been reduced. In cases where the problem cannot be solved immediately, scheduling time to address it later can have a similar effect. Writing “handle client issue tomorrow at 8:45 a.m.” into a calendar signals to the mind that the concern has not been ignored. The worry is parked for later rather than allowed to circulate endlessly. Another element involves the structure of the workday itself. Many people respond to overwhelming workloads by pushing forward without pause. They move from meeting to meeting, task to task, trying to survive the day. Ironically this behavior reduces productivity. Cognitive performance declines as fatigue accumulates. Creativity, judgment, and executive functioning all deteriorate when the brain remains under continuous strain. Short restorative breaks can interrupt that decline. A few minutes of physical movement, a brief walk outside, or a supportive conversation with a colleague can reset mental resources. What matters is that the break genuinely restores energy rather than adding more stimulation. Doomscrolling through social media or reading the news rarely qualifies. These techniques are modest but practical. They require attention rather than radical lifestyle changes. Most people already spend hours each evening mentally revisiting work problems. Redirecting a fraction of that time toward structured reflection can produce a noticeable difference. The deeper question that emerged during our conversation concerns the future of work itself. If automation eventually provides widespread basic income and eliminates many traditional jobs, what replaces the psychological role of employment? Winch does not pretend to know the answer. Work provides purpose, competition, creativity, and social structure. If those elements disappear, people will almost certainly invent new forms of aspiration to fill the gap. Humans rarely remain idle for long. The shape of those aspirations remains unclear. They might emerge in artistic communities, local organizations, scientific exploration, or forms of competition that do not yet exist. What matters is that the underlying psychological drive toward goals and progress will remain. For now the immediate challenge is simpler. Work has always demanded effort and attention. What has changed is the degree to which it invades the rest of life. Phones keep us connected to the office at all hours. Global competition raises expectations. AI adds uncertainty about what the future holds. The result is a quiet epidemic of dread that many people treat as normal. It is not normal. It is a signal that the balance between effort and recovery has collapsed. Rebuilding that balance does not require abandoning ambition or disengaging from work. It requires noticing how the mind responds to pressure and intervening before the grind becomes the only thing left. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.keepgoingpod.com/subscribe

    46 min

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About

When you're going through Hell, keep going." This is a podcast about failure and how it breeds success. Every week, we will talk to amazing people who have done amazing things yet, at some point, experienced failure. By exploring their experiences, we can learn how to build, succeed, and stay humble. It is hosted by author and former New York Times journalist John Biggs. Our theme music is by Policy, AKA Mark Buchwald. (https://freemusicarchive.org/music/policy/) www.keepgoingpod.com

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