Nanxi and Xiaojiao are the co-hosts of sisreads (姐姐好读), a Chinese-language podcast about literature, art, and contemporary life told through the perspective of women readers. The show has become one of the leading Chinese-language cultural podcasts with more than 350,000 followers and has been named one of Apple Podcasts’ Top 10 Arts Shows in Chinese. You can find the show on YouTube and Instagram.

This interview has been edited for length and clarity.

Anna Burgess Yang: How did sisreads start? What was the original idea, and how has the podcast evolved over time?

Nanxi: The first episode came out in February 2024. Xiaojiao and I were postdocs, co-teaching a course at a university in Shanghai. In our casual chatting, we found a lot of mutual interest in each other’s reading — especially in women writers we wanted to talk about. We were in my office, and Xiaojiao and I were brainstorming authors we wanted to read together. So it really started as a private interest in starting a book club and reading great books together.

Xiaojiao: The postdocs performed in front of students that semester. Nanxi and I did a skit and revised the idea of A Doll’s House by Ibsen and combined it with Barbie, because that was a time when Barbie was in cinema. That was our first collaboration, to some extent.

There are a lot of works by male authors. So we thought there could be more female writers that we could read. And we wanted to do something more public-facing — to give a broader audience the opportunity to listen to us talk about female writers.

ABY: What’s a typical format of the podcast? How do you decide what to talk about or what to cover?

Nanxi: Overall, I would describe it as a book podcast, although we do cover other topics like art, films, or even popular culture. Most of the time, we consider this a chat among women readers. Each episode is about 60 minutes long. We have a third co-host, a screenwriter living in Beijing. Sometimes it’s the three of us chatting, and sometimes we have great guests who are women creators in different fields.

We try to introduce the book a little and open with a brief description, but it’s not really a summary of the book. Overall, we try to make it a free-flowing conversation, more spontaneous and fun to listen to. We laugh a lot. We try to make it fun and engaging. Our other co-host is so funny. She’s the best storyteller I’ve ever met, and she always turns something dense into something delightful and vivid.

Podcasting is very public-facing, and people usually listen to it while they are doing laundry or driving. So the entertaining aspect of it is so crucial in planning our content.

Xiaojiao: We also broadened our scope a little. It’s not exclusively female writers. We do a little bit of comparison — I work in comparative literature — and we combine books with film adaptations or other pop culture references.

In an episode we recorded recently, we talked about the summer vacation in Proust’s In Search of Lost Time alongside a book called Sommarboken (Summer Book), written by a Finnish female writer, and a Japanese film about summer in the countryside. It’s a mixture of different things, but the theme is about how we have a good time in the summer. Because it’s August, we want our audience to have a summer reading list. Each of us recommends a work that we hold dear to our heart for the summer.

ABY: At this point, you’re navigating very different professional paths — Xiaojiao still in academia and Nanxi building sisreads into a platform. How do you think about the relationship between your primary work and the podcast?

Nanxi: I started doing sisreads full time after I finished my postdoc program, and of course, it’s a very different career trajectory. I was not 100% committed to academia towards the end of my PhD. I also have a background in media — I did journalism for my undergrad. So this is a natural detour, a shift of my focus. Preparing for one podcast episode is quite similar to the workload of preparing for one class. It comes out as a natural evolution.

I have to handle a lot of the business side. I have to try to get sponsorship for our show, and I have to coordinate when we do the recording and plan the next season. We’re still a tiny team, but it’s still a small business.

That aspect, for me, is challenging, but also a lot of fun. I enjoy this very steep learning curve. I’m absorbing a lot of new information, and sometimes, especially when you talk to marketing people or to PR and brands, you have to adopt a different tone. How do I convince them that this would be a worthwhile investment to sponsor us? It’s definitely been a very fun journey, and we have an amazing team to work with.

Xiaojiao: I’m still in a literature department, in academia. The difference is that in academia, when we write or when we speak in a seminar, we always want other people to think that we are the smartest person in the room. But with this type of public-facing communication, the most important thing is for the audience or the reader to think they are smart enough to absorb this information. Instead of feeling, “I don’t know anything about this topic” or feeling intimidated by the conversation. So I think the shift in mentality, to think about the audience before myself, has been helpful.

As postdocs, there was a lot of doomsday discourse around academia falling. There weren’t many jobs out there. Even today, especially in the humanities and social sciences, the fields are shrinking — no funding sources, few jobs available out there. So everyone’s stressed. Having sisreads really took some of the pressure away. It opened up this new world to us, saying that you don’t need to be a scholar to survive.

ABY: You have 350,000 followers and a Top 10 Apple Podcasts recognition, so sisreads clearly resonates with listeners. Why do you think that is?

Nanxi: We didn’t really plan it when we started in our office. We couldn’t have imagined we would have a solid base of listeners. If you look at our listener demographics, it’s 96% women. And 70% from the age of 23 to 40, so it’s young women, and a lot of them are professionals. It’s really amazing that there’s this virtual community of young women who are eager to learn but who are also thinking about how to live their lives.

I think the amateurish vibe, or the kind of playfulness we want to highlight on this show, is also partially why it resonates. But we are being very serious about the production and about how to make it a better cultural product. We spend tons of time editing because it’s very hard to edit a conversation. But 60 minutes is a long time, and I want the listeners to have a quality 60 minutes with us.

Xiaojiao: Young women in China are the future of China, from my perspective. They are curious, because these days I think there are more women in universities in China than men. So there are a lot of highly educated, forward-looking, bold, curious women out there, and they make up the majority of our audience. And I think reading — that’s my hope — has been revived to some extent. I hope this trend goes on.

ABY: How do you pick a book or a topic that you want to cover?

Nanxi: We’ve been thinking about it more seriously now that we have more people listening to our show. We now have our shows on a seasonal basis with about 10 episodes, and then we take a break. During that break, we collectively decide what books or topics to cover for the next season.

We try to figure out what books we are personally interested in. For example, Xiaojiao would propose Proust’s In Search of Lost Time because she has been a reader for a long time, and she’s really familiar with the work. And sometimes we also try to talk about topics that have been widely discussed, like a hit movie or some social phenomena.

Although we are a small team, we kind of work like an editorial board. We sit together and think about the best way to approach this topic or the best way to plan the episode.

Xiaojiao: We also want some diversity in the authors and the content. For instance, each season we want to have some American writers, and then Japanese, and writers from China. So it’s a combination of literary works in different languages and cultural backgrounds, so that our audience can have a more diversified exposure to the cultural products that we’ve been discussing.

We have long, really long outlines and scripts that we prepare and books we read for those episodes. But the eventual effect that we want our audience to have is this playful, easy-to-listen-to, easy-to-get-into episode. Behind it is a lot of pre-production and post-production work. A lot of teamwork.

ABY: Do you assume the audience hasn’t read the book you’re discussing, or do you assume they have read it, or maybe have heard of it?

Nanxi: If we are teaching any kind of class, it’s required reading. The students have to come into the room prepared to discuss the reading. But when it’s a podcast, you cannot require your listeners to have done the reading before listening to the show. So we would not assume they have read the book.

Maybe they have heard of it, and that’s what makes them interested in listening to this particular episode. But the way we tackle it is that in the first 15 minutes, we have to build this common ground. Even if you haven’t done the reading, you will have an idea of what is going on.

Xiaojiao: A lot of our audience will comment saying, “I’m going to buy this book and read it.” It’s more like a promotion of certain literary works, instead of a classroom where students have read the book and then we analyze it together. We give them a sense of what this book is like, and then some of them would afterward get the book and read it.

ABY: What has building sisreads taught you about work, ambition, or success that’s been different from other points in your careers?

Xiaojiao: For me, as a literature scholar, it really helps me to unlearn a lot of things. Recording the episode on Proust, I was thinking about how I need to forget a lot of the theoretical things that I have read about Proust.

This journey has dragged me out of my niche of literary scholarship and theoretical research, and really broadened my understanding of literature. It brings back my childhood reading experiences. Like your first encounter with a great author, when you don’t know anything about other people’s writing about him or her. That’s the passion that I regained from doing this.

Nanxi: I’ve been learning so much. It’s not like academia, where you work on a topic for years, trying to write about it and trying to be at least among the top people who know about the subject. In podcasting, that’s impossible. You have to put out an episode every week. It cannot be perfect, and you cannot be the expert on this book. But it is about a continuation of how to produce work that you feel comfortable sharing with the world.

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I’ve never been good at asking people for help. Then I lost my job, decided to start a solo business the next day, and needed clients… fast. I turned to my network to ask for both referrals and recommendations to jump-start my business.

Asking for referrals is uncomfortable. Most solopreneurs would rather wait for business to come to them than put someone on the spot. But referrals are one of the most effective ways to grow a solo business. A warm introduction from someone who knows your work carries more weight than any cold pitch or LinkedIn message. Now, a few years later, most of my business comes from referrals.

The trick is knowing who to ask, when to ask, and how to make it easy for the other person to say yes.

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Ask executives how much interest their CEO takes in improving the work environment, and 69% say it’s high or very high.

Executives think they’re building workplace culture, but “wanting to develop culture” and developing and sustaining a particular environment is more than simply a mandate from the top.

When companies notice a workplace culture problem, the response is usually a project. New values get announced, or an executive committee is formed to brainstorm ways to improve company culture. Sometimes there’s an all-hands meeting about who we are and what we stand for (with slides!)

One review of workplace culture found that executives who rolled out new values reverted to old habits and a focus on tasks the moment they were under pressure. The supposed values or emphasis on company culture were nothing more than a communication exercise.

I’ve experienced this disconnect many times in my career: the company that proclaims to be people-first, and then lays off employees with no notice and no severance. It’s left me feeling like company culture is a farce, because when push comes to shove, the company will always put itself first.

Yet, I’ve seen companies that — at least from the outside — have amazing company culture. Employees seem to love working there, as evidenced by how much they talk about their employer online and the average employee tenure.

We assume that company culture flows downward from the top. And true, leadership sets the tone. But does everyone else simply absorb it? Or is workplace culture created by everyone?

How organizational culture is created

Sociologists settled on what culture means a long time ago: the shared values, beliefs, behavioral expectations, symbols, and artifacts that make up a group’s way of life. Organizational culture — aka workplace culture — is a bit different. It can run independently of the wider societal culture or alongside it. A company doesn’t invent a culture from nothing. It develops one through the way it interacts with the people who work there.

Company culture lives in the ordinary stuff. Hallway conversations and Slack channels. Emphasis on quality versus taking shortcuts. Whether people collaborate or throw each other under the bus.

Dr. Marcus Collins, a clinical associate professor who studies the influence and impact of culture on human behavior, told me:

Most organizations describe their culture by way of celebratory rituals (happy hours), objects (foosball tables), or perks (summer Fridays). Their articulation hardly ever constitutes the underlying cognitions that inform these kinetics, the shared thinking that drives our shared doing.

This omission, unfortunately, often prevents corporate leaders from rolling out a desired cultural state for the organization.

A company’s leadership sets the conditions, without question. There are absolutely situations where the problem starts at the top — operating in a culture of fear is a real thing, and one executive’s behavior can set the tone for everyone reporting to them.

But setting the conditions isn’t getting at the root of what leads to a positive workplace culture, as Dr. Collins notes. It’s missing the “shared thinking” and “shared doing.”

Starbucks has long set the narrative that it’s a great place to work. Once upon a time, that may have been true. But more recently, one journalist argued that “many employees went from feeling like they had ‘the coolest job on the planet’ to something closer to a third-shift factory worker.” The company shifted drastically over time — whether intentionally or not.

Culture sometimes shifts because of external forces. Technology changes. So do regulations, or the market. Any of those can reshape what the work feels like day to day. Explosive growth can also impact culture, if you look at companies like Meta or Google, once heralded as great places to work. Few would say that now.

What this means for employees

Most workplace commentary, including a good deal of mine, focuses on what companies and leadership get wrong. That criticism is warranted: leadership failures are real and expensive, and the people most impacted are those with the least power.

But even if leadership determines a company’s direction, that doesn’t mean change will actually happen. Dr. Collins points out:

When a company says it’s “changing its culture,” the change is predicated on how the organization ultimately responds to said forces. This response is not determined by leadership mandates pushed from the top down but by a collective negotiation that happens from both ends. Just like the marketplace when new ideas are introduced through media or industry, the population decides if the idea sticks.

That negotiation plays out all the time. A company’s “About Us” page may describe the company culture and values one way, and the employees describe something completely different. That disconnect is what people are pointing out when they say a company “lost” its culture. The company keeps broadcasting one version of itself, but that ideal did not permeate through the ranks through collective negotiation. The employees either rejected it or recognized that it was nothing more than lip service.

I’ve written about what happens when employees stop caring and about how management needs to stay connected to the team. Both are relevant to workplace culture: it gets made at the level where the work happens.

None of this means employees should be handed the job of fixing a broken workplace. Some companies like to say that “culture is everyone’s responsibility.” Employees may have some agency, but ultimately, the people responsible are those whose paychecks support that level of responsibility.

I asked Dr. Collins what happens when people feel like a company’s culture and values are no longer aligned with their own. He replied,

When people feel like their values no longer line up with their place of work, what they really need to evaluate is (1) whether they believe what the organization believes and (2) if the organization is living up to it.

If the answer to the first prompt is “no,” then it’s definitely a mismatch, and that person should go find a better fit. If the answer to the second prompt is “no” but the person aligns with the organization’s beliefs, then it’s worth trying to make a change. In fact, this is a potential opportunity to lead.

One of the interesting things about leaving a job — for another job, or to work for yourself — is finding out how much of the culture came with you. You have assumptions about how work is supposed to feel. I remember leaving a toxic job, and when I went to my next employer, I said, “Wait… people are actually nice to each other? On purpose?”

You can walk out of the building and still be running the “how to survive” playbook you learned while there. Which is worth knowing, because that’s the part of the culture that will change, no matter where you land.

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From 1870 to 1930, the U.S. census counted “gainful workers.” The definition was purely a data point: a gainful worker was anyone who reported an occupation in which they earned money or a money equivalent, or in which they assisted in the production of marketable goods.

The government wanted a number for how many people were attached to paid work, and “gainful” was the word that separated earners from non-earners. (I’m not a census historian by any means. But the language we inherit comes from somewhere, and this one came from a form.) In the 1940 census, the Bureau replaced the whole approach with the “labor force” concept, which asked about employment status instead of occupation.

But yet the words “gainful employment” never dropped out of our vocabulary. In fact, it’s taken on a different shape. Look up “gainful employment” in Wikipedia today, and the definition goes like this: an employment situation where the employee receives steady work, payment from the employer, and enough income to be self-sufficient.

Look at who is the giver and who is the receiver in that sentence. The census was describing a person who earned money. The current definition describes a person an employer pays.

I ran into the difference in a conversation a few years ago. I was talking about burnout and leaving a job I’d been at for 15 years, and the response was, “Sure, but your prior employer kept you gainfully employed for a long time.” On the spot, I didn’t know how to reply — but knew that the phrase made me feel uncomfortable.

Reflecting on the exchange, the word that’s off-putting in that sentence is kept. Somewhere between the original census and that conversation, “gainfully employed” implies that because the employer provides, the employee should be grateful.

The transition from earnings to a provider

The original census data point looked at the worker’s side of the equation. The gain in “gainful” was money the person earned or goods the person helped produce. The employer doesn’t appear in the definition at all, because the employer wasn’t the thing being counted.

In ordinary use now, the phrase describes what a company did for a person. Companies provide gainful employment. Workers have it — they’re on the receiving end. (And self-employed people are… somewhere else?) It’s not about the worker’s accomplishments at all.

Perhaps I’m reading too deeply into an old phrase. But U.S. employment law supports why the phrase feels icky. At-will employment means an employer can end the arrangement at almost any time for almost any reason. Outside of mass layoffs covered by the WARN Act, there’s no federal requirement to give notice or pay severance. The employer holds all the power to provide employment.

In today’s labor market, workers feel increasingly like they have little control. Whether the job continues really does sit wholly with the employer. Employer mismanages the company? Layoff. Employer wants to hand roles over to a bunch of AI agents? Layoff. The employee is screwed. When one side holds that much power in the arrangement, calling that side the provider is pretty accurate.

In the conversation I had many years ago, I’d been talking about burnout and about watching people get treated badly for years. “Gainfully employed” was the rebuttal. My steady paycheck was supposed to offset the question of whether all those years had been good ones.

A two-way transaction, not a favor

A paycheck is what a company owes you in exchange for your time and expertise. Mine was money I could have gotten somewhere else, and my employer was never the only option. Saying an employer “keeps you gainfully employed” — under today’s definition — erases the worker’s side of the equation, and what the employer gains in return.

There’s plenty to say about what money does to our sense of a job’s worth (I’ve written about that before.) But the transaction itself is simple. I gave 15 years of work and was paid for 15 years of work.

Nobody was doing anyone a favor.

The things I gained from those years don’t appear anywhere in the phrase. I learned what I won’t tolerate in a workplace anymore, which turned into boundaries I still maintain to this day. I can also recognize a good colleague immediately now, because I spent many years around the other kind.

Under the original definition, “gainfully employed” describes the worker’s position in the labor market. You work, you sustain yourself. But today’s framing of the employer at the center of the universe reinforces the structural imbalance. It’s time to retire the phrase.

As a self-employed person, nobody says I’m “gainfully employed.” Since the employer — a company — is now the primary driver in the definition, self-employment falls outside of that (apparently). I talk a lot about how self-employment isn’t as risky as people think, especially when you consider the employer’s power in an employer-employee relationship.

The relationship works when both sides can clearly state what they’re getting out of it (gaining). Trouble starts as soon as one half of it gets called “generous” and the other side is “lucky” to be on the receiving end. So when someone tells you that a company kept you gainfully employed, think only of the math. If you got paid, you came out fine.

Thinking about a career change? Download my guide: 5 Types of Career Pivots.

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Nearly every solopreneur starts their business saying “yes” to everything. After all, you’re trying to get clients and build a business. Revenue is unpredictable, and your brain treats every opportunity like it might be the last.

But when you work for yourself, every “yes” comes at a cost. Agreeing to one project means declining another — or giving up time you can’t get back. Defaulting to “yes” is how solopreneurs end up overcommitted, underpaid, and working on projects that don’t move their business forward.

Saying no is a business skill and, like any skill, it gets sharper with practice.

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This weeks’s Perspectives is an interview with Scott Siff, the founder and CEO of Pivoters, an AI-native job-matching platform built for workers 55 and over. He is also the Managing Partner of Quadrant Strategies, a Washington, D.C.-based strategy research and communications firm. His professioanl and personal experiences led him to see the structural forces operating against older workers and inspired Pivoters.

This interview has been edited for length and clarity.

Anna Burgess Yang: Tell me a little bit about your career.

Scott Siff: I founded a company called Quadrant in 2015. We work with some of the biggest companies in the world on their toughest problems, and we do it using data. So, through my job, I’m constantly exposed to the most interesting trends and issues in the corporate world. Earlier in my career, I worked in political strategy, which helped me see what the levers are for making things better.

I will admit I’m a bit of a workaholic. I just kind of like getting stuff done. I like feeling in the morning when I wake up that I have some cool things I get to do. Things that could make a difference. And I like feeling at the end of the day that it was a good day. I’m conscious of how many days we have left, and I want to make sure I’m doing something fun and worthwhile with each one of them.

ABY: What made you decide to do something different with your career?

SS: The initial spark came from my father. He is my hero. He’s been an inspiration my whole life, and he continues to be. He’s showing me how to age gracefully.

When he was in his 70s, he was looking for a new job. He wasn’t one to retire; he’s a workaholic like me. And so he came to me and said, “Could you help me find a new job?”

I thought to myself, I solve problems. I know data. I know how to find solutions — this should be no problem at all. My dad’s one of the smartest, hardest-working, dedicated, amazing people. Who wouldn’t want to hire him?

So I started diving into it, and it turned out the opposite was true. It was impossible. The existing resources that help people get jobs are biased against people 55 and over. And it’s partly institutional. They might not be set out to be biased, but if you look at the stats, the people that use the big job matching sites tend to be in their late 20s, early 30s.

When you show up as somebody 55+, 60+, 70+, you’re going to stand out as a little odd on those sites. And if you combine that with the natural ageism that exists in society, it makes it really tough.

ABY: What did you learn throughout that experience of working with your dad?

SS: I initially started as a son trying to help his father get a job. And then I switched to my Quadrant hat: this is an issue that needs to be solved.

It’s actually a really interesting set of problems. The idea of retirement itself is a new concept. It didn’t exist through human history. The first spark of it came in the late 1800s from Germany, from Otto von Bismarck. He thought this would be a nice giveaway to people in society.

In the beginning of the 20th century, a bunch of big institutional actors in the US picked this up. Companies liked it because it gave them a chance to get rid of older workers and instead hire cheaper, younger workers. Financial companies liked it because the idea of retirement was going to give them billions of dollars to manage. Eventually there was a whole retirement industrial complex: retirement homes, travel, financial management.

The last actor to come on board was the U.S. government. In 1935, it passed the Social Security Act as part of the New Deal. At the time, the average life expectancy was 61. Now, fast forward almost a full century to today. The retirement age is still basically 65. It hasn’t moved. But if you’re 55, your life expectancy has gone from 61 to your mid-80s. People now live decades past retirement. And it set up this huge problem.

Everyone thinks that once you hit 65, you ought to be done. We think 65-year-olds probably don’t have the physical or mental capacity to continue working. All of our conceptions of what people can contribute in those years — all wrong. Part of it is because we have this legacy legal structure. There’s ageism built into the framework with Social Security.

ABY: From your work at Quadrant, how do companies approach the workforce in that age group?

SS: Let me talk about the macroeconomics and why this is such an important problem. The US economy has outperformed most other economies because of population growth. Population growth means more people creating more GDP.

The two drivers of population growth have both ended. Birth rates now in the US are about 1.6 births per woman. The replacement rate (the number of births needed to sustain the population) is 2.1 births per woman. Around the world, economies with low birth rates are really stagnant because of population decline.

The second driver is immigration. Previously, it’s been masking our decline in birth rates. 2025 was one of the few years in US history when we had net negative immigration. That means we don’t have enough people to fill all the jobs. To keep the economy growing, we need more people in the workforce.

So how do we solve this problem? We can’t easily get people to have more babies. Countries have tried to do that, and it’s really hard. And the political winds have changed on immigration. The solution is right in front of us, and it’s workers 55 and older.

I have a goal to change attitudes about people in that age group. Businesses around the country are struggling to fill jobs, despite all the talk about AI, and we’ve got the workers. It’s a giant gap in the labor market.

ABY: What does career pivoting look like for someone in that age group?

SS: It is very hard to pivot. There’s so much working against you. With employers, there’s a strong bias in favor of looking for somebody young, even though they’re working on hundred-year-old assumptions about age. And the second problem is the job boards. Most people in the country rely on job boards to get jobs, but the big job matching platforms cater to people in their late 20s and early 30s.

At the moment, the shorter-term approach is the old-fashioned way: networking. Ask your friends’ friends. Try to get a chance to make your case live. Let them see how healthy and smart and capable and experienced you are. Because if they only see you on paper, they’re going to write you off.

Longer term, I hope that Pivoters and other similarly focused platforms will solve the problem. Once we get them into the workforce, the tide will turn. People don’t want to retire at 65, or most people can’t retire at 65. They don’t have enough money for retirement.

The truth is, people in that age group — 55 and over — actually have longer tenure in jobs than other people. They are also the happiest cohort of anybody else in the workforce. If you want a happier workforce, a more loyal workforce, you want to have more people in that age group. When you have happy employees in the workforce, there’s a ripple effect.

ABY: How do you think about finding the right job and accepting a job in that age bracket?

SS: I would say rush to accept the first thing you’re offered and don’t worry about the fit. This idea of fit is a little bit of a young person’s game, in the sense that young people tend to be looking for careers. They want a job that’s meaningful, that they can grow with, that offers professional development.

People 55 and over — they’re looking for a job, not a career. Most of the benefits that you get from a job come from having a job, not from having a specific job. Most of them will find that most jobs are better than no job.

Don’t pass unless it’s a completely horrible option. Most of the time, it’ll be better than not doing anything.

ABY: You’ve built Pivoters as an AI-driven platform. How do you think about the role of AI and its impact on work?

SS: AI is actually really good in the workplace for people 55 and over. Up until just a few years ago, one of the most important things employers looked for was being tech-savvy. To be tech-savvy five years ago meant you needed to know how to code or use different tools. People 55 and over didn’t know how to do that. With AI today, all you have to do is talk. The technology has become so simple and accessible that the theoretical barrier against people 55 and over disappeared.

For the job-finding process itself, AI is a disaster at the moment. You can get a bot that will scan the Internet and apply to every job out there with a customized resume and letter for you. So where people used to apply to three to ten jobs, now they can apply to thousands. On the other side, employers are getting flooded with applicants. And they’re using AI to sort through them, because there’s just no other way to do it. The system is really creaking and starting to break down. I’m sure it will sort itself out in the next few years, but at the moment it’s making the problems worse.

ABY: Tell me about what makes Pivoters different from traditional job boards.

SS: We reverse the process. You won’t apply to a job — cutting-edge AI technology will go and search different job listings for you and match you. It’s also going to look at things beyond just your resume or work history, such as your strengths, your skills, your work style.

So it’ll make the employee experience better. They don’t have to sort through thousands of job listings. On the employer side, we’ll tee up the very best person in the whole database as your first candidate. Instead of sorting through thousands of applications, you’re going to sort through two to five, because it’s going to be the best ones on the first try.

ABY: If someone reading this is in their 50s or 60s and feeling stuck in their career, what advice would you give?

SS: Jobs provide lots of the important things you need in life to feel happy and useful. You have purpose — a reason to get up in the morning. You have structure — it just gets you out of the house. And the last, which may be the most important, is social interaction. For most of us, your job provides a core part of the people you interact with on a day-to-day basis. If you lose that built-in social interaction, a lot of people get lonely.

The rates of depression for people in that age group who have retired have increased significantly. People who feel a sense of purpose live longer and feel better.

Keep an open mind and don’t rule things out too quickly. The concept of pivoting is really important — don’t assume that your only job option is what you’ve been doing for the last 20 years.

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If you’re self-employed and spend any time on social media, you’ve seen the debate. One person swears you need a professional website from day one. Another says a logo is the first thing to invest in. Someone else is selling a $500 course that promises to “elevate your brand’s presence.”

Everyone has an opinion about where your money should go first (and they’re usually selling whatever they’re recommending).

I’ve been running my own business for three years. I’ve run the branding gamut from DIY templates in Canva to hiring a professional brand designer.

Here’s what I’ve learned: the right branding investment depends entirely on where your business is today. When you’re spending money, you need an actual payoff in your business. Branding investments might not turn into specific dollars, but they should make sense for your business and the clients you want to attract.

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For more than seven years, I was a product manager at a software company. Product managers guide the direction of the product based on feedback from customers, sales, and leadership teams. They keep the company updated on the progress of projects and initiatives. And they constantly juggle tasks and deadlines when projects go off track or something unexpected comes up.

It often felt like herding confused cats out of a building that’s always on fire.

A significant amount of my time was spent buried in documentation. Preparing reports for the leadership team, reviewing spec documents for new features (or writing them myself), and preparing release documentation for customers that explained new features and bug fixes.

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I look back at the amount of time I spent on much of this work and how it limited what I could get done during the day. Today, that role would be incredibly different, thanks to AI.

David Pierce, Editor-at-Large at The Verge, said in an interview:

The thing that I am hopeful for, and frankly already grateful for in the technology, is that it can do a lot of the busywork I don’t want to do. It’s not creative. It’s not even thoughtful. It’s just administrative.

We can all find better things to do than turning an Excel file into bar graphs in a PowerPoint. So if we can automate that out of existence, I’m actually extremely hopeful for what we can all go find to do instead.

Product management is a critically important role in many companies, but also one that is drowning in tasks. The sources of data are scattered, like customer data, the upcoming project plans, a calendar of due dates, analytics, and more. It’s a chore to pull everything together.

What I would hand over to AI

The same job, today, would be almost unrecognizable. I’d have more time for the things that make a product manager role interesting (thinking about the direction of the product) and spend less time on “paperwork.”

For example:

• AI could spot patterns. I used to pore through hundreds of customer support tickets, looking for things that customers were complaining about or asking for. Those with the most requests often received higher priority, but identifying them was an intensely manual process.

• AI could create a design prototype. For new product features, developers would work from a mock-up that was painful to create. AI could create this in seconds.

• AI could write reports. I produced a monthly report on each project’s status for the leadership team, but the data lived in multiple systems. On top of that, the CEO liked to see the report in a very specific format. All of that could be handed over to AI. I could have even produced more frequent reports with the time saved.

• AI could write release notes. AI could determine from the project management and coding tools which features and bug fixes actually made it into a release and draft the release notes into a format suitable for customers. This process used to take hours (if not days) to compile.

What I could have done with the extra time

At a guess, I think the current version of AI tools could have saved me at least 10 hours per week. Maybe more, during the weeks when I was creating design prototypes or writing release notes.

And none of these required human creativity.

• Spotting patterns is simply compiling data. The judgment for “What should we build?” is still human.

• Design prototypes were based on well-established product specifications, just applied to a new feature (like “This button always goes in the upper-right corner, and when you click it, it does XYZ thing”). Developers simply needed a visual reference so they could code the new feature.

• Reporting was also mainly compiling data, with the addition of formatting. Explaining the project’s progress to the leadership team would still come from a human.

• Release notes were taking a description of a bug fix written in “developer speak” and translating it into something a customer could understand.

Without the hours spent on these tedious (but necessary) tasks, I could have:

• Talked to customers. Product managers at bigger companies with larger teams often talk to customers to understand their pain points. As the sole product manager, I rarely had time for this and had to rely on support tickets written by the customer service team.

• Made better product decisions. Since my process of looking through support tickets was so manual, customer needs and pain points were often missed.

• Fixed things myself. The company had hundreds of outstanding bugs to fix at any given time. Some were incredibly minor, so they were never prioritized. But with vibe coding, it’s likely that I could have learned to apply a fix myself and let a developer review it. Fewer outstanding bugs, happier customers.

I’ve always tried to automate repetitive tasks throughout my career. I did as much as I could back then, but there were simply limits to what I could do — especially with some of the most time-consuming tasks. Generative AI has changed that.

Of course, I recognize that this also blurs the lines for different roles. Should a product manager be expected to code bug fixes? Maybe not (though I would have enjoyed just fixing something rather than letting it linger).

My point is that I would have found the job much more fulfilling if I had been able to spend more time on the work that required human judgment. Talking to customers would have been incredibly valuable, but it wasn’t a requirement to move forward. So it got pushed to the bottom of the list. Creating a report for the CEO — while tedious — was an expectation of the job.

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A survey found that one in four workers think using LinkedIn for dating is fair game. This is despite the fact that LinkedIn’s own community guidelines explicitly prohibit romantic solicitation. And a 2023 study found that 91% of female LinkedIn users had received unwanted romantic advances at least once. (Myself included.)

Unlike other social platforms, LinkedIn has largely stood on its own as a place for professional networking. There’s no anonymity: everything is tied to your name and work history. People who are active on the platform aren’t the traditional “creators” you might see on Instagram or TikTok. The platform’s algorithm was designed to primarily show your posts to your connections and their connections — making it a hub for networking.

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Until recently. The algorithmic feed has shifted away from professional connections, and LinkedIn shows you what it thinks you’re interested in. (Spoiler: it’s pretty bad at this.)

The dating angle is one data point in a much bigger shift: LinkedIn stopped being a professional network and became a social media platform like any other where people compete for attention. It just happens to have your resume attached. And the people paying the highest price for this change are the ones trying to find jobs right now.

How LinkedIn’s algorithm rewired the feed

LinkedIn replaced its old retrieval system with a unified, LLM-powered architecture. As a result, only about 31% of the average feed now comes from first-degree connections. Some “Suggested Posts” from complete strangers that the algorithm has decided are relevant to your interests.

The feed responds to engagement sequences. If you start clicking on personal stories, you get more personal stories. More of whatever kept you scrolling last time. The job-relevant content and updates from your actual network get buried.

It reminds me of when Facebook introduced content from strangers in its feed. I’d always used Facebook to connect with friends and family. Content from strangers fundamentally changed what I was seeing.

For LinkedIn, this is a significant shift. LinkedIn moved from a connections-based graph — showing content to the people who know you — to an interest-based graph that functions identically to every other social platform. Your feed is now shaped entirely by what the algorithm predicts you’ll engage with, regardless of whether it has anything to do with your career.

Richard Van Der Blom, whose annual LinkedIn algorithm report is one of the most cited independent analyses of the platform, points out that while LinkedIn may be called a social media platform, it “never reacted like the other platforms do.” It lacks the collaborative attitude toward creators that Instagram or even X/Twitter developed over time. LinkedIn also actively shuts down third-party tools and targets “LinkedIn experts” creating a walled garden that it tightly controls.

And now, LinkedIn has rebuilt its algorithm to reward the exact social-media behavior it claims to discourage. The move from a connection-based feed to an interest-based one has turned LinkedIn into a stage where everyone is performing.

Of course, LinkedIn has always had personal content — people share career stories, celebrations, even grief. I’ve shared my own stories of pregnancy loss, because I advocate for more bereavement support in the workplace. The difference is that the old algorithm primarily showed the content to your network and your network’s connections. The new algorithm pushes personal content to strangers who see the post but have no connection to the person behind it. That changes the incentive structure for posting entirely.

The worst timing for the people who need it most

People used to dunk on LinkedIn because of its cringe factor: the inspirational posts, the humblebrags, the “I’m thrilled to announce” posts. (There’s a reason an entire “LinkedIn Lunatics” subreddit exists.)

But, for better or worse, connecting with people on the platform used to matter. This algorithm shift arrives at the worst possible moment for people who actually need the platform to fill its role as a professional networking tool.

LinkedIn’s own research found that nearly 80% of people feel unprepared to find a job in 2026. Applications per open job in the U.S. have doubled since spring 2022. People are competing harder for fewer positions, dealing with AI-driven screening systems — all while the platform that was supposed to help them now optimizes for time-on-site, not job outcomes.

When I log in these days, I can barely find the people whose content I used to enjoy. The feed is now a combination of AI-generated slop and a feeling that LinkedIn’s algorithm hasn’t quite figured out what I’m interested in.

LinkedIn is actively making job hunting harder by rewarding content that has nothing to do with professional competence. And it has zero competition for its place in the market. There is no professional alternative.

For employees: If you’re job hunting right now, the feed is, unfortunately, working against you. You need to engage deliberately with content and people who are related to the type of job you want and build your professional network with intention, because the algorithm won’t do it for you.

For self-employed people: LinkedIn was once the most reliable organic channel for finding clients and building professional credibility. The algorithm shift means your posts increasingly reach strangers who may not be your target audience. It’s worth taking a step back and rethinking your content strategy — or even considering what a pipeline looks like if LinkedIn no longer works the way it once did.

The strain is real right now because the platform can’t have it both ways. You can’t claim to serve professionals while burying any professional utility underneath a feed that’s designed to keep people scrolling.

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When I worked a corporate job, I had unlimited PTO. And I easily took 6+ weeks of time off every year. I have kids and followed their school schedule, taking time off for spring break and Christmas (for example).

Now, I’m a solopreneur. When I started my own business, I was certain that I wouldn’t want to change how much time I take off each year. But to make that happen requires a bit more planning.

In a corporate job, PTO just exists. You request the days, someone approves them, and your paycheck stays the same. As a solopreneur, you have to create that infrastructure for yourself. On top of that, you don’t have coverage or backup when you’re gone.

A fellow solopreneur polled her audience recently and found that one-third of solo business owners never take time off. If you don’t actively build time off into your business, it simply won’t happen.

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In June 2026, two major publications ran stories with a similar message: remote work might be hurting you. NPR published “People Love Working From Home. But Does It Love Them Back?“ The New York Times followed with “We Liked Remote Work. Then We Looked at the Data.“ Both cited the same study — Emanuel, Harrington, and Pallais, published in Science — which surveyed 588,000 Americans and found that workers in remote jobs experienced a 58% rise in hours spent alone and a 72% rise in spending their entire day with no human contact. This led to more anxiety, more depression, and more medication to treat these things.

The data is real. And the findings around isolation absolutely deserve attention.

But these articles treat isolation as though it’s baked into remote work itself, rather than examining what companies and workers can do about it. The headlines imply remote work is the villain — not the way companies have implemented it (or, more accurately, failed to implement it). Nor do they look at the broader question of whether the office was ever providing the social connection it’s now being credited with. And certainly not in the context of the “loneliness epidemic” that many experts agree is prevalent in American society as a whole.

The arguments against remote work are so predictable at this point: find a downside and frame it as “proof” that the whole model is broken. Meanwhile, there’s no discussion around whether the tradeoffs are worth any downsides. And all of these arguments pretend to put the employees’ interests first in RTO mandates, rather than looking at the company’s motives. (Spoiler: they’re not thinking about employee well-being at all.)

It was never about your loneliness

Every argument about remote work isolation rests on the assumption that in-person work provides positive social connection. The office is where meaningful human interaction happens!

But what about the interactions people are relieved to avoid? Microaggressions. Hostile managers. Office politics. The energy required to context-switch all day. The NPR piece quotes a researcher lamenting that remote workers miss out on casual interactions: “not even a wave to a barista.”

That’s the bar we’re supposed to use to measure wellbeing?

These articles pretend to care about people. We’re looking out for your loneliness. Or perhaps the reporters and researchers truly care about people and the impact of loneliness. But that’s not at all aligned with what CEOs have in mind when they order people back to the office.

The business case for bringing everyone back also doesn’t hold up. Studies consistently show that return-to-office mandates don’t have any impact on productivity or financial returns.

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Maybe these companies believe that they will benefit. Maybe they’re truly concerned about employee isolation (though doubtful). But research published in 2026 found that the only personality trait that consistently predicted objections to remote work was narcissism. The more self-important and entitled the company leaders, and the more they coveted power and status, and the more they favored return-to-office mandates.

Psychologists have long suggested that narcissism operates like a drug. Narcissists crave a regular supply of attention and validation. Remote work deprives leaders of that supply. These leaders see any kind of remote work as a threat to their authority and attention, and ordering people back to the office full time is a power and status move.

Loneliness is a convenient argument for something much simpler: leaders perceive remote work as a loss of control.

What remote work actually supports

“But people need human connection — the data is clear!” Yes. But conflating “human connection” with “office presence” is a faulty argument. People who study the loneliness epidemic in the United States find that the leading causes are technology, insufficient time with family, people being overworked, and living in a society that’s too individualistic. Remote work is not one of them.

In fact, if “being overworked” is a cause of isolation, that’s an argument in favor of remote work. Removing a lengthy commute from the day leaves more time to interact with other people. People can also get more rest if they’re working from home.

The loneliness framing fails to ask a basic question: what is gained? Remote work provides structural support for the people who need it most. Women choose remote work because remote work makes it possible to manage caregiving responsibilities (that still disproportionately fall on women). People with disabilities may find commuting draining or offices inaccessible. People face discrimination at the office (racism, misogyny, microaggressions) that drains energy and erodes mental health over time. The disparate impact of return-to-office mandates falls hardest on these groups.

Even if companies are well-meaning (and the narcissism research suggests many are not), the argument assumes that “loneliness” outweighs accessibility, safety, caregiving, and basic equity. When my kids were little, I had to drop them off and pick them up at day care. I had to take them to doctors’ appointments during the day. Even if I’d felt lonely, I wouldn’t have traded the flexibility that remote work gave me. The logistics of my life would have been exponentially harder if I were working in an office.

Some in-person connection with coworkers is valuable. But full-time office attendance is unnecessary. Atlassian found that a quarterly gathering does more for connection and belonging than daily commutes to the office.

So instead of asking “Is remote work bad for workers?” companies should be asking what they’re doing to support remote workers. The answer, for most, is: very little. Culture requires intentionality from leadership — whether the team is in one office or spread across ten cities.

If remote work is what allows you to be present for your family, manage your health, or do your best work without the overstimulation of an office — that’s reason enough. It’s worth being aware of the risks of isolation (as a whole, not just tied to remote work). But no one should pretend that isolation is the only — or most important — factor in someone’s work life.

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Solopreneurs make dozens of business decisions every day. Which client to prioritize. Whether to raise rates. Which tool to try. In a corporate job, there are committees and approval chains to share the decision-making load. When you’re running a solo business, every call is yours.

When I was a product manager, I learned to sort decisions into two categories: ones you can easily reverse and ones you can’t. It sounds almost too simple, but it changed how quickly I moved and how much I deliberated. That same framework can be applied directly to running a solo business.

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Early in my career, I had to travel a lot. I was working for a financial technology company. A bank or credit union would buy the software, and I would travel to the customer’s location. These were mostly really small banks, with maybe only a few branches, in small towns.

Getting to them was an entire production, often involving a flight to a major airport, then renting a car and driving for a few hours. I started working for the company in 2006, before the iPhone. Heck, I wouldn’t even own a smartphone for another four years.

As such, I had to carefully prepare how to get around. I’d print stacks of Mapquest directions. Airport to hotel. Hotel to bank. Exploring the city was too risky (what if I got lost)? But there usually wasn’t much to see anyway. Food was limited to whatever was in my line of sight between the hotel and the bank.

I traveled heavily for about three years. Once I had my first baby in 2009, the company changed its overall method of delivering training to a web-based approach. My boss realized that she wouldn’t be able to retain a lot of the company’s talent with roles that required 50% travel. After the change, I only traveled a few times per year.

The towns I visited were sometimes so small that there were only a few main roads. Even so, I simply wasn’t brave enough to explore. I’d get done working for the day, grab a sandwich from Subway, and collapse in my hotel room with CNN and my laptop.

I thought about this while I was in San Francisco this past week. I bounced all over the city, relying on a combination of Google Maps, Waymo, and public transit. I looked at Yelp reviews of local restaurants, eager to try a little dive dinner in Haight-Ashbury or a walk-up dim sum place in Chinatown.

I wonder about everything interesting I probably missed in these small towns. Navigating the roads, restaurants, and landmarks was just so different back then.

On one of my first trips, as a new employee, I was headed to western Kansas from the company’s headquarters in Topeka. Another employee was with me to show me the ropes of working on-site at a customer’s location. He drove, and we sat in silence for most of the trip. We barely knew each other and had little to talk about (though we later became friends). He would often call his girlfriend on his cell phone and talk to her for hours at a time while I sat, listening to his half of the conversation.

We were driving along the roads of Nowhere, Kansas, when he announced that we were taking a detour to visit the world’s largest ball of twine. There was nothing I could do but agree. We got out of the car and walked around the “landmark.” In today’s world, I would have been snapping photos. But back then, I didn’t have a smartphone, and it never occurred to me to bring a digital camera on my trips.

Part of me is sad that I have no documentation of my travel. I never wrote anything down, even though I experienced a lot. The only time I took photos was when I was sent to Kalispell, Montana, and planned ahead to visit Glacier National Park.

I don’t even remember what the world’s largest ball of twine looks like... only that we made the stop.

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In February 2013, Yahoo CEO Marissa Mayer banned all remote work. The move surprised everyone: Mayer was a new, young CEO, and Yahoo had a well-established remote work policy. The stated reason was collaboration and innovation, which Mayer thought was lacking.

The real context was much simpler: Yahoo was losing the competition with Google and Facebook, and Mayer needed to look like she was doing something. The RTO mandate was the “something.”

Fast-forward thirteen years. The mandate didn’t save Yahoo. Verizon acquired it for $4.5 billion in 2017, merged it with AOL, then wrote down the value by more than it paid. At the time of acquisition, Forbes reported, “The biggest story is how Yahoo squandered its massive head start and let each wave of new technology in search, social, and mobile pass it by. Yahoo remains largely the same company it was a decade ago.” Yahoo was sold again in 2021, and the Forbes sentiment remains true.

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When companies are struggling, they change the rules workers operate under and call it “strategy.” But these moves are almost always a cover for a business problem leadership can’t figure out or won’t name. And, over and over, we’ve seen that the companies that abandon their core principles under pressure don’t save themselves. They just lose what made people want to work there in the first place.

When the company you joined stops existing

The company formerly known as Facebook (now Meta) debuted at number one on Glassdoor’s Best Places to Work in 2011 and held the top spot three times. By 2023, it had fallen off the top 100 list entirely.

In April 2026, Meta deployed what it calls the “Model Capability Initiative”: software that captures employee keystrokes, mouse movements, clicks, and periodic screenshots. CTO Andrew Bosworth confirmed there is no opt-out. (European employees are exempt, because GDPR won’t allow it.) Employees have said that the initiative makes them really uncomfortable.

In June 2026, Meta laid off 8,000 employees, and several thousand more were reassigned to the Applied AI Engineering unit — and had no option to transfer elsewhere. Some have reportedly taken to calling themselves “draftees.”

The company that once topped every “best workplace” list is now tracking every keystroke in some type of nightmare dystopian workplace and telling thousands of employees they can either accept a role they didn’t sign up for or leave. The company still exists. But the company people joined? That’s long gone.

Starbucks has drifted from its own identity, too. For years, Starbucks built its brand on being the “third place” — a community space between home and work. But Starbucks has had an identity crisis over the years, amidst sagging performance. Should it optimize for mobile orders? But then that detracted from the “third place” vibe. Should it add more seating inside the stores? But then that made the stores more crowded. Employees have been dragged along for every iteration, and meanwhile, the company has taken a strong anti-union stance, trying to prevent workers from organizing to protect themselves.

The Starbucks experience changed, and so did the working conditions. What was once a company built around the idea of community became, for many of its workers, a volume operation that happened to sell coffee.

Nothing tells you more about how a company’s values than how it treats its employees when it is struggling. Webflow, once a company known as a great place to work, laid off employees in May 2026 by locking them out of their laptops at 7 am with no advance notice. Employees discovered they’d been impacted when their Slack and email access vanished — before any email from HR arrived.

And I’ve personally experienced this. I worked for a company that proclaimed to be “people-first.” The company began to struggle during my year there, leading to me losing my job unceremoniously. I was shocked by how it unfolded, since I had believed that this company cared about its employees — that’s what it had proclaimed, every step of the way.

Your values are the only constant in your career

Roger Lynch, CEO of Condé Nast, was recently on the podcast “Channels” with Peter Kafka. In 2020, the employees indicated that they wanted the company to focus more on diversity initiatives and sustainability. The global media conglomerate put together internal teams to address both. In the interview, Lynch said:

“It’s discouraging to see all these other companies dropping these initiatives, but it only says one thing: that it never was a core value, it was a convenience.”

“Companies have to adapt to survive — you can’t expect them to stay the same forever.” That might be the claim of Meta, Starbucks, or even my former employer. True. But there’s a difference between adapting your strategy and abandoning the principles that attracted your workforce. Yahoo opted for command and control of the office. Meta turned to surveillance.

You can’t get attached to a company’s stated principles. Unfortunately, there’s no way to predict which companies will abandon everything when the market gets rough or the industry changes. Companies may last decades and go through several iterations, and new leadership may usher in entirely new values (just look at Twitter, now X).

Every company will put itself first. The question is whether you’re building a career that depends on a company continuing to be the company you joined. Because if there’s one pattern that holds, it’s this: you can’t trust the company not to change in ways that you fundamentally disagree with.

The only thing you can truly depend on is what you build for yourself. That’s not saying you should quit when there’s company upheaval (that’s not realistic in the current job market). But it’s worth asking whether the stability you think you have is real, or whether it’s contingent on a company continuing to honor the values it used to recruit you. And it’s worth thinking about what you’re willing to tolerate to stay, even if the company has changed.

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\Most people use AI like a search engine: type a question, get an answer. It’s an easy, well-understood use case for tools like Claude, Gemini, and ChatGPT.

But for solopreneurs, the real value is in setting up dedicated projects with a lot of background information about your business. Most AI tools let you create project workspaces where you can add context about who you are and what you do. You can attach relevant files, and keep the conversation focused on one specific idea or area of your business.

I have 23 AI projects in Claude for everything from strategic planning to building a website. Some are used a few times per month, while others I rely on almost daily.

Here are a few of my favorites.

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Every promotion moves you one step further from the work itself. First, you’re doing the work. Then you manage the people who do the work. Then you manage the people who manage the people who do the work.

At each step, the daily reality of the job gets a little further from your line of sight. You may no longer be aware of the tool that no longer meets the team’s needs, or the client requests that have started absorbing entire afternoons.

I went through a few iterations of this throughout my career. I moved from a role in enterprise software implementation to the company’s product manager. Though I was no longer talking directly to customers, I was still “touching” the product constantly as I tried to figure out how to make it better.

Then I moved to an executive role. Though I was still the product manager (dual role), I no longer had time to tinker with the product. I was meeting with my team of seven people, preparing reports, and organizing vast swaths of data for the development team. The longer I was in the role, the more I realized that I no longer understood what the new features of the product did. I was also removed from the pain points that customers were experiencing — the kind that the customer service team had to deal with every day (and made their work harder).

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The further you move up in an organization, the easier it is to lose sight of what the people below you do all day. It’s even true of self-employed people who may start to outsource some work. It’s imperative to stay in touch with the work in some shape or form. Being too removed from the work is what causes bad decision-making.

The disconnect happens because of distance

Each rung up the ladder adds a layer of abstraction between you and the work.

When I was an individual contributor, I lived inside the daily friction of customers. As a manager, I was only hearing about it. My boss (COO) and the CEO only heard the summaries I provided. At larger companies, these are reduced to quarterly metrics.

By the time the information reaches the top, it’s been compressed so many times. The context is gone, and the context is how people actually understand the problems. (This is part of why so many people feel trapped in the middle as a middle manager.)

When I moved into a product manager role, I was responsible for reviewing issues reported by customers. I wasn’t receiving them directly, but I looked at the tickets. The tickets would contain notes from the customer support rep (if a phone call) or the direct emails from the customers. I could get a sense of the urgency or level of pain that the issue was causing. But the other members of the executive team (the COO and CEO) only saw numbers: how many customers reported the issue? It was my job to convey urgency, but this was often stacked against other priorities.

In Glassdoor’s Worklife Trends 2026 report, mentions of “disconnect” in reviews that reference leadership rose 24% year over year. “Miscommunication” rose 25%, and “misaligned” jumped a whopping 149%. Employees are well-aware of the structural distance — and when they feel like they’re not heard, they may check out entirely.

Part of the problem for managers is the endless barrage of meetings and reports. Your calendar is filled with strategy reviews, daily standups, and quarterly planning, and you stop having time to understand the work itself. You spend your days staring at dashboards and tracking outputs instead of staying tuned in to how work actually gets done.

A manager who only sees the metric can’t tell the difference between “the team is behind schedule” and “the team is behind schedule because something in the process is completely broken and the workaround takes three times as long.”

Freeing up time to stay involved in the work

I remember the intensely uncomfortable feeling that I no longer understood the product that I was supposed to manage. My days no longer had any time built in to get my hands on the product and play around.

But the fix isn’t to swing to the other extreme and do everyone’s job for them, which is what some managers do. That’s a failure mode all on its own: the leader who refuses to let go and hovers over every decision. (And founder mode is the worst version of this.)

Stepping back so people can do the work they’re good at is the entire point of building a team — you hire smart people precisely so you can let go.

The ideal is informed distance: close enough to understand how the work actually gets done, far enough to let people do it without you breathing down their necks. You step aside on every single detail, but stay connected to the how.

I’m an advocate for AI when it’s actually useful (i.e., not slop), and it has a place here: buying back in a manager’s day. I think back to the hours spent prepping for meetings, compiling information scattered across five different systems, and turning raw numbers into a summary for the CEO — a lot of that is now work that can be done with AI.

And the point isn’t more output. If done correctly, that reclaimed time flows back into understanding the work itself. In an episode of the podcast How I AI, host Clare Vo says:

I know so many people who feel like they’re in meeting after meeting after meeting. And when they’re not in meetings, they’re preparing for meetings… You would much rather your managers be hands-on doing the work, filling a creative impulse, than prepping for meetings.

Management roles can often suck the fun out of work. There’s creativity in being an individual contributor that disappears with a promotion to a manager role. Imagine if managers actually had the time for creativity. They’re more connected to the team and get to keep work interesting.

Most of the conversation about AI at work is about cutting headcount or increasing output. But for managers specifically, the most valuable thing added is giving them more time for attention — the time to actually watch (or put their hands on) the work again.

For managers

The structure of most managerial roles causes a disconnection that most managers feel. The system moved you away, then handed you responsibilities that make it impossible to stay connected.

The best leaders stay curious about what the work feels like, not just what it produces. They know the difference between a number on a report and the context behind it. They get that story by talking to the people living it. That only happens when you have time in your day for curiosity. The management team above you won’t give you that time, so you’ve got to find ways to claim it for yourself.

For self-employed people

The same management scenario applies the moment you stop being a team of one. When you hand off work — to a contractor, a VA, or a subcontractor — you need to understand more than just the end result.

You should absolutely hire people more capable or more specialized than you, but it’s too easy to forget about the work altogether. Distance creates the same blind spot for a solopreneur, the same way it does for a VP. You stop thinking about the “why” or “how,” and the work loses meaning.

So as you hire help, resist two urges: the pull to micromanage (let the person do their thing!) and stepping so far back that you lose sight of the work. Stay close to the process even when you’re no longer the one doing it.

The goal is always to keep your eyes on the work without constantly putting your hands all over it. And to build time into your day that lets you do just that.

Thinking about a career change? Download my guide: 5 Types of Career Pivots.

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Have a work story you’d like to share? Please reach out using this form. I can retell your story while protecting your identity, share a guest post, or conduct an interview.

When I worked a corporate job, I was often in charge of purchasing decisions. At one company, my team had inherited a lot of homegrown solutions. I saw the limitations of these products and was quick to replace them if the budget allowed.

In corporate settings, “build vs. buy” is a well-known decision framework. Companies weigh the cost of developing something in-house against purchasing an outside solution. It’s often simple math: how much time and resources does it take to maintain this internally versus what does it cost to buy or outsource?

Solopreneurs face the same decision constantly. However, the stakes are a lot higher when it’s your own time and own money as decision factors.

Knowing when to DIY and when to hire out is one of the most important operational decisions a solopreneur makes — and one that’s hard to figure out until you’ve been through it a few times.

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A few days ago, Webflow laid off a significant portion of its workforce with no warning. Employees found out when they couldn’t log in to their work laptops or Slack for the day.

It was so bad that one employee posted this on LinkedIn, tagging the company CEO Linda Tong:

Webflow, a tool for designing websites, was once considered a great place to work. Now, it finds itself in the spewing the same BS that we hear from startups every few days: “Today, we’ve made the difficult decision to reduce the size of our workforce.”

It happens over and over. Abrupt layoffs repackaged as “restructuring” or “adapting to the world of AI.” Every time, the response follows the same script. We share the LinkedIn posts, we express outrage, we say, “This is horrifying.” Then we move on until the next company finds itself in the temporary spotlight when it makes a similar announcement.

And yet we keep not asking the obvious question: why does this keep happening?

The answer is brutally simple. The only reason this keeps happening in the U.S. is because nothing prevents it. Outside of unionized workers — which account for just 10% of the U.S. workforce — American employees are largely at-will. They can be fired at any time, for any non-discriminatory reason, with no notice and no severance required. We’ve built an entire employment system around the assumption that workers are disposable. All the power is held by the employer.

I’ve written before about how we underestimate the risks of traditional employment. The never-ending barrage of tech layoffs has proven to be one of the starkest examples of how this can play out.

What worker protections actually look like

I’ll frequently share screenshots like the LinkedIn post above. Without fail, someone will comment, “If you don’t like the way these companies function, start your own business.” (I did, as a matter of fact, but that’s not the point here.)

The power employers hold is a uniquely American experience, as is the idea that employees are entitled to nothing when their employer decides to cast them aside.

As part of my client work, I’ve spent a lot of time researching employment laws in other countries — particularly around how termination works. The contrast with the U.S. is striking.

Here are a few examples from my research.

Japan

Japan takes worker protections very seriously. Employees can only be dismissed for “objectively reasonable grounds.” Employers have to demonstrate they’ve done everything possible to avoid termination — document issues, offer performance improvement opportunities, consult with labor unions, consider reassignment — before resorting to it.

The standard notice period is 30 days (or 30 days’ pay in lieu). Japan even offers Employment Adjustment Subsidies to help companies retain workers rather than lay them off. (Imagine if that existed here.)

Netherlands

The Netherlands doesn’t allow at-will employment. Employers typically need permission from a government agency or a court to dismiss someone, and they need a valid reason. Notice periods range from one to four months depending on tenure, and employers are required to pay mandatory “transition compensation.”

Philippines

The Philippines has enshrined “security of tenure” in its labor laws. Employees can only be dismissed for legally recognized causes. For business-related reasons like redundancy, the employer must give 30 days’ written notice to both the employee and the Department of Labor. The employee is paid severance based on the length of their tenure.

South Africa

South African labor law requires dismissals to be both “substantively fair” (valid reason) and “procedurally fair” (proper process). For redundancy, employers must go through a formal consultation process — notifying affected employees, applying fair selection criteria, and considering alternatives to termination.

Turkey

Turkey requires valid reasons for all terminations, with notice periods ranging from two to eight weeks based on tenure. Employees with at least one year of service receive one month’s gross salary per year of service in severance. Pregnant employees, those on parental leave, and union representatives are protected from dismissal except in cases of gross misconduct or company closure.

This wouldn’t fly anywhere else

Every one of these countries requires a valid reason for termination. Most mandate weeks to months of notice. Most require severance. Several give employees the right to challenge their dismissal and be reinstated with back pay.

This is the polar opposite of U.S. at-will employment, where most workers can be let go at any time with no notice, no reason, and no recourse.

Japan’s framework is particularly striking when held up against what happened at Webflow. Japanese courts allow redundancy as a valid reason for dismissal, but with strict restrictions. Employers have to demonstrate a genuine business necessity. And they have to prove they did everything in their power to avoid a layoff first.

Now think about Webflow. Webflow said it was restructuring “because AI.” This is a company that has raised hundreds of millions of dollars in venture capital funding and had a $4B valuation in 2022. If AI truly was the reason (and that’s a generous reading), they could have chosen to do more with the same people. Instead, they chose to do the same with fewer people.

Under Japan’s labor laws, that argument would fall apart. Under the Netherlands’ system, they’d need government permission first. Under Philippine law, the dismissals could be invalidated for procedural failures alone (no notice period).

But in the U.S.? Nothing. No mandatory notice, no required severance, no mechanism for employees to fight the layoff. Hundreds (if not thousands) of employees have their lives upended. And once the company gets past the bad PR, they get to operate as they were before.

Power is 100% in the hands of the company. And when fear of a layoff becomes the driving force in how people think about their jobs, that’s not an individual problem. It’s a structural one.

These companies deserve to be publicly dragged. Because right now, nothing else is holding them accountable.

Thinking about a career change? Download my guide: 5 Types of Career Pivots.

If you want to support my work as a writer, you can subscribe to receive additional issues I publish.

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Have a work story you’d like to share? Please reach out using this form. I can retell your story while protecting your identity, share a guest post, or conduct an interview.

A lot of people go out on their own after a layoff, especially in the current economy. And when they do, they tend to focus on what they don’t know: how to find clients, how to set pricing, how to market themselves. But a long corporate career also builds some core competencies that translate directly into running a solo business.

I spent 15 years in a corporate environment, including a role on an executive team. I pivoted to a new career, and then found myself laid off 18 months later. I made the snap decision to start my solo business the next day.

While a lot of aspects of starting a solo business were intimidating, there were a few things I knew I could do well, based on my corporate experience. If you find yourself in a similar situation, here are a few corporate skills that might lend well to your solo career.

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The other day, someone asked me if my clients would start demanding that I lower my prices “because of AI.”

The primary way I earn money is by working as a freelance content marketer for B2B SaaS companies. It’s a question that a lot of people are facing right now — freelancers, employees, anyone whose work has gotten faster or more efficient thanks to AI tools. The assumption baked into that question is that if something can be produced faster, it must be worth less. Or that workers should be producing significantly more of it for the same price.

The pressure to lower prices or produce exponentially more “because AI” rests on a specific assumption: that the value of work is measured by how long it takes to produce it. If something gets done faster, it should “cost” less in some shape or form.

That assumption was always wrong.

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The “do more with less” trap

The demand that AI should make workers cheaper or exponentially more productive is the latest version of a pattern that has been squeezing workers for years. Automation did it before AI. “Lean” management did it before automation. CEOs have long demanded “more with less” — AI is just the latest mechanism.

The basic way economists measure productivity is in output per hour. If you produce more output in the same number of hours, that makes you more productive. No wonder CEOs are salivating.

I had written almost this entire draft and was ready to publish when the CEO of ClickUp (a project management software) decided to further illustrate my point. He wrote on X/Twitter:

Today we reduced headcount by 22%. The business is the strongest it’s ever been. So I think it’s important to be direct about what I’m seeing and why.

This wasn’t about cutting costs. Most savings from this change will flow directly back into the people who stay. We’ll be introducing million-dollar salary bands. If you create outsized impact using AI, you’ll be paid outside of traditional bands.

The primary change is that we’re reconstructing around what I call 100x org. The goal is 100x output. The roles required to build at the highest level are fundamentally different than they were a year ago.

The 100x org is actually heavily dependent on people — infinitely more than today. This is only possible with 10x people that have embraced and adopted new ways of working.

(There was a lot more after this about the 100x org… it was a long post.)

Translation: “This isn’t about cutting costs. I just don’t give AF about the people who work for me.”

He doesn’t care about the former employees and families of nearly 25% of people who are now unemployed at the whim of the CEO.

He doesn’t care about the employees left behind, because 100x output is insanity. And even though he says that they will be increasing the salaries to match the impact… is it 100x? No. The difference between the impact, what flows to the company, and what flows back to the employee is what’s outsized.

He said the quiet part out loud (at least, according to a CEO’s way of thinking): AI isn’t about freeing up anyone’s time, as it promises. It’s about creating and requiring more work.

The infuriating part of his word salad of a statement was saying that the 100x org is “heavily dependent on people.” Just… not the people that the company had already hired, apparently.

How to think about your value at work

100x org aside, productivity gains that flow entirely to the employer or client have absolutely no benefit for the worker. What is the point of a 100x org? It’s a means of extracting more output for the same money (or the same output with fewer people, or for less money).

The conversation about AI and compensation — whether that’s salary negotiations, freelance rates, or even workload expectations — needs reframing now, before this intense and unrealistic focus on increased output becomes the new baseline.

For employees: When a manager suggests that AI should allow the team to take on twice the workload, that’s a change in the requirements of the role — and workers need to treat it as such before it becomes the default expectation. 100x is ridiculous. He’s probably blowing smoke, but it’s smoke he chose to blow in public. I know for many people, quitting is not an option, but I hope the CEO’s post scares away any new talent.

If you take AI out of the picture and were asked to take on more responsibilities, you are being asked to do more for the same pay (which isn’t right). Even ClickUp’s promise of higher salary bands isn’t aligned with the 100x output the CEO is expecting.

I’ve long advocated that people research a company before applying for a job, and public statements like this are self-filtering. Don’t apply unless you plan to create value only for the company, and not for yourself.

For the self-employed: Thinking about client expectations in a world of AI, the frame is simpler (though the stakes may feel high because your livelihood depends on clients). The deliverable is the deliverable. If the quality hasn’t changed, the price hasn’t changed. No “extra output” for the same cost, and certainly not a lower cost. How you produce the work is your business — literally.

I’ve used AI in many parts of my business. I used to have a manual process (copying/pasting) from client briefs to my own project management tool. Automation and AI now do that formatting for me, saving time with every deliverable. I have one client who requires heavily researched articles. Claude now does the bulk of the research, and I check the results to make sure it’s correct and relevant to what I’m writing. These are process improvements, not a devaluation of my work.

If you’re navigating these conversations right now, don’t concede the premise that “faster” means “cheaper.”

This latest wave of “do more with less” doesn’t have to be the one that pushes people over the edge.

Thinking about a career change? Download my guide: 5 Types of Career Pivots.

If you want to support my work as a writer, you can subscribe to receive additional issues I publish.

Subscribe now

Have a work story you’d like to share? Please reach out using this form. I can retell your story while protecting your identity, share a guest post, or conduct an interview.