In October 2022, I became self-employed. This month marks four years of working for myself.

I could write about the different things I’ve done to make it work, running my own business, but I’ll save that for LinkedIn…

Instead, I want to reflect on how much my perception of work has changed in that time. And not just because I now work for myself: because work has changed. I lost my job at the start of a downturn in the job market, and it has only gotten worse. Many people, like me, choose a path of self-employment because it seems preferable to finding a new job. A choice born from necessity isn’t really a choice (though it forced me down a path I was likely headed anyway).

Fear drives a lot of what we do with our careers. Fear of the unknown. Fear of discomfort. Fear of giving up job security.

So whether you’re considering a voluntary career change or are pushed into one, here are four things to keep in mind.

1. The beginner phase is shorter than you think

When people consider a career change, they tend to assume that everything about the new career will be unfamiliar. That was certainly my assumption when I left a tech job I’d been at for 15 years and pivoted to a new career in content marketing.

And some parts of a new job will make a newcomer feel inadequate. Every industry has its own jargon, for example, and not knowing it is a fast way to feel like the least experienced person in the room. (Imagine my adjustment when “SQL” went from meaning “structured query language” to “sales qualified lead.”) But jargon can be learned. It usually just takes a few months of listening and asking questions.

And you’re never truly a beginner again, even if you start over in a completely new industry. That assumption ignores everything a career pivoter already brings. Someone a decade into their career has made hard decisions and kept complicated projects on track. Those skills take years to develop, and someone at the start of their career hasn’t had as much exposure to a wide range of experiences.

The beginner phase is real, but it tends to be short-lived.

2. What you take with you are your boundaries

People always have a specific reason for leaving a job, and a lot of the time that reason is a boundary that got pushed or crossed. Maybe it was a boss who expected answers late at night. Maybe it was an ever-increasing workload without an increase in pay. Maybe it was an intolerable co-worker.

These days, finding a new job takes months of effort. Nobody wants to go through all of that only to end up with the same problems at a different company.

So people hold on to the boundary. What you didn’t tolerate at one job becomes something they actively try to avoid at the next one. Plenty of people leave a job with a very clear list of what they won’t tolerate.

That list — whether it’s actually written down or exists only in your mind — is the most portable thing anyone takes from an old job. Titles and skills may vary between roles and industries. But a firm grasp of what you want and what you’re willing to give (and give up) won’t change.

Boundaries also make it easier to see the employment relationship for what it is. Companies hire people because they need the work done, and nobody employs anyone as a favor. You’re trading your time and talent for money. Holding firm to a boundary ensures the exchange stays fair on both sides.

3. Security doesn’t come from structure

For a long time, a full-time job with a salary and benefits was the safe choice. Working hard inside that structure was supposed to add another layer of protection, via promotions or, at least, respect.

Layoffs have shown us that the social contract is broken. Companies have zero loyalty to their employees (yet still expect loyalty). Staying late or picking up extra projects often doesn’t change the outcome of who is impacted by a layoff.

For years, tech, in particular, was the industry that was supposed to be safe. At this point, outside of unionized jobs, nothing seems to qualify.

Some will argue that a steady paycheck is still safer than self-employment income. But a paycheck can disappear without warning, and then a person has lost 100% of their income.

A lot of people have been mistaking survival mode for stability. They hold on to a job because leaving feels riskier than staying.

Self-employment carries its own risks. Clients leave, and projects end. Both paths of working carry risk; it’s just a matter of choosing your risk — and building your own forms of a safety net if needed.

4. Ambition changes shape

Back in 2021, I wrote about redefining ambition.

The title-and-promotion version of ambition is what society has historically decided to value. A title gives people clout when they introduce themselves, telling everyone in the room how important someone is.

But titles are often meaningless. I held an executive role at a tech company and had a title of Director. After I left, my replacement — who was given less responsibility than what I had — was offered a title of Vice President. At first, I was miffed. Then I realized that he was probably lured with a title in lieu of compensation. The company didn’t want to pay him as much, so the title was a consolation prize.

Four years out, my ambition looks different. I don’t call myself a “founder” or “CEO” of my one-person operation. My goals have shifted to being recognized for the value of the work itself. That kind of ambition is certainly harder to show off at a networking event. But success for me comes from doing good work without sacrificing everything else for it.

If you’re thinking about a pivot, you’ll still have your ambition. It may just start taking on a different shape.

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.

Note: October is Pregnancy and Infant Loss Awareness Month.

In 2015, I had a stillborn baby girl. I found out during a prenatal appointment that my daughter had no heartbeat.

Because I was in my second trimester, I was admitted to the hospital’s Labor and Delivery ward. The same ward where women deliver living babies. Except I did not get to bring my baby home.

I’ve talked openly about pregnancy loss for many years. I’ve advocated for more openness in the workplace. It’s a way to honor my daughter: to use my voice to make things better for other grieving parents.

Bereavement policies should cover pregnancy loss

My employer at the time had a very flexible leave policy. I ended up taking nearly three weeks off from work after my daughter’s stillbirth. My entire world felt like it didn’t make sense anymore. My body needed to heal.

Unfortunately, pregnancy loss often falls into a gap in companies’ bereavement policies. They don’t allow any time off for a miscarriage or stillbirth. I met a woman through a support group who delivered her stillborn baby via c-section and had to go back to work mere days later. When there’s no living baby, maternity leave does not apply. And the standard 3-day bereavement leave that many companies have is wholly inadequate.

Only a few states in the U.S. provide any guaranteed bereavement leave, and even fewer specifically include pregnancy loss as a qualifying event. It’s mostly up to individual employers to craft their own policies.

Many years later, I was working for a young company that was working to solidify its leave policies for the first time. I asked the HR person to include pregnancy loss leave specifically. I said, “You don’t want to wait until a situation comes up and then be scrambling to define the leave.”

I fear that happens too often. Companies don’t include pregnancy loss in their bereavement leave until an employee asks about it. At that point, the employee is in the throes of grief, which is the worst time to wait for HR to figure out a leave policy.

In 2022, TheSkimm launched a Show Us Your Leave campaign. Pregnancy loss leave was included in the data collected. If you can influence HR policies and are unsure what type of bereavement support to offer, TheSkimm’s database is a place to start.

How to support a coworker who has experienced pregnancy loss

Pregnancy loss is incredibly common: 20% of pregnancies end in miscarriage, according to WebMD. Some researchers believe that the number is much higher.

Yet, pregnancy loss is still a taboo topic, especially in the workplace. As a result, parents feel isolated in their grief.

Recently, a friend came to me because one of her employees had a miscarriage. She asked me, “What can I do to support her?”

I believe that caring, compassionate co-workers often don’t know what to do, especially if they’ve never experienced pregnancy loss themselves.

Here are my suggestions:

• Review this list from the Miscarriage Association of what to say (and what not to say)

• Listen to this podcast episode: How to Support Someone Experiencing Pregnancy and Infant Loss

• Set a reminder on your calendar to check in on a regular basis — even weeks or months later. Offer to listen if the person wants to talk.

If you’ve experienced pregnancy loss yourself, I’m so sorry. I know how devastating and isolating it is. I highly recommend resources from Share Pregnancy and Infant Loss Support.

I want to see the narrative around pregnancy loss change, especially in the workplace. I didn’t simply “lose a pregnancy.” My much-loved child died, as did all the dreams I had for her. There’s a hole in every family photo, because she isn’t there.

Workplaces can – and should – do better. Pregnancy loss isn’t rare. The workplace shouldn’t be a source of awkwardness or additional pain. Companies and coworkers need to figure out how to support someone, because it will inevitably come up.

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Right now, I have (checks computer) more than a dozen scheduled tasks that AI handles for me. Plus, countless other saved instructions to run repeatable processes on the fly.

Most AI advice focuses on content generation or chatbot conversations. But what a large company needs and what an individual consumer might do with AI are vastly different from a solopreneur: one person, with some business use cases.

Solopreneurs can get a lot of benefit from handing off specific operational tasks. This type of work keeps your business running smoothly, but it isn’t the best use of your time.

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When I was in college, I was working at a community bank in Wisconsin. In the summer of 2003, I was given the task of converting the bank’s paper loan files to digital files. I sat at a desk with one other person, and we ran thousands of pages through a desktop scanner, organizing them into different folders.

At first, the work was awful. Not unbearable — we had a radio and listened to music while we worked — but monotonous. But eventually, I saw the end result. Loan officers were able to pull up documents without leaving their desks. Paper files were messy; scanned versions weren’t. And a few months after we started, the entire project was done.

Of course, not everyone liked the change. Once scanned, the paper files were stored where the officers could no longer access them, to force the change to digital files. One loan officer started hiding files under her desk because she didn’t want to give up the paper versions. During her lunch break, I would retrieve the files and scan them.

After graduating from college, I went to work for a software company (the same company that made the loan imaging platform I’d been using for years). My first role was implementation specialist. I traveled around the country, helping community banks learn to use the product they just purchased. Not just for scanning loan files, but a whole suite of loan management features.

Without fail, I’d encounter bank employees resistant to change. Some thought their current process was better. Some didn’t like the disruption to their routine. A few were uncomfortable with computers in general and struggled to navigate a new piece of software.

After getting through the presentation part of training — showing employees how the software worked — I often sat next to them. I’d gently guide them: click here, now click here, see how that works?

Throughout my career at the software company, which ended up lasting 15 years, I was the person who pushed for internal change. Much as the company wanted its customers to abandon manual processes, its own internal systems were lacking. I always wanted things to be better: to eliminate anything tedious or manual, so everyone could focus on the more interesting parts of their job.

I don’t get to do much of that now. Hardly any, in fact. Working for myself, I can make any changes I want, any time I want. But it’s not the same as listening to and solving for other people’s problems. Banks would often present me with complex workflows that I’d have to “translate” and reshape into the software I’d shown them. I occasionally consult with other solopreneurs and help them figure out their tools and systems, but those projects are very short-lived.

Nilay Patel, editor-in-chief of The Verge, talks about people who have “software brain.” He wrote an entire essay, The people do not yearn for automation. He writes,

“So what is software brain? The simplest definition I’ve come up with is that it’s when you see the whole world as a series of databases that can be controlled with the structured language of software code.”

It’s true that I spend more time tinkering with tools and automation than I’d care to admit. I have a ring that connects to my to-do list. I’ve vibe coded a menu planning app for my family.

But, as Patel points out, software eventually collides with human reality. In the business world, you can tweak the database or the software code to match the business use case. Human life outside of work is much different.

And in the work I do with fellow solopreneurs, it’s more like a personal life than a business use case, because work and the human are deeply intertwined. It’s not solving for a large team moving a loan file through departments. It’s solving for one person, who has fewer dependencies and limited bandwidth. All the automation capabilities in the world have to be accompanied by a force function for change.

Earlier this week, a repair person came to my house to fix my garage door. At the end, I asked if he’d prefer a check or a credit card. He told me a credit card, because otherwise he’d have to call the main office with my card number to run the transaction.

Of course, there are plenty of apps and tools that would allow him to process the credit card with his cell phone. He was halfway there: I signed for the work on an app and was emailed a receipt, which was more than the dishwasher repair person a few weeks ago who handed me a paper copy. The garage door company is quite large, but must not be feeling enough pain from the current way of doing things. So the technician has to call the main office a few times per day to run a credit card… not a big deal (to them).

Always and forever, I want to make processes and the way things work better. But I recognize that not everyone has the same desires or motivations.

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.

Is burnout an inevitable part of success? A survey found that 40% of workers believe this is the case. That’s far more than a fringe belief: it’s a working assumption that almost half of the workforce ascribes to. We’ve absorbed the idea that achievement requires running ourselves into the ground.

Over the past several years, I’ve watched the anti-hustle culture movement push back hard against the “rise and grind” mentality. Fewer social media posts celebrating 80-hour weeks as proof of dedication and sacrifice. People sharing their experiences of stepping away from work to recharge.

The criticism is warranted (and overdue). Chronic overwork does lead to burnout. The culture of pushing through when our bodies and minds are telling us to stop has long been a structural problem, even though the hustle bros would have you believe it’s a personal failing.

But somewhere in the backlash, the conversation fell into two camps. Either grinding is the path to success, or intensity itself is the enemy. You can’t have both. Both sides treat work intensity as a permanent setting — you’re either “on” or “off.”

That framing misses how we move through different seasons of life. Including dialing up and dialing back as needed.

In my career, I worked intensely at a tech job for 15 years. In many ways that I won’t enumerate here, that was bad. The pandemic hit, and I was tired of it all. But I had to keep hustling and pushing myself in order to find a new landing place in my second career.

That season of intensity was necessary. Not because the hustle-culture crowd was right, but because building toward something new or different requires it.

The question should be: Is this hustle temporary? Or a permanent fixture in your work life?

Hustle has its place when it’s temporary

Hustle mentality is usually seen as a character trait. And, of course, some people will still pursue relentless hustle in pursuit of their goals.

But for many people, hustle might be tied to circumstances. Two situations come up again and again that look nothing like “hustle culture as a way of life.”

Trying to leave a job

When I knew that I wanted to leave my tech job, I put in long hours. I had my regular 9-5 job, and then was freelancing in the evening, often for several additional hours per day. This was necessary to build the writing portfolio I needed to change careers. Then I added applying for new jobs into the mix.

It was utterly exhausting. But I knew it wouldn’t last forever, and I was right. Three months after I started freelancing, I landed a full-time job at a content marketing agency and a retainer agreement at a magazine.

That kind of intensity has a clear purpose (build the skills necessary to get out) and a clear end point (the new job). If I’d only said, “I’m working 60-hour weeks,” it would have looked like hustle from the outside. But it didn’t feel like hustle because it was temporary, and saying otherwise would have been performative. I wasn’t trying to prove anything to an employer. I was doing it because the alternative was staying “stuck.”

Unfortunately, the current job market demands even more of this kind of effort. Job searches may stretch into months of interviews and take-home assignments. Or a job-seeker may spend a ton of time networking. Anyone in the middle of a career transition knows this. The work of finding a job is a much longer season of intensity and can be hard to sustain.

Trying to build something of your own

The same principle applies when someone is building a solo business or pivoting to self-employment. The early days are intense by nature. You’re taking on the work of finding clients and building systems, often without support. There are months when the hours are long, and the to-do list feels absolutely endless.

This was my second season of hustle in recent years. I lost my job and decided the next day that I was going to freelance full-time. Even though I had some pieces in place from freelancing alongside my 9-5, it was a mad scramble to build up a full roster of clients and pull in the income to support my family.

But the early hustle of building a business on your own terms is completely different than corporate overwork. Every client relationship and everything you create is an asset that belongs to you. Corporate hustle often comes without a reward proportional to the effort an employee puts in. Employees trade their nights and weekends for what? A modest raise or a new title? In far too many cases, they get nothing at all.

When the intensity is in service of your own thing, there’s a direct relationship between what goes in and what you get in return. I’m not a fan of never-ending hustle, but the connection between effort and outcome makes a temporary hustle season tolerable… maybe even energizing. And unlike a corporate environment where the expectation of intensity never slows down, the self-employed person’s hustle phase can dial back when they reach the point of a sustainable business.

Building so you don’t have to hustle (as much)

The anti-hustle crowd gets one thing right: permanent intensity is destructive. Without an end date or a target in mind, it becomes a state of being that leads to burnout. We’re simply not designed to operate that way.

Ask yourself: Am I choosing this intensity, or is it choosing me?

Corporate hustle is often unchosen or a baseline expectation. Seasonal hustle is deliberate and has a particular outcome.

Jay Clouse, founder of Creator Science, put it this way on his podcast:

“I want to be world-class at something, but I want to be world-class on my terms. I don’t want to be world-class in a way that requires me to build a business that I don’t want to build in a way I don’t want to build it. … And in this season, I just don’t want to [do more].”

My days now look so different than the way they did in 2020 (at a corporate job) and in 2022 (when I first started my freelance business).

That’s the whole point. Hustle seasons should have boundaries. You push hard and work toward what you need, and then your hustle season ends. It’s not because your ambition disappears, but because the season did its job. Your goal is to create a season that means the next phase of your career can look different than the last.

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.

There’s a popular narrative around starting a solo business: quit your job, take the leap, figure it out along the way. It sounds bold. It also ignores what many successful solopreneurs actually do: start while they still have a paycheck, figure it out, and then quit.

I freelanced alongside my 9-5 for two full years before going solo full-time. That runway gave me time to figure out my offer and ideal clients, build a portfolio, and develop the confidence that I could make it work. As a result, the transition didn’t feel like a free fall.

If you’re thinking about solopreneurship, a side hustle might be a smart way to get started.

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The word “freedom” shows up constantly in conversations about work — everything from debates about return-to-office mandates to freelancer lifestyle content.

A 2025 Randstad report found that more than half of workers would give up higher pay for more control over their working hours. But what most people describe when they say they want “freedom” what they actually mean is flexibility. They want the ability to take an afternoon off for their kid’s soccer game or maybe skip the daily commute when the weather is bad.

Flexibility is what an employer offers you, most often with constraints. You might have a hybrid schedule that requires an in-office presence three days per week or working core hours. Workers have to operate within those constraints.

Freedom is something else. Freedom is the ability to make the choice yourself — not just when and where the work happens, but what the work is and who it’s for.

Most conversations about work don’t make that distinction. Flexibility is certainly one component of freedom, but freedom goes further. And once you start thinking about what you’re choosing between, you realize that every work arrangement trades one kind of freedom for another.

Every work arrangement is a trade

For more than a decade, I worked in a very unique setup, called a Results-Only Work Environment (ROWE). Even though I had an employer, I had complete autonomy over when and how work got done. Only the results — a designated end point — mattered. If I wasn’t feeling well, I could simply take the day off and wouldn’t need to ask for permission. Working around my kids’ school calendar was easy.

I had the ultimate flexibility, and for a long time I mistook that for freedom. It was hard to imagine working for another employer where my working hours might be constrained in some way. But the tradeoff was working toward an employer’s goals, which eventually became misaligned with my own.

Subsequent employers (two of them) imposed the exact constraints I feared. My last employer before going solo had a four-day workweek. At first, that seemed amazing, but eventually I realized that the other four days were a grind. Butts in chairs at 8:00 am, working nonstop until the end of the day, to cram five days’ worth of effort into four days. The tradeoff was less schedule control for other things I valued. Eventually, that was no longer enough, and the best option, for me, was to work for myself.

But no work arrangement gives you everything. An employee trades full autonomy for stability: someone else sets the direction, but the paycheck is predictable. A self-employed person trades stability for control: the income fluctuates, but the work is self-directed. There’s no safety net, but also no ceiling.

We talk about these arrangements as if they exist on a spectrum from “less free” to “more free,” with self-employment sitting at the top for people who want to maximize their freedom. But that framing is wrong, because there are still trade-offs. The question is which trade-offs you’re willing to make.

I have to look at money differently than someone who has an employer. For some people, that’s unfathomable because they like the “freedom” that a reliable income brings.

Instead, I think it’s wrong to pit self-employment and working for an employer as more or less freedom. Instead, the actual freedom comes from the ability to choose.

The difference between choosing and settling

The real dividing line in all of this is whether you chose your trade-offs from a position of genuine options… or if you’ve accepted your current work situation because you felt like you had no good options.

There are two versions of being trapped. The first is staying at a job you’d leave in a heartbeat if you could, because you rely on an employer’s health insurance (a structural constraint). The other is being self-employed, not because you chose it, but because the labor market sucks and you weren’t able to find a full-time job. In both cases, the arrangement chose you.

The freedom conversation often assumes that self-employment is the destination. That if you just had enough savings or enough clients or enough grit, you’d obviously prefer to work for yourself. But that’s not true for everyone. The trade-off of instability — unpredictable income and no employer-sponsored benefits — may not be worth it. The constant mental weight of running everything yourself is its own kind of cost.

On the podcast The Vergecast, senior reporter Elizabeth Lopato said:

“I don’t want to make a business. I have a job because I don’t want to think about accounting, and I don’t want to hire my own libel lawyer. I want to write things that are meaningful, and the more time I can spend doing that, the better. And one easy way for me to do that is to have a job where all I do is write. And somebody else takes care of the business stuff.”

Choosing to stay with an employer because you want stability is a valid choice. Freedom at work is what you choose to build your career around. The trade-offs don’t disappear — whether you’re employed or working for yourself, something is always being exchanged for something else. But when you’re making decisions about trade-offs, when you pick them from real options and decide you can live with whatever you’re giving up, that’s real freedom.

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.

There’s a popular narrative around starting a solo business: quit your job, take the leap, figure it out along the way. It sounds bold. It also ignores what many successfu…

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I’ve written many times about how I started my own business in 2022 after I was laid off from my marketing job. But in reality, that’s not struck out on my own. The first time was when I was 23 years old.

I was working for a financial technology company. I liked the company and the product, but I got a new boss, and she was awful. I was so stressed all the time. As much as I liked the job, I didn’t think I could keep working there.

The company was located in Kansas, but let me work remotely from Wisconsin. I loved the arrangement. Remote work was uncommon at the time. I knew that if I left, finding a similar job might be tricky. There were no tech companies in my small hometown in Wisconsin, and my husband was still finishing college. I felt like I was stuck, at least until my husband was done with school and we could move elsewhere.

At the time, I was leading software implementation for community banks. Projects were often up to 6 months long, complex, and involved many people. The culmination of the project was traveling to a bank location and spending 3 days on-site, training employees.

One bank mentioned in passing that they would love to hire me as a consultant to get more dedicated help. It seemed like a way out of my current job situation. I spoke to the bank’s vice president and said, “Were you serious about that offer?” and he told me, “Yes.”

I decided to quit my job to work as a consultant. Once I was done with that project, I would move on to the next one.

When I told my boss that I was quitting, the company’s COO reached out to me. She told me that she thought we could work together. I could stay on payroll and keep my health insurance. The company would process the payments from my consulting contracts, take a cut, and pay me the difference as a bonus. There was a benefit to the company also: they could offer their clients my services as a consultant. I agreed.

I spent six weeks at the first bank location. Another bank ended up hiring me for almost three months. They put me up at a corporate apartment near their headquarters in Jefferson City, Missouri.

It always worked out, and I was able to get the “next project.” I did everything myself, from scoping the agreement to negotiating with the bank. I rarely interacted with my employer-on-paper. I even read a book about consulting. When one bank wanted to extend my contract, but for less money, I replied, “Sure, that’s fine. Then let’s figure out how to reduce the scope.” They re-signed at the original amount proposed.

But being on the road 100% of the time was really hard. Corporate apartments were boring. Since each stint was temporary, I never got to know the town or found anything interesting to do. And I frequently went back to Wisconsin on the weekends.

Then my direct boss quit. The COO reached out and asked if I’d like to return to my prior role. I negotiated a salary that was equivalent to what I was earning as a consultant and agreed.

Once I became a regular employee again, I stepped into more contract negotiations and defined the scope for custom projects. That work excited me because I was good at it. I stayed at that company for 15 years in part because they gave me opportunities over and over to define my own path. I became the company’s first product manager. Later, I managed the entire customer service department and carved out what that role would look like for me. I left, in part, because I ran out of ways to grow.

So while I wasn’t technically self-employed as a consultant, I was functionally on my own. I had mentally prepared for self-employment at the time I quit. Even though it ended up being a brief stint, it was an indication early in my career that I wanted to chart my own path.

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.

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.

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.

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.

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.

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.

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 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.

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.