When you talk to Maya, you can tell she’s alive-capital-A. Her true love is writing fiction (and she’s always writing). She’s published several books and a few years ago one of them even sold 13,000 in six months. But that doesn’t like…pay the bills.

These days, she works several types of jobs to make ends meet, but they all revolve around her writing, and trying to stave off the debilitating depression that has come and gone over her lifetime.

I met Maya through mutual friends and adored her instantly. We’re now in a writer’s group together, working on our books, which is how I knew she had a story worth hearing.

This conversation is pulled from a transcript of our conversation. Edited for clarity and length.

“My most traditional job was when I went into the schools. I became a teacher, taught Kindergarten through fifth grade for ten years. I love children. I don’t have any. It was wonderful.

“At the time, we had real freedom to teach in Florida schools. I had about 30 kids a day, the usual suspects. These were the kids who were left behind. Kids who had moved six times in a year and lived in their auntie’s car. Drug raids in their neighborhood. These kids were way behind, and I loved working with them. It was a great gig, but it paid next to nothing.

“I was only able to do it because I had saved some money. I was 15 minutes short of full time — it was a federally funded program, and they structured it that way deliberately so there were no benefits. So I depleted my savings.”

“You did this for ten years?” I asked. Surprised that she’d made it work.

“Oh, yeah. I could be creative every day. We co-created theater for the rest of the fifth-grade class. It was amazing what these drama scenes would do for the kids. It lifted them up. Gave them self-possession and self-reliance. They each had to be in charge of something — props, script. “With freedom comes responsibility” was always my phrase for them. If they forgot a prop, that was on them. I wasn’t their mama. Actualization. Self-actualization — which is a big word for fifth graders.

“There was a time when it all changed and became more data-driven.The freedom to actually teach where the child was taken away. Children are not data. I used to go into the school and say, “Okay, 20% academics today, 80% behavior.” Parental involvement was basically nonexistent, so we had to meet them where they were.

“The teachers were being pushed to churn out numbers. Kids needed to operate at grade level, but you can’t just can’t take a kid who’s been living in a car and make them operate at grade level. My boss — who was smart and had been in the business thirty years — said to me, “If he trusts one adult, you’ve done your job.” Not what’s coming out on the data. And yet the data drove the funding.”

Maya paused to sip her coffee.

“I remember you mentioning one time that there was one school that did it right.”

“Oh yeah. The schools got graded, A through F. There was one school I worked at that went from a D to an A.”

“Fascinating,” I said. “What changed?”

“The principal actually created a physical space with coffee, a copier, all the mailboxes. A true teacher’s lounge. So the teachers could actually confer about what was going on with their students, because that is their product. A first-grade teacher knows Johnny. She can help the fifth-grade teacher that Johnny is new to. That communication was critical. When it came together, you could see the relief.

“She also knew what the school needed and how to delegate. She had a behavioral support manager with a walkie-talkie who roamed the school and helped in classrooms when needed. She had a data manager who handled all the state requirements.”

“There was a K through eighth-grade school I worked at that had a F grade and remained at an F. They turned the teacher’s lounge into a gym. It was tiny. Nobody went in there. The teachers had no way to discuss things. They were alienated from each other. They couldn’t coordinate, couldn’t collaborate. It was a breakdown.

“At the end of the year, graduation rates were too low. The school was shut down, funding was shifted to the local high school, and the teachers’ jobs were cut.”

Listening to her reminded me of this book I’m reading, The Empathy Advantage (by Heather E. McGowan and Chris Shipley) which is all about what empathy, baked into a workplace, looks like. They looked at health systems as an example: certified nursing assistants and pharmacy techs, often paid well, but treated poorly and undertrained. Most quit within a year.

The authors asked this, “What would happen if an empathetic leader invested time on a nursing ward to understand daily work environment and endeavor to build a culture of support, understanding and respect?” And they cited research that showed workplaces that invested in understanding and meeting employee needs increased revenue and profits by nearly 50%.

Not surprising that Maya’s school with the teacher’s lounge and an engaged principal, who understood people, got an A grade. The students performed better when the teachers had a natural place to connect and collaborate.

“Can you tell me about what you’re doing these days? How you’re making it all work with housing, food, everything?” I asked.

“I had to get over myself,” she said. “I clean Airbnbs — that’s where the majority of the income comes from. I sing, so I make good money at certain events. I sell the band.

“I had to see all things as work. Everything provides for the machine. I also have an Airbnb room in my own house.

“Everything is spokes on the wheel — it all feeds to the center. Just because something is mindless cleaning work doesn’t mean it’s not valuable. It actually gives me time to do the writing. I listen to my research with an AI voice on the laptop while I clean. I might be mopping the floor and working on a scene in a book.

“The center of the wheel is my health and well-being. Because I have coped with severe, chronic, recurring, debilitating depression since I was five years old. That has really determined much of my work. There are times I’ve been almost catatonic — I can’t read, I can’t speak, I can’t process language. So my health has determined my work choices.

“Thank God for the Affordable Care Act. Obamacare made it possible for me not to deplete my savings. I have the best healthcare I’ve ever had.

“Fifteen years ago, I was spending nine hundred dollars a month on healthcare because of pre-existing conditions. You could have a mortgage for that. I finally found a balance. All my choices are related to keeping the wheels on the bus. I have to manage my health, or I have nothing.

“What about people?” I asked. “You said you’d really enjoyed working at the school when there was a teacher’s lounge and the collaboration space made all the difference in the work. Do you find ways to collaborate now?”

“I do have a writing group that’s important to me. And with the cleaning, I feel part of a team, though I don’t fully trust them. I found out my male coworker was getting paid more than me. So even being ‘part of a team’ doesn’t necessarily mean the relationship feeds you or helps you grow…

“Gig work has more respect these days than it used to. But yeah, I regret not having comrades to share the journey with, celebrating a victory, or changing the toner together. I really need more of a team. I do have an artist I work with on book covers, and an accountant for my taxes. But on a daily basis, it’s a solo effort. It’s really lonely.”

Maya was quiet. I was quiet with her. Letting the space breathe to see what came next.

“I do have mentors and friends outside of work who encourage me that I do enough, I am enough, I have enough. These are people who are going back to school, starting small businesses, taking the risk to go in for a big corporate job, it allows me to take risks.”

“In all those people, in your work-life or outside of it, is there any person who helped you see yourself?”

“My dad. He made me a shingle, a cypress shingle, like the old-fashioned ones you’d hang outside your place of business with your trade on it. Mine said ’Artist.’

“He carved it with a wood carving knife and then shellacked it. He could see me when I couldn’t see me. He knew I was an artist even when I was little. And I was too afraid to embrace that. I didn’t go to art school.

“But the other thing he did was — when my brother and I were in business together, he would come to our little tiny office and put stamps on envelopes for our marketing campaigns. He believed in me. He never put us down. He was an attorney. He saw me when I was afraid to see myself. And I have that shingle in my bedroom over my door to this day.”

“Do you own it today? The artist identity?”

“I do it every time I sit down and write. I give a lot of time to it and a lot of thought. I’ve given up other things to create space for it — to have the imagination be free. I guard against negative influences and time sucks. And there comes a point of do it or don’t. Is this ever going to make money? I don’t know. But I’m going to do it whether it makes money or not.

“Why?” I asked.

“Because it’s fun. Because I’m actually good at it. And why not? I’m as good as anybody else. When I sing, I’ve got an octave and a half range, I might as well sell it if it feeds me.

“And being an artist keeps me from being dead in depression. When I’m working on a new fiction story, it’s a grand obsession. It’s a joy. It’s endless research. I learn about the whole world. I was studying emeralds in Colombia. Betrayal in Miami. Yesterday I was studying Looney Tunes characters and Moana and Disney characters because they’re part of my story. It’s a constant evolution of learning. I’m always traveling through my imagination.

“And it costs, because that’s what I’m supporting with my income. Not a 401k. Not a two-week vacation. But on a daily basis, it’s really fun. And it gives it back to me.

“I don’t know. If there’s one thing I could say about all the work I do, it’s that I don’t compartmentalize. Work is not separate from life. It all contributes to one thing… your family, your business, your health, it makes up your life. This is it.

“How do you spend your day?” she asked. “It better be something that works for you.”

When I got to my car I sat in silence for awhile, feeling so many things all at once. Not trying to make sense of it, just trying to let it move through. I felt sadness for the depression that had disabled Maya throughout her life and the determination with which she wrote her books because it kept her moving. I felt grateful to know her, because she has a way of inspiring you with just a turn of phrase or with stories about her days researching for her current book project. She takes road trips all over so she can meet people, see specific buildings, and decide on details for her characters. She holds my dream of this project, Human Doings/Human Beings. I’m glad she agreed to be in it.

If you’re interested in sharing an anonymous story with me, please reach out. Email me at humandoingshumanbeings@gmail.com. Let’s set up a Zoom chat so I can hear about how your work life has shaped who you are today.

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• Alice Shin worked at Flatiron School, a WeWork company, during peak IPO chaos

• Her boss, Eli Bohemond, created a rare environment where it was safe to say “I need help.”

• Now, with AI advancing fast, the world feels like it’s moving at startup speed. Alice explains how to stay grounded.

Why it matters:
This piece is a real-world look at how trust can fuel performance.

Human Doings / Human Beings is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

The Boss Who Made It Safe to Say

“I Need Help”

Originally posted on Flllow with Alice

It was 2019, and I was working at Flatiron School — a WeWork company. That summer, Adam Neumann announced a “quiet period” at our all-hands. IPO ambitions were in full swing.

At Flatiron School, we were developing future tech talent. And as a WeWork company, we were also part of something bigger: a movement to redefine how people learn, live, and work.

At least that’s what I believed. And the story the media told.

Inside, we were paddling full speed to stay afloat.

A few years earlier, I was on the other side. A founding member of a small startup, crammed into WeWork’s very first location in Soho — an unassuming red-brick building on 154 Grand Street in New York City.

I remember walking the long hallway, breathing in the scent of La Colombe cold brew and ambition, catching glimpses of dreamers and builders through glass walls. There was a quiet energy in the air — a mix of excitement and nerves. We were taking big bets and building something from nothing.

So when I joined Flatiron School, it felt like a full-circle moment.

💁🏻A Masterclass in Compressed Chaos

During my 23 months at Flatiron, I experienced eight major changes — nearly triple the industry average.

We expanded markets, restructured the organization, changed ownership, went fully remote — and rode a rollercoaster of hiring and layoffs.

Externally, we faced a pandemic and cultural reckonings like Black Lives Matter — reshaping our customer behavior overnight. “Business as usual” stopped making sense.

It became a masterclass in what I call compressed chaos — a Harvard Business School case study, unfolding in real time.

In the thick of it, I learned something I still carry: speed matters in the startup world. But speed paired with psychological safety? That’s golden.

🌊 Today’s AI wave feels eerily similar — but it’s global, and faster.

One week, I’m deciphering multi-agent systems.

Another week, I’m learning about “vibe coding.” At first, I thought it meant casually coding together, given Gen Z’s slang, “it’s a vibe” is their catch all for anything cool. But as of last month, it’s now Merriam-Webster official, and it means prompting AI to build software for you!

This sort of rapid evolution can still feel overwhelming. But instead, I’m experimenting and learning with a sense of play.

But it wasn’t always this way.

✅ From Threat to Safety

Early on, I didn’t have the capacity to dive deeply into AI. I was managing product discovery, driving feature adoption, and adapting to shifting priorities.

I entered the world of tech to be at the forefront of innovation, and share knowledge and access to others.

But the daily AI breakthroughs made me feel increasingly behind.

That pressure triggered a familiar anxiety.

Fortunately, I had experienced years ago at Flatiron School how to overcome this and thrive.

Understanding how the brain works under pressure gave me a roadmap.

🧠 The Brain’s Organizing Principle

At the NeuroLeadership Institute, I learned in the face of threat - the amygdala fires, cortisol spikes in our brains.

We get tunnel vision.

We become reactive.

Decision-making and collaboration suffer.

We enter survival mode.

This is called an away state. In an away state, even high performers underdeliver. Sometimes, a robot might do better — unbothered by emotions .

But we have a choice.

We can build the conditions to thrive in uncertainty — psychological safety, a belief that one will not be punished or humiliated for speaking up with ideas, questions, concerns, or mistakes (Dr. Amy Edmondson, The Fearless Organization).

Psychological safety shifts the brain into a toward state, where we’re open-minded, cognitively sharp, curious, creative — and far better collaborators.

What that meant for me was to prioritize, focus, and build the conditions to learn AI.

🧔🏻 The Human Variable — Psychological Safety in Action

In the midst of compressed chaos, it would’ve been easy to slip into an away state .

But at Flatiron School, we didn’t — we had Eli Bohemond

Eli didn’t shield us from challenge.

He was honest.

He didn’t have all the answers — but he made it safe to say “I don’t know” and “I need help.”

He acknowledged reality and supported us through it.

Fear was minimized, not ignored.

That safety made us sharper, and faster, because we weren’t stuck in survival mode.

That made all the difference.

Many leaders dismiss psychological safety as too soft — or too slow. But let’s be honest: it’s easy to write it off if you don’t know how to build it.

🙈 So Why Do So Many Leaders Get It Wrong?

Many leaders dismiss psychological safety as too soft — or too slow. But let’s be honest: it’s easy to write it off if you don’t know how to build it.

Blame and control often feel easier than vulnerability. But that’s the paradox: the higher the pressure, the more safety matters.

Especially in startups, where a founder’s personality often defines the culture, psychological safety must be built deliberately — for stronger teamwork, faster learning, sharper decisions, and more creative problem-solving.

Eli modeled it masterfully:

• He was transparent and courageous. He named the challenges ahead — and what he didn’t know.

• He knew our personal and professional goals, so he linked our personal growth to business goals.

• He set clear expectations.

Not all people in leadership positions are leaders. Eli was an exception.

But even without one, you can build psychological safety for yourself.

👏 PAT Yourself on the Back

When I found myself in an away state — falling behind in AI — I felt anxious.

To shift into a toward state, I used a process I call PAT:

1. Purpose → Anchors you.

🧠 When you know why you’re doing something, it calms the threat response, and gives your brain a sense of control.

For me, the purpose was clear: I wanted to learn AI, because I believe it’s a game changer — like the internet and social media were. It will reshape the future of work — my domain.

2. Asset → Reframes the discomfort.

🧠 By identifying how an experience adds value — even when it’s hard — you shift away from fear and anxiety, towards curiosity.

I saw AI as a way to save time, improve workflows, and boost creativity.

3. Tools → Leap you into action.

🧠 Structure, systems, and support reduce cognitive load, build a sense of agency, and turn intention into momentum.

For me, safety meant gathering what I needed: a learning community to stay motivated, a strong foundational course, and a project to test and apply what I was learning.

PAT helped me reduce the cognitive load and shifted me into a toward state — one fueled by confidence and curiosity.

🤝 Growth Bonding — Our Team’s Legacy

Psychological safety made our team at Flatiron resilient. We trusted each other.

At our peak, our team of six supported 150+ coaches, who in turn guided over 5,000 students — many navigating identity shifts and stepping into the unknown of tech.

That kind of transformation required real connection. And we could only create that for others because we had it within our team.

Some might call it trauma bonding.

I call it growth bonding.

In a previous post, I introduced SSCALE, my framework for building connection.

The first “S” is self awareness. The second, safety.

Our team was one of the most self-aware groups I’ve worked with. And Eli’s leadership created the conditions for us to stay in a towards state.

We built trust, resilience, and clarity — together. And we emerged stronger for it.

To this day, our leadership team of six keeps in touch.

💙 Sharing is Caring

I’m sharing my AI learning journey to create a space where it’s safe to be curious — to not know yet, to ask questions, to learn out loud.

If you’re leading a team, I hope you consider Eli’s model when you start conversations about AI adoption. Because safety isn’t just about moving slower — it’s what makes deeper learning, faster adaptation, and real connection possible.

And maybe, in reading this, you feel a little more connected — to your own journey, to your team, and to me.

👀 Next Up in SSCALE: Curiosity and Adaptability

Next week, we’ll explore how these two skills helped me connect with a bodega storeowner in Barcelona — and how that small moment challenged my assumptions and deepened my empathy. In an AI-driven world, where algorithms often reinforce our biases, curiosity and adaptability are how we keep our humanity — and stay truly connected.

Alice Shin, Product Strategy & Change Management in Learning & Development Tech who writes the blog Flllow with Alice

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If this resonated, the best thing you can do is pass it along to a colleague, a friend, or anyone who’s ever felt like work should be more than it is.

Share Human Doings / Human Beings

And if you have a story of your own, about a workplace that shaped you, a manager who saw you (or didn’t), a moment that stuck, I’d love to hear it. Anonymously, over Zoom. Reach me at humandoingshumanbeings@gmail.com.



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Jackie went on to describe a routine team meeting that made her point especially clear.

Nothing on the agenda had suggested anything unusual was coming up. Then a senior teammate publicly blamed a very junior teammate for an issue that wasn’t theirs to own. “It wasn’t subtle,” she said. “It landed hard. And everyone in the room felt it.”

“The junior teammate was thrown under the bus in a really horrific way, and they just shut down. The rest of the team went quiet, too.”

She went on. “I think there was some shock at the more senior person’s behavior. But it was also quiet watching. Everyone was waiting to see what leadership would do next.”

Jackie knew immediately this wasn’t just about a comment. It was about what the team would learn from it.

Her leader didn’t address it in the meeting or make an example out of anyone on the spot. They moved on in the moment and followed up privately with the senior teammate. They were direct about how that senior teammate’s actions weren’t up to the company’s expectations around communication. No ambiguity or hedging. “They basically were like ‘That’s not how we do things here. Our culture is kinder and more generous. You don’t get points by throwing people under the bus.’ ”

At the same time, Jackie reached out to the junior teammate, who she’d mentored in several projects. She reassured them about the team’s standards, the company’s values, and how development was handled there. She made it clear that this moment didn’t define how things ran at the company.

Then her team’s leader did one more thing that mattered for the rest of the team.

They sent a message to the full team that reinforced the culture they were trying to build and what good communication looked like in practice. It didn’t name names or rehash the situation.

“It was fast,” Jackie said. “And it was clear. Everyone knew we meant what we said about our culture.” That clarity stuck with the team, and there weren’t any more incidents like the one they experienced.

Jackie has lived through the opposite, too. A major reorg where people were reassigned or laid off, but little else was explained. Folks were moved to new teams without introductions, guidance, or a sense of where they fit. For weeks, people were trying to orient themselves, unsure who they reported to or what success looked like.

“It honestly felt like that John Travolta meme,” she said. “Everyone was looking around, trying to figure out where they were supposed to be. It was wild how much time was wasted. And how much confusion there was. It all could have been prevented.”

“Good communication,” Jackie explained, “could have created better guardrails. It could have helped people understand expectations and anticipate what was coming, even during times of change. That visibility makes it easier to stay grounded and do good work.”

The difference between her two experiences wasn’t talent or intelligence… It was care.

When I asked her about the times she felt most valued for her individual perspective at work, she told me about improvements she made to her team’s process. Not only did the improvements help her own team, but they were adopted by other teams. “It was super validating to see my work scale like that,” she said.

The best managers Jackie has worked for shared a few things in common. They were clear about expectations. They allowed room for mistakes. They didn’t try to mold people into copies of themselves. They listened, gave thoughtful guidance, and were generous with praise.

“They paid attention to how it felt to work there.”

When leaders get that right, people don’t have to spend energy protecting themselves. They can spend it doing the work.

Jackie is in her early forties and queer. She’s spent twenty years in the same industry, moving between companies of all sizes. She’s seen how leadership shifts as organizations grow…and how communication, for better or worse, shapes what it feels like to be on a team.

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If this resonated, the best thing you can do is pass it along — to a colleague, a friend, or anyone who’s ever felt like work should be more than it is.

And if you have a story of your own, about a workplace that shaped you, a manager who saw you (or didn’t), a moment that stuck, I’d love to hear it. Anonymously, over Zoom. Reach me at humandoingshumanbeings@gmail.com.

I met Eric on Substack, where we read each other’s writing. He spends his days in a tech company doing the corporate thing. His Substack, I’m sure you’re right, is where he writes under a pen name, so he can take the corporate guy mask off and publish things like “New Guy, New Rut - Figuring out why the new guy bummed me out so much” and “How to avoid your job stealing the prime of your life.”

I expected him to be loose and irreverent, the way his writing is. But the Eric I met took his time. When I asked what something felt like, he stopped to think. When I pushed a little, he went there.

Here’s our conversation, edited for length and clarity.

“You’re an interesting guy,” I started. “You have this split that a lot of us have. The person that has to perform at work, and then you have this strong internal voice that’s often at odds. But when you talk about it, you don’t sound conflicted… Are you?”

Eric paused and thought for a moment. “I have this thing that I say to customers sometimes, and it’s a sports analogy. Basically, there’s the name on the front of my shirt, which is my jersey name, right? This is the team I work for, the company…”

I nodded to the letter E on my screen. Eric agreed to meet with me virtually, but he kept his camera off. “And then there’s the name on the back of my shirt. These are two different people talking to you. So there’s the stuff I gotta say to you based on the name on the front of my shirt. And that, in my mind, is like, it’s my job. I’m here to represent that name. So I take a lot of pride in doing that. That’s what I consider a good job, making my team represented well in the world.”

“Right, got it.” I said.

“But it doesn’t stop me from knowing I have to take care of the name on the back of my shirt. I’m going to have certain relationships that run in contrast to those, or in tension with that. So there are moments I have to be like, look, me as a reasoning human person — name on the back of my shirt — I understand what you’re saying. Me as a representative and team member — name on the front of my shirt — this is how we feel. And I guess I have learned to exist with that cognitive dissonance.”

He truly didn’t seem in conflict. Maybe because he had such a clean tidy metaphor... But there had to be more to this, because his Substack publication existed as a place for him to take the “team jersey” off. I wanted to know more about that.

“Tell me a bit about why you write on Substack?”

“Having to keep a mask on at work, it’s like playing chess. I’m just thinking, what am I doing to maximize the chances I get more out of this? But if I’m in that mode all the time, I can lose track of what I actually think or feel about a situation.”

“I can get too focused on what I would do to maximize my chances of a promotion or a raise or whatever and not even ask myself ‘What do I actually like or dislike about this person?’

“I started my Substack because I needed a place I could go to just be authentic and really work things out and decide what I actually feel. I needed to try to find that true north again. What’s moral, what’s not. Not what do I have to do, but what do I want to do. And because there’s not a lot of room for that in the world — let alone at work, which is taking up so much of my life anyway — the Substack has really done a lot for me.

“I feel like authenticity can be a muscle. And if you don’t use it, you start to lose it. And I think being able to find that true north and really reinforce who I am outside of work — knowing more about myself by just exploring that — has made it easier to navigate a world where I can’t always be that way.

“Because I don’t have to sit there and wonder, okay, I’m saying this because I think it’s what I need to do for right now to be successful at work, but have I lost track of what I really think? Have I lost track of what I really feel about this? With Substack, I’ve had the opportunity to explore those scenarios and find that compass again. And that part has made it easier. It’s definitely taken weight off those hard interactions I’ve had at work.”

“This makes so much sense to me,” I paused and glanced at my list of prepped questions for Eric, but decided to follow my curiosity instead.

“What would the best possible workplace be for you? From benefits to management to leadership…what would it have in order for you to feel like you’re thriving?”

“Well, I recognize it’s not necessarily something that works for everybody, but for me — I would like to be someplace that is absolutely transparent. The good, the bad, the ugly. I want to know if we’re losing money, I want to know if we’re making money. I just want to know what the deal is from all sides…”

“It’s really hard to tell what’s going on in a lot of companies in corporate America, it’s just so opaque. It’s a lot of like reading tea leaves and wondering if you’re okay.

The guessing and wondering can waste a lot of energy, I got that.

And then Eric went into personal dynamics and culture. “And if someone thinks I’m doing a terrible job, they should just tell me. We’ll just talk about it. I thrive in that degree of honesty. Maybe it’s just I’m from the northeast, so I’m kind of used to that environment. So for me, it would all start with that.

“From there, trying to find a place that is about mutual gain. I worked for a couple of places where, and some people hated this — when you talk behind someone’s back, they say, hold on, let me get that person on the phone and so we can hash it out right now. I love that. That to me is such an essential part of a successful work culture that’s going to actually grow. Because I just feel like people get stuck and it’s easy to get complacent in an organization that isn’t adapting in a way it needs to. You end up with people in the same position having the same problems and complaining about the same shit 10 years from now that they’re dealing with today.

“And it’s one of the funny things that puts people off a little bit when they interact with me, even in my current job, because I really have a hard time with that. If people want to complain about someone else, I’m just like, look, anything I’m saying to you right now is something I would say to them, and anything I would say to them is what I would say to you. I just want to work it out with you.”

“There’s just so much opportunity to find common ground with people and recognize that you feel the same things. I just feel like it doesn’t happen enough.”

“What do you mean?” I asked.

“Like, I have a guy that I work with right now. I’m feeling really bad for him because he is being so punished right now for being so authentic. He has a very common name, right? We’ll just say his name’s Danny…”

“Danny gets on calls — these giant calls — and we had one not long after I started this job where the senior leader of our biggest enterprise customer, his name was Dan, basically the same name. So we’re getting on a call. There’s like 200 people on this call. Dan, the senior leader, is like, alright, I’m just waiting for this one other person. Danny, the person I’m referring to — the person getting punished for his authenticity — he gets on the line. He’s like, ‘Oh Dan, don’t worry. Danny’s here.’ Zero sense of being afraid to joke to a higher-up in that moment.

“He treats everyone the same — from the janitor to the CEO. And because of that, he doesn’t play that game. He doesn’t put the mask on. And for that reason, people are afraid of putting him in front of certain types of leaders and customers.

“But this dude Danny and I have crushed it. Like everywhere that he goes, he’s the mayor of that place. He’ll be talking to the person at the Dunkin’ Donuts and in the bureaucratic offices in the back and everyone’s like, oh, Danny. He’s charming. And then you come back into our internal corporate world and people are just like, oh my god, Danny put his foot in it again. He’s going to say something embarrassing. And I don’t know, I just think it’s a story that’s very reflective of one of the things that I think is the easiest to change and the most in need of change — people being more forgiving of others being real like that.”

The Danny story made me think about job security and if Eric had ever been on the wrong side of a layoff himself.

“You know, I worked for a large insurance company that ended up moving a lot of our staff to like two hours away from where it originally was in a major city, and then they had us start training a remote office — I think it was the Philippines. And of course, all along, they’re like, ‘Oh, don’t worry, we’ll never have layoffs. We’ll never have layoffs.’ And lo and behold, a year later, the whole crew is laid off.”

He clarified. “It was one of my first jobs. I had gotten the job in the mail room, moved up into some of these, like, sort of adjacent positions, doing still, like, menial sort of administrative tasks.

“And for me, I was very young at the time, so being a little bit brash — I felt this coming, and I would ask in, like, town halls, ‘Isn’t this gonna mean layoffs?’ I would never do that now, right?

“But at the time, I wasn’t as keen to how much that could negatively impact me. And obviously you get the answers you’d probably expect, which is, ‘No, of course not. You know, we’re just trying to maximize and optimize and all of the efficiencies and things that come with that.’

“So having somebody stone-faced telling me one thing and knowing intuitively that it was something else — I mean, this was one of my first real corporate job, so I knew that that was a thing, but it’s not until you really see it that you’re like, wow, that’s real. That’s actually how it is.”

“And then, you know, we moved the office to a cheaper location and a lot of the people ended up uprooting their whole lives to move to this place. And I remember kind of feeling like a fool on a pulpit at the time, trying to tell people, well, you know that we’re also training our replacements. Like, this has gotta be just a step on the way to that outcome, you know?

“I started looking for another job back in the city where we were originally working, and eventually I did move back there before the layoffs came, so I was fortunate for that. But it was tough. It was hard kind of seeing the punch coming, and seeing so many people that I cared about not getting out of the way.

“I ended up leaving right before the layoffs but I took a huge demotion to do so. I ended up jumping into a job at a company where we did legal documents. I was like, driving a truck and then going into law firms and stuff. It was just kind of out of my field. But I knew I needed to go. It was one of those, like, even if this wasn’t great, it’s better than the nothing I see coming.”

“It sounds like your inner voice was louder than what everyone around you was willing to hear,” I said.

“You know, one of the people I worked with in the mail room — he ended up being my boss in the mail room. His wife was the head of HR for the whole insurance company and he had worked there for 20 years or something. He was still convinced, ‘Oh, there’s no way they’re going to do these layoffs.’

“And I remember saying, you know, ‘Tom, like, come on man. All the writing’s on the wall.’ It was sad when the layoffs happened. I was so early in my career, it didn’t cost me nearly as much as it did a lot of these folks that were close to retirement, or had been there 15, 20 years in some instances.”

“What about today, in your current role?” I asked. “You’re doing well... You’ve been promoted a few times in a handful of years. How secure do you feel?”

“I think it’s a really tough time to feel secure,” he said. “I work in technology.”

On Substack, Eric Bourgeois is , and he publishes: I’m sure you’re right. He also collaborates with on As Per My Last Newsletter and As Per My Last Podcast.

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If this resonated, the best thing you can do is pass it along to a colleague, a friend, or anyone who’s ever felt like work should be more than it is.

And if you have a personal story, about a workplace that shaped you, a manager who saw you (or didn’t), a moment that stuck, I’d love to hear it. Anonymously, over Zoom. Reach me at humandoingshumanbeings@gmail.com.

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I was out to dinner about six months ago with several friends. One friend, Devon, had been laid off from his job that week.

He was a bit in shock, fluctuating every few minutes from “I’ll be ok” to “I should move to a less expensive place next week…” and back to “I know I’ll be ok.”

I realized, as we listened and shared stories of encouragement with him, that every single one of us had been laid off in the past 2 years. None of these layoffs were personal or a reflection of our work (as everyone’s manager stated at the time, per legal instructions); they were the result of reorganizations and company cutbacks. But each layoff hit each of us REAL hard.

“Something will come of this time,” I told him. “We can’t know what it will be but…” I paused. “This ending will bring you a shake-up and…eventually… you’ll be better for it.” I felt this. I said this. I’d had my own experience with this. But I also questioned my own words as they came out of my mouth. We can never know what a layoff will bring for another person.

When you are passionate about the idea of work (a weird passion to be afflicted with, to be sure), you can’t help but zoom out and see the patterns. I looked around the table at my friends…one had worked in education and nonprofit organizations and had been laid off twice, even with his Ivy League education and high standards. Another friend, who has worked in dermatology offices and was downsized out of her office manager role, was out of work for nearly a year. And Devon, who had worked at major health insurance companies. Each layoff was like a long-term romantic relationship break-up that had taken time to work through. We had all been on that journey to some extent, and now Devon was beginning his.

“I was unhappy there, I know,” said Devon. “But I’m still so pissed. It’s like I wanted to be the one who broke it off.”

I know I always write about how work should be more than a transaction. That employees should be seen, paid, and treated as human beings, not “human doings.” That’s my thing.

But I’ve never talked about why it’s my thing.

The truth is that every job left fingerprints on me that continued into the next one. Sometimes I was proud of the way I’d been shaped. But I also carried some scars. Jobs can do real damage and make it harder to show up fully in the next one, just like romantic relationships can.

Our jobs shape us in ways we don’t always see coming… through the culture, through the people who notice us or look right past us, and through the way it all ends.

My 25-year-old self at work was fearless. My 40-year-old self, after a layoff, felt suddenly unsure about all I had done and accomplished. I had to rebuild with the help of people who knew and loved me. I even bought a nameplate for my desk where I did job searches and applications. Instead of my name or title, it said: “I’m kind of a big deal.” I needed the laugh. I also needed the reminder.

I write because workplaces don’t have to inflict damage in the first place. I write because there is always the possibility of another way.

Several weeks ago, Devon and I met for coffee. Sitting outside, with the spring sun warming us, he seemed pretty relaxed. Still between jobs, but interviewing.

I found myself curious about the jobs and people in his past work life that had shaped him before this one. So I asked. And he let me hit “record.” These are Devon’s exact words, edited for clarity…

“Well, I was working in a call center at [company name removed], and there was this call center leader. Rarely to never had she ever said hello to me. She was professionally nice. But it was like she didn’t see me.”

“Until I started having more access to leadership, and she needed me in order to be seen by some of the VPs. And she just came right out and asked me to take a suggestion directly to Michael, a VP. Just said it. Point blank.”

“And I thought: this is a woman who never even spoke to me when I was on the calls…”

I asked him if others had built him up instead of trying to get something from him.

“Alicia saw different things in me that I didn’t even know existed. And she was high up in leadership. I worked with her on some of our company’s charity projects. And I didn’t want to let her down because I felt like she had given me a shot that not everyone gets after working in a call center for six months.”

“And I saw that as: okay, she believes in me. There’s something she’s seeing in me that I’m not believing in. So I need to maybe think a little differently…about myself.”

“I’ll never forget this one time when I walked in about eight minutes late to one of our meetings, and I was so embarrassed. There were two seats directly next to Alicia, and I walked all the way to the end of the table and sat off to the side. And she said, in front of everyone, ‘You don’t have to be afraid to sit next to me. Ever again.’ Lesson learned.”

I could hear the gratitude in his voice as he talked.

“She picked up on this drive, this hustle, in me, and she molded it. When I started there, I didn’t know how to express it or go about it. And she just... molded it.”

I loved how Devon described this relationship with Alicia. He saw her seeing him — and growing him into a team member who was even more confident.

Devon sipped his coffee and looked toward a noisy flock of birds that had just taken flight from a tree nearby.

“These stories are so interesting when you tell them back-to-back like that,” I said.

“Well, Alicia really saw me, and how I could potentially be successful and good for any company in any future role. The call center lady didn’t see me at all until I was useful to her.”

Mic drop. That was the major truth under all of it.

“And as I grew, I was afforded many opportunities. I’ve learned through the experiences that I’ve had since that time. One, that I’m valuable. Two, that I should believe in my own abilities. Three, it helps to know people. And four, success is also a double-edged sword. Because there’s gonna be knives out for you, and you have to be able to see.”

“See what?” I asked.

“It taught me to be able to see through that bullshit. That fakeness at work. I’m able to read people on a corporate level now. Whereas before, I wasn’t. Before, I thought everyone was just a friend.”

I drove home thinking about how much he’d learned — about power, about who sees you and who doesn’t, and about what kind of person he wanted to be on the other side of all of it.

If you know Studs Terkel, you know that he created an amazing book in the 70s called Working. It’s a book of oral histories from people talking about their jobs…everything from stone mason to barber to janitor to ad executive. In the introduction, he tells a story that has been haunting me as I write this.

A college president decided to take a sabbatical. Rather than vacation or work on a book, he wanted to try out a variety of “menial jobs.” He did fine in most of them, but in one job as a porter-dishwasher, he was actually fired. Not laid off. Fired.

“I’d never been fired and I’d never been unemployed,” he said. And he was devastated.

“For three days, I walked the streets. Though I had a bank account, though my children’s tuition was paid, though I had a salary and a job waiting for me back in Haverford, I was demoralized. I had an inkling of how professionals my age feel when they lose their job and their confidence begins to sink.”

He eventually finished his sabbatical as a ditch-digger, then returned to his role as college president — and later became chairman of the Federal Reserve Bank of Philadelphia. He described white-collar work as surreal after his experience. I’m guessing he returned with newfound empathy for people who grind versus people who decide.

Studs Terkel knew that stories were data. They provided almost photographic proof of what working in the U.S. was like. And now, with my Inside Voices series, I’m attempting to do the same. The anonymous stories you share with me will live in this newsletter and my in-progress book as part of a bigger picture about working in the U.S. today — and the way our past jobs have shaped us.

It’s all in service of the idea that stories are the only way to make people who lead truly understand how their power and decisions impact their employees. And that a mindful, conscious business can have ripple effects that extend beyond each employee’s life to their family, their community, and eventually the world.

I don’t know if these stories will be read by the people who need them most. But I’ll keep collecting and keep shining a light. Not because it’s easy, but because I have a hope that things can be better. I’m not sure they will be. But I have to do what I can to try.

If you’re interested in sharing an anonymous story with me, please reach out. Email me at humandoingshumanbeings@gmail.com. Let’s set up a Zoom chat so I can hear about how your work life has shaped who you are today.

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“Across companies that had launched formal culture initiatives since 2022, 72% showed no meaningful improvement in employee trust, engagement, or retention one year later.”
- Harvard Business Review

That’s a wild statistic... So can we agree that companies have a blind spot when it comes to how to improve culture? And through culture—engagement? And through engagement—performance?

In my experience, it all starts with the vaunted employee engagement survey.

Here’s what happens:

• Run engagement survey

• Engagement scores are low

• Divide and conquer—task your corporate teams to address their relevant metrics (example: Talent Development asked to improve sentiment around career growth)

• Spend the year building and socializing solutions for executive approvals

• Develop your communications plan for said solutions (often all landing on Internal Comms’ plate around the same time)

• Launch solutions (usually new apps, platforms, guides, or intranets)

• Frontline adoption is underwhelming

• Repeat

We named this The Survey Trap (clever, I know).

But like every good trap, it doesn’t feel like a trap. It feels like human-centric leadership.

So why doesn’t it work?

We have another clever name—Experience Blindness.

Engagement surveys tell you what your teams think, but they don’t tell you why.

And for whatever reason (I have theories but I’m not a psychologist so I won’t subject you to them), this assumption is made over and over again, by most cdepartments, in most organizations:

“It’s an awareness issue. We have to communicate [your thing] more/better.”

And in the six+ years I’ve been fortunate enough to work with companies eager to escape the survey trap, and in the hundreds of hours I’ve spent talking directly with frontline leaders—it’s almost never an awareness issue.

It’s an experience one.

It’s not that they don’t know career development happens at your company.

It’s that they don’t believe it’s accessible to them because they don’t experience or see it firsthand.

It’s not that they don’t know you have annual rewards and recognition programs.

It’s that they don’t feel recognized day-to-day.

It’s not that they haven’t read your core values.

It’s that 20 practices and policies they experience every shift contradicts them.

“59% [of employees] told us that senior leadership actions contradict stated values at least weekly” —Harvard Business Review

That’s Experience Blindness.

This is so common. But it’s not normal.

It’s not normal in any other industry or function to pour endless time and money into a solution when you don’t really understand the problem.

And when you don’t understand the problem, what was meant to signal we see you ends up proving the opposite: we don’t understand what it’s actually like to work here.

Over the years this tireless activity creates engagement bloat & fatigue—a costly buildup of disconnected efforts that overwhelm teams, stall performance, and breed organizational cynicism.

Programs aren’t unimportant. But they don’t matter if the basics aren’t there. Employees want to finish their shift without systems that set them up to fail, policies that imply mistrust, or contradictory priorities.

There’s got to be a better way.

If culture is what happens in the day-to-day, then improvements have to impact that.

Borrow our framework and focus on the three “channels” that matter most:

• Managers: 70% of the variance in team engagement and performance is determined solely by the manager.

• Operations: Often overlooked but this is Where Promises are Kept (or Broken) Daily

• Then Comms & Info Hubs: Reinforcing the experience with consistent, unified messaging.

Put each of the above in a column and for each value or brand promise, ask yourself:

• What daily behaviours do managers need to carry out for this to be true?

• What needs to be operationally true to achieve this perception?

• How do our communications support this directly and indirectly?

Important note: do that all the way up the ladder!

“69% of middle managers said they felt solely responsible for delivering on cultural commitments. Yet only 14% believed senior leaders were modeling those same behaviors themselves” —Harvard Business Review

There can’t be any broken links in that chain from Frontline Manager to CEO.

The Outcome

When you fix the day-to-day systems, all the things you’ve been trying to do with campaigns finally start working:

• Recognition feels real, not performative.

• Employer brand promises actually line up with employee experience and can actually be used by talent attraction.

• People stay long enough to grow in the company.

You turn the trap into self-reinforcing system that improves retention, reduces friction, and turns daily work into a driver of profit—not a risk to it.

Engaged teams deliver:

• 17% higher sales

• 13% higher productivity

• 10% higher customer loyalty

• 78% lower absenteeism

• 26% lower shrinkage

And those are wild stats we can all get behind.

Bekki Cait is the founder of CATO Creative. Connect with her on LinkedIn.

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If this resonated, the best thing you can do is pass it along — to a colleague, a friend, or anyone who’s ever felt like work should be more than it is.

Share Human Doings / Human Beings

And if you have a story of your own, about a workplace that shaped you, a manager who saw you (or didn’t), a moment that stuck, I’d love to hear it. Anonymously, over Zoom. Reach me at humandoingshumanbeings@gmail.com.

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One of the most formative parts of my childhood was a twice-a-year tradition my family kept.

My parents, who were free-spirited and music-loving people, would pack up the car and take us to a folk and bluegrass festival in the mountains. For four days, we camped in this pop-up town in the trees, complete with music stages, food stands, a general store, and a pirate radio station that aired music from the main stage, announcements, and storytelling. As you walked around, every campsite had that radio station playing in the background.

The daily radio host, who looked like he rode a Harley and spoke like a sage, told simple, grounding stories. “We don’t rush. We share resources. We help each other out.” His voice gave shape to the culture. It turned a gathering into a community. Even cautious parents like mine felt safe letting their kids roam. I’d run barefoot, swim in the lake, sing harmonies at jam sessions, and feel part of something joyful, expressive, and shared. It was a Technicolor world, so different from home (a tidy little suburb outside of San Francisco with very uniform beige houses). My parents loved the feeling of safety they felt there, except we didn’t quite fit in, and our colorful house paint triggered a slew of neighborhood complaint letters.

That festival showed me what a living, temporary culture can feel like when it’s built on shared values, generosity, and rhythm. It also made returning to “regular life” feel stark. My middle school years were marked by a cluster of student suicides. Our town looked very polished on the outside, but carried a quiet undercurrent of disconnection and grief. That contrast really sharpened my instincts around what gets said, what stays silent, and how community norms can shape people.

Today, I work at the intersection of internal communications and employee experience. That idea of shared, temporary culture still lives in the back of my mind. A workplace environment (including its leaders, norms, and how employees understand their roles) has enormous influence on a person’s productivity and even their quality of life. When culture is done well, employees feel seen and valued, and they are more engaged in bringing a company’s vision to life. They can even help expand what’s possible for the business.

Read my full interview on Authority Magazine.

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If this resonated, the best thing you can do is pass it along to a colleague, a friend, or anyone who’s ever felt like work should be more than it is.

Share Human Doings / Human Beings

And if you have a story of your own, about a workplace that shaped you, a manager who saw you (or didn’t), a moment that stuck, I’d love to hear it. Anonymously, over Zoom. Reach me at humandoingshumanbeings@gmail.com.

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The story below came from Marisol, a woman in her mid-thirties who has worked in tech sales for many years. She shared this with me in writing, with permission to use it anonymously (her name has been changed). All the words are hers, edited lightly for clarity.

Being trusted changes how you show up

Recently, my manager handed me a big project. I assumed someone with more experience would take it, but she had no doubt I could handle it. I gave it my best shot. Later, I found out my work had been shared with the CEO and the board, and they praised it.

That felt amazing, but what mattered more was knowing she had my back the whole time. I never felt like I was walking a tightrope alone. When your manager believes in you and actually supports you, it’s easier to take risks and do great work.

She’s actually a manager I returned to because I remembered what it felt like to be led by someone who listens, makes time, and treats support as a priority.

She doesn’t micromanage. She doesn’t act like she’s above the work. It feels like you’re in it with her, working through the process side by side. That kind of leadership sticks with you. Once you’ve experienced it, you don’t want to settle for anything less.

When communication breaks down, trust goes with it

At a tech startup I worked for, I was on a tiny sales team working for a CEO who had a really hard time delegating or empowering her team to work together to make a bigger impact. She was under a lot of pressure, and very anxious, so she got into micro-directing, pushing, causing confusion by meeting with leads outside of the sales appointments we’d already arranged. It was bizarre. A lot of zigging and zagging. A lot of emails and calls. Constant pings. Constant second-guessing. One day I counted: 21 emails and 7 calls from her in seven hours. “Why this?” “Why that?” “Did you do this?” “Where are the notes?” It was nonstop. And then blame when any sale didn’t work out. She had zero awareness that her panic spiral was destabilizing the team. It freaked everyone out and made it nearly impossible to focus or perform.

On top of it, she made two new hires to help with operations and improving the sales funnel process, but then told us (sales team) not to worry about collaborating with them, and not to connect with them, or ask them questions. It’s hard to do your job well when the person leading your funnel is a black box and leadership won’t let you ask questions. It felt weird and isolating. I kept wondering why I was being left out.

It was by far one of the most stressful jobs I’ve had. When the stress was at its worst, I was running on fumes, my brain would randomly go into “freeze mode,” and I literally could only just stare at the screen. By the time I left, I was losing hair from the stress. I’d started drinking buckets of wine on the weekends just to cope. (Spoiler: it didn’t help.)

When I finally quit, I was beyond burned out. I was crispy. I didn’t have another job lined up but I knew the situation was spiraling. Everyone at the company had absorbed the CEO’s panic. There was no room to think. I couldn’t work that way or live that way anymore. I went without work for four months while I looked for another job. My husband and I tightened our belts and had to borrow money just to make it through. I prioritized getting back to better health. I quit drinking entirely, started sleeping a full 8 hours a night again, began to exercise, and I got back into therapy.

But the biggest shift actually came from finding a role at a company where I’m actually supported. My manager checks in, communicates clearly, and makes it clear she would never want any of us to operate in survival mode. I still put in long hours when we have a deadline or when we need “all hands on deck” for a major effort, but I can now see how much more successful I am when I work for a smart-and-kind person with realistic, human expectations.

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If this resonated, the best thing you can do is pass it along to a colleague, a friend, or anyone who’s ever felt like work should be more than it is.

Share Human Doings / Human Beings

And if you have a personal story, about a workplace that shaped you, a manager who saw you (or didn’t), a moment that stuck, I’d love to hear it. Anonymously, over Zoom. Reach me at humandoingshumanbeings@gmail.com.

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Let’s get into it.

Studs Terkel did it in 1974. He sat down with hundreds of ordinary Americans (stone masons, waitresses, corporate executives, janitors) and asked them what it was like to do what they did every day. The result was Working, one of the most important books ever written about American life.

He knew something that data dashboards don’t: that stories are the only way to truly understand what it feels like to be a person inside a system.

I’m doing a version of that. Smaller, more focused, and specific to this moment, because this moment deserves to be documented. And I hope that the stories might be persuasive to people who make decisions about their workplaces and how their employees experience them.

We are living through a profound shift in how work is designed, valued, and experienced. AI is accelerating everything. Trust between employers and employees is eroding. Layoffs are being announced alongside record profits. And the people living inside all of this (doing the work, managing teams, trying to hold their humanity together through reorgs and return-to-office mandates and engagement surveys that go nowhere)… their voices are largely missing from the conversation.

I want to change that, by listening to and sharing one anonymous story at a time.

Here’s what I’m looking for:

I want to meet with you over Zoom and hear about the jobs that shaped you. The managers who saw you, or didn’t. The moments when something shifted. The workplace that left a mark, good or hard or both.

Your stories will become an anonymous part of the Inside Voices series, which lives in this publication and in my in-progress book about the state of work in America today.

You just need to have worked somewhere that left a mark on you. This is not about trashing companies or former employers by name. This is about mapping patterns and sharing what we find.

If that’s you, reach out. I’d love to hear from you.

humandoingshumanbeings@gmail.com

The story below came from a leader I know—let’s call him Miles.

He’s in his mid-forties and currently holds a C-level role at a global company. He shared these memories with me during a conversation about what great workplaces actually feel like. All the words are his, lightly edited for clarity.

Early Career Curiosity

I’m trained as a scientist and I’m very curious. In one of my early career roles as a scientist developing products [at a global household products company], I wanted to know about all of the other parts of the business. I had a marketing partner—her name is Jillian, and we’re still friends today—and we worked together on launching a whole line of products.

What I really appreciated about Jillian was that she recognized that I was very interested in a lot of the consumer research and the marketing. I had all these questions I was really curious about: how do you decide what to name it? How do you decide what words to put on the bottle? Why did you decide to go this or that direction with the marketing?

And so she (in a way that was not normal at that company) went to her boss and was like, “Hey, I want to bring Miles to the focus groups. I want to fly him to meet with consumers two states away. I want him to meet with our creative directors. I want him involved.”

She expanded my role on the team beyond what was typical for someone in my position because of my interest. I was able to bring a unique perspective. I could translate science in a way that a lot of people found useful. But it was also very personally fulfilling for me, and really formative for my career.

Now I try to do that with people who work for me. If I see somebody who’s interested in something, and I have the power and the ability to help get them exposure to that, I do it. Because I think the most important thing for any employee is to be really engaged in their work. I’d rather take someone who’s engaged than someone who’s good—because an engaged person is really going to try. Honestly, the work that I do isn’t really rocket science. So engagement, and being interested in the work, is actually really important to me as a manager.

That experience was really special for me and was part of what made me want to pursue an MBA several years later. I always appreciated Jillian for doing that.

The Manager Who Told Me the Truth

When I got hired at [company], I had this manager for a while, who was later in his career and he had this very professorial vibe—and we really got along.

What was so incredible about him was, first, he made me feel so comfortable because he had such a good grasp of what mattered in life and what didn’t. I’d be stressing about an upset customer or something, and he’d just say, “It doesn’t matter enough to get upset over it,” like to help me keep perspective.

He just saw so much that he kind of knew what mattered and what didn’t (like check-box tasks that frankly didn’t really need much attention), and he taught me a lot about perspective. I’d be like, “Hey, can I have $1,000 to go to this conference?” And he’d say, “Yeah, Miles, of course. It’s $1,000. It’s no big deal.” Like he never blinked, in fact, he almost waved the question away.

Every other manager I’d ever worked for would’ve said, “Oh my God, we need 12 levels of approval,” blah blah blah. And these are multi-billion-dollar companies I’ve worked at. But he was like, “Nobody cares. If you want to spend $5,000 and go to a conference, go to the conference.”

It wasn’t that he was flippant with money—he just knew that nobody cared. And he didn’t need to create some kind of drama in the asking. I really liked that.

The other thing I really, really liked was that he was the first manager who kind of pulled me aside and told me how it really works. He put it like this: “you want to be noticed, you want to get promoted, you want to rise in your career—but here’s how it works.”

He said, “We have calibration meetings a couple times a year where people managers all talk about people on their teams, as part of succession planning and gearing up for making promotions. And we only talk about a few people. If we’re not talking about you, you’re not going to advance.”

Of course, that’s shitty to hear—because it means most people aren’t being talked about, and most people aren’t going anywhere. But it’s the reality of the world. He and I continued working together and I was eventually promoted there. I learned how it really worked, though. Relationships with your supervisor are everything.

The people above him didn’t really know me. I mean, they kind of knew me, but not really. They just listened to him. And if he said I was the one, then I was the one. He just said, “This guy’s great, we need to promote him, we need to get him these experiences, we need to put him in this special program for future leaders.” And that’s what happened.

It was kind of shocking, honestly. On one hand, it took what looked like a meritocracy and made it into: if your boss isn’t advocating for you in a room full of other people, you’re going to have a very hard time progressing. Learning that was a wake-up call and one of the most valuable lessons I’ve carried with me.

I felt like I was given information that helped me see advancing at work so differently. I shared that insight with other people whenever I could.

Putting it into practice

In my next company, they assigned me a group that had been pulled together from different teams—it was a brand new group and there was a woman who was going to start reporting to me, named Priya. She had been at [company] for eight years. She started as a temp—which is common—and got hired full-time after a year. She had moved up a level, but she was making the same amount of money I made at my first job—doing the same kind of work, 10 or 12 years later. She wasn’t being paid fairly. She was good. She was dynamic. Tons of energy.

When I went to my first calibration meeting, I talked about promoting her, but the people above me didn’t really know who she was, so they pushed back. It reminded me again about how things work in these massive companies. You have to introduce the person’s name to the people above you to get them used to the idea that your team member is exceptional. Then you have to give that person the opportunity to shine so that the higher-ups could feel ok giving you the green light to make the promotion.

Since I’d already brought her name up, I assigned her to a high-visibility project. I had her mentor others. I gave her exposure. And of course she nailed every project and assignment. I never had any doubts because she was always great. I was able to promote her, and very quickly, her career started taking giant steps forward because someone above her advocated for her.

I think that young people, who are early in their careers sometimes think that work is like school, and everyone’s getting graded. The people with “top-marks” or perfect scores get to advance to the next grade. But that’s not really it, from where I sit. Success at work is not about being perfect or never making a mistake.

In regular corporate America-type jobs, if your boss doesn’t like you or feel connected to you, you’re going to stall out. And that can happen at any time in your career. As someone who manages teams and mentors early-career professionals, I always try to be aware of who is the quiet—maybe overlooked—member of the team. I look at how long it’s been since they had a raise or promotion. I talk with them about their career goals and let them explore projects that will help them get there, because that’s what helped me.

I know not everyone gets a manager like I had, or someone ready to advocate for them. That’s why I try to be that person now.

I didn’t rise in my career just because I was good at my work. I rose because someone believed in me. That’s the part we don’t talk about enough. So I talk about it as much as I can role model it, and try to make it normal for other managers who don’t already think that way.

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If this resonated, the best thing you can do is pass it along to a colleague, a friend, or anyone who’s ever felt like work should be more than it is.

Share Human Doings / Human Beings

And if you have a personal story, about a workplace that shaped you, a manager who saw you (or didn’t), a moment that stuck, I’d love to hear it. Anonymously, over Zoom. Reach me at humandoingshumanbeings@gmail.com.

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