In this 4-part compilation of clips on interviewing, Molly shares insights to help people on both sides of the interview table. For Molly, hiring someone and being hired require the same skill in many ways: getting to know a person deeply enough to know if the fit is real.

For interviewers, Molly walks through how she runs a “motivation interview” to get past a candidate’s resume to what actually drives them and how she vets for hard-to-measure traits like “comfort with ambiguity”. And for those being interviewed, Molly describes the green flag she would advise looking for and the importance of avoiding a squishy yes.

P.S. If you liked this video, you may also appreciate Molly’s piece on Fit.

For Interviewers:

Molly’s Approach to the Motivation Interview

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With Amazon Music, you can discover the WorkLife episodes most relevant to you. Listen to WorkLife on Amazon Music.

I don’t have many work regrets. I’m actually not a big believer in the word “regret” — I think every experience gets you to where you are now, and you can learn something from basically anything if you’re willing to look at it honestly.

But when I look back over my career, the regrets I do have almost all come from the same place: how I treated someone, or how I behaved, when things were hard.

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There was a phase at Facebook on a project I was on where things got very political. It was a clash between various teams, a power vacuum, and a frantic energy in general. I definitely let it get the best of me. I have a memory of yelling during a meeting, which for those of you who don’t know me, is not something I do. I also have a memory of treating some folks with a lot of arrogance and dismissiveness, among other things. In short, I’m really not proud of how I handled it.

What situations like that taught me, at least in retrospect, is that when there’s conflict, or things get political, you want to be able to look back — regardless of the outcome — and say “I did my best.” That phrase implies a bunch of stuff. You’re accepting that you can’t control the situation or the outcome. You’re accepting that you can’t control other people’s behavior. All you can control is what you do and how you comport yourself in a hard moment. You want to look back and feel mostly proud of how you handled yourself, regardless of how things turned out.

I talked to Don Faul about this on the most recent episode of WorkLife. Don is the former CEO of CrossFit, former operations exec at Pinterest, Facebook, and Google, and a great friend of mine. Don started his career in the Marines, and I wanted to know what leading under real pressure — the kind where people might die — taught him about this.

Threaded through every story he told was some version of the same conclusion: you can’t control the circumstances, but you can control how you respond.

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He told me a story that’s basically the same shape as mine, just wearing a different uniform. Don was planning a mission with a commanding officer he didn’t respect — they disagreed regularly, about tactics and about values. In one specific moment, he found himself thinking, I’m going to fight him on this. And then, almost as quickly: what am I doing? I’m making this worse. He caught himself, and instead of asking “how do I win this,” he asked, “what can I do to create the best possible outcome?”

Same issue as mine, in a lot of ways — except he caught it in the moment, and I didn’t. The disagreement with his commander was real, and it stayed real. He couldn’t change that. The only thing he could control was whether his ego was about to turn a bad day into a worse one.

Don got an early, pretty blunt version of this training at the Naval Academy. Freshmen are only allowed four responses when a superior addresses them: yes sir, no sir, I’ll find out sir, no excuse sir. That’s it. No “well, actually.” No story about why. Don said he’d spent his whole life up to that point explaining why things weren’t his fault, and those rules just took the excuse off the table. It’s one of the lessons from the Marines that’s translated most directly into his business leadership: you find a way, or you make one.

Don’s had to practice this — by his own account, thousands of times — until it became something closer to instinct. You don’t get to choose what happens to you; you get to choose how you respond. And I can vouch for the fact that, despite going through lots of incredibly challenging moments in business (where I might be curled up in a ball on the floor), he’s one of the most even-keeled people I’ve spent time with.

The other thing he said about how he manages to stay calm in the face of chaos: adversity is about perspective. For some reason, that sentence has stuck with me since. A couple of years ago, I was leading a company through a really tough phase, and someone mentioned that I didn’t seem stressed about it. It made me stop and reflect. Similar to what Don said — I think in that moment, all my prior experience had already told me that whatever we were going through was going to be fine, one way or another. It wasn’t actually that bad. No one’s life was on the line.

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That’s the thing about perspective — it’s not a mood or a personality trait. It’s something you build, usually by going through hard things and finding out you survived it. You also typically figure out that none of it was quite as bad or important as you thought it was. I clearly hadn’t built enough of it yet during that political mess at Facebook. I have more of it now. I’ve been through enough bad moments to know that most of what feels unbearable in the moment is survivable, and most of what I’ll actually regret has nothing to do with how things turned out — it’s about whether I liked who I was while it was happening.

Don and I also recorded a second episode together, because there’s one more story from his time at Facebook I wanted him to tell in full. It’ll be live next week. Don was layered — his job was split in half — and I asked him to walk through what that actually felt like, how he responded, and now that he’s been on the other side of it too, how to handle it well if you’re the one doing the layering. Not surprisingly, one of the things he talks about in that episode is how emotional the experience was for him, but how he realized that the only thing he could control – given that it wasn’t his decision – was how he responded.

If you’d like to hear some thoughts about layering before the episode next week, take a look at this article I wrote recently.

You can listen to the full WorkLife episode anywhere you get your podcasts or watch it on YouTube.

What else?

• If this resonates with you, here are things you can do next:

  • Subscribe to Lessons to get new posts. I post at least 2X per month for all, and paid subscribers also get access to video courses and the full library of content.

  • Listen to the WorkLife podcast, where I talk to brilliant leaders and builders to untangle the messy, human side of work.

  • Follow me on LinkedIn, where I share more tools, thoughts, and a little of the day-to-day chaos.

  • And if you’re a leader looking for a community of peers to lean on and learn from, come find out more about Glue Club over here.

A month ago, a friend of mine was working through something with a member of his team. He’s a CEO, and this was a strategic decision – should they shut down this business line and use the resources to launch something new? The person on his team was senior and fully responsible for the decision – whether to shut down, how to iterate, the direction and scope of whatever came next. This employee sent my friend a slide deck explaining what the new business could look like. The email had no context, and the deck was very clearly AI-generated – it only reflected some of what the two of them had actually discussed in previous meetings. Left with a lot of questions, my friend sent back a long email full of feedback.

A couple of days later, an email back in response. Again, zero context – just “how about this?” with a link to a completely different slide deck, pitching a completely different business. No explanation of how he’d addressed the earlier feedback, or why this concept was better. No way to follow the logical thread that had gotten them here. It was like starting the conversation over from zero.

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Now, all of us who work with AI know what happened here: this employee had a conversation with AI based on the previous meetings and discussions about the business problem. He asked the model, whichever one it was, to help him come up with an idea and generate a slide deck based on whatever parameters he fed it. Then, when he got feedback from his CEO, he fed that feedback into the same conversation and it spit back a new concept. Who knows how much he iterated or went back and forth with our robot friends on either deck, but what came out was a pretty useless waste of time for everyone involved, because it lacked judgment, context, and the connective tissue that makes these conversations move forward.

As Hilary Gridley pointed out recently, in the last year, the problem has moved from “how do I get people on my team using AI?” to “how do I get people on my team to stop using AI so badly??”

A lot has been written about the concept of AI slop, but I want to talk about this workflow and ones like it because I think under the label “AI slop,” there are a lot of different problems. I have taken to calling this one the “Lazy Fucking Interns” problem.

You know that behavior that used to drive you nuts when you were training interns? You’d sit an intern down, give them all the context you thought they needed and pretty clear instructions (in your mind, anyway) of what you needed, and then ask them to generate a first draft of a report or an email or a project. Once they were done, they’d send you an email that was one sentence – the equivalent of “here you go” with no further explanation – and attach a first draft that was missing detail and context, hadn’t been thought through all the way, and generally didn’t “show their work.” One of the hardest things about coaching interns, for me anyway, was explaining the gap between their definition of “good” and mine, their definition of “done” and mine. Interns often think the point is completing the project, not solving the larger problem. Progress for the sake of progress. Sometimes, it seems, they don’t even grasp what the larger problem is. Teaching someone judgment is exhausting. Sometimes the gap was so big I didn’t even know where to start with coaching them.

That same gap is exactly what’s playing out right now in organizations everywhere. There are essentially two entangled problems coming together to create a lot of stupid behavior and wasted time.

The first is that people are treating AI chatbots and agents as if they are highly skilled senior employees when, in most cases, they aren’t. They’re interns. Often sycophantic and kinda lazy ones.

AI’s job isn’t to think critically about what’s right at the highest level – it’s to deliver an answer. If that answer gets treated without a critical eye, without human judgment, the Lazy Intern vibes just get passed along. Just like interns, AI is great at useless productivity – shipping something regardless of whether it actually answers the question or meets any bar for quality. When someone copies and pastes the highly-confident-and-very-pretty-but-full-of-holes deck or email or doc that AI generated, you get a chain of Lazy Intern work.

And that’s exactly the second problem: somehow AI is making smart, skilled, senior people lazier. I can’t quite tell if it’s a pass-through effect, or if working with such a confident, seemingly smart intern like Claude or ChatGPT just makes us feel smart, so we’ve stopped asking questions. Either way, the downstream effect is that behavior that never would have been acceptable before – passing your manager a report an intern wrote with no significant editing or vetting – is somehow becoming commonplace.

The Lazy Intern pattern we’ve been talking about a lot in Glue Club is senior people sending over work with very little context that’s clearly AI-generated, and then, when you start asking questions about it, immediately naming or blaming the robots. “Oh, I didn’t write that section, that was Claude” or “Yeah, ChatGPT put that in.” As if there’s an autonomous third person in the room who can take the fall for being thoughtless, or… lazy.

We are managing Lazy Interns, and we are becoming Lazy Interns. Lazy Fucking Interns everywhere!

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Ok so how do we combat this Lazy Intern problem? Some ideas:

1. Treat AI like an intern, and train your team to do the same. Interns need to be MANAGED – lots of onboarding, context, coaching, oversight, feedback, and vetting to be useful. Prompting better and being critical of the quick answers your robot gives you will help, but it’s actually much deeper than that. The skills of management just got a lot more important, because now they apply to robots too. Make sure everyone on your team understands this dynamic. That includes ICs, not just managers.

2. Create a “show your work” rule with every artifact generated. We’ve started doing this on our team, and it’s been really helpful. So has my CEO friend. It was getting to a place where I just assumed that docs or dashboards or slides were AI-generated without much oversight, which caused me to react and respond in a different way. Now, on my team, when we send each other things, we explain what we used AI for and how we editorialized it.

3. Make a rule that the human is accountable for the work, regardless of what the AI contributed. Someone in Glue Club flagged this, and I think this might be the most important thing. Part of the Lazy Intern madness is the excuse that “Claude wrote that.” If you create something and choose to send it to me, I’m holding you accountable for it, however you made it. If it’s shitty, that’s on you.

4. All of this matters EXTRA if you’re in a senior leadership role (looking at you, CEOs). One of the lessons every leader learns the hard way is that people hang on every word you say. That means being thoughtful about every word that goes out under your name. If you have a habit of copy-pasting AI output without heavy vetting, change now. Sending out lazy intern work at that level does two things at once: it sets an example that this behavior is fine, and it causes real confusion, sometimes real chaos.

5. Make expectations like this a part of your definition of performance. For my friend, he now treats employees differently if they behave like Lazy Interns. It changes how he delegates work and which work he delegates, and he’s been explicit about that. That isn’t new – low-quality work has never gotten you promoted in the past – but it needs to be more explicit in the age of AI.

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One of my biggest theories about AI, at least the way most people are using it right now, is that it isn’t creating new problems at work so much as multiplying the ones that are already there. Lack of clarity becomes ten times more expensive when hundreds of agents are following unclear instructions. Weak management, poor judgment, and sloppy communication scale faster. AI isn’t inventing these failures; it’s accelerating them. Everything I wrote about in the Waterline Model just gets worse and faster with AI in the loop.

The organizations that get the most out of AI will be the ones that are best at the deeply human parts of work: defining success, setting context, exercising judgment, giving feedback, and producing work that someone else can actually build on. The management skills we’ve spent decades learning to use with people now apply to robots too.

What else?

• If this resonates with you, here are things you can do next:

  • Subscribe to Lessons to get new posts. I post at least 2X per month for all, and paid subscribers also get access to video courses and the full library of content.

  • Listen to the WorkLife podcast, where I talk to brilliant leaders and builders to untangle the messy, human side of work.

  • Follow me on LinkedIn, where I share more tools, thoughts, and a little of the day-to-day chaos.

  • And if you’re a leader looking for a community of peers to lean on and learn from, come find out more about Glue Club over here.

With Amazon Music, you can discover the WorkLife episodes most relevant to you. Listen to WorkLife on Amazon Music.

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One of the questions I get asked a lot (because of my TED talk and all the writing I’ve done on taking risks) is “how do you know if it’s a bad idea to take a risk?”

It’s such a good question, because one of the predominant feelings when you’re staring at something that feels risky is fear. It’s the emotion that frequently causes people to not take risks — fear of failing, fear of feeling incompetent, fear of leaving safety or surety. And part of my point when I talk to people is that to get good at taking risks, you need to start seeing fear as a green light. If your body or your brain is saying “I’m scared, I can’t do this,” that’s a sign to run toward it, not away from it. One of the biggest benefits of taking risks is proving to yourself that you’re capable of much more than you know – of overcoming fear.

But how do you know if the fear is a different kind of fear? One that’s telling you this is actually a bad idea?

Because the truth is, there’s a type of fear that will make you bad …

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With Amazon Music, you can discover the WorkLife episodes most relevant to you. Listen to WorkLife on Amazon Music.

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You can listen to the full WorkLife episode anywhere you get your podcasts or watch it on YouTube.

I’ve made most of the decisions in my career based on intuition. I listened to thoughts and advice from the people around me, but in the end, I just went with my gut. And luckily, for many years, they turned out to be great decisions. It really made me trust my gut and also trust myself. I got to the middle of my career and felt like I had an almost infallible sense of the decisions that were right for me.

But then I made a career decision that turned out to be a mistake.

On paper, it looked like a great job, but fundamentally, for many reasons, it was the wrong one for me. Making that decision based on what I thought were the same instincts that had previously felt infallible, only to have it be wrong, was one of the most confusing moments I’ve ever had in my career. I’d finally gotten what I’d always thought I wanted, and it made me miserable. How did I end up here? And why?

I got lost.

Not burnt out. Not overwhelmed. Lost.

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I was literally crying at my desk most Mondays on this job — a sure sign it wasn’t right — and I felt completely paralyzed. I had no idea how to move forward. I was completely disoriented, and taking any step felt terrifying because I no longer trusted myself or my instincts. Fundamentally, I felt like I really lost my sense of who I was, not just what work was right for me.

The thing about getting lost in your career is that it is very easy to feel like you are the only person who has ever felt this way. Everyone seems to be striding forward confidently, and you are just stuck in a mud puddle, possibly full of quicksand. It is a very lonely feeling. And that loneliness can compound the sense of stuckness.

I did a lot of work to get myself out of that stuck moment. It honestly took me years. But it wasn’t until I met Ify Walker that I shed the loneliness, embarrassment, and confusion that came with what I experienced. Because she had a name for it! Ify calls it “The Work Twisties.”

Now, a moment to just say that Ify is one of those people you meet and immediately feel seen by. She makes you feel calmer. In our first conversation, I felt like I’d met not only a lifelong friend but also someone I could learn from.

She described her own experience of getting lost in her career using a gymnastics concept made famous by Simone Biles at the Tokyo Olympics: the twisties, where a gymnast loses their sense of place and position in the air. Simone said her mind and body had disconnected, and she felt she couldn’t trust either. That’s the twisties: not a lack of skill, but a disconnect between what you know how to do and your ability to actually do it. For gymnasts, it’s incredibly dangerous.

Hearing Ify describe “The Work Twisties” and her own experience of losing herself after her father died made me understand my own experience better. Ify’s dad was the person who told her to go play football when her mom said no. He was the one who made her feel like the rules didn’t fully apply to her — or that she could figure out whatever the rules were. When he died, she didn’t just lose him; she lost her compass.

Our triggers were completely different, but our experience of feeling lost was incredibly similar. Ify said that for most of her life, purpose, place, and protection had just come to her. Just like I was able to make intuitive decisions without overthinking, Ify didn’t have to look for her source of conviction or confidence. And then all of a sudden, she did. She had to rebuild her own sense of safety and clarity rather than inherit it.

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I invited Ify to come on the WorkLife podcast to talk about “The Work Twisties” because hearing her story was so helpful to me. Giving my disorienting experience a name and language made me feel more sane. Realizing that lots of other people go through this made me feel less lonely.

In the episode, we also both talk about what it took for us to find ourselves again.

For Ify, getting out of her twisties meant two things: she stopped outsourcing her judgment to other people’s advice, and she learned to trust the smallest, most factual step in front of her instead of the story she was telling herself about how things would go.

For me, it meant realizing the different voices in my head weren’t all pulling in the same direction — and that some of the parts of myself I’d always trusted weren’t serving me the way they used to. I left that job, and then I spent years and made plenty of mistakes, relearning how to make career decisions I could actually trust again.

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We’re both out of our twisties now. I don’t think I’ll ever fully forget what it felt like to be in them and how much I wish I’d heard Ify’s story earlier in my journey. That is exactly why I wanted her on the show.

What else?

• If this resonates with you, here are things you can do next:

  • Subscribe to Lessons to get new posts. I post at least 2X per month for all, and paid subscribers also get access to video courses and the full library of content.

  • Listen to the WorkLife podcast, where I talk to brilliant leaders and builders to untangle the messy, human side of work.

  • Follow me on LinkedIn, where I share more tools, thoughts, and a little of the day-to-day chaos.

  • And if you’re a leader looking for a community of peers to lean on and learn from, come find out more about Glue Club over here.

In this course, Molly shares her framework for managing up — not as a set of tricks for handling your boss, but as the ongoing work of decoding another human being. Every new boss comes with a new playbook: how they process information, what they care about, how they build trust, and what they need from you in order to make better decisions.

Molly walks through five rules for managing up, from building trust and adapting your communication style to disagreeing effectively and knowing when to put a fight down. Ultimately, she frames managing up as one of the most important skills for senior operators.

P.S. If you liked this course, you may also appreciate these related pieces from Molly.

Introduction

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You can listen to the full WorkLife episode anywhere you get your podcasts or watch it on YouTube.

Also, the next start date for Glue Club is around the corner (July). Applications are due on June 26. If you’re a leader in a fast-changing company looking for peers to learn from and lean on, come join us!

Talking about culture makes me want to scream.

Which is ironic because I used to have “culture” in my title at Facebook.

It drives me nuts for two reasons. First, culture is a black hole word — it means something different to every person who uses it. Second, I see so much energy invested in the wrong things when it comes to “culture”: beautiful values statements that make great posters; consulting firms hired to run employee surveys and bottoms-up processes that create principles no one remembers.

I spent a lot of time and energy at Facebook — which had a VERY strong culture for better or for worse — trying to help craft and shape the culture, which was mostly a waste, but it left me with some very strongly held beliefs about what culture is and what it isn’t. They are:

1. Culture comes from the top.

2. What you do matters more than what you write down.

3. The best cultures are repellent to some people.

4. Anything you write down only matters if people can remember it.

5. Culture has to evolve as you grow.

This week on WorkLife, I talked to Mike Schroepfer — Schrep to me and many others — Facebook's longtime CTO and current founder of Gigascale Capital, about the best part of Facebook's culture: its ability to learn, fail, and move on to more learning. The stories he told made each of these points more clearly than I ever have. Here’s a clip of the convo to give you a taste:

1. Culture comes from the top.

This was one of the most humbling lessons I learned while trying to shape Facebook's culture from my cute chair in HR. That is not how this works.

The vast majority of culture is shaped by the personality and behaviors of the founder. After that, it’s reinforced and reverberated by the senior leaders around them. Schrep said it simply: “Most cultures are a direct reflection of the founder. It’s really hard to build a company culture with an involved founder that’s orthogonal to how the founder feels.”

What that meant at Facebook was that Mark embodied the learning culture before it was ever written down. He was unsentimental. When something went wrong, he never asked who was responsible — he asked what happened and what do we do now. As Schrep put it: “I don’t ever remember Mark saying ‘who was responsible?’ It was more like, ‘what happened, and what do we do now?’” That consistency made everything else easier to build.

When you’re choosing where to work, you’re basically choosing a personality to work inside of, weird as that might sound. The more senior you get, the more carefully you need to think about that.

This is also why I don’t believe in bottoms-up culture exercises. If you want language, values, and principles, start with the CEO. It will get you most of the way there.

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2. What you do matters more than what you write down.

This is probably the belief I feel most strongly about. You could never write anything down — no values, no posters, no principles — and you would still have a culture.

Culture is crafted through the behavior of the people at the top. Your culture already exists; you just have to figure out how to articulate it.

This also makes it clear how cultures get broken. When there is dissonance between what you say and what you do, people get lost. You say you value bottoms-up feedback, but you fire people who give it. You say you want transparency, but you make decisions behind closed doors. The larger that gap, the more distracting and demoralizing it is for everyone inside it.

Schrep understood this deeply. You can hear it in how carefully he thought about everything — the format of every All Hands, how he reacted when things went badly — because he knew his behavior created ripple effects.

On the show he tells this story — he considers it one of his proudest moments at Facebook — about a worldwide outage that was costing the company millons of dollars. And in the middle of all of it, someone pipes up and basically says “I think it was my diff that took the site down.”

Think about what it takes to say that. In the middle of a disaster. In front of your boss’s boss. When people are already stressed and losing money and looking for answers.

The only way that happens is if the person raising their hand already know what’s coming next. And what happened next at Facebook was: zero blaming. Zero yelling. “Thank you. You got us back up faster. Now let’s figure out how this never happens again.”

That safety wasn’t built by a policy or a values statement. It was built by a thousand small decisions — who got celebrated, how failures got examined. Learning culture vs. blame culture. The difference isn’t philosophical; it’s what you actually do in the room, every day, when it’s hard.

3. The best cultures are repellent to some people.

This is the one that gets the most pushback when I say it out loud. People conflate psychological safety with belonging, and I think that’s a mistake. Psychological safety — people being able to show up and do their best work — is something every culture should strive for. But wanting everyone to belong? That’s not the goal. The goal is to be opinionated about who does and who doesn’t belong.

Great cultures attract the right people precisely because they repel the wrong ones. The job description that tries to appeal to everyone only does you a disservice.

I told this story a long time ago in a First Round article, but when I was rewriting the Facebook values with Mark in 2009, he pulled out an old list called “one of us”. It was something he had written when he was first trying to put words to the culture at Facebook. The list was:

• A very high IQ

• Strong sense of purpose

• Relentless focus on success

• Aggressive and competitive

• High quality bar, bordering on perfectionism

• Likes changing and disrupting things

• New ideas on how to do things better

• High integrity

• Surrounds themselves with good people

• Cares about building real value over perceived value

If you read the list, it’s very controversial (or at least it felt that way to me when I first read it), but it also sounds a lot like Mark. It’s a list that a lot of people would read and think: “not for me.” That is a GOOD thing. You want the right people to think “Yup!” and the wrong people to run.

Schrep makes this point through the lens of trade-offs. If you describe your culture and can’t name its downsides, you don’t fully understand what you’re building. Every real culture embodies trade-offs — and the leaders who’ve built the strongest ones are unafraid to name them.

4. Anything you write down only matters if people can remember it.

I’ve written about this one at length — go read it here — but the short version is: if people can’t hold something in their head, they can’t use it to make decisions. Schrep has the same instinct. He calls it the “rules of three” — most humans can remember three to five things, so if you have a seven or eight or twelve-tenant culture, pick a random employee and ask them what number seven is. You already know the answer. Fewer, simpler, and more specific beats comprehensive every time.

5. Culture has to evolve as you grow.

People think evolution means losing something. Maybe it does, but it’s a necessary shedding. Evolving means staying in dialogue with your organization about what still serves you and what doesn’t.

The culture that gets you to 100 people is not the culture that gets you to 1,000 or 10,000. At Facebook, there was real pride early on in shipping fast, breaking things, moving on. Interns shipped code to production in their first week. The site went down sometimes. And for a while, that was exactly right — speed mattered more than perfection, and the cost of downtime was low enough that it was worth it.

Then you get to hundreds of millions of users. Whole businesses depending on your platform. And suddenly “don’t be afraid to break things” means something different than it used to.

Schrep describes this as inertia — the most powerful force in the universe, as he puts it. A group of people who have been very successful doing something a certain way will resist changing it, even as the world around them changes. The job of a leader is to notice when that’s happening and nudge the org in a different direction. Not bulldoze. Nudge.

What I watched happen at Facebook — and what Schrep articulates better than I ever have — wasn't abandoning the culture. It was Mark having a real conversation with the company about what we still were and what we needed to shed.

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Schrep said something that stuck with me: when that engineer raised his hand in the middle of a crisis and said “I think it was my diff,” it saved the company hours of downtime and millions of dollars. That happened because of culture. Not a poster and not a values doc. A thousand small decisions made by leaders who knew their behavior was the message.

That’s why it matters.

You already have a culture. The only question is whether you’re being intentional about it — and whether what you’re doing matches what you’re saying.

Culture isn't a project. It's what happens every day whether you're paying attention or not.

What else?

• If this resonates for you, here are things you can do next:

  • Subscribe to Lessons to get new posts. I post at least 2X per month for all, and paid subscribers also get access to video courses and the full library of content.

  • Listen to the WorkLife podcast, where I talk to brilliant leaders and builders to untangle the messy, human side of work.

  • Follow me on LinkedIn, where I share more tools, thoughts, and a little of the day-to-day chaos.

  • And if you’re a leader looking for a community of peers to lean on and learn from, come find out more about Glue Club over here.

Nothing burns great people out faster than what I call “work whiplash.”

People can handle hard work. They struggle when priorities constantly reverse, decisions get made and un-made, and goals keep changing underneath them.

One of the most demoralizing things that can happen to someone at work is spending weeks pushing something uphill — only to find out the strategy changed, the project no longer matters, or another team was quietly working on the same thing on the other side of the building.

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The most common versions I see inside scaling companies:

• The strategy changed during an offsite or in a leadership meeting, but nobody told the three teams who were already heads down executing the old one.

• A decision got made, then un-made, then made again. No one doing the work knows which version is real.

• Two teams were handed the same problem. Both built solutions. Neither knew about the other until someone gave a demo.

• A person busts their ass to get something across the finish line… and their bos…

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You can listen to the full WorkLife episode anywhere you get your podcasts or watch it on YouTube.

Also, the next start date for Glue Club is around the corner (July). Applications are due on June 26. If you’re a leader in a fast-changing company looking for peers to learn from and lean on, come join us!

My first two years at Facebook were 2008 and 2009. When I started, we were smaller than MySpace. Everyone thought Microsoft was going to buy us. There was nothing obvious or inevitable about Facebook — not from the outside, and honestly, not from the inside either.

But there was this conviction. We knew what we were building was bigger and more important than anyone understood yet. And still — some of my most vivid memories from those years are of feeling like we were about to drive the car off a cliff.

Like we were one bad decision away from destroying everything we’d built and all the opportunity in front of us. When I give my Legos talk inside rapidly scaling companies, I usually put up that picture ^^ and this one:

These are my best explanations of what building something feels like most of the time. Even the wildly successful companies that look so fancy and inevitable from the outside feel like a messy chaos-fest on the inside.

So: how do you know the difference? What’s normal mess — the kind that’s just part of building something real — and what’s the kind of mess that should send you running for the hills?

I invited Claire Hughes Johnson, the former COO of Stripe, on the WorkLife podcast to talk about this. Claire joined when Stripe was around 200 employees and roughly $30–50M in revenue. She still sits on the board today — now it's about 8,500 employees and valued at $159B.

From the outside, Stripe’s story looks inevitable. But a while back, Claire had mentioned something to me offhand that I couldn't stop thinking about. She and Patrick Collison (Stripe’s co-founder and CEO) had been talking about the most surprising thing about their Stripe journey, and they agreed: it was that they just kept going.

I don’t think anyone would guess that answer. That’s the most surprising thing??? But that answer gives you a glimpse of how hard it was from the inside.

So I wanted to ask her about it. What does building something successful actually feel like when you’re in it? And how do you tell the difference between mess that’s normal and mess that means something’s actually wrong?

Here’s a sneak peek of the convo and some takeaways:

Look at the whole board, not just the square in front of you

Early at Stripe, there were so many crises. When things were blowing up, Claire would zoom out and ask herself one question: is this existential, or is it overcomeable?

Those are really different things. And most of what feels existential… isn’t.

Claire tells a great story in the episode about a moment when Stripe went down. Payments not processing, customers freaking out, support teams getting hammered. For a company that is effectively infrastructure for other people’s businesses, downtime is very bad for your reputation.

Claire had left a very stable senior role at Google to bet on this company, and there were definitely moments where it felt like it might all fall apart.

But when she zoomed out, she knew that the business was fundamentally strong: the product was real, the customer base was growing, and the people around her had the conviction to fix it. So yes — there were brutal moments, but it was also overcomeable.

The mess was bad. The fundamentals were good.

I just want to add my own note here to say that I think this is probably the most important thing, and one that I haven’t paid enough attention to at times. Is the business truly strong and growing despite whatever chaos you are currently in? There are going to be really bad moments in most businesses, but if you zoom out and look at the overall trajectory — years, not days — what does it look like? That is the trend to pay attention to when you are thinking about normal mess versus bad mess.

Know your “keep going” criteria before you need them

In addition to the business fundamentals, there’s the personal side. Is it worth it for YOU to keep going through all the hard?

Claire has two questions she goes back to when things get hard:

Am I still learning? Am I still having an impact?

If yes — and she can see a path where she has some agency — she keeps going. Even through really rough stuff.

If the answer to one or both is no, that’s gut check time.

Her other point is that it’s important to think about this — the criteria — before you’re in crisis. Because when you’re in it, you won’t be able to think clearly. You need something to anchor to ahead of time. What does “worth it” mean to you?

I think this starts in the job search and acceptance process. I wrote about it in a different Substack article, but my favorite test for taking a job is: If this company struggles or fails, will I still be glad I took the job? That gives you such solid ground for choosing your role and knowing your why regardless of whatever tornadoes or hurricanes come your way.

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When you’re stuck, go outside your own head

Claire mentioned a boss she had early in her career who, whenever she’d come in panicking about something, would say (somewhat snarkily): “Huh. Has no one ever experienced this before???”

Meaning: go find them. Someone else has been exactly where you are right now.

When you’re stuck, you’re probably not going to unstick yourself. I’ve made this mistake so many times. It can feel like a black hole; it can feel embarrassing. It’s really hard to reach out (or to even think straight), but if you can remember to do it, it is one of the most powerful tools for perspective. You’re closer to the problem than anyone, which means you’re also the least qualified to see it clearly.

Sometimes the answer is “run”

I want to be clear: the message here is not “just keep going.”

Claire and Patrick’s answer wasn’t that they powered through on grit and conviction alone. It was that when they zoomed out, the ground was solid. The fundamentals were real. That’s what made keeping going the right call.

Claire actually tells a story in the episode about someone she was advising who was in a hard situation at work. Her advice wasn’t “keep going.” It was: run. Because when she looked at the fundamentals — the leadership, the traction, the trajectory — they were off. Keeping going there wasn’t resilience. It was just wasting that person’s most precious resource: their time.

So the question isn’t: can you muscle through this? It’s: what does the ground actually look like under your feet?

Check the fundamentals. Know your criteria. Find someone who’s been there. And then — if the ground is solid — yeah. Keep going.

What else?

• If this resonates for you, here are things you can do next:

  • Subscribe to Lessons to get new posts. I post at least 2X per month for all, and paid subscribers also get access to video courses and the full library of content.

  • Listen to the WorkLife podcast, where I talk to brilliant leaders and builders to untangle the messy, human side of work.

  • Follow me on LinkedIn, where I share more tools, thoughts, and a little of the day-to-day chaos.

  • And if you’re a leader looking for a community of peers to lean on and learn from, come find out more about Glue Club over here.

This week, we’re introducing a different kind of episode: Frequently Asked Questions. We want to create a two-way dialogue with you, so our hope is that these episodes can allow you all to ask questions that are top of mind for your work life. If folks like it, we’ll keep doing it.

To kick us off, Ashley Murphy and I chose a bunch of questions that we hear regularly from folks in our community, Glue Club. Glue Club is a leadership development community built for mid-career leaders seeking support and growth as they build rapidly changing companies. Over the last 3.5 years of working with folks in that community, some of the same sticking points come up time and time again, so we’re using some of those as a starting place.

In the future, we’d love for these questions to come from you, the WorkLife listeners. You can submit questions by replying to this email, messaging me on LinkedIn, emailing worklife@ted.com, or leaving a voicemail at 347-377-2938.

You can listen to the full WorkLife episode anywhere you get your podcasts or watch it on YouTube, but here’s a sneak peek:

Key Takeaways

1. “Disagree and Commit” is harder than it sounds — try “Disagree and Let’s See” instead

The well-known framework, “Disagree and commit”, sounds clean in theory but it can be hard in practice. My reframe: approach disagreement as a genuine experiment. The shift isn’t just semantic. It requires believing that neither you nor your manager (or whoever the decision-maker is) has the full answer. You might not agree with the path forward, but if you see everything as an experiment, then it matters a little less. You just need to set clear metrics, define a time horizon for the experiment — and actually let it play out. Sometimes, you’ll be surprised by the result, and sometimes it will play out exactly how you thought, but mostly, this approach just turns the temperature down on the fight.

2. The best culture actively repels the wrong people

Leadership consultant Marcus Buckingham once told me that the best job descriptions should be repellent — written to attract the five (or some small number) people perfect for the role, and to repel everyone else. The same is true of culture. Trying to make your values universally appealing makes them meaningless. Honest, specific, even uncomfortable values help the right people opt in — and everyone else opt out. Clarity, even the uncomfortable version, is the goal.

3. What’s the difference between a therapist, a coach, and an advisor? And which one do you need?

There are three distinct types of support, and it is so helpful to be clear about which one you need in a given moment.

• A therapist helps you unpack your past, often your parents, your patterns, what triggers you, and why. I call it your programming. But typically therapy is a deep dive into who you are, what made you that way, and why you react the way you do to certain things (also how to get better at it).

• A coach typically helps you better understand yourself as a leader — strengths and weaknesses — and uses smart questions and frameworks to draw answers out of you. They are not there to tell you what to do, nor do they usually have relevant experience to your domain. A great coach can help almost any leader in the world.

• An advisor has experience directly relevant to your job. They have been where you are, have tried things and succeeded and failed, and will tell you what they’d do. An advisor is full of practical, experience-based guidance.

A lot of people think they’re trying to look for a coach when they actually want an advisor. Trying to find all three (or even 2) in one person often means getting a suboptimal version. Figure out what you actually need before you go looking.

Submit questions for future episodes

There’s a lot more inside this episode, so give it a listen. If you want a question answered by me on a future episode, feel free to reply to this email, message me on LinkedIn, email worklife@ted.com, or leave a voicemail at 347-377-2938.

And if Glue Club sounds like the kind of community you’d like to be part of, applications close on June 26 for the New Member group kicking off in July. This is the kind of conversation that happens there daily.

What else?

👋Hi! I’m Molly. This is where I share the lessons I’ve learned from building fast-moving, messy, ambitious companies. If you’re new here, here’s what you can do to stay connected:

• Subscribe to Lessons to get new posts. I post at least 2x per month for all, and paid subscribers also get access to video courses and the full library of content. We’ll also post here every time a new episode of WorkLife comes out.

• Follow me on LinkedIn, where I share more tools, thoughts, and a little of the day-to-day chaos.

• And if you’re a leader looking for a community of peers to lean on and learn from, come find out more about Glue Club over here.

A friend of mine — Toyin Ajayi, founder and CEO of Cityblock Health — shared a metaphor with me a few weeks ago that I haven’t been able to stop thinking about. I’ve probably reshared it a dozen times since, so I wanted to give it to all of you. It’s a metaphor that’s wildly helpful when thinking about what is and isn’t your job as a manager and a leader.

When Toyin started her company, she thought her job as a leader was like hosting an intimate dinner party. Every detail mattered — the invitations, the drinks, the seating, the way the conversation flowed. She felt like she was responsible for making sure every single person had a great time. And if anyone was unhappy — if the food was wrong, if the conversation lagged, if someone felt left out — she was failing. As CEO of her company and maybe particularly as a manager, she thought that described her job.

It’s a natural way to think about leadership, especially early on. In my first few management roles, I was convinced my job was to …

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Most people I talk to are exhausted by their work in some way — they're running too fast, chasing the wrong thing, or measuring themselves against everyone else. Mark Rober seems to be a genuinely rare exception. He's one of the most-watched creators on YouTube — 75 million followers, 16 billion views — and he got there by posting one video a month for 15 years. Slow and steady. And in an industry that seems to push creators toward unsustainable habits, somehow he seems more energized than burned out, more focused than scattered, more inspired than ever.

I wanted to understand how that's possible and what all of us can learn from him. Turns out it has almost nothing to do with YouTube, and everything to do with how he runs his life.

You can listen to the full WorkLife episode anywhere you get your podcasts or watch it on YouTube, but here’s a sneak peek:

Key takeaways

1. Know your why before the incentives get their hooks in you.

Mark started posting on YouTube before you could make money on YouTube. That timing matters more than it sounds — his motivation was set before fame or money were even on the table, which is why neither one distorts him now. He told me there are a thousand great reasons to start a YouTube channel and only two bad ones: to get rich and to get famous. “Because you’ll never be rich enough. And when you get famous enough, you’re like, why did I ever want this?”

Most of us don’t set our principles before the incentives arrive. We take the job, feel the pressure, start optimizing for the metrics in front of us — and then wonder why we feel hollow. Mark’s version: decide what you’re for before the system decides for you.

2. Sustainability is a competitive advantage

Mark has this image that I’ve thought about a lot since our conversation: keep the treadmill at a speed you can actually maintain for years. Not sprint speed, not the pace that feels exciting when you first get momentum — the speed you could keep going and going. He watched a lot of creators do the opposite: get traction, hire a team, crank up the output, and burn out before the dopamine caught up.

His sustainability isn’t just about personal energy — it shows up in how he built his businesses too. He didn’t quit his day job until he had 10 million subscribers. Didn’t launch Crunch Labs until he could fund it himself. He frames this not as caution but as how you maximize total output over a lifetime. Slow and sustained beats fast and collapsed.

3. Emergence: Get the principles right and the destination takes care of itself

Mark doesn’t have a ten-year vision. What he has instead is a clear set of principles — and he trusts that if he keeps making decisions based on those principles, something good will compound out of it. He borrowed a word from biology for this: emergence. The way a beehive produces something extraordinary without any single bee having a master plan. Each bee just follows simple rules, consistently, and the whole becomes something none of them could have designed.

We put so much pressure on ourselves to have The Vision, The Plan, The Five Year Goal. Mark’s point is that if you get your principles right and apply them consistently, the destination takes care of itself. You don’t need to know which rock you’ll be standing on in ten years. You just need to know which principles you use to choose the next rock.

What Mark Rober is doing with Class CrunchLabs — building a free, open-source science curriculum for third through eighth graders, giving it away to teachers — is what happens when someone builds patiently, stays rooted in their original purpose, and eventually has enough to give something meaningful back. It’s inspirational.

Try this

Similar to the episode with Patty Stonesifer, do you have a few principles that help guide how you choose the work that you want to do? Do you know why you do the work you do? Are these answers leading somewhere you want to go?

Identify one place in your work where you've cranked the treadmill past a pace you can sustain. What would it look like to dial it back — not to stop, but to find a speed you could imagine keeping for five more years?

If this conversation sparked something, share it with a leader in your orbit who needs to hear the treadmill idea or the emergence idea.

What else?

👋Hi! I’m Molly. This is where I share the lessons I’ve learned from building fast-moving, messy, ambitious companies. If you’re new here, here’s what you can do to stay connected:

• Subscribe to Lessons to get new posts. I post at least 2x per month for all, and paid subscribers also get access to video courses and the full library of content. We’ll also post here every time a new episode of WorkLife comes out.

• Follow me on LinkedIn, where I share more tools, thoughts, and a little of the day-to-day chaos.

• And if you’re a leader looking for a community of peers to lean on and learn from, come find out more about Glue Club over here.

I’ve watched leadership teams spend days creating six strategic pillars, fourteen objectives, and beautifully designed documents. Three months later, almost nobody can tell you what they were.

If people can’t remember something, they can’t use it.

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It sounds almost insultingly simple: make things memorable. But I’ve watched smart leaders at good companies invest enormous energy into goals and values that don’t actually have any effect on behavior — not because they got the strategy wrong, but because they made things too complex for it to stick.

If your goals aren’t memorable, they’re not useful. If you have fourteen company values, people will remember three. And they won’t all remember the same three.

When people can’t hold something in their head, they can’t use it to make decisions. They fall back on something else — their own instincts, their manager’s preferences, whatever feels urgent in the moment.

Ultimately, your job as a leader is to create structure that shapes the decisions pe…

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If you’ve been asking yourself whether the skills you’ve spent years building still matter in an AI-shaped world, this episode was made for you.

In our latest WorkLife episode, I sat down with journalist, podcast host, and author Manoush Zomorodi — a woman who has watched the media industry get dismantled and rebuilt multiple times over — to talk about what it actually takes to keep moving forward when the ground won’t stop shifting under your feet.

(Side note: Manoush also just published an awesome book called Body Electric: The Hidden Health Costs of the Digital Age and New Science to Reclaim Your Well-Being. It’s a science and data-backed analysis of what our sedentary lifestyle is doing to our health and practical tips on easy ways to reverse it.)

You can listen to the full episode anywhere you get your podcasts or watch it on YouTube, but here’s a sneak peek:

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Top 3 Takeaways

1. Know your mission. Stay unattached to the how.

Manoush has been in journalism for thirty years. She’s watched wave after wave of disruption roll through — the internet, social media, podcasts, now AI. And her work keeps changing shape around her.

But the thing that struck me is what hasn’t changed. She’s always been trying to help people make sense of the world. That’s it. That’s her mission.

The vehicle keeps shifting. Radio to podcasts, broadcast to newsletters. But she doesn’t seem especially tied to any particular format — only to the work itself.

For people navigating disruption right now, I think that’s really worth thinking about. You might not need to reinvent yourself as completely as you think. The craft underneath your role is often more durable than the current version of the job.

2. Stop talking about it. Go make something.

When people ask Manoush for career advice, she said she often gets frustrated. There’s so much theorizing — who should I talk to, what should I do, how do I figure out the right move?

Her answer is usually some version of: just go make something.

You don't have to publish it. You don't even have to know if it's any good yet.

For her, clarity tends to come from motion, not from analysis. You learn more from making one real thing than from spending six months talking about whether you might make it someday.

3. Failure is part of the story you’re telling.

Manoush spent two years deep inside the world of crypto and blockchain journalism — and then the company at the center of the story imploded.

But she doesn’t describe that as wasted time. She knew the whole time, whether or not it worked, it was going to be one of the most interesting stories she’d ever tell. The failure just made the story better.

There’s a lot of fear right now. A lot of people are terrified of making the wrong bet. What I took away is that if you stay curious about what you’re learning instead of just judging the outcome, almost everything that is interesting to you is worth trying.

Try This

I left this conversation with such an interesting question about all this disruptions happening and coming with AI:

What would you do differently if you believed that the craft you’ve built — the thing you’re actually best at — is never going away? That people will always need it. It just might look very different over the next 10 years.

If this one resonated, forward it to someone who’s asking themselves whether their skills and experience still matter. Chances are, they need to hear this too.

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What else?

👋Hi! I’m Molly. This is where I share the lessons I’ve learned from building fast-moving, messy, ambitious companies. If you’re new here, here’s what you can do to stay connected:

• Subscribe to Lessons to get new posts. I post at least 2x per month for all, and paid subscribers also get access to video courses and the full library of content. We’ll also post here every time a new episode of WorkLife comes out.

• Follow me on LinkedIn, where I share more tools, thoughts, and a little of the day-to-day chaos.

• And if you’re a leader looking for a community of peers to lean on and learn from, come find out more about Glue Club over here.

In this course, Molly shares her framework for using goals as a communication tool — not just a management ritual. She argues that the real purpose of goals is to create clarity for everyone in the company about what winning looks like.

Molly outlines six rules for effective goal setting and ultimately frames goals as a learning mechanism. The real quest isn’t writing them down, but figuring out what it takes to move the number — and building the operating system to do it consistently.

P.S. If you liked this course, you may also appreciate this companion piece.

Introduction

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If the conversation around AI has been making you tired, this episode might actually help.

This week on WorkLife, I sat down with Max Mullen — co-founder of Instacart, investor at Workshop, and one of the few people I trust to give me straight, practical answers and not make fun of my stupid questions. This episode is a bit different than the usual format, but I really want to take a few episodes this year and try to cut through the noise and the hype and figure out what's real. I'm calling them AI curiosity episodes — I'm going to find areas that I'm curious about and talk to people who are deeply immersed in the AI world to help us understand what's really going on. Max said something I hadn't heard anyone say quite this way before: you are probably closer than you think — days not months — to being an AI expert.

You can listen to the full episode anywhere you get your podcasts or watch it on YouTube, but here’s a sneak peek:

Key Takeaways

1. The Six-Week Rule. If you tried an AI tool more than six weeks ago and it didn't work, try again. The models are improving so fast that what felt clunky or unreliable two months ago may now do exactly what you'd hoped. Max thinks we may soon need to reduce it to the six-day rule. The bottleneck right now isn't the technology — it's already capable of more than most of us are using. What's lagging is adoption, inside companies and inside ourselves. That's not a reason to feel behind; it's a reason to start now.

2. You’re closer to an expert than you think. The people considered “AI experts” right now? Most of them learned a month or two ago. The gap between beginner and fluent isn’t a four-year CS degree — it’s hours of genuine curiosity. And here’s what makes this moment different from every previous computing shift: you don’t need to learn a new language or interface. You just have to be able to articulate what you want — clear thinking and clear communication, which are things you already do every day.

3. AI gets you to 80–90%. You still do the last mile. AI isn’t replacing your judgment — it’s handling the drafts, the research, the first pass. The curation, the taste, the final edit? Still yours. Max still edits every piece of AI-assisted writing and so do I, heavily. And if anything, Max would say, AI makes the human work sharper — you have to be more deliberate about what actually sounds like you, what you actually believe. The value isn’t in removing humans from the loop. It’s in removing the tedious parts so the human in the loop can do better work.

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The Bigger Point

What I kept coming back to after this conversation is how much of the exhaustion around AI is about feeling behind — like everyone else is ahead and you’re scrambling to catch up. The pressure to spend your Saturdays learning the latest tool, the constant drumbeat of “you need to be doing this” or “everybody else is doing this”… it’s a lot.

But Max pushes back on that framing, and I think he’s right. The people who seem like experts right now started recently. The tools are becoming more intuitive, not more complicated. And the skills that matter most — thinking clearly, asking good questions, knowing what a great answer looks like — are already in your toolkit.

He also made the point that this isn’t Saturday optional work. It belongs in your Monday as part of your job. And the best employers are already treating it that way.

Try this

If you’re ready to stop avoiding it and start actually using it: pick one problem you’re working on right now, open ChatGPT, Claude, or Gemini, and just describe what you need. Don’t over-engineer the prompt. Just talk to it like you’d brief a smart colleague.

Then try it again in six weeks. You’ll be surprised by what’s changed.

Listen or watch the full conversation with Max on WorkLife.

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What else?

👋Hi! I’m Molly. This is where I share the lessons I’ve learned from building fast-moving, messy, ambitious companies. If you’re new here, here’s what you can do to stay connected:

• Subscribe to Lessons to get new posts. I post at least 2x per month for all, and paid subscribers also get access to video courses and the full library of content. We’ll also post here every time a new episode of WorkLife comes out.

• Follow me on LinkedIn, where I share more tools, thoughts, and a little of the day-to-day chaos.

• And if you’re a leader looking for a community of peers to lean on and learn from, come find out more about Glue Club over here.

In our latest WorkLife episode, I sat down with Julie Zhuo — co-founder of Sundial, former VP of Product Design at Facebook, and author of The Making of a Manager. Julie thinks of herself as a scared-y cat — someone who is full of fear — and yet she’s done things like switch from engineering to design, write a book, and found a company.

Most of us think about risk-taking at work as something big and dramatic — quit your job, make the leap, bet everything. We also think of it as something binary: you’re either a risk-taker or you’re not.

But I think that framing hurts all of us, and Julie does too. Because it turns out risk-taking is a muscle: you build it with small, unglamorous reps, not one giant leap. That's what this episode is about.

You can listen to the full episode anywhere you get your podcasts or watch it on YouTube, but here’s a sneak peek:

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Top 3 Takeaways

1. Fearlessness and courage aren't the same thing. The goal is courage. We tend to admire fearlessness — acting like nothing scares you. But Julie made a distinction that I haven't been able to stop thinking about. Fearlessness means the thing wasn't actually scary. Courage is different. Courage is when you know exactly what could go wrong, you're scared, and you still do it anyway — because it matters. Courage is actually the thing worth building.

2. Confidence comes after risk, not before. One of the things I see people get stuck on is wanting to feel ready before they take the leap — one more class, one more job, before they do the thing they actually want to do. Julie flips that. When she looked back at the moments she was proudest of — switching from engineering to design with no formal training, stepping into management without knowing what she was doing — confidence wasn't what got her there. It's what she found on the other side.

3. You can actually get better at taking risks. Julie dedicated a whole year to what she called "everyday risks" — picking one thing to do every day or every week that scared her. Noticing the moments that felt uncomfortable and choosing to lean in anyway. These were usually not big things, and often really small ones: saying "I'm not doing well" when someone asked how she was; taking an unscheduled afternoon with her kid instead of following her calendar; surfing for the first time. The point wasn't the action — it was the feeling. Recognizing the twinge of discomfort and using that as a signal to do something instead of avoiding it. And over time, because she made it a practice, she built the muscle of courage.

Try this:

If this episode resonated, here’s a place to start.

In your journal — or just in your head — think of three places in your life right now where you’ve been avoiding something. A conversation you keep putting off. A decision you’re not making. Something you want to try but haven’t let yourself begin.

Write a bit about each one. What you’re feeling and what you’re avoiding.

Pick one. What’s the smallest possible move you could make toward it this week? You don't have to tackle the whole thing at once. Just find one small thing to try — a rep.

If this episode resonated with you, share it with someone who might need it!

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What else?

👋Hi! I’m Molly. This is where I share the lessons I’ve learned from building fast-moving, messy, ambitious companies. If you’re new here, here’s what you can do to stay connected:

• Subscribe to Lessons to get new posts. I post at least 2x per month for all, and paid subscribers also get access to video courses and the full library of content. We’ll also post here every time a new episode of WorkLife comes out.

• Follow me on LinkedIn, where I share more tools, thoughts, and a little of the day-to-day chaos.

• And if you’re a leader looking for a community of peers to lean on and learn from, come find out more about Glue Club over here.

A founder friend of mine — she runs a multi-billion-dollar company — said something recently that I haven't been able to shake.

A few years ago, she was completely gripped by the outcome. She wanted to build something huge, and she felt personally responsible for everything — every decision, every number, every swing in the business. You could feel it when you were around her — how much she cared, but also how much it weighed on her.

Fast forward to now. It’s the same company, though now it’s actually a much harder macro environment. But she’s different. Being around her, you can tell she feels calmer and less reactive, like she has more ground under her feet.

She told me: “I think I’m actually a better CEO now because I care a little less.”

What she meant wasn’t that she lowered her standards or stopped showing up. It was that she stopped needing the company to turn out a certain way. She accepted that there are things she can’t control, that she’s going to do her best in the face of chaos, and that there are a lot of possible good — even great — outcomes. Once she let go of needing it to be one version, her decision-making got clearer and her energy got steadier.

That shift is subtle. It’s also, I’d argue, a sign of someone becoming a better operator.

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For most of my career, I would have told you the exact opposite.

One of the things that made me effective early in my career was how much I cared. I cared about everything! Every project, every detail, every deadline as if it were my responsibility and mine alone. That caring showed up in very concrete ways — I was the person making diving catches, pushing on decisions that needed to be made, making sure the right thing happened, regardless of whether it was technically my job.

And it got rewarded. Not because anyone said “you care so much” — but because things got done. Problems got solved. Fires got put out. My bosses loved it. Over time, the message I internalized was: hold on tighter, care more, this is what good looks like.

And for a while, that’s true. Caring is a genuine superpower, especially early in your career or inside a smaller company where individual effort can still meaningfully change outcomes. The surface area is small enough that stepping in everywhere isn’t just possible — it’s often necessary. Caring deeply is often what gets you into the room in the first place.

But there’s a version of it that backfires.

I burned myself out twice in large part because of this. I was carrying way too much of the company in my head, taking mistakes personally, fighting every fight, operating at full intensity all the time. It didn’t feel like a choice — it felt like what being good required. When I finally recognized the burnout, it was too late. The only way I could recover was to leave.

As my brilliant friend Wendy Chow puts it: “Care less, so you can care longer.”

Burnout is the obvious cost, but there’s a subtler one that I think matters more: caring too much about outcomes you can’t control eventually makes you worse at your job. You end up more reactive and emotional. You attach yourself — your self-worth — to every decision going your way or everything going right. It becomes harder to see what actually matters. It’s so hard to realize this when you’ve built your career and your brand on caring, but the person who takes everything personally, who needs things to turn out a specific way — that person isn’t more invested than everyone else. They’ve just lost their objectivity. And objectivity is what you actually need to make good decisions.

There’s one more layer to this that I think is easy to miss, and it’s where many operators specifically get hurt. If you care deeply about a company, it’s very easy to start believing the relationship is mutual — that if you show up with loyalty, the company will show up with loyalty. Sometimes that’s true with individual people. It’s almost never true at the system level. Companies are systems designed to survive and succeed. They will reorganize, change direction, and let people go — even people who care deeply and have given a lot — because that’s what the system requires. If you’ve been operating as if the relationship is personal and mutual, those moments feel like betrayal. Not because anyone intended it that way. Because you gave more than the system was ever designed to give back.

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