B (4:15)

There's a lot of pressure around what it takes to build a great career. And it all comes back to this idea that you're supposed to know what you want to do. It's an idea that I like to call the stairs. Here's how the stairs go. You show up in college and you're supposed to know what you want to major in. That major is supposed to lead you to your first job and then you get another job and you get promoted and promoted and promoted forever. The best part about the stairs is safety and security. It feels like you know what you need to do to get ahead. The worst part of the Stairs is that it's like a weird video game that you can get stuck inside of for years. The stairs will make you feel like your self worth is tied to your title or your last performance rating or your next promotion. But the truth is that the stairs are an illusion these days. Excellent careers are not built by excellent stair climbers. Said differently, one of the most important things you can get good at in your career is taking risks. Or as I like to call it, jumping off cliffs. Let Me Explain what I mean with a story. When I was 25, I got offered a crazy job. I had spent a couple of years climbing the stairs in human resources at Facebook when the leader of another department came to me and asked me to help him start a new project doing something that I knew nothing about. It was a long term project, it was risky, and a lot of people told me it would probably fail. I was intrigued, but I was also scared. I talked to a bunch of different people and I have to admit, a lot of them told me not to take it. But there was this little voice inside me that just kept saying, I wonder. I wonder if I can be capable in this completely new environment. So I took a risk and I took the job. Now, I'd like to say that what happened next was that it was obviously a great decision and I was immediately successful. But actually, the first nine months on this project felt a lot more like falling off of a very steep cliff. I had gone from feeling competent and capable in HR to feeling like an absolute idiot. All the time I was sitting in rooms with brilliant people asking very dumb questions. Six months into this job, I got the lowest performance rating of my entire life. I had so many moments when all I wanted to do was run back to the safety and security of the stairs. But about nine months in, something interesting happened. I had to lead a meeting. It sounds simple, but it was a big meeting. It was a complicated debate about a nuanced part of this project. I was successful. And I so vividly remember walking out of that meeting feeling like myself again. I had gone from feeling like a beginner in this new environment to feeling confident and capable. I spent another three years on this project learning and growing. And on the other side of it, I was a completely different person. I was offered jobs that no one would have offered me if I had stayed in hr. That's the thing about jumping off cliffs. It doesn't just take you a couple flights up on the stairs. It's like a weird elevator that takes you to a whole new place. Cliff jumps teach you who you are and what you are capable of in ways that the stairs can never. To get good at jumping off cliffs, you have to get good at three things. The first is actually jumping off the cliff. After many years of coaching people through career decisions, I know that sometimes it is just not the right time to take a risk. But I can also tell you that most people do not stay stuck on the stairs out of necessity. They stay there out of fear. The trick is to learn to Tell the difference between the kind of fear that says, I'm scared I might run out of money, which you should actually listen to, and the kind of fear that says, I'm scared I might fail, which you should take as a giant green flashing light to jump. Cliff jumps teach you what you are capable of in spite of fear. The second thing you have to get good at in order to get good at jumping off cliffs is surviving the fall. Jumping off a cliff is taking a giant step backwards into the land of being a beginner again. That means it's a very big learning process. And with that comes a huge emotional rollercoaster. Daily, weekly, sometimes hourly. All of my jumps have involved vacillating wildly between feeling like, oh, maybe I'm going to be good at this, and then immediately feeling like, who the hell

C (9:55)

even gave me this job in the first place?

B (9:58)

All of that is normal, and it doesn't actually mean that anything is wrong. You have to learn to expect the rollercoaster and ignore it at the same time. The most valuable mantra for me in this phase has been give it two weeks. A lot of people will tell you to sleep on it. I can tell you most of these emotions don't go away overnight. Two weeks is a great barometer for things that you should actually pay attention to. The third thing you have to get good at in order to get good at jumping off cliffs is becoming a professional idiot. I can tell you that this is one of my greatest strengths. I am comfortable sounding like a moron. I am great at sitting in rooms with brilliant people asking very dumb questions. But what that actually means is that I have become an extraordinary learner. My favorite phrase is, sorry if this is a stupid question, but when you ask it that way, everybody wants to make you feel better. They're like, no, no, that's not a dumb question. And then they would love to teach you what they know. People love being teachers. It makes them feel smart. The other thing you discover is that most stupid questions aren't actually stupid. So many people are afraid of sounding dumb that the world is littered with important questions that never got asked. Questions like, can you define that word for me? Why are we doing this?

C (11:51)

Why are we having this meeting?

B (11:55)

Embracing being a professional idiot often actually makes you the most valuable person in the room. There's a last thing, part of the illusion of the stairs that becomes really obvious the more cliffs that you jump off of. And that is the idea that there is one set of stairs, one definition of success. I have a lot of friends that have climbed up the stairs to some version of the top, a fancy title, a lot of money, fame, and then they've realized that they're miserable. One friend described becoming CEO of her company and immediately thinking, is this all there is? You know what she did next? She jumped off a professional cliff. She went from being the CEO of a marketing agency to helping people who were dying in hospice. Success is not the same for everyone. I know that what I'm talking about isn't easy. It takes bravery to trade the known for the unknown. It takes courage to do something that might seem like a step sideways or backwards to someone else. But you will never really know who you are or what you are capable of until you learn how to try. Thank you.

A (13:36)

Don't go away. My conversation with Molly Graham is coming right up. This episode is brought to you by LinkedIn. Running a small business means every hire matters. A bad hire can cost you time, money and momentum. A good hire? They can help grow your business. But finding great talent isn't easy, especially when you don't have the time or resources to sift through piles of resumes to find the right fit. That's why LinkedIn built Hiring Pro, your new hiring partner that screens candidates for you. So instead of sorting through applications, you spend your time talking to candidates who are actually a good fit. With Hiring Pro, you can hire with confidence, knowing you're getting the best talent for your business. In fact, according to LinkedIn, those hiring with LinkedIn are 24% less likely to need to reopen a role within 12 months compared to the leading competitor. Join the 2.7 million small businesses using LinkedIn to hire get started by posting your job for free@LinkedIn.com TEDTalk terms and conditions apply. This episode is sponsored by Defender. Summer is on its way, and now is the time to start planning your next great outdoor adventure. If you're setting your sights on higher peaks, deeper rivers and bigger dreams, embrace the impossible with Defender. Built with legendary capability and tested on some of the most difficult terrain, Defender brings the toughness you need in a vehicle to take you to faraway places with the comfort and and smart tech that makes the journey feel luxurious. Choose between the sleek two door Defender 90, the purposeful Defender 110, or the Defender 130, with seating up to eight people. For bigger expeditions, Defender's robust materials mean you can adventure without compromise, and innovative driving aids like Clearsight technology help you view the world around you in powerful new ways. With the available three models, you have the potential for up to 89 cubic feet of cargo space. This summer adventure with confidence, Explore the full Defender lineup@land roverusa.com. Molly, welcome to the show.

C (15:43)

Thanks, Elise. I'm happy to be here.

A (15:46)

Listeners just heard your talk again, so they know the general framework. And the new season of Work Life with you as host just launched.

C (15:55)

Yeah.

A (15:55)

You have spoken openly about the fear that you felt taking this on, but that it was also a risk worth taking.

C (16:03)

Why? Ooh. I mean, I think most risks are worth taking, unless there's some, like, real fear that you should listen to. But, like, I think most risks are worth taking just to say it. And then this one, like, when I got the offer, it really triangulated for me on, like, is this the work I do? You know, is this the thing that I want to spend time and energy on in the world? And is it a kind of learning that I want? And for me, those two things together, like, it was such a powerful combination, because the work that I do right now, the thing that I love, is helping people feel less lonely, more sane, more seen, and also more confident at work. And then I think for me, it's like, I just love doing things that I feel highly unqualified for. I love the learning curve that's like, I don't know where I'm gonna end up on the other side of this. And this really felt like that. Like, I was literally like, I might be terrible at this. Let's go find out. It felt like a risk very worth taking.

A (17:06)

You know, you have said that you want Work life to kind of be a mentor that not everybody gets access to. And when you think about the mentors who've shaped your own life and your trajectory, what do you feel like they have given you?

C (17:20)

Oh, man, there have been so many, and I feel really lucky for that. I mean, I think that's important, by the way, that, like, it's not usually one mentor. It's, like, a lot of them. And for me, it's like, these conversations that just landed the right thing in the right moment. Like, you know, the. There's a woman coming on Work Life named Patty Stone Safer. And she. I remember when I left Facebook, I don't even remember what question I asked her, but I was just telling her about leaving and feeling scared because I didn't have another job lined up, and I didn't. That felt, I don't know, crazy or something. And she said to me, you know, the hardest thing for me in my career has been letting go of one rung of the ladder without having your hand on the next rung. And she was like, it really shows up in cocktail parties when, like, people say, what do you do? And you're like, like, what do I do? I don't know. But it's just those moments when somebody kind of gives you a language for what you're feeling. Those have really big unlocks for me. And there's just so many examples of somebody saying the right thing to me at the right moment. And. And for me, that's what mentorship is, is kind of like somebody that sees you and can feel what you're going through, but then can push you and nudge you and unlock things for you. Because they've been there, you know, they've seen it and done it maybe a hundred times where it feels new to you.

A (18:38)

And then ideally, the show serves that kind of role for some listeners as well, and hopefully has the topics that folks are needing to hear in the moment. They need to hear them.

C (18:48)

Yeah, exactly. I mean, I think, you know, there's so much wisdom in the world that people don't have access to, right. These. There's so many incredible leaders that have had such amazing experience, but haven't had time to write the book or don't have time to go on the podcast or just don't prioritize that because it's not what feeds them. And, you know, my hope is that I'm going to convince a bunch of wonderful experience leaders to come on and get some of the stuff that's in their brain out. And hopefully, you know, in listening to this show, like, each episode, what I'm trying to do is get stories and frameworks and lessons and metaphors that will feel really tangible to people so that they can leave and take something away that they can, like, kind of quickly put into action if it speaks to them.

A (19:31)

We noticed that the show's description says the full range of human emotion can happen at work and that those messy feelings can actually be a roadmap. What does that mean to you?

C (19:43)

Oh, man. Feelings at work. You know, it's so funny. At least early in my career, I felt like I was sort of given the message that you were supposed to come into work and, like, leave a lot of the human behind. You know, you were. Come in and be a professional. Same. Yeah. Put on your suit and, like, get your. Together am.

A (20:01)

I swear, worse you are. And we're similar ages, so.

B (20:04)

Yeah, yeah.

C (20:05)

And it's like, I think we were taught, like, be polished and be like, you know, whatever. Just, like, show up like a professional, whatever. That meant, and this really interesting thing happened for me. So, like, you know, I spent five years building at Facebook and I went through this very specific experience that comes with, like, going through, like a high velocity of change all the time, which is, you know, what scaling companies are, but really it's just change. And. And you get tackled by all these emotions all the time, and you're constantly sort of questioning yourself and wondering if you are in the right job or who's going to figure out that they shouldn't have hired you in the first place or whatever. And I wrote this article after called give away your Legos. And I meant it just for, like, people going through rapid scale. Like, I meant it for the people that were going through an experience like what Facebook had gone through, but really what giveaway your Legos talked about was the emotional experience of scale. And I got emails from all over the world. Like, I got all these emails from people that you wouldn't predict would have resonated with the article. You know, it taught me that not enough people talk about the emotional side of work and that so many people are experiencing the emotional human reaction to change. And I think that's even more true today because there's so much going on in the workplace and there's just not enough people out there saying, hey, this is hard and it's emotional, and yes, you're a professional and yes, you can be buttoned up and polished, but you will be a better leader, a better worker, a better professional if you are able to sort of acknowledge and manage all that humanness that comes with you to work. Yeah.

A (21:42)

What is the difference to you between good fear and bad fear?

C (21:47)

So I've been thinking a lot about this lately because I just did an interview with a woman who, she says she's the scaredy cat and she's taught herself to be good at risk by taking daily risks. She literally created a journal and challenged herself to take one risk every single day. And she was talking about the fact that she pushed herself to do it. So, like, she learned this set of feelings and triggers where if something was uncomfortable and something was sort of making her almost like, want to run away, that she was like, that's the sign that I have to do it. And so we had a conversation, and it made me even think more deeply about when should you not, you know, when is the discomfort telling you you shouldn't? And to me, taking risks means taking on a bunch of emotions and a bunch of anxiety and a bunch of just human chaos on your side in your like internal life. And to be able to do that well, you have to like, both have a clear why. You have to know what's in it for you and why you're putting yourself through all this kind of like pain and fear and, and anxiety. There has to be something that you're shooting for on the other side so that when you're having a bad day, you can be like, remember we're doing this for a reason, blah, blah, blah, blah, blah, whatever that reason is. But also you can't do that well if you're constantly being attacked by fundamental needs. So to me, some of the, like, clearest fear that you should really listen to and might be telling you you shouldn't take a risk are things like financial anxiety, right? Or anything that attacks, you know, what I would call like the Maslow's hierarchy of needs. Like, I'm scared I can't feed my family. I'm scared I'm gonna lose my house. Those are things where you're not gonna be good at taking a risk if that level of anxiety accompanies it. And I think that kind of fear might be telling you, hey, like, now's not the moment. You know, now's not the time to quit your job or challenge yourself in this way. And there will be a moment, but maybe now's not it.

A (23:58)

You've also talked about having to sort through which voice in your head is talking. Like, is this an ego driven decision or is this an authentic sort of soul driven decision? How do you help folks be able to tell the difference?

C (24:13)

Woof. It's the work of a lifetime just to say it. And you know, I did a lot of this work or started on this work because I made a career decision that ended up being a mistake. And sort of on paper it was like perfect. The job was fancy and I thought I'd always wanted that job. And if I reflect backwards, I would say that there was a very strong voice that was ego driven, what I would call my like, achiever voice, saying, you should do this, like, it's shiny and everybody's gonna think you're cool and you're gonna put it on your LinkedIn and everybody's gonna be like, woohoo. You know, it was like almost so excited about having had the job that I never stopped to ask, are you excited to do the job? And eventually a friend showed up that said, are you excited about the day? Like, are you excited about the hours in the day? And I remember that he asked me that at a bad time. Talk about a misplaced mentor piece of advice. It was, like, two weeks before I started the job, but I remember having this sinking feeling of, like, oh, I'm not sure I am excited about the day, but it caused me to do a bunch of work to try to sort out these voices in my head of, like, what are they each doing? And my. I. I had a coach at the time who gave me this really great metaphor of, like, it's like a car, and you have voices that are in the front, and they're driving, right? And you have voices that are in the back seat, and they might be shouting things, but they're a little softer. And then there's voices in the trunk. And she literally had me do these amazing exercises where I took people out of the trunk and talked to them about why they were there and how they got put there, and also talked to the people in the front seat about what was important to them and why they were driving. It's. You know, but it's like piecing apart these different parts of yourself and realizing that they have very different motivations. And over time, it's taught me to be a lot better at recognizing which voice is talking. And it's not like you ever get rid of them. You know what I mean? Like, the voices are still there. I think you just get better at recognizing which ones you should listen to in which moments and which ones maybe are, like, healthier at certain times. And I. You know, years later, I got this job offer, and I. My achiever voice was very loud, was very much like, you should take this job. It's really cool. Like, everyone's gonna think you're awesome. Like, you know, it'll be fancy and all these things you'll get on all the lists, whatever. But I had strengthened this other voice that was like, hey, what does this get you that you don't already have? Why, why, why? Why are we doing this? Like, why would we put ourselves through this again?

A (26:41)

And is the general idea to let the quieter voice or the voice that might be farther away in the trunk speak more loudly?

C (26:51)

So I think there can be a lot of power in asking, you know, whatever voice tends to drive, to let go of the steering wheel and to put a new voice in there? So I'll give you an example. Like, one of the voices that's always been in my trunk is my creative self. I have a very creative older brother. So I think I've always defined myself as not creative. But my coach was like, who is this person? Like, why are they in the trunk? And I Was like, they're in the trunk. Because, you know, brother, creative, not me. And she was like, what would happen if they were behind the wheel? What would they want? What would they say? What would they say you should do? And for me, that exercise was very uncomfortable. I was like, I don't know. I don't even know how to talk to this person. They've been in the trunk for years, you know. But it did lead to a very different set of conversations than it letting this sort of like ego driven achiever voice guide.

B (27:38)

So it's.

C (27:39)

It doesn't mean the creative self should always be, you know, in my case, like always be in the driver's seat. It's more like the act of giving that voice a louder seat, a more prominent seat. Really bring stuff out of you that you're like, huh? These are questions I never ask.

A (27:53)

Yeah. Especially when we define some of our preferences or what we think are dynamics of our personality against a sibling. Because it happens a lot with birth order and siblings, if we grew up with siblings. Because, for example, my brother was always the athletic one. And so I thought of myself as uncoordinated and often didn't try new sports or activities because I was never, quote unquote, the athletic one. But it was not actually because I was substantively unathletic. It was just because of the way maybe I defined myself against somebody else. And so it's really worth questioning those kinds of scripts.

C (28:29)

Yeah. And I think, where does that script come from? You know, it comes from siblings, it comes from parents. Right. I always call it your programming. Like you grew up somewhere, someone gave you a set of messages. It can come from school too, and things like that, but most often it comes from something in our family. And I feel like making some of these decisions often forces you to ask, like, who's in charge and who should be in charge? And like, who's the healthiest voice to listen to? And like, what if that wasn't true? Right. What if I was athletic? What if I believed I was athletic? What would I do differently? What if I believed I was creative? What would I do differently? You know, what if I believed I was like, I've just self defined as someone that doesn't take risks. What if I took a moment to say, what if that's not me? What if I am something different? And even just asking that question can really lead to a different conversation about what the best thing for you might be.

A (29:16)

You know, I was about to ask you how we begin to separate what we actually want from Our programming, it sounds like just beginning to question the programming itself is the first step.

C (29:29)

Yeah, totally. And, you know, I think that that idea of, like, just asking what's underneath it. And also I think sometimes just what would you have to believe for that to not be true? You know, for me, like, my achiever self got me great things in life.

B (29:47)

Like it.

C (29:47)

It charged for years, and it created all this, you know, quote unquote success professionally. And I'm like, so grateful for that. And then I think I just realized it was chasing something that was going to end up being toxic, you know, and. And that's, I think, very complicated and confusing, which is, like, for a while, some of these things really serve you, you know, and they really are good

A (30:11)

forces or culture is rewarding you.

C (30:14)

Yeah, totally. They can be productive, but at some point they become unhealthy, and you get the signals of unhealthy, like whatever it is for every different person, right? Burnout or depression or anxiety, that's just not. That's showing you that this voice or person has been driving for is. Is no longer really serving you. And then I think asking questions, sort of challenging your fundamental assumptions. What literally my coach did was make you sit down and have a conversation with that voice, like, define where it came from. Which, by the way, can also be really confusing. I can't remember what the name of the voice was, but a voice that I would have said came from my dad, came from my mom and I. And once I asked it questions, I was like, oh, you totally came from a different place than I thought you did. I think it was a little bit of a people pleaser voice, if I remember correctly. But then asking it sort of like what it wants and what's it trying to do for you? Because, like, I think a lot of these things are built to protect you. You know, they're built to help you, and. And in their best use, they're helping you, and in their worst case, they're actually holding you back, you know?

A (31:16)

Yeah. Yeah. I feel like in my own personal work with my therapist, we work on how I sort of as a journalist my whole life, I like having a dark side. I like having a sort of cynicism and skepticism about things because I feel like cynics are always right. It's like, so long as you think doom will happen, it generally does. And you're like, I'm never wrong. But he was like, I can see how that protects you, but how might that hold you back? Like, how might that hold you back from hope? And earnestness, you know, and kind of wonder. Right. Because you, like, hold on to that particular.

C (31:59)

Yeah, man.

A (31:59)

Idea.

C (32:01)

So it's so funny you say that because there's this quote in this book. It's like actually a throwaway quote in this book. But the book is called the Five Regrets of the Dying. It's by this woman, Bronnie Ware, and she was a. She was like a death doula, essentially, in Australia. And in this book, again, a throwaway line in the middle of the book. But she said everything in life is either love or fear. It's like, wildly overly simplistic. But it is totally fascinating to watch people make decisions and realize that so many people make decisions out of fear. Right. And I always love asking the question, what would it look like to do this from love? Do you know what I mean? From a place of excitement, from a place of joy, versus that sort of like protectionist instinct, you know?

A (32:44)

Yeah, I like that. And with respect to our work choices, this kind of goes back to some of your TED Talk and the idea of taking risks and kind of getting off of the stairs, if you will. But we are in this. I think it's unavoidable that we are in this job market and in an economy that feels really precarious. It's really brutal for a lot of people right now. AI is rapidly changing so many industries. So I can imagine that for a lot of listeners, the idea of choosing to take a risk and make a choice out of love rather than fear might feel practically impossible. Right. How do you hold this message of making choices in the direction of love and not fear alongside the reality of our precarious economy right now?

C (33:37)

It's such a real thing. And, like, you know, I spend a lot of my days working with leaders that are both leading teams through this, but experiencing it themselves. And I was just talking to someone who was like, I got laid off for my last job and it's left me terrified. You know, basically you tell me, you know, to challenge my boss. You tell me to push back. Like, you tell me to, like, fight these fights and try to build a better company. And I want to. And I'm also like, what if I get fired? Right. You know, and so couple of things. On the risk taking point, I would just say there are big risks and there are small ones. And actually, a lot of my early risks were inside the same company. They were just pushing myself to say yes to an opportunity that I was like, I don't know if I can do this. So it doesn't always have to be leaving a job. It doesn't always have to be, you know, starting a company or going back to school. It can be like, this makes me uncomfortable to lead this meeting. This makes me uncomfortable to give this person feedback. You know, somebody asked me if I want to, you know, do the presentation or give the speech or take on a new project, and I don't know if I can do it. Those are all great risks that just start to build a muscle of building tolerance for discomfort and risk and also proving to yourself that you can do things that you didn't know you could do, which is actually like a really powerful muscle and one that comes in handy, you know, when I, like, you get pushed off the stairs.

A (35:04)

Right.

C (35:04)

If you get laid off or fired, which happens to a lot of people. But for me, and I said this to this leader who was talking to me about the trauma from her layoff, like, there's a lot of stuff you can't control in the job market right now. You know what I mean? Like, you can't control if you're gonna get laid off or not. It actually, most of it right now is not. It's not performance. It's business.

A (35:22)

It's not personal.

C (35:22)

You know what I mean? Yeah. And so you can choose to do your job trying to kind of protect yourself against that, but actually, like, no matter what you do, like, it still might come for you. So how do you focus on the things you can control? You know, the main point is how do you make the most of where you are today? How do you leave? Whenever you leave, however, you leave with a great story. And, like, that does come down to pushing yourself to take advantage of the role that you're in now, whatever that looks like. And it can be small, iterative risks. It can be slightly bigger risks inside the company that you're in, where you're proving to yourself that you can do a whole role that you didn't know you could do. But I would just say, like, this job market, there's a lot of stuff that's out of people's control. So I would really focus on the things that you can control, which is your own experience at your current company. And, you know, the other thing I'll just say is, like, you think when it happens, it defines everything. Like, suddenly you think it's like this Scarlet A or whatever the right metaphor is that you're going to carry with you forever. And the truth is, it's. I always say it's just a chapter. It's not the whole book like it's just a thing that's going to happen. It's going to be part of your story. The question is how you move through it and you are better prepared for the other side of it. If you've learned to live with discomfort and challenge yourself and and stretch yourself to do things that you're unsure about, you know, so that risk taking muscle is developed in small moves and is so valuable for moments of uncertainty.

A (36:56)

This episode is brought to you by Amazon Health AI Let me ask you something. Why does getting care so often start with paperwork forms that ask for the same information over and over as if your story has to be retold from scratch every time? We've come to accept that friction as part of the process. But it doesn't have to be. Amazon Health AI is built to change that. It can understand your health history so you can spend less time repeating yourself and more time actually getting the care you need. Amazon Health AI Healthcare just got less painful this message is brought to you by Apple Card Apple Card members can earn unlimited daily cash back on everyday purchases wherever they shop. This means you could be earning daily cash on just about anything, like a slice of pizza from your local pizza place or a latte from the corner coffee shop. Apply for Apple Card in the Wallet app to see your credit limit offer in minutes subject to credit approval. Apple Card issued by Goldman Sachs Bank USA Salt Lake City Branch terms and more at applecard.com

D (38:00)

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A (38:40)

As for proactively leaving jobs, which I know this isn't just the only thing that you're talking about or the only kinds of ways that we can take risks, a lot of times we're told by our career counselors or by our parents that you shouldn't leave a job until you have the next one lined up or definitely have a safety net of a certain amount of savings. When you're coaching someone who might not have another job lined up or not have the safety net, does your advice about their next step or the decision matrix leading to their Choices change.

C (39:18)

So, first of all, I think taking time off between jobs, if you can afford it and if you can do it without significant financial anxiety, is one of the most powerful things you can do. Because jobs are like relationships. And we all have that framework of the rebound relationship, right, where you, like, you're like, dating the person and it's toxic or whatever, it's just not it. And you break up with them and you jump right into another thing that really, that next thing isn't a healthy relationship. It's just the opposite of whatever you just had. You're running away from something versus running towards something. And sometimes I've seen a lot of people take the rebound job right, where it's like, I just had to get out of there. And first of all, I wanna say financially, if you're in a toxic or not great job and someone offers you an exit, and financially that's the best decision for you, rebound jobs could be great for that. And it's unlikely that that's going to be, like, the best job for you right now. So space in between jobs kind of lets us shed whatever baggage and trauma we're bringing from that last relationship so that we can kind of like, take the space to be, like, what's right for me next. But I do think you can only take healthy space between jobs if you are not constantly terrified about money. And so a lot of the work that I do with people when they're thinking of leaving and sort of asking what's the best way to le is really go through the math with them of, like, what would have to be true for you to take, you know, a month or two months or three months off between jobs or a year sometimes. How much savings do you have to have? Really? It comes down to, like, what is the dollar amount that you need per month to make you feel safe? And that word is very vague for a reason. Because what makes you feel safe, like, what makes Elise feel safe is not what makes Molly feel safe. It's not what makes someone else feel safe. It's, we all have different budgets, different lives. But also it comes back to the programming. Like, what our parents taught us is safe. So it can be about savings. It can also be about, like, I had a friend that left a job that she'd been in for 10 years, and I was like, what do you need to feel safe? And she was like, I need something that I can do in, like, half my time or less. So I have some space that covers my rent, you know, that covers my mortgage, and we did some brainstorming and figured out a job that could pay her that amount per month.

B (41:31)

And it.

C (41:31)

It wasn't like it was. It was like more like consulting. You know, it was something where she didn't give away all of her time, but that gave her a year of half time work. And that was enough space for her to, like, pick up music and remember who she was, you know, before she founded a company. Which I think is really the other value of that space, which is like, you know, we spend so much of our lives at work that sometimes we forget that we're a whole human outside of it. And, you know, often when people take time off, I'm say, even if you could just take like a couple of weeks to remind yourself who you are outside of work. And that can be so powerful because it discharges your job a little. It lets you put less of your identity into your work, which can make that relationship way healthier.

A (42:11)

Yeah, I like that. Molly, it sounds like so many lessons you've learned about yourself and how you think about work actually came from some missteps, right? Or heading in some directions that you later realized weren't right for you. So in your coaching, how do you navigate helping someone kind of build their own compass without having to take missteps along the way in order to get those lessons? Or is maybe the only way that we truly understand ourselves from making some mistakes along the way?

C (42:44)

Yeah, screwing stuff up. So it's actually a question I've been asking myself a lot lately, like, do

A (42:50)

you have to put your hand in the blender to learn that you shouldn't put your hand in the blender? Like, how do we get wise?

C (42:56)

I just want to say I have to put my hand in the blender. Like, I feel like, you know, a lot of people will tell me, don't do this or whatever, and sometimes I just have to. Like I always say I have to touch the stove in order to realize that it's hot. Even if you told me, even if there's a sign above it that says that it's hot. But, you know, I think that for me, the mistakes are part of who you are. Right? And they're part of how you learn. And that's, you know, I don't really have. I don't really believe in regret just because I think you are who you are because of the things that got you there. Mistakes and successes. There were some decisions I might not make again, knowing what I know now. But I only know what I know now because I made those Mistakes, you know? But I think that people gain wisdom from lots of different things. Like, there's lots of different types of learners in the world. I'm an experiential learner. I need to, like, experience things in order to, like, truly internalize them. Yeah. So some folks can really learn from a book or learn from a podcast and decide not to do the thing. But to me, more, what I find with listening to other people's stories or watching folks that I work with in my communities learn is like, it's so valuable to hear other people's stories because often it sort of helps you orient yourself like a little bit of a compass. Like, sometimes you're in a little tornado, and you're like, I don't know which way is up or down or sideways or north or south or east or west, and. And somebody tells you a story of a time that they were in a tornado, and it might not be exactly the same tornado, but it just lets

B (44:26)

you be like, oh, I know which

C (44:27)

way north is all of a sudden, you know? So it isn't to say that it saves you. It's more that it, like, helps you make sense of your own experience. I think sometimes, at least for me.

A (44:38)

And it's less isolating. I think it makes us feel less alone to know that we're not the only ones going through things, but that we all have this bias or negative bias that, you know, I'm the only person on Earth who has ever gone through this.

C (44:53)

But it's just giving you that, like, relative sense of, you're not the only person that's ever gone through this. Somebody else has gone through something, and you can learn something from that. But to your point, like, you can feel seen because of it, you know?

A (45:07)

All right, one of your first jobs was actually leading wilderness tours in Patagonia, which is amazing. And you majored in African history, you worked in Silicon Valley, and now you're hosting a podcast for Ted that sounds like at least three or four completely different adventures and lives. And yet a lot of people feel that by the time they're in their 40s or 50s, it's maybe too late to reinvent. What do you say to someone who's at midlife and feeling kind of stuck?

C (45:38)

Woof. Elise, I want to hear your answer to this. You know, I actually think reinvention is part of midlife. It's one of the things that I'm really witnessing in, like, all of my friends. I think it hits people at very different times, and there's, like, a different Cause, you know, but for me, midlife has been about realizing that what matters to me is different and that what I thought mattered to me when I was 20 is just different. I was leading wilderness trips, which was a form of teaching, and I was like, this feels too narrow for me. I only want to, you know, I want to work at scale. I want to impact more people. And so I, you know, ended up in tech, which is a lot of scale and a lot of impact. And I'm right back there now. Like, I really find that the kind of impact and the kind of work I want to do is so different than it was in my 20s. And I care a lot more about depth than I do about breadth, which was, again, not what my 20 year old self would believe. But. But to me, you change as a person and that means that reinvention is of your career, you know, and of relationships.

A (46:40)

A lot of people get divorced or separated at around this time.

C (46:44)

Yeah, yeah. And like, how you see yourself in the world, like, it changes and you want to be able to, like, move your life and your work in association with that. And I think my experience of watching it for, you know, myself and a lot of friends is it's very confusing. You know, I think I started my sort of reinvention like eight years years ago, and the last three and a half years in particular, I felt very lost. Like, very, very lost. Like, so confused, both about what I wanted to do, but also, like, whether I was on the right path and all these things because I was shedding a lot of programming. But I kept thinking, like, if I could just do X, I would have an answer. If I could just do Y, I would know what this next phase was going to be. But it's really taught me that everything is just about steps. What's the next step that is going to teach you the thing that you need to know. And I think if you can let go of that sort of like, fixed identity of like, here's who I am or here's what I am in the world and just say, what's the next step I need to take to learn who I'm becoming or to learn what work feeds me? Sometimes it can just be a step inside your current job, slight shift in a role, you know, taking on a different challenge like that teaches you what the next step is? And it actually, like, I've been, I've been on this journey for a while, but like, certainly the last three and a half years, I'm still taking steps. Like, this podcast is came out of nowhere and for me was like, oh, that's the next step. That's the one that's going to teach me all sorts of stuff that I could not have imagined. And I think there's incredible power in that, in sort of not trying to predict what the destination is, but just finding the right next step.

A (48:11)

I am motivated in a similar way in that I often ask myself before I make a decision, how much will this help me learn and grow? And is it in the direction that I want to learn and grow, you know, or maybe need to learn and grow? And so that's an orienting question for me. And then also, who are the people that you're surrounded by? Like, who are the other players in this band? And one thing that I generally talk to my kids about is you don't want to be the strongest player in the band. You want to be, like, mid tier or the weakest player in the band, because that means you'll level up.

C (48:45)

Yeah.

A (48:45)

Or they'll help you level up.

C (48:48)

And I also think, like, you know, one of the things that midlife made me ask is how do I want to spend my time? You know, I think I hit 40 and I was like, man, if I'm lucky, I'm going to live till I'm 80 and be healthy and all that. And so, like, I'm halfway through my life, which, you know, again, who knows me? I. Lots of people don't live till they're 80. But I was like, okay, then we only have so much time. Like, how do I want to spend my days and my hours? And for me, people is a huge part of that, which is like, you know, who are the people I want to surround myself with and learn from and get to work with? And I think that it's like, at the end of the day, life is just made up of hours. And who you surround yourself with has a big impact on both what it feels like, but also, to your point, like, what you learn, you know, and how you push yourself. Yeah, yeah.

A (49:27)

Molly, what do you think is a conversation about work that is most consistently avoided? What's the thing that all of us experience? Maybe, but we don't say out loud or we don't talk about enough.

C (49:40)

What a good question. To be honest, I hate being repetitive, but, like, the number one most valuable thing to me has been normalizing the emotional roller coaster of work. I think that's such a consistent theme in everything that I do and sort of talk to people about, and that makes them take sort of the sigh of relief. Of like, oh, I'm not crazy. I'm not, you know, doing the wrong thing. Like, I do a lot of speeches and stuff inside of mostly tech companies, although now more and more companies all over the world. Because I think the experience of change is highly emotional, and it feels like a giant mess. And you're sort of, like, successful. Things can't feel this messy, can they? And, you know, a lot of what I'm here to say is, the most successful companies in the world feel like a mess all the time. And part of it is because they're changing pretty rapidly. And the question is, you're going to have that experience of change and sort of, like, the emotional experience of work. Really, what defines the difference between successful people and folks that get crushed by it are the ones that are able to, like, manage their emotions and, like, have all those experiences but not let them dictate their actions. I always say, you have this little monster. And the monster for me is, like, this really helpful way to externalize those emotions. I give my monster a name. Mine. Mine's name is Bob. Yours can be named whatever you want. Sorry, all the Bobs out there. But, like, I grew up on the Muppets, so I think it's basically a Muppet that, like, travels with me. And I always think he's, like, on my shoulder. He's on my toes. And unfortunately, this monster's job is to basically make you the worst version of yourself. You know what I mean? And it's like, he's there just being like, who gave you this job? Like, why? Why are you, like, did a really bad job in that meeting. Like, don't speak up. Like, you're gonna get fired. Whatever. And I think part of maturing at work, part of learning how to get good at change, is essentially not letting that monster dictate your actions. Like, you can have the feelings. Let me tell you, I've been giving speeches about Bob for 20 years, and he's still there. But I've learned what is a Bob moment. You know, what's him talking and then what's me? And I think that's been really helpful to me. And it's not something that people talk about enough, which is that there is this whole emotional human life of work that we have to learn to get good at in order to handle the kind of change that everyone's going through right now in the world, you know? Yeah.

A (52:08)

Because what is work or a workplace, but it's just a collection and a series of relationships that we have to navigate.

C (52:14)

Absolutely.

A (52:15)

And relationships are hard.

C (52:16)

Totally. No, I mean companies are just a structure that's basically to organize humans to be greater than the sum of their parts. So at the end of the day, the work of building companies and businesses and the work of work is about humans and interrelations. And yes, there are robots, but the humans are still the main show. And that means the main, you know, sort of experience of work is a human experience.

A (52:39)

Molly Graham is the new host of Work Life, one of our ed podcasts. Molly Graham, thank you so much.

C (52:48)

Thank you so much, Elise. This was so fun.

A (52:54)

That was Molly Graham at Ted next 2024 and later in conversation with me, Elise Hu. Our conversation was recorded in April 2026. If you're curious about Ted's curation, find out more@ted.com curationguidelines and that's it for today. TED Talks Daily is part of the TED Audio Collective. This episode was produced and edited by Lucy Little. The TED Talks Daily team includes Martha Estefanos, Oliver Friedman, Brian Greene, and Tanzika Sangmarnivong. Additional support from Emma Tobner and Daniela Balarazo. I'm Elise Hu. I'll be back tomorrow with a fresh idea for your feed. Thanks for listening.

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