Start With Yourself: A New Vision for Work & Life by Emma Grede - 12

I never dreamed about success. I worked for it.

—Estée Lauder

There’s an amazing scene in Sex and the City where Carrie and Miranda are sitting in a shoe shop. Carrie’s trying to figure out how to buy a house after her breakup with Aidan. I’m paraphrasing from memory here, but she turns to Miranda and asks, “When was everyone buying houses? Nobody told me. I must have earned some money?”

Miranda says, “Well, of course you earned some money. How many pairs of these shoes do you own? Fifty?”

“Oh, come on, more like one hundred.”

Miranda responds, “Well, there you go—one hundred times four hundred—that’s your down payment.”

“Well, that’s only four thousand.”

“No, that’s forty thousand. ”

“I spent forty thousand dollars on shoes and I have nowhere to live?”

This is funny because for many women, it’s true. When we pull a Carrie and refuse to think about money, neglect to plan financially, or assume someone else will figure out a house for us, it stops us from really thinking about money as a tool.

I’m an employer; I rely on excellent employees. My ability to build an incredible team is part of what has enabled me to be successful. And I still don’t want anyone to sacrifice the vision for their life to my business plan—good employer/employee relationships work when everyone is being served by the partnership. Any job you have is an excellent training ground for becoming the type of leader or thinker you feel destined to be—and I would recommend approaching your career through that frame. What would you emulate, and what would you leave behind? Which decisions would you have executed differently? Where would you have invested, and where would you have pulled back? Use your current career as both a sandbox and school—a place to learn, to play, to test, to grow. And use it to wrestle some of the stories you might have playing in your mind to the ground. After all, if you don’t attend to them now, these stories will grow bigger in your mind when you’re on the hook for meeting payroll yourself. So let’s start with one of the biggest stories of all: You’re an impostor.

1. Old Thought: You don’t know enough, and you’re not qualified for the role you want.

Work ethic eliminates fear.

—Michael Jordan

At 9:00 a.m., my investors thought I was a genius. At 11:00 a.m., I was a CEO who was not fit for purpose. And to be fair, this was kind of true: I had no idea what I was doing. I had never done it before. But as I’ve come to understand, while my inexperience might have been really obvious that fateful October morning, nobody really knows what they’re doing. And if they’re doing something interesting, they’ve likely never done it before either.

Let me back up. On this particular day in 2016, I was huddled with five other people in a conference room at Frame, a denim brand cofounded by my husband, Jens. Jens and I had moved to LA not long before, and I had just had Lola, my second child. I had recently sold my first company, the agency I built under the Saturday Group umbrella, and I was itching to do something for myself. I had grown tired of seeing my ideas build brands for other people. Besides the initial booking fee, I would see zero upside for my ideas and my work; it was starting to create resentment and irritate me to the extent that I knew I needed to do something different.

I had also started doing equity deals for clients—I had cut Pharrell Williams and Will.i.am into businesses, for example, and I knew that this would be the future. I had also watched as those businesses ballooned. This happened again and again. But because of the structure of ITB, my agency, potential upside from equity couldn’t be our future—we were set up for fees, not equity—and so there was no functional way for me to benefit from this shifting business ecosystem. The world was changing. Nobody wanted to just be a face anymore; they wanted real skin in the game. And I did, too. Because I functioned as an exporter of US talent to the rest of the world, I handled a lot of brand work for celebrities outside of America—and I had been doing business with Kris Jenner and her lawyer Todd for many years. Over time and trust, we had become friendly. I wanted to create an inclusive denim brand—in a much wider size range than what was generally available—because almost every woman I knew struggled to find jeans that looked good and didn’t make them feel bad. I knew Khloé Kardashian would be the right person to partner with and bring it to the market.

First, I went to Jens and Erik and pitched them to invest in me. I asked for $3 million, and they gave me one. (Jens’s response: “You’re an unproven apparel person, so go elsewhere and raise the rest.”) I raised the rest in a friends-and-family round mostly composed of clients I’d done great work for over the years. At the beginning, I flew back and forth from London to Los Angeles, eight months pregnant, I spending most of my time in the factories in Vernon, where I learned the process of how to make denim. I watched them wash denim, I watched them distress denim, I watched them construct pockets. I realized I had no clue what I was doing. I would stand there and watch how many pocket squares could be sewn in a minute, not knowing how to put the whole process together or how to price it. I had a lot of questions: What’s the cost if you change the way the belt loops are sewn in? What’s the cost if you do something special on the hem? What’s the cost if you change the construction of the waistband? The level of my naivete was stunning.

But I also knew Good American could be huge—and different. I wrote a mission statement for the brand, and Khloé went on the radio and read it. It described how ridiculous it is that so many women can’t find clothes anywhere that fit well—and there was a massive resonance and response. People rushed to follow the brand on Instagram, and when we held an open casting call at Milk Studios, thousands and thousands of women applied. We wanted to find women to represent a brand made to fit them, and not the other way around. I’d been present at so many marketing campaign shoots over the course of my career that advertised “inclusivity,” knowing that if you turned the few plus-size models on set around to the camera, all the clothing had been cut down the back to make it look like it fit. This was the opposite of that. That day at Milk Studios was one of the most emotional days I’ve had in my career: Are you really going to make jeans that will fit me? Is this actually going to happen? The women were cautiously excited, wondering if we were really going to stay true to our word. We were addressing a profound need. That was also one of the most clarifying days in my career: I knew that Good American was going to work.

Launch day came, and I was very nervous. The team was tiny: just me and a handful of people, along with Jens to offer emotional support. We set up a TV screen for the Shopify dash and started testing the site at 6:00 a.m. to make sure the checkout worked. Even then, we could see the customers sitting on the home page waiting for launch, and I panicked: We aren’t going to have enough stock. Eventually, there were fifty thousand people on the site waiting for us to release the collection. At 9:00 a.m., when we launched the site, everyone thought I was a genius.

At 10:00 a.m., one of my investors, Andrew Rosen, called: “Oh, darling, you may have underestimated the opportunity a little bit.”

At 11:00 a.m., another investor called to tell me I was a fucking idiot and that I didn’t know what I was doing.

And I really didn’t. I had worked with a merchant named Melissa Anderson on the collection, and she had warned me that we were “off-calendar,” which means we didn’t have production cycles lined up, but I didn’t know enough to take her seriously. I had used all my start-up capital to make this first collection of jeans. Not only did I not have any more collections planned out, I didn’t even have any fabric ordered and on hand to meet the demands of the first day. My inexperience could only afford me visibility to the launch.

I did some things right, even though a seasoned denim merchant probably would not have made the same choices. In my naivete, I only made nine SKUs total, three fits, in three washes: Good Legs (skinny fit), Good Cuts (tailored boyfriend), and Good Waist (high-waisted skinny). But I made these three fits in an unprecedented range of sizes, which went from 00 to a plus-size 24. I based the launch on the iPhone: We told a story about the unique features of our product—the difference in our denim—and we showed the product from all angles on three different size models, which at the time was totally unprecedented. We explained how it was made and, better still, how it would make you feel. We told our story, how we wanted to make a jean that’s a perfect fit for women’s bodies, especially women who have curves and encounter a lack of options when they go shopping.

We promised we would never make them feel bad. We named the fits after what we knew customers would want to achieve: a Good Waist, Good Legs, Good Curves. We also stressed the differences in the smallest details we had spent a year perfecting, like our signature recovery fabric, the reinforced belt loops, and our four-piece trouser waistband, which ensured you’d never have that gap in the back. Our concepts were so simple, it was memorable for customers: The names of the jeans stuck, and women felt to the core that we had seen them. I learned, then and there, that people don’t buy when they understand what you’re doing; they buy once they feel understood.

We sold $1 million worth of jeans on day one and were out of stock by hour two. I had to frantically figure out how to reorder and make more. Except I didn’t have any fabric, and I didn’t have any factory space. We wouldn’t have any stock for at least twelve weeks. I sat there for three days straight and emailed, texted, or phoned every single disappointed customer, telling them that I would get them their jeans… eventually. I didn’t realize it at the time, but that original group of customers—those who heard from me directly—would become key advocates of the brand as we grew. They never forgot the direct contact.

Understandably, I was in a panic, so I started calling everyone I knew in Los Angeles, asking if I could buy fabric or factory space from them. I had some relationships from Jens and my ITB days, but largely I was a stranger in a strange land. It was a great forcing mechanism to put me more deeply into the denim community, particularly because I had just moved to LA and was running a business I fundamentally did not know how to run or fully understand. Though I was theoretically a competitor, people were really kind. They gave me information, they gave me space in their factories, they gave me advice for getting my costs down with the logistics provider (every time they “touch” your product, it costs a buck—so if they’re folding your jeans into thirds instead of in half, or adding a paper insert, or including fancy packing materials, you’re suddenly blowing your product margins with costs you don’t really need).

We got a ton of press about our “Million-Dollar First Day”—and we experienced some backlash. I knew the Kardashian family did well at an accessible price point, and that’s what people expected from them, but we were selling $300 jeans, priced at $179 because they were direct-to-consumer. Even then, I had not properly thought through my margins (unsustainably small!), which took a long time to clean up because these jeans were of a quality that was expensive to make. No one knew what “four-piece trouser waistband” meant, but everyone knew about a gap in the back, or sitting down and exposing your thong to the world. I remember going to a Forbes conference and saying that women didn’t need to experience that anymore and hearing a gasp from the audience. They understood what we were doing straightaway. One of my sole focuses was translating all the knowledge about denim and pant construction I was accruing into problem-solving for women—specifically for women who had never been considered.

It was an interesting moment in my life because I was being praised left, right, and center for making something women loved and wanted, but behind the scenes, my investors thought I was a not-fit-for-purpose CEO and that I was wasting a massive opportunity because of my inexperience. But I knew, despite the company being teeny-tiny, the launch wouldn’t be a flash in the pan and that we were holding a really big, if not revolutionary, idea. These days, it’s somewhat inconceivable to build a brand without including a much wider array of sizes. But back then, we were the only one taking this on.

The team at Nordstrom believed in it, and before we even launched, they told me they’d put the brand in fifty stores. I negotiated it down knowing that I would need to manage the growth and test and learn in a wholesale environment. I had gone to them with a half-made prototype and convinced them to believe in the vision: an incredible fabric, a size run not seen before, and an incredibly desperate customer who was entirely underserved by the existing market. II

Some companies believed in it less. After the launch, Net-a-Porter wanted to put in a sizable order, which would have been validation for Good American from a fashion point of view, but they refused to take all the sizes: They wanted sizes 2–10, so I told them no, as that undermined the entire principle of the brand. “Have you been listening? Have you read any of the press? I’ve taken a pledge , a pledge of fucking allegiance, to do nineteen sizes.”

After the launch, everything got very serious. We launched in October, and if we had managed to maintain inventory, we would be on a $40 million trajectory for the year—if full inventory had been available, I could have done $60 million in the first six months. As one of my investors said, “Emma, you have a tiger by the tail. Please don’t fuck it up again.” As soon as we were able to get Nordstrom their inventory, they blew out of it, too, but they had bought in a much more considered and better way, with a more accurate size curve. They have a powerhouse team of planners and merchants who really understand the American customer, and I credit them with teaching me almost everything I know about the denim business. I was lucky to encounter a team of incredible women at Nordstrom—Trisha, Holly, and Shea—who took me under their wings. I ate up everything they were willing to teach me. (Coincidentally, these women now run the biggest retailers in the US.) At the beginning, I didn’t know anything . They sat me down and really helped me understand what the customer in America goes for from a wash point of view, the fabrics I should be developing, and what fits might be next. It was Denim University at Nordstrom, and I was their best student, in part because I knew I didn’t know shit, and I was open to learning.

Nordstrom also asked me to go to stores all over the country to meet and talk to customers and train the staff. I jumped at every opportunity to learn about my customer. I gave away as many jeans to the retail team as possible, pinpointing people on the shop floor who I knew would be good advocates for the brand: “You—you’re a size 16, put these Good American jeans on.” From that one experience with the brand, they’d sell Good American all day. I learned so much about the country, about people’s tastes in different markets, and about what people want. In reality, I’ve come to understand that operating a business requires this type of mindset: If you go into every encounter with a beginner’s mind, believing you have so much to learn, you will.

When Michelle Obama talks about her own impostor syndrome, that maybe she doesn’t have anything wise or relevant to share, she offers a “secret” to the rest of us: “I have been at probably every powerful table that you can think of. I have worked at nonprofits, I have been at foundations, I have worked in corporations, served on corporate boards. I have been at G-Summits, I have sat in at the UN: They are not that smart.” 1 I honestly think that when you think you have it all figured out, when you’re certain that you are a fit-for-purpose CEO and absolutely the right person to take on the job, you might be screwed. Our world and culture are shifting and evolving dramatically fast. Anyone who thinks they know how to steer a business with complete certainty is full of it, for one, and if you don’t take the attitude of being a perpetual learner, the world will pass you by. The only thing you need to continually cultivate throughout your life is curiosity, the belief that there’s more for you to learn and plenty of people to teach you, and that you can’t be complacent. If you can master those three things, you’re in good shape.

In Mindset, Carol Dweck tells the story of George Dantzig, who was a math graduate student at Berkeley in 1939. She writes, “One day, as usual, he rushed in late to his math class and quickly copied the two homework problems from the blackboard. When he later went to do them, he found them very difficult, and it took him several days of hard work to crack them open and solve them. They turned out not to be homework problems at all. They were two famous math problems that had never been solved.” 2 I love this story because it underlines the formative power of a growth mindset. If you assume that every problem is solvable, you’re much more likely to figure it out. On the flip side, if you think something is too difficult, and everyone’s already tried, and what do you know, you’re never going to succeed.

New Thought: Nobody knows what they’re doing; your only job is to figure it out, day by day. Do the work, and keep your antennae up and your mind open and curious.

2. Old Thought: You should naturally be good at things. If it doesn’t come easily, it’s not for you.

Knowing what you don’t know is more useful than being brilliant.

—Charlie Munger

I want to double-click on education because it’s one of the things I’m asked about a lot. I am not a naturally gifted learner, school was incredibly hard for me, and I ended up not finishing. To that point, I’m not “naturally” good at anything. Not a sausage. This doesn’t mean I’m not really good at a lot of things, but you would never take someone like me and pattern-match me against anyone else in the industry and say, “Ah, there’s a winner.”

In the earliest stages of my career, I felt a ton of anxiety about my lack of higher education. It felt like such a void in my life because I left school when I was sixteen and have always felt “behind” everyone else, and that they learned things I’m also supposed to know. Even though I got a head start in the working world, I felt like everyone who went to university had a head start in life. On some level, I knew this wasn’t true, but I still struggled to shake the belief that everything would have been better if I’d been able to stay in school. Though when I reflect on this now, I recognize that following a preordained path—you go to a good college, you get a good job, you retire—can create complacency and passivity. If you assume it will work out because it works out for everyone else, it’s less likely that you’ll figure it out for yourself.

So, first, yes, get a good education. This is one of my priorities for my kids, and while I have a lot of thoughts about not giving my children money, as I don’t want to deprive them of the opportunity to figure their lives out themselves, I will always pay for their education, including any graduate degrees they might want to pursue. While it’s not “formal,” I am educating myself all the time. I’ve put myself through college courses, like Yale University’s African American History from Emancipation to 2010. I read compulsively, both newspapers and books. And, if you haven’t noticed, I make a lot of phone calls and ask a lot of questions.

Back in the day, when I was trying to figure it out, I got out the Yellow Pages in London and tracked down all the PR agencies. Then, after landing a one-week placement at one of those agencies, I’d take the fashion industry contact bible, Le Book , and copy the entire thing. I started calling and writing to people asking if they needed help. It worked—people needed help—and so I did a year unpaid anywhere I could lend a hand. I’d work at various PR companies or designer studios for four days a week, and then I’d spend the weekend working retail to make money to survive.

Often, I’d find myself in a cupboard packing up samples to send out with a twenty-two- or twenty-three-year-old recent college graduate—at first, I felt “less than” because of my accent and lack of education, but pretty quickly, I realized I should probably get out of my own way on that. We were all equally clueless about life, and none of us had any work skills. In some ways, I knew more than they did, as I had been out for myself for a while. Over time, I came to realize that my lack of education wouldn’t be a massive factor in the potential for success—nobody was résumé-checking me for a college degree. I had worked my way beyond that expectation and was on the same path as these other girls.

Since I wasn’t overly formed by a specific college degree in, say, marketing or journalism, I used my internships to help me figure out what I didn’t want to do. I knew I wanted to be in fashion, that’s it. At first I thought I wanted to do PR, then I thought I wanted to be a buyer, then I thought I wanted to be a journalist. Over time I managed to gain a cursory understanding of a lot of different functions while ticking things off my list of career possibilities. I ruled out a lot of jobs via experience. The other upside is that I came to fundamentally understand the business of fashion. I worked every dogsbody job out there. III I really came to know the sausage quite intimately—and how the sausage is made.

Besides getting a taste of every part of the fashion industry, every once in a while, if you were lucky, you’d get a sign of something you were good at. I believe enormously in signs and that the universe is in constant communication with you, if you care to pay attention. At one job, someone complimented me on how enormously organized I am, in another how I could always see around corners and understand the bigger picture and end goals of the clients. I took notice of this and realized I might have a talent to cultivate there—one of my points of genius now is that I can pull many, many strands together at relative warp speed and then sell you on the vision. I see the story, I see the journey, I see how everything is connected, and then I can bring people along on the ride. This is possible only because I have the mentality that keeps me focused on the bigger picture—I’m not sure if I would have focused so intently on developing and maintaining that skill if it hadn’t been called out as special early on. In my early days, I used to be in charge of posting health and safety manuals backstage at the shows and making signage—one day, someone pointed out that spatially, from a graphic design point of view, I had done a really nice job. My response: “I don’t think you should put up an ugly sign in a really beautiful environment.” And from this, I noticed that I pay more attention to small details than the average person. To this day, I am really, really good at understanding the visual language of an email, store signage, or a landing page—I know how to present product really well. I learned I had a knack for negotiation because in the chaos of backstage, I could always bring people together, whether it was the designer’s team, the PR team, or the production team, and get everyone to cohere and be okay together. This signaled another skill.

When I worked at Quintessentially with a bunch of Eton and Harrow grads, I really became disabused of the idea that I wasn’t smart. I loved a lot of them, but those toffs couldn’t organize a piss-up in a brewery. I didn’t know until I was an adult with kids of my own who share my diagnosis, but I’m dyslexic. The minute I understood this though, I felt a flood of self-belief that I could figure out how to work with my dyslexia—and that it gives me special powers in the way that my mind is organized. I realized then that I’m not stupid, I just learn differently. I also let go of the belief that everything would have been better if I had been in a fancier school, because it would have still been me in the fancier school—and I still wouldn’t have understood how I think or learn. I came to understand that the only person who could affect my reality is me, and that I needed to sharpen up and get really good at working with my mind and how it uniquely functions.

One of the superpowers of dyslexia is that I see through problems: I can make everything very uncomplicated and distill it down to its essential nature. I don’t get confused or stuck in a bunch of dark side alleys, and it’s also why I’m good at identifying all the thoughts that I don’t want to entertain.

Every superpower in my life and work is based on my relationship to the world. It has all come from understanding myself through experience. I am incredibly organized, but this goes beyond Excel. It’s about seeing the underlying system, what’s important and what’s extraneous, what’s essential and what’s a 1 percent distraction. I care a lot about beauty and small details because aesthetics are critical to customer experience and the success of the product. And I really believe that there are creative solutions to every problem where everyone wins, meaning I’m exceptional at bringing unlikely partners to the table and making people happy. Nobody taught me this, and you won’t find it on any school curriculum. It’s an attitude. I figured it out by observing myself and the way other people responded to me. I urge you to do the same.

I also urge you to move past the discomfort of asking a million questions. Think about your career as your opportunity to study and learn, with no graduation in sight; because the world is constantly evolving and shifting, your skill set must expand and grow to keep pace. In the time of permanent disruption and change, what works today will not work tomorrow. The people who thrive in this environment are those who live in a growth mindset, continually adapting to the world by paying attention and assuming they know nothing. In my experience, perversely, men are more comfortable in this stance: They don’t believe they should have all the answers. As women we need to move past feeling like we are stupid or inadequate for not knowing everything, or that the wrong question will give us away as a fraud.

Again, education is important, but there is no educational degree that will deliver you certain success. I’ve worked with enough highly pedigreed people that I’ve learned having all the right degrees from the right schools will not solve your underlying anxiety about not knowing enough. And it shouldn’t. What you need to do instead is transform that anxiety into curiosity: Ask questions, lean into the valuable white space that’s left when you don’t rush to fill it because you immediately assume you know best and must have all the answers. What you need to discover is a fundamental faith in your own ability to figure it out . Not to have the solutions, but instead to have the mindset required to discover them repeatedly and recurringly. It’s important to remember that the solutions will shift and change.

New Thought: You will bring a particular genius to your career, and it’s your job to figure out what this is.

3. Old Thought: Part of your job is to make other people comfortable.

Your energy is your most expensive currency. And not everyone can afford it.

—Déjà Rae

This is what I’d like to hear women start to say: Instead of I can’t ________________, I’d like to hear I won’t ______________. Or even I don’t want to ______________. Because you know what happens when you tell someone you can’t do something? They push. They suggest ways in which you might be able to accommodate their desires by rescheduling your life, or breaking a boundary, or pushing past your own values or limits. I’ve been trying this for a minute, and when I tell someone I won’t come to an event or shift my schedule around, they offer zero retort. It’s so final, so assured, so clear. If you don’t feel ready for the directness of I won’t , you can modify the script: I’m saying no to everything right now, or I’m heads-down at the moment. Please ask me again in the new year.

I understand this might sound stark and maybe even mean in a culture where we are conditioned to be so goddamned nice all the time, but we need to give ourselves and each other a break. While you might think it’s your job to serve other people’s needs and make other people happy at your own expense, it’s actually not. Not only that, it’s not even your job to ensure that other people are comfortable. I want you to sit with that for a minute because this is big in the psychology of women: So many of us have been convinced by the culture at large and maybe even our parents, teachers, or friends that we should sacrifice our preferences, goals, and desires to keep other people happy. We steamroll ourselves in the process.

Now, I get that within the function of having a job and being a reliable employee, you will need to do things that you don’t want to do. This is a reality of working for other people. But there is a line that I want all women to find between work that can sometimes be irritating or an inconvenience—and soul obliteration. When there’s choice, make sure you bring yourself into the decision as well: Do I want to travel and I’m making my kids an excuse for not pursuing more, or do I not? Do I want to take on this additional project, or do I not? Do I want to work on Sunday night, or do I not?

Saying no for many of us is a new skill, possibly one that’s never been exercised before. It’s okay to practice in less consequential ways, rather than steeling yourself to defy someone who has more power than you right out of the gate. Practice with your friends—instead of telling lies to get out of Friday night plans, tell them you’re trying to be more direct and give them a straight No, thank you, I don’t want to go. Or Thanks for the kind offer, I won’t be able to make it. In time, a simple “no” will become more and more accessible. Don’t offer an abundance of excuses; don’t justify your “no”; don’t hem and haw; don’t apologize. You can be polite and even grateful for the opportunity (you don’t want) without selling yourself down the river.

The instinct to dwell on the way other people feel about us is not always a great survival skill—spending a lot of energy trying to make yourself perpetually palatable can really fuck you up. I’ve heard stories from women who found themselves being convinced to sign additional yearslong contracts for jobs they despised. I’ve heard stories from women who got screwed in their marriages because they were embarrassed to get advice from others. I’ve heard stories from women who felt like they were being an encumbrance or taking up too much time with questions, so they rushed through the paperwork to please the person offering the pen. And I’ve heard stories from women who didn’t want the person they were negotiating with to think they were mean because they were pushing back. When we don’t stay connected to ourselves, we’re much more likely to get screwed because we know . At some level, you always know. Find that part of you.

Sunita Sah, a physician and professor at Cornell’s school of management, explains that insinuation anxiety is that feeling you have when you don’t say something for fear of making it clear to the other person that you hold a negative opinion of them. Insinuation anxiety is the reason why we can struggle to speak up about a bad haircut, or send an undercooked meal back, or tell someone we think they might be giving us a raw deal on a car, or a salary, or a term sheet. She writes, “Insinuation anxiety encourages us to act against our values and preferences in order to protect another person’s feelings. We do not want to insinuate that we think the other person may be biased, corrupt, or plain incompetent. So we often comply with a suggestion, keep silent, or accept a bad piece of advice, just so that the very person who is hurting us, costing us, or putting us at risk can ‘save face.’ ” 3

I don’t really struggle with insinuation anxiety. I push back, though it’s a muscle I had to build. When I’m uncomfortable, confused, or I feel like something is off, I ask for clarification — and I always ask for time so I can look things over on my own clock (and have my lawyers look, too), without feeling watched for my response. I do this nicely enough—sometimes I even crack a joke or a smile—but I don’t rush to please, and this has kept me safe.

I’m somewhat convinced that one of the reasons we hate to say no, or make ourselves say yes to things we want to reject, is that we hate to hear “no” ourselves. I still find it hard to hear no , yet I’ve trained myself to look for the lesson and what the no is there to teach me. There’s some magical thinking involved where if we say yes to everyone and everything, we’ll only get yeses to our requests in response. That, and we sometimes take care of the needs of others, hoping they in turn will then take care of ours (again, magical thinking in action). Hearing no can be painful because it suggests that you’ve over-asked, or been presumptuous, or are pushing too hard—and for many of us, it can be excruciating to hit that type of boundary or wall. This is another reason it would be good for all of us to practice this powerful two-letter word with each other; think of it as exposure therapy.

“No” is not death. A no is not the end of the world. A no doesn’t mean that you don’t have incredible value, or that people don’t want to have dinner with you, or don’t want to have you around. A no—particularly in a high-stakes situation like your salary negotiation or when you’re doing a deal—can feel scary as fuck, but don’t give that word so much power. Ultimately, it’s just information, signaling a boundary or line—it doesn’t need to shut the conversation or the negotiation down. Use a no to a request for a promotion as an opportunity to ask where you can improve, where you’re falling short, and what you could do differently. Then drop the defensiveness and listen. Sometimes a no is easy to digest and recover from, but when I hear a no that causes me to stop short, I pause and take a deep breath, and then I ask questions, looking to understand where the other person sits and why. Keep reminding yourself that this is not the end of the world, nor is it the end of your opportunities. As the saying goes, Rejection is God’s projection. I’m so grateful my first bosses gave me a big, fat, heartless no when I asked them for more money—I’m not sure where I would be today if this hadn’t pushed me out the door and onto my own path. There’s no version of business and life where you get successive yeses until you die. If you’re not hearing no from time to time, you haven’t found the edge of what’s possible. It’s now your job to find that edge and pursue it.

New Thought: Your wants and needs are as important as everyone else’s—in fact, for you, when it comes to work, they come first. If you’re not hearing “no,” you’re not pushing hard enough for those wants and needs.

4. Old Thought: You should strive for work-life balance.

Whenever you see me somewhere succeeding in one area of my life, that almost certainly means I am failing in another area of my life…. That is the trade-off. That is the Faustian bargain one makes with the devil that comes with being a powerful working woman who is also a powerful mother.

—Shonda Rhimes

In 2025 I went on The Diary of a CEO and the host, Steven Bartlett, asked me about interview red flags. I offered that a big one for me is when someone asks me about work-life balance in the organization. I said, “Work-life balance is your problem. That’s yours to figure out.” This line got picked up everywhere , and you would have thought I’d canceled Christmas. Some people were outraged, while others slid into my DMs to thank me, as it’s something that they de facto ask in interviews without really thinking about why. I get this: We’ve been programmed to say it. My issue with the ask in an interview context is that it signals a lack of personal responsibility and autonomy, two qualities I expect from my team.

If you come to work with me, yes, you come in, and yes, you have set hours, but there will always be flexibility within your working life in the same way that you need to be flexible in your home life. Nobody is looking to see who is or is not sitting at their desk—we don’t work like that anymore. I don’t know if anyone works like that. But there is a quid pro quo expectation, if we’re being honest, that if you’re going to use work hours to do personal things, you’re probably using some personal hours to do work things. There’s also an understanding that some people are exceptionally efficient and focused and boundaried with their time, and they might get a majority of their work done between the hours of 9:00 a.m. and 5:00 p.m., while some of us are more fluid and unstructured. I don’t really care. It’s none of my business. My business is that you do your job. And if you have a lot of ambition for yourself, you’re probably going to want to do your job and then some.

I know that people prioritize the mythical “work-life balance,” though everyone struggles to define what this means. 4 The lack of definition makes sense, as theoretically this balance is different for everyone, and it brings me back to the idea of trade-offs: You’re not going to get everything you want all the time. I can assure you that you won’t be running a massive company maintaining a personal policy that you’re done working at 6:00 p.m. every night and are unreachable every weekend. Sure, fine, we’d all vote for a perfect, mythical “work-life balance” in a vacuum. But if you rank work-life balance on a scale against earning substantially more, year-over-year, or getting a really meaningful bonus, people’s priorities would change. Those achievements correlate with working really hard. To run an organization where people get great work-life balance, you need to be profitable. The company needs to be in line with, if not beating, its competition. It’s not realistic to imagine that you’re going to work at a start-up with the potential for huge upside and be home by 5:00 p.m. every night when there aren’t that many people to get the huge amount of work that needs to be done done . It is realistic to earn a nice salary at a stable business with limited upside and expect to be home at 5:00 p.m. every night. Every job is different, with different trade-offs.

I am in the business of delivering huge upside, and with that comes an expectation that my people are not going to be watching the clock but doing what they need to do to get the job done. This isn’t for everyone, but it is the right fit for people who have a similar ambition. When we’re talking about a traditional job, I don’t think there’s an expectation anywhere that you need to work seven days a week. But if you have ambition, if you want to do the most , if you want to grow, if you want to be one of the people on the top of the organization, chances are good that you’re going to have to work a little bit more. We shouldn’t be angry about that; we should be honest about it! That’s the truth. I’m sick of people lying about it. Everyone I know who is extremely successful is a little bit of a workaholic—they work on Saturday or Sunday if necessary. They’re looking at emails at night. I do this. I also put my phone down for three hours every evening to have dinner with my kids. I completely check out for vacation a few times a year. I have many great weekends up in Malibu on the beach where I’m not thinking about work at all. This happens. But I do not lie to myself or other people about shutting work out of my personal life. It’s all one thing.

I get that people are tired of hustle culture. People are burnt-out and tired of thinking about being burnt-out. I get it. But figuring out your own limits and your own ambition is a big part of your responsibility to yourself. And my part here is to deliver a level of honesty about what it takes to be really successful. I see it as an obligation not to lie. I refuse to tell people that they can be really successful without giving 150 percent, without waking up most days and doing some type of work or at least thinking about work. It has not been my experience that people achieve great things doing less. People chafe against this because they don’t want to do it. They want all the benefits, but they don’t want to do the messy part in the middle of creating success, which requires a lot of monotonous and endlessly grinding work. I cannot stress enough that you will not be able to skip out on this level of consistent intensity and succeed. I get it, it’s not for everyone. And if it’s not for you, don’t do it. That’s your choice. But an extraordinary career is always the result of extraordinary effort.

It’s not the right call for a lot of people. The reality is that most of your colleagues and coworkers don’t actually want the tippy-top pinnacle of success. Most people want the security of a well-paying job that allows them to pay their rent or their mortgage. They want to have a nice life, and a nice car, and educate their kids, and go on a couple of vacations. That’s what most people want. And should you be able to achieve that without working every night and weekend? Yes, definitely. But if you want an extraordinary life, it will require extraordinary sacrifice.

If you run a modern organization, chances are nobody in your company will miss a dentist appointment, their turn to be the surprise reader at their kids’ school, or a parent-teacher conference. If someone’s kid is sick, their kid is sick and will need a parent to be home. Nobody who works for me is waiting to go to the doctor for three months because they can’t duck out for a 3:00 p.m. appointment. That’s just not how we work anymore. We have a flexible way of working. But do I think that working from home for three days a week is conducive to becoming a leader? No, I don’t. First of all, there’s an urgency and an immediacy to being together with people that you cannot approximate on Slack. You’ve got to gather people quickly and do things fast. That is one of the qualities that’s made me so successful: We move, we get stuff done. We tolerate mistakes because we optimize for speed. We don’t sit and strategize and figure it out three months later. There is an urgency with which we work. There’s also proximity, which is key in business, especially in the earliest parts of your career. If you want to sit at the leadership table, remote work isn’t going to be in the cards for you—that doesn’t mean that you can’t anticipate a certain amount of flexibility, but you’re not going to run a team effectively from your bedroom. You have to be in the room. You need to be seen. There’s a middle ground situation where all employees are able to balance their career aspirations with their home obligations. That was already happening before COVID hit. But I’d be lying if I said that I don’t really worry that putting women back at home is not putting women forward.

I actually lose sleep worrying about the impact of remote work on women who want leadership roles. On the one hand, I recognize that it creates slack and relief—chances are, you can swing more pickups or take a break and head down to your kids’ preschool to serve snacks. But then you are literally not in the room. Ultimately, I don’t think women are served by it because there’s a sneaky presumption in our culture that mothers are default caregivers, and that they should be able to do it all—also, that work is kind of a “bonus job” on top of the primary duties of being a mother. I’ve heard from very senior leaders at my companies that their husbands argue with them about the necessity of paying for childcare on WFH days, somehow laboring under the belief that being in the house means you can do your job while executing drop-off, pickup, and after-school programming. I worry that shit like this is disproportionately going to affect women’s ability to step up and become leaders of organizations. There’s the belief that if they’re working from home, they don’t need the help. But they do need the help! Women need all the help they can get!

We’ve really wrestled with the WFH question at our companies. On any given Friday, the product teams are likely in the office. Otherwise, the office is largely empty. Post-COVID, we’ve given everyone the liberty of working in the office four days a week, with the expectation that they’re putting in a fifth day from home. I have really, really mixed feelings about this. We talk so much about the flexibility of working from home and what Zoom has enabled in business, but we don’t talk at all about the rigidity of it, and what it takes from work, and what you miss out on. I can guarantee that if I had been WFH in my twenties, I wouldn’t be anywhere close to where I am now. And I don’t just mean professionally. I met my husband at work. I made some of my best and strongest relationships at the office, relationships that are the foundation of both who I am and how I find my happiness. The friendships I made early on in my career are some of the most important in my life.

It’s so interesting that we have an aversion to the office now, and all want to be as far away from it as possible. I just don’t really get it. I’m an in-person person. I want to be with people. I want to collaborate. I love detail and specificity. I want to do things quickly. I mentor a lot of young men and women inside my own businesses. Work culture right now makes this very hard. I can’t teach you through a screen—if you’re not with me, you won’t see how I move or operate. You need proximity to me. You need to understand the flow of what’s happening. The way we work now makes me a little sad because I don’t think we’re having all of those exchanges that are the result of being in a really dynamic environment where you’re able to learn from people on the fly. We’re simply not together as much as we used to be, and our professional relationships are suffering because of it. Also, it just isn’t as much fun: Drink after work, anyone? Now I’m really showing my age.

If you work in a business with other people, or you want to build a business of scale someday, the idea that you can do it alone is a joke. You are not going to get far unless you surround yourself with people, because nobody is successful working on their own. If you want to lead, or be at a decision-making level at any company, you need to be with your people. I haven’t seen it work any other way.

New Thought: Work-life balance is the wrong focus—alignment to your ultimate ambition is the right one. If you want to go big, what you lose in remote work is profound. The downside is deceleration—a curse for ambition.

5. Old Thought: You’re owed mentorship and opportunity.

Nothing will work unless you do.

—Maya Angelou

While mentoring as many people as possible is now one of my primary intentions in this phase of my life, in my own experience, I didn’t have any mentors. I held Oprah in my head as a paragon of what was possible for a woman, and I watched her on TV whenever I could (often when I was cutting class, after dropping my younger sisters at school), and I picked up what she was laying down about gratitude, mindfulness, self-actualization, and manifesting your life through action. I wanted to be thoughtful and articulate like Oprah, and I wanted to move like Oprah because I thought she moved so well. She was kind of it for me because, as they say, You can’t be what you can’t see . We didn’t have podcasts and endless online content when I was coming up, and I’m really someone who learns from watching other people operate. Absent a lot of people to look to in the wider culture, I used what was immediately available. If you’re smart, you will make whoever is around you your mentor—both in what you want to adopt and what you don’t.

I started my first real salaried job in the fashion industry when I was eighteen, and I just happened to sit directly in front of my boss. All my friends at the office thought this was unfortunate because she could see my screen—while they were online shopping at Net-a-Porter, I was relegated to work, and this was good for me. I listened to every phone conversation she had. When she had a great call, I’d write down what she’d said so I could adopt parts of her pitch. She’d walk out of the room, and I’d pick up the phone to dial for new business, adopting her lines and then making them uniquely my own. She wasn’t my mentor, she was my boss (and a bitchy one at that), but I learned a lot from her. I even copied her outfits. She was incredibly formative in my own early success. Look around: There must be people, whether they’d be your first pick for a mentor or not, who can teach you. Emulate what they do. Ask them for feedback on your work and what you could do better. Practice leads to mastery. Everyone starts somewhere, so start by studying the best people in your midst. While we’re trained to look at women who are senior to us to teach us things, I’ve learned just as much from women who are my employees, like Mel Anderson and Lindsey Frawley.

Honestly, anyone who would be a good mentor probably doesn’t have time to mentor you. And depending on who you are and your level of exposure to best-in-class businesses and leaders, you’re probably not going to be surrounded by the right people anyway. Almost every one of my podcast guests has told me that their mentors all came out of books, and Mark Cuban told me he is currently being mentored by AI: “If you learn how to prompt it… it’s like having an entire staff of a thousand business professors.” 5 (He also makes the point that if you’re using your job correctly, you’re being paid to learn, regardless of where you sit in the company.) So start exactly where you are and figure out whom you have contact with who can teach you things—they don’t even need to participate; you can simply study them. They could be colleagues, teachers, or even friends. Early on in my career, I’d look for mentorship from my clients, too—if I encountered the CMO or the CEO, I’d ask a question at the end of the meeting. I’d say, “I have two other questions that have nothing to do with the work we’re doing or the brief I’m here to deliver, but I’d love to ask you…” Invariably, they’d answer and give me really generous and thoughtful advice. I never wasted the opportunity and asked good questions. In my experience, people are happy to share their wisdom if they have the time and you ask in a nice way. IV

Throughout my life, I’ve had an insatiable appetite to learn. When you are building something, you don’t get to stop growing. You need to stay in learning mode. It helps ensure that you are always asking better questions. You’re staying curious. You’re refusing to let your ego block your evolution. For me, this boils down to a lot of reading, a lot of self-reflection, and a lot of listening. I often have a lot to say, but sometimes I need to stay quiet and observe people operate whom I aspire to be like so I can better understand how they do what they do. Commit fifteen to thirty minutes a day to intentional learning—read a book, listen to a podcast, take a course, or watch someone you admire speak. At the end of every day, ask yourself some questions: What did I learn today? What challenged me? Where are my gaps? What could I do differently or better next time? These simple prompts keep your brain in learning mode and bring some awareness to how you’re operating in a way that’s very healthy and hygienic.

Find some teachers in your life—a group of friends, a coworker who is wise and thinks bigger than you do, a more formal mentor if you can find one. But think deeply about where you’re spending your time and with whom, as it can really expand or limit your growth. I’ve been quite systematic throughout my life about shedding people who were not good for me, or who dragged my energy down. You might need to shed people who carry low expectations for you or are narrow-minded. It’s just not worth it to stay loyal to people who don’t want the very best for you. Throughout it all, stay rooted in your curiosity and remind yourself frequently that you don’t know everything—if you can do that, you’ll go much further than most people.

One of the most foundational parts of my success has been that I’ve never felt like anyone automatically owes me anything—I’ve never had any entitlement about what my career should look like, or which opportunities should be rolled out for me. I’ve forged my own path. I knew it started and ended with me. I meet a lot of people who expect a lot simply because they show up. Maybe they’re right to have that level of entitlement, but in my experience, you need to make a career yourself and prove yourself worthy for advancement. It doesn’t just happen because you’ve been there the requisite number of years. It requires an active desire to get better and grow. Nobody can do that for you. You must be devoted to curiosity, learning, flexibility, discipline, and hard work if you want to advance.

The three most important words for the advancement of my career were: I’ll do that. That was me. My whole life, I’ve had my hand up, offering to do the thing. It didn’t matter which workplace I happened to be in; I’d put my hand up. These boxes need to be packed up and shipped. “I’ll do that.” These samples need to be steamed. “I’ll do that.” We have a client in town who wants to see the sights. “No problem, I’ll take them around.” People started to look at me as someone who would always get it done. It’s not that I had any particular skill. I simply put myself in the space of giving it a go, every single time. Because I’d never been trained to attack a problem through the lens of a business school, I’d go straight into figure-it-out mode. Nowadays, we call this “test and learn,” but at the time I was just known as a person who would solve the problem by throwing a bunch of things at the wall to see what sticks. I grew a reputation as someone who could make shit happen; from there, my confidence grew that I could, in fact, make shit happen.

If you’re hoping to be noticed, if you’re hoping to be promoted, the most surefire way to ensure that this happens is to be excellent at what you are doing. I find it really difficult when people come to me and ask me for a promotion, or an expanded job remit, or to do a different function altogether— I’d really like to do this thing over there; I’d like this bigger opportunity— when they’re not blowing my socks off. I then have to tell them that they’re only 70 percent good at what they’re currently doing. On the other hand, I’m always looking at the 120 percent people in the organization and thinking about how to grow them. Those people get much wider remits because I trust them to be excellent at whatever it is that they’re doing. I don’t care so much about whether they have the expertise required, as I’m confident they will figure it out and learn quickly on the job.

I’m much more inclined to hire for attitude over experience. For this reason, I’m very open to moving people around to different functions on the team—and other good leaders share this willingness—because the more the team understands the business as a whole, the better they can function with increasing responsibility and an understanding of the organization and our goals. If you’re an amazing wholesale salesperson who really wants to learn e-commerce and how to buy for DTC channels, I’m going to support that mission. I’m very invested in team members who are interested in the entire business and want to see the structure from outside of their current lane or division. I have done sidesteps from one department to another in a few of my jobs, and it has always served me well.

Another essential quality to cultivate is flexibility. This comes back to knowing what you don’t know, and acknowledging that the world is changing so quickly, what you know today might not be relevant tomorrow. You’ve got to always be learning , always trying new things, and looking for novel solutions. I hire a lot of people who are in their forties and fifties for senior executive leadership roles, and I’m conscious to rule anyone out who adopts an attitude that’s overly fixed, rigid, or certain. If you come from a competitor and say, “The only way to get from here to there is the way I’ve been doing it for the past twenty years,” we’re not going to be the right fit. I want that vast experience to be paired with flexibility, because technology means the customer expectations change all the time.

I’m a generalist who came up in an unexpected way, but most people take a more typical path: They’re specialists. If you’re working in a function in an organization, you’re a specialist. And some leaders are specialists, too, like Mellody Hobson, who is the co-CEO and president of Ariel Investments. When we spoke on my podcast, she talked about cultivating her expertise in finance—and how she’ll never, ever be done becoming an expert. She talked about how when you survey the greats, whether it’s Steve Jobs, or Walt Disney, or Warren Buffett, “they did one thing extremely well and they went deep. An expert is someone who knows more and more about less and less. There’s a difference between a general practitioner whom you go to for your routine checkup and brain surgery. I wanted to be the brain surgeon of my field.” Mellody went on to explain that she “wanted to be known for something that [she does] so well it distinguishes [her].” For her, one of those distinguishing points, in addition to her financial chops, is that she can explain money and financial concepts to anyone, making a complex industry transparent and understandable. And she focuses on this in particular because once you can teach something, you really own it—it forces her own learning and question asking. 6

If you want to run the place in time, or if you want to start and run your own thing, Mellody agrees with me that you need a level of intensity, a sense of urgency, an indomitable work ethic, and a desire to be great. She believes what Jim Collins, author of Good to Great , writes: “Good is the enemy of great.” You can’t be a B+ player because then you’ll be satisfied with a B+ result. I know I just belabored this in the section on work-life balance, but you’ll likely need to be a little bit of a workaholic if you’re going to make your dreams come true. And she feels you need to be incredibly disciplined. This is industry-specific advice—my emails are not like this—but Mellody has someone copyedit every single one of her emails because she feels that an error there could create the idea that she’s not fastidious and detail-oriented—and when it comes to people’s money, they expect precision and care, not sloppiness. “A typo could kill an opportunity for us because they will think you’re half-assed—as my husband always jokes, ‘She does not like half-assed—she likes whole-assed.’ ” 7 While spelling isn’t important to me, my team knows that I am incredibly disciplined about every aspect of each product. I believe this is a huge part of my success. I sweat every single, solitary detail and rarely use the apparel phrase “correct and proceed.” Instead, I want to see it, wear it, test it, and likely change it again! I will obsess about every part of a store’s design, and any copy that touches product, the website, a swing ticket, or any part of our business. I don’t feel I need to do all the work, but I do need to respond to the work and give feedback and direction. I out-care everyone else. I pay maniacal attention, so my team does, too. Discipline is contagious in an organization, and it’s contagious in your life. When you take this approach, it will start to positively affect other parts of your life. As the saying goes, How you do anything is how you do everything .

Wherever you are in your career, treat every opportunity and experience as leverage—even if you hate it in that moment, skip the sour attitude and think about what it’s teaching you, and what you’ll eventually be able to bring forward. Early on in my career, I realized that every client who had a show could eventually be useful to me in some way, shape, or form. I cultivated all those relationships. Eventually, when I left that company, not only did I have contacts to leverage but I had my reputation, which ended up being even more valuable. I was known as a hard worker, diligent, perfectionistic, and someone who would get the deal done. I was also known as having a lot of passion and enthusiasm for the industry and for making the entire experience as joyful and fun as possible. Those contacts became my clients at my agency ITB; those clients then gave me bigger and bigger projects and opportunities once they were certain I would deliver. And eventually, when I needed to do my first raise, I didn’t go to a VC or a fund—I went to my clients. I had long working relationships with all of them and a reputation for always delivering on my word. Many of them are still my trusted advisors to this day. So what I’d offer is that rather than getting too fixated on your next step, or where you want to be, think about where you are today and make sure you’re as excellent as possible. Start with yourself, and use that as a springboard for your next move.

New Thought: You are the creator of your own career, and the responsibility for it is yours, too.