In September 2015, Molly Graham shared a new article with her Twitter followers, writing that it contained “All the things I know about scaling and how to try to do it well.” As it turned out, this collection of lessons from her experiences building teams at Google, Facebook, and Quip would strike a chord in the startup world. Her mandate charging readers to give away their Legos is still one of the Review’s most widely read articles — and it’s become a timeless, oft-cited metaphor for how to thrive inside of a rapidly scaling company.
The message seemed to hit a nerve because it gave voice to the emotional realities of startup life that often go undiscussed. “You go to cocktail parties and people ask you how it’s going, and you have to fake it. You say that everything is great even though it often feels like the world is falling apart. You think it’s just you that’s struggling,” says Graham. “It mattered to a lot of people, I think, to hear that feeling is actually completely normal.”
But in her view, recognizing the normalcy of these emotions is just the first step on a long journey. “We need to flip the switch from gritting your teeth and muscling through to acknowledging and managing your emotions,” she says. “And it can start small: What would happen if we all talked more openly, even just to our friends, about the emotional rollercoaster of work?”
In the three years since the Legos article first came out, Graham has made a side project of researching and leading discussions on these very questions. She’s given numerous talks at scaling companies such as Stripe, Slack, Convoy, Drift, and Pinterest on what it really feels like inside rapidly growing companies. And she’s also added a few more personal data points to her own collection of scaling experiences, from a successful exit (when Quip sold to Salesforce for $750 million) to a stint on yet another rapidly growing team (the Chan Zuckerberg Initiative, where she served as VP of Operations while the team scaled from 30 to over 200).
Now, as a startup advisor (and future founder mulling over company ideas of her own), Graham is back to dive even deeper into tactics for handling the emotional rollercoaster of scaling with grace. She covers why the whirlwind of emotions we face at work are “normal, but not useful,” and shares the strategies that have helped her keep her head on straight. Graham also frames up the tools she’s relied on to defang especially challenging emotions and cultivate a mindset that enabled her to thrive amid the twists and turns. Let’s get started.
WELCOME TO STARTUPS: MEET YOUR EMOTIONS
There’s a wellspring of intense emotions underneath the surface of every growing startup. For founders and early employees, company building life is intense and chaotic, but in Graham’s view, that’s not necessarily a negative signal in and of itself.
“You’re fighting to survive and for people to give a shit about your company. There’s no way that the stress of building something from scratch doesn’t affect your emotions. You’re cycling through anxiety, fear, euphoria, boredom and then back to fear again as the situation changes, and that’s completely normal,” she says. “But if you don’t know that’s normal and how everyone secretly feels, well then you can add feeling isolated and discombobulated to the list, too.”
When you’re at an early-stage startup, a significant percentage of your time is spent feeling like the whole thing might go off a cliff.
Out of all of her scaling experiences, Graham’s time at Quip felt the most intense. The difference? She joined Quip three months before launch when there were only nine people, as opposed to the 500 that were already on board at Facebook when she joined in 2008. “I was prepared for the emotions that come with giving away your Legos, which I had become familiar with from all the scaling at Facebook, but I was deeply unprepared for how different and emotional the process of helping to start a company is,” she says. “At Quip, I was more personally invested — and when you’re more connected, the highs are higher but the lows seem lower."
Graham points to the particular emotional turbulence that followed Quip’s July 2013 launch as an example. “After the pop, things started to slow down, which is normal. But I wasn't sure how we were going to follow it up and I found myself kind of spiraling,” she says. Over lunch with a friend, however, Graham got the reality check she needed.
“I opened up about how ambivalent, insecure and uncertain I was feeling. He just looked at me and said, ‘Welcome to startups.’ That was the moment that unlocked it for me; it’s what made me realize that what I was feeling was normal. I was like, ‘Oh, a lot of people at baby startups feel this way!’ And that realization sucked the power out of the emotions and made them less intense. How much healthier would everyone be if they realized that people at all the startups they admire also feel terrified half the time?” says Graham. “There’s so much power in admitting and sharing that, in recognizing that it doesn’t actually mean that the company is driving off a cliff.”
Take a breath and realize the rollercoaster — the highs and the lows — is normal.
WHY YOU NEED TO MAKE FRIENDS WITH THE MONSTER CHEWING ON YOUR LEG
To encapsulate how these emotions show up and how we can ride out the roller coaster’s twists and turns, Graham leans on another colorful metaphor: If learning to scale yourself and your job at a startup makes you feel like a kindergartener forced to share Legos, then all the emotions that come with navigating a fast-growing company are like a monster chewing on your leg.
“I call mine Bob,” says Graham. “He’s a tiny little monster and he seems friendly — I imagine him as a kind of muppet — but the truth is that Bob’s sole job is to make you the worst version of yourself. He aims to make you feel like you don’t know what you’re doing, to ask who even gave you this job in the first place, to behave in ways you’ll regret.”
For Graham, Bob represents all of the emotions and insecurities that can get the best of you at work. “It could be territorialism, anxiety, fear, doubt, politics, envy, FOMO, you name it. He’s like a backpack you can’t take off, a weight that you carry around with you,” she says. “Sometimes Bob is just nibbling on your toes, but other times, he’s eating your whole leg. And those territorial people that are making everyone’s life miserable at work? Bob is probably driving their car.”
And it’s not a feeling that will dissipate with time or experience. “I started talking about Bob to help people realize that you won’t outgrow or shake off the feelings he represents," says Graham. "No matter how hard you try to ignore him or get rid of him, he’s always going to be with you. You need to make friends with the monster because like it or not, he’s on this journey with you. The skill you need to develop is managing him."
At any given moment, ask yourself: Is your monster mostly well contained, chewing on your toes and smiling up at you? Or is he making his way up your whole leg? "Who is driving your car? It’s okay to have all of these feelings, but you can’t let your emotions sit in the driver's seat. You can’t let Bob win,” she says.
Your number one job in a rapidly scaling startup is to not let the monster eat you alive.
But how do you keep Bob down at your toes with so much change, ambiguity, and chaos swirling around you? Here are three guiding principles that Graham has relied on over the last decade inside scaling companies:
1. Observe, don’t act.
Simply put, the first step is to recognize that all of the emotions that accompany scaling are normal — but also that they’re not useful.
“Whether it’s fear, stress, anxiety, territorialism, or insecurity, these emotions themselves aren’t wrong. To be clear, it would be impressive if you didn’t feel them on a daily, weekly, or monthly basis inside a scaling company. Acknowledging that they’re normal, that everybody else is feeling them too, is helpful in making them feel less dramatic,” she says.
But that recognition of those emotions and their normalcy is only half the battle. In Graham’s view, what matters more is how you respond to them.
“You’re in the middle of a tornado and there are all these feelings that go along with that. But none of those emotions provide cues or advice for how you should act. On any given day, feeling territorial doesn’t mean you should grab all the Legos back. Feeling insecure doesn’t mean that you’re not qualified for the job. Feeling anxious doesn’t mean that the walls are actually falling in. You shouldn’t try to avoid the emotions or ignore them, but you shouldn’t necessarily act on them either.”
Just observe the emotions – ‘Today I’m feeling territorial’ – but wait to act on them until you know what’s real.
“I can say unequivocally that all of my biggest mistakes and things I regret the most are the times when I let Bob take the wheel,” says Graham. “Whether it was my ego taking over and saying ‘I need to make that presentation,’ or ‘I need to do XYZ to prove I'm important’ in a moment of insecurity and ambiguity, acting on that initial emotion never turned out well. But I’ve never regretted pressing pause to reflect.”
2. Give it two weeks.
But how can you tell when the timing is right to take action? While the phrase “Why don’t you sleep on it?” rings true in some cases, in Graham’s view, this approach needs a little fine-tuning to better adjust to the startup context.
“A lot of these emotions last longer than a day. If you slept on it and you're still anxious or scared, that doesn't mean you should go talk to your boss or grab all the Legos back. It’s not a sign from the startup gods that you should send that angry email,” she says. “Instead, observe any emotion or reaction you’re having to change around you, acknowledge it, shake Bob’s hand and say, ‘I get it, today I’m feeling territorial’ and then move on. Do that every day and if the emotion is still the same after a two-week period, then you should consider doing something about it.”
More often than not, this exercise allow these turbulent feelings to fade into the background. “You’ll be amazed at how many emotions pass in a two-week period. Something that feels dramatic and all-consuming in May will be gone by June, and you’ll be grateful that you didn’t act on it,” says Graham.
With startups, the only constant is change. Operating on a two week time horizon creates space for that change to take place, and more importantly, settle.
Graham readily acknowledges that some situations are not a “Bob problem” as she calls it, but rather a real one. “If you're still feeling almost exactly the same way after two weeks, that’s a sign that something deeper is going on. You should talk to someone — your manager, someone you trust, a coach, a mentor. While you don’t want to act on every impulse, you don’t want to go to the other extreme of never flagging what could be a serious problem for you or for the company,” she says.
3. Remember that everyone is battling a monster.
When it feels as though the monster may be winning, Graham’s advice is to go back to work and practice empathy, for yourself and others. “It doesn't matter what day of the week it is, it doesn't matter how well the business is doing — everyone feels like a fraud. It gets worse the more senior you get. It can also be worse for women and minorities,” she says.
The key is to recognize that everyone has their own version of Bob weighing them down. “Be kind to yourself by reiterating that, in all likelihood, you aren't an impostor and there isn't someone better than you for the job you're in,” she says. “And if your colleague is behaving weird or getting territorial, try to remember that it's because they're scared and have a monster eating their leg, not because they're an asshole.”
I have spent a significant chunk of time at every job feeling like I'm failing at everything. Ask every successful, competent person you know who has a the tiniest bit of self-awareness, and they’ll tell you that it has been the same for them.
MAKING SURE THE MONSTER DOESN’T WIN: THREE CHALLENGING EMOTIONS AND TACTICS FOR MANAGING THROUGH THEM
Recognizing the monster’s presence and making him your friend is key to surviving startups. But for Graham, it's not just about making it through. "If you deal with your emotions properly while scaling, you can work towards cultivating a mindset that allows you to thrive. Even in the thorniest of startup situations, I've found there's a way to focus on the positive and on what you can learn," she says.
Here, Graham identifies three common (and uncomfortable) emotional hurdles that the monster can throw in your path and gets tactical on how to manage through them — and come out the other side even stronger.
Challenge #1: When things feel competitive and political
In rapidly scaling startups, fixation on titles and power struggles can start to develop. “It’s one way that people try to control the chaos, but this tactic is straight out of Bob the monster's playbook,” says Graham. And she’s the first to admit that it’s all too easy to get pulled in.
“I’ll own up to the fact that I got annoyed that I wasn’t a Director at Facebook. I felt like that recognition of my skills and contributions came too late,” she says. “It’s completely normal to feel this way, we’re only human. But you have to recognize that it’s because Bob is driving."
And things can quickly get out of hand if you don’t beat him back. "If you let Bob win, your startup’s culture will devolve into a place where people waste time fighting for credit, control, or recognition for themselves rather than focusing on what’s right for the company," says Graham. "If people give in to their fears, hold on to their Legos, fight other people for jobs, remain overly fixated on their title and who gets the credit, they usually don't scale with the company. You have to adjust your mindset if you want to succeed at scaling.”
In her experience, obsessing over credit and titles is a sideshow that’s not worth the distraction. “Everything is going to change in two weeks or three months anyway. Sure, you might win this battle today, but you’ve burned bridges and everyone knows you’re out for yourself, so what happens in two months when everything changes? No one wants to work with you. That’s why I recommend swimming in the opposite direction,” she says. “My golden rule is to focus on being useful. Give away the credit and just worry about making the right thing happen. Be the person that makes everyone else look good, and you’ll be amazed at the opportunities that come your way over time.”
Focus on being the most useful person in the room, and the rest will follow.
To put a point on it, Graham underlines her own experience. “Let’s be real that, looking back now, no one — including myself — gives a shit what my title was at Facebook," she says. "Ultimately, I collected a set of experiences that have been invaluable to me in everything I’ve done since, and that is far more important than any title could ever be. Concentrate on making the company as big and successful as it can be — that is ultimately what will make the biggest difference to your career.”
Challenge #2: When fear and insecurity take over
When you step into a new role or join a startup in a different space, the intimidation factor immediately sets in. While impostor’s syndrome looms large in the background for almost all of us, it’s terrifying to admit out loud that you don’t know what’s going on. But in rapidly growing startups, Graham has come to value a willingness to learn, evolve, and sound like a moron more than established experience or deep expertise.
“Many believe that they have to be an expert in order to lead something, but I’ve found that no one can truly be an expert in the face of rapid scale — and pretending to be one leads to far worse outcomes,” she says. “All too often, people are so worried about sounding smart. So many important conversations aren’t had because people are so afraid of seeming dumb. The little insecure voice in your head telling you to stay quiet and nod along, that’s Bob taking control. Asking the right questions and learning to ‘figure it out together’ is actually the most important muscle to develop. ”
Graham has learned to put Bob back in his place with a trick she picked up from Chris Cox at Facebook.
“One of my favorite tools is the ‘Sorry if this is a stupid question but…’ line. When Chris was running HR, experts would come in to give us advice and he was unafraid to say, ‘I don’t know what that term means’ or ‘Can you explain that to me?’ It immediately caused incredibly smart, talented people to slow down and use smaller words to explain complex concepts,” she says. “I’ve used questions like this almost every day since. I used it to learn about mobile at Facebook, about SaaS at Quip, and I used it literally every day to educate myself at CZI about things as complex as biomedical research and criminal justice reform,” she says.
It's incredible what you can learn when you’re willing to suspend your ego, quiet that insecure voice, acknowledge that you’re a moron and ask people to teach you.
Aside from generating learning for yourself, this tactic is also a helpful tool for sparking conversations that otherwise wouldn’t be had. “If I sit in a room and I’m confused about what’s going on, I have two choices: I can assume that everyone else knows what’s going on, and just let it the conversation happen without me. Or, I can stop the conversation and ask a potentially stupid question. It can be terrifying, but try it a couple times — you’ll be shocked at how often the confusion wasn’t because you’re a moron, it was because no one understood what was going on,” says Graham.
Challenge #3: When you get caught up in envy and comparison
“People forget that building companies from scratch is really fucking hard, even if it’s going well,” says Graham. “In some ways, success is almost scarier. Your inner monologue is: Can you replicate it? Can you beat it? Can you sustain it? That’s why the worst thing you can do is rewrite history after success. When I look back at my experiences, most of the time I'm like, ‘Jesus, that was really hard.’ I spend a lot of time inside scaling companies talking about all the things we did wrong at the places I’ve worked, all the ways in which things looked far better from the outside than they truly were on the inside.”
This is why Graham encourages others to leave the comparison game behind. “On the individual level, we idealize successful founders. But the truth is, their life is usually more uncertain and more insecure. Bob's with them every day. He may be chewing on their leg for different reasons, but he's there,” she says.
This pattern emerges on the company level as well. “You spend so much energy thinking, ‘If only we could grow like they're growing,’ or ‘If only we had made that hire instead.’ But the reality is that you have no idea what’s going on in that building and whether it’s even worth your envy,” says Graham.
“A couple years ago, when I was in a dark moment, my brother reminded me of that saying from third grade, ‘Keep your eyes on your own paper.’ I now have it as a poster on my wall," she says. "For me, it’s a reminder that the only thing that matters is that I love what I do and am proud of what I build. Nothing else.”
In short, Graham says, for startups of every shape and size, it’s essential to realize that mess itself doesn’t mean something is wrong while success on it’s own doesn’t indicate that everything’s smooth sailing behind the scenes.
Worrying about failure and comparing yourself to the success of others isn’t useful. No matter what the rate of growth or revenue looks like, the truth is that on the inside, it always feels like a mess.
THE FINAL TAKEAWAY: REMEMBER THAT YOU’RE LUCKY
To thrive in the midst of that startup scaling mess, when the walls are threatening to cave in, lean on Graham’s tactics. Think of the emotions weighing you down as a little monster chewing on your leg — but remember that you need to keep him in check. Don’t push your emotions away, but don’t act on them either. Instead, observe how you’re feeling for two weeks to give change a chance to settle. Avoid getting sucked into power struggles by giving away the credit and focusing on being useful. Fight fear and insecurity with a willingness to play the role of the moron, and deflate feelings of envy by remembering that every successful founder is weighed down by their own monster.
And above all, remind yourself that the opportunity to build and scale a startup is a privilege. “Many small companies never get funded, and many of the ones who get funded never get to scale. Even when it’s exhausting and hard, it’s important to remember that if you’re getting to build and scale a company, you’re lucky,” says Graham.
“Take advantage of this opportunity. Give it everything you’ve got, but take care of yourself, and potentially even more importantly, be kind to yourself. Don't let Bob the monster get the best of you. And if you want to do something good for the world, maybe the next time you’re at a cocktail party and someone asks how it’s going at your company, talk about the chaos and what’s hard in addition to what’s fun and going well.”
Images by ZoneCreative/Getty Images and Drawkman/Getty Images.