Sarah Robb O’Hagan is the CEO of Flywheel Sports, has served in executive roles at Nike, Gatorade, and Equinox, and is the author of ExtremeYOU: Step Up. Stand Out. Kick Ass. Repeat. She recently joined Simon Sinek, bestselling author of Start With Why and Leaders Eat Last, for a live conversation on why our relationships are the key to resilience, courage, and fulfillment—and why we so often mistake glamorous jobs for fulfilling ones.
This conversation has been edited and condensed. To view the full conversation, click the video below.
Sarah: How have you developed your own resilience? There were many months when Start With Why was not so well known. How did you stick with it?
Simon: I made the single biggest mistake any individual can make, especially a small business owner, which is I thought I had to know all the answers, and if I didn’t, I had to pretend that I did. It’s very lonely. I would present myself as knowing all the answers, and so people wouldn’t help me.
It became lonelier and lonelier, to the point where I hated going to work. The whole of my energy went into pretending I was happier, more successful, and more in control than I actually felt. It wasn’t until a close friend came to me concerned that there was something wrong, did that give me the courage to admit that I couldn’t do it. My resilience is not some deep down internal something, it comes from the people around me. We’re all surrounded by people who want to help us, if we would just admit that we needed help. But if we fake it, nobody shows up.
That’s how Start With Why was born: I never expected it to become what it became. It was just a solution for me; I shared it with my friends. The whole speaking thing started when I would go to somebody’s apartment and stand in their living room and talk about this thing called “the why,” and [help] people find their why for $100 on the side.
But I had a clear vision and sense of what I could contribute. Having gone through this transition from hating my work to loving my work, I learned that fulfillment is different than excitement or happiness. You can be excited or happy if you get a promotion, get a book, or get a bonus, but it goes away. Nobody is walking around with a sense of accomplishment for that goal you hit a year ago.
Fulfillment is different. It’s like love: you don’t like your children every day, but you love your children every day. I firmly believe that fulfillment in our work is a right and not a privilege, and we treat it like a privilege. You go out with friends and somebody at the table says, “I love my job”, and the rest of us go, “you’re so lucky,” like they won something. I wholly reject that. We have a right to demand that those for whom we work give us an environment for which we love showing up every day. And if we are the leaders, we have the responsibility to provide that to the people who are in our charge.
“We have a right to demand that those for whom we work give us an environment for which we love showing up every day.”
Sarah: Statistically, [there is] a lot of job hopping going on right now, particularly among the younger generation. Like, “I’m not at the perfect job. It’s not meeting my expectations. I’ve got to move on.” [But I’ve learned that] you can’t find your passion by putting it into a Google search. You actually have to make your passion.
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Simon: Here’s a true story: a friend of mine, who’s 30 years old, called me up. She was contemplating quitting her job and wanted my advice whether she should quit or not. My first question is, “How long have you been there?” She says, “Four months.” I said, “Is your boss a horrible human being who’s abusing you every day?” She goes, “No, he’s a nice guy.” I said, “Is he supportive of you?” She goes, “Yeah, he is.” I said, “Are you not getting paid enough to pay your bills?” She says, “No, I’m making more money than I’ve ever made.”
I said, “Work me through this one, I’m struggling.” She goes, “I’m not doing the work I want to do,” which is a very common thing I hear in the millennial generation right now. So I said, “Have you told your boss?” She said, “Yeah.” What did he say? “Okay, I get it, but I want you to do this for now.” So I said, “Are you telling me that he sees potential in you that maybe you don’t see?” She said, “Yes.”
I said, “Get over yourself and stay in your job. It’s really good. Stick with this, get good at this, he clearly sees something in you. There may be some lessons to learn here.” She goes, “Thank you,” and a month later she quit. Without another job! The option for nothing was better than the story that she was telling herself that her life was over because she was “doing something I don’t want to do.”
I’m fascinated by this, and it’s very common in this younger generation. Nothing is the better option, or as they call it, “entrepreneurship.” Not having a job and saying you work for yourself is not the same thing. You actually have to have a business and sell something of value, and then you may have a business.
The work that you talk about is profoundly important: not all lessons are obvious to us and not all work is work we want to do. Nobody likes being junior. When you get senior, you get to be good at one thing. But when you’re junior, it sucks. I think one of the reasons for the job hopping is because they don’t like the suck, so they leave. I’m lucky that I had a boss who cared about me, who wanted to see me grow, who saw potential in me that I didn’t see, and I sucked it up because I trusted them. There’s a weird lack of trust that somebody is looking out for you and you don’t have all the answers.
Sarah: I also think it goes hand in hand with our culture of perfection. If you come out of college today, you have to be perfectly coiffed on Instagram, have a perfect resume, have the perfect first job. I don’t remember ever feeling any of those pressures. Today there’s so much pressure to keep up with the Joneses. Yet if you just dig in and do what might not look perfect, it will help you in the end. What’s your thought on the perfection issue?
Simon: There’s an irony, because everybody knows intellectually that perfection is not true. We’ve all been sitting on a sales call where whoever is trying to sell something has every answer to every problem we have: they are un-credible, right? We know that perfection is impossible, and so when you go on a date and somebody tries to convince you they’re perfect, we all know it’s a scam, it’s a lie, they’re broken, don’t trust them.
When somebody says, “I don’t know,” or “I’m not really that very good at that,” it’s somewhat endearing. That doesn’t mean that they’re secure—sometimes they are, sometimes they’re not. The thing is, to admit imperfection actually makes us trust them more, because we know they’re imperfect already.
[With] the rise of suicide amongst teenagers and Gen X-ers, the neighbors all say the same thing: “on Instagram they looked like they were happy,” and, “they were Grade A students and on the varsity team,” and everything was “so perfect,” and then they killed themselves. It is an unfair standard.
“Every generation, from Boomers to Gen X to Millennials, has become more and more risk averse. The fear of failure is one of the single biggest things that holds people back.”
Sarah: One of the things that I’ve found from my research is that every generation, from Boomers to Gen X to Millennials, has become more and more risk averse. The fear of failure is one of the single biggest things that holds people back. You made some big decisions early in your life, like the decision to get out of the agency business and go out on your own. Where does the courage to take risks come from?
Simon: I do not believe that courage is some deep down internal thing that you find. I think courage is external. I’ve had the privilege of getting to meet people who have actually risked their lives to save the lives of other people. I’ve asked them, “Why did you do it?” and they all give the same answer, “Because they would have done it for me.”
BUD/S is Basic Underwater Demolition, the [Navy] SEAL selection process. You may have seen documentaries of them lifting telephone poles and sitting in the ocean freezing cold. There was a former SEAL who was asked, “Who makes it through BUD/S? Who’s good enough to become a SEAL?” and this was his answer: “I can’t tell you who makes it through BUD/S, but I can tell you who doesn’t: the preening leaders who like to delegate all of the responsibility, the star college athletes who’ve never really been tested to the core of their being, the guys covered in tattoos and bulging muscles who want to show you how strong and tough they are. None of them make it through.”
Some of the guys who make it through are skinny and scrawny. You will see them shivering out of fear. But when they are physically and emotionally exhausted, when they have nothing left to give, they’re able to dig down deep inside of themselves to find the energy to help the guy next to them. Those are the ones that become SEALs.
Being the biggest and the boldest and the strongest is not what makes them elite. It’s the intense energy they have to protect each other. Yet we have the completely opposite standard in business: we reward the one who presents himself as the biggest and boldest, but ignore the ones who would sacrifice themselves to take care of each other. If our most elite warriors are caregivers, maybe we should learn something from them.
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Anything that I have ever done that others would label courageous, I had people to the left and right of me [who] said, “No matter what happens, we’ve got your back.” That is the only reason I had any strength to do anything perceived as “risky.” No trapeze artist would ever try a death defying new act without a net. So why would any of us? That net is called a friend, a trusted leader, a trusted colleague. If we don’t work hard to cultivate those relationships, if we as leaders do not work to build those cultures, and as we as employees do not demand that our leaders provide those cultures, then no one has any courage to do anything. It’s not a surprise why most businesses aren’t as innovative as they’d like to pretend they are.
“You know what happens when you only work with people who believe what you believe? They become your single biggest champions.”
Sarah: It goes hand in hand with the idea of vulnerability, because when you’re vulnerable and open and willing to say, “Here’s what I’m not good at,” that’s when you can build those great relationships.
Simon: Brené Brown talks about this. We don’t actually build trust when we offer our help, we build trust when we ask for it. When people in positions of authority ask for help, it’s even more amazing.
Sarah: Yeah. Sometimes being the boss, you have this feeling of, “Oh my God, I’m supposed to have the answers,” and it’s so intimidating. But when you just come out and say, “I really don’t know, can you help me?” it’s incredible. Suddenly the whole conversation opens up.
In the early days of starting your own business, when you had peers who were doing similar things and seemingly accelerating faster than you were—
Simon: Not seemingly, they were.
Sarah: They were giving you advice, and you knew to stick with what you were doing. I talk a lot about this need to not try to keep up with the Joneses, because we’re never as good when we’re an imitation Jones as we are our best selves. But you were young. How did you know to stick with what you felt was right?
Simon: It was very scary. As I was getting going with this whole Start With Why thing, I made no money. We could barely pay our bills. There were friends I had who were consultants making $200,000 to $300,000 a year, and were giving me advice about what I should be doing.
I knew that if I just did what they said, I, too, could be making coin. But their way felt smarmy—and I wasn’t driven by the coin, that was the other problem. I’d rather struggle and do the right thing and be happy than not struggle, do the wrong thing, and ultimately not be happy. I knew that if I ran out of money I wouldn’t die. I’d be humiliated, I’d have to sleep on a couch, I’d have to move back in with my parents, but death was not immediate.
I believed in something. There’s a reason why people do crazy, irrational things for love. It was like a religion for me, this “why” thing, and so I ignored all the advice and it hurt until things started to go. People would call me to hire me and I would turn them away, because I knew that they were the wrong people for me to work with. If somebody said, “Convince me why I should hire you,” I would say, “Don’t.” Because I’m not convincing anybody. I’m not in the sales business. You either believe what I believe or you don’t. Eventually, I only attracted people who believed what I believed. You know what happens when you only work with people who believe what you believe? They become your single biggest champions.
[But it took a while.] I made the decision because it was the right decision, even though the appearance was really bad. I was working by myself out of my sister’s living room. I used to have an office and blue chip clients and employees.
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Sarah: I think a lot of us go through that. I quit my job a year ago, and I remember suddenly going from being a highfalutin corporate person with all the trappings, to backpacking around to Starbucks to have my meetings.
“It’s time we started having an honest conversation about what it really takes to be fulfilled. It’s okay not to know at the age of 20 where you’re going. It’s okay to screw up, to do not sexy jobs.”
I’d had this really uncomfortable experience seven or eight years earlier: I was giving a speech to a thousand people and the projector broke. [There was] sweat on my forehead, it was not going well, but then the girl comes out to read my bio and says, “Fast Company‘s Most Creative People in Business and Forbes‘ Most Powerful Woman in Sports.” I remember sitting there squirming, because she’s saying all this shit that makes me sound amazing and she’s missing “got fired twice in her twenties, was very average in childhood, bushy eyebrows.” It led me to this realization that our culture of success has taken us to this crazy place. It’s all about perfection, and we put people on pedestals: the 40 under 40, the 30 under 30, the 20 under 20. My literary agent was asked to do a deal for a 12 year-old YouTube star’s life story, for shit’s sake.
It’s time we started having an honest conversation about what it really takes to be fulfilled. It’s okay not to know at the age of 20 where you’re going. It’s okay to screw up, to do not sexy jobs. And it’s okay to have huge feet if you’re a woman. Embrace your imperfections, and be the best of who you are. Because if you aspire to leadership, you have to have a strong foundation to have courage when the winds are coming against you.
Audience: There’s this underlying assumption that I’m hearing, that [you have] to be passionate for your work in order to have a meaningful life. That’s great if we’re in a room full of educated people, but do you really think you cannot lead a meaningful life without being passionate about what you’re doing?
Simon: What’s that got to do with having a room full of educated people?
Audience: A greater amount of opportunity to do their passion.
Simon: I know a lot of really educated people with lots of opportunity who have no fulfillment in their lives, and I know some janitors who love what they do. I’ll tell you about a company called The Luck Company: they own quarries, which means they smash rocks.
We went out and visited them and sat around a table with their frontline employees—most don’t have high school educations. None have college educations. They fit every stereotype you can imagine: baseball cap, dip in the cheek. I said to them, “Tell me what you love about working at Luck Companies?” One guy leans forward and says, “Working here I’ve learned to communicate my feelings. I can say to my colleagues if I’m feeling frustrated, angry, or how I can say thank you. It’s been amazing. I love coming to work here, and I feel like I’m part of a team. It’s actually improved my relationship with my wife and my kids.”
That guy has passion like you can not believe. There are plenty of jobs that are not glamorous, but it’s the people with whom we work, the way our leaders make us feel, that [makes us] do our work with passion even if the work is unglamorous. Sometimes we’re attracted to jobs that are in tech or television; we think that because it has glamour, we will be passionate. Nothing could be further from the truth. It is always the people.
