At only 28 years of age, Ryan Holiday has achieved more than most. After dropping out of college at 20, he took mentorships with bestselling authors like Robert Greene and Tucker Max, became director of marketing for American Apparel in 2008, and released his own bestselling book “Trust Me, I’m Lying” in 2012.
Currently, Holiday runs his own marketing firm, Brass Check Marketing, whose clients include Tim Ferriss, Mark Ecko, and James Altucher.
However, despite all of his successes, Holiday at one time felt unhappy and unfulfilled. According to Holiday, he was doing things he didn’t want to do and his life became full of noise. Worst of all, American Apparel, the company he saw rise to the top, went bankrupt. It’s founder, Dov Charney, whom he used to look up to, was ousted from the company and left with nothing.
American Apparel’s stock graph all the way until it went bankrupt.
“Work can become this kind of addiction.” Holiday told NextShark. “The more work you do the more work it creates for you. I remember having a panic attack because I had gotten off a flight where there wasn’t Wi-Fi and so I’d written a bunch of emails. I could just feel my mind and my heart racing.
“Wait, you’re telling me that I’ve worked hard, accomplished these things, and the reward is that I’m going to have a panic attack because I didn’t send eight fucking emails about something that nobody else cares about but me? That’s not a way to live.”
Holiday’s experience, which he explores in his new book “Ego is the Enemy,” will surely resonate with many.
“There’s a certain amount of ego in saying yes to everything.” Holiday said. “You’re afraid that if you say no then you’ll miss out or be left behind. Ego drives people to sometimes tremendous success. Then it also undermines that very success.
In an interview with NextShark in 2014, acclaimed venture capitalist Brad Feld said he disliked the amount of “bullshit” and “happy talk” in the startup space. Holiday, an admirer of Feld, echoes this notion.
“What happens is you see other really successful people get media and think that if I get press attention, then I’ll be the same as them. You take your eye off the ball,” Holiday explained. “Instead of making your work 5 percent better or pouring that time and energy into the company, you’re pouring it into pursuing some reporter or doing something that gives you the appearance of success without the actual validity behind it.”
In his new book, Holiday tells a story about World War II General George Marshall, who had to sit for a painting that took a week to finish. After the artist finished, Marshall immediately got up to leave. When the painter asked whether he wanted to see the painting, Marshall supposedly replied, ‘Not really.’
“I think early on in your career you’re obsessed with getting attention, recognition and building your profile,” Holiday said. “But as you become successful and fall in love with this thing that you’ve dedicated your life to, you start to see these things as a distraction.”
Focusing too much on the vanity in what you do as opposed to being authentic is something Holiday believes can hold people back from success.
“People are afraid to be real because they see so many people around them not being real,” he explained. “You think, ‘Hey if I’m honest and say this is hard or I’m struggling or not working out, then everyone is going to laugh at me.’ In fact you typically have the opposite reaction. The public finds authenticity and honesty refreshing and unique because so few people do it.
“Ego is this haze between us and the real world. It disconnects us from this vulnerability and the human experience entirely. You have to strip away that bullshit ruthlessly or the creative part of your brain isn’t able to operate.”
Holiday, now 29, currently lives in seclusion on a ranch in Austin, Texas with his wife Sam after having lived in Los Angeles and New York City. He raises animals including donkeys, goats, geese, chickens and ducks. He regularly goes fishing on the lake in the back of his house and hunts wild boar and turkey for food. Holiday says his new lifestyle has made him feel happier and more fulfilled than ever.
“One of the reasons I live in Austin instead of NYC or LA is that it’s much easier to say no to things,” he said. “It’s a calmer pace of life; it makes me more reflective and forces me to work more. Out of that bubble of trying to impress all of these people that you don’t really care about.”
Another obvious reason is that the cost of living in Austin is much more manageable than other major cities, which helps Holiday focus on what’s truly important in his work.
“I think as a creative person and living in a place where there’s an incredibly high cost of living, it forces you on this treadmill that forces you to say yes to projects that you really don’t want to do, or working harder than you need to work just to make ends meet,” he said. “That’s not good for your art.
Now more aware of the things that have brought him true happiness, Holiday shared advice for anyone looking to pursue some level of success:
“I remember telling myself that I wanted to be a millionaire by the time I was 25. It wasn’t some burning ambition of mine, but I remember thinking about it. I remember 25 coming and going and not being there. I wasn’t super far from it or impoverished, but I wasn’t there. I remember thinking, ‘Why did I have that goal to begin with?’ I didn’t want a million dollars to pay for cancer treatment for my mom or want it so I could so some important thing. I wanted a million dollars because I arbitrarily decided that’s an impressive number. That’s a bad way to live your life.”
“There’s that line in ‘Fight Club’: ‘We buy things we don’t need to impress people we don’t even like.’ I feel like it’s so easy to get on that treadmill and the more you can find out what you actually like and what your dream life is, it’s much better. People don’t want a million dollars. They want what they think a million dollars will get them. There’s often other ways to get there other than having the cash.”