It was April 2009, and Srini Rao graduated with an MBA – and no job offers.
The economy had just crashed.
So when he heard about someone creating a website called “Twitter Should Hire Me” that got a ton of press and subsequent job offers, he thought, why not try something similar?
He called his website “100 Reasons You Should Hire Me.”
There was just one problem: “I couldn't come up with 100 reasons.”
He moved back in with his parents in Riverside, California and with free time for the first time in a long time – no classes, no job – he channeled all his energy into learning how to surf.
He went out to the ocean every day.
He got beaten up by the waves every day.
But he kept returning. Again and again.
He got better.
He wanted to write about what he was feeling – enjoying something so much that even getting pummeled by waves felt worth it.
He started a blog called “The Skool of Life” and enrolled in a blogging course; he hoped that starting a blog would both give him a creative outlet and serve as a platform that might finally get him a job.
He wrote posts like “Why the 8-hour Workday Doesn't Make Sense” and “The Ego Driven Pursuit of a Life that Looks Good on Paper.” He was wrestling with society’s expectations and his own drive to create, and doing it all live.
The blog did make him stand out – he got job interviews.
But he couldn’t seem to make it past that phase.
It seemed the very thing that drew employers to him was also the thing that made them hesitant to hire him.
As one interviewer said about his blog: “You don't need a job. It looks like you have a job.”
That’s when Srini realized they were seeing what he hadn’t quite been able to admit yet: this is what he really wanted to do. He wanted to be a creator.
Why, then, I asked, did he apply for jobs for two years while building his blog and popular companion podcast?
Money. I needed money.
“What would happen if…?”
To help with that, Srini started taking freelance jobs he found on Craigslist. He got one freelance gig that paid $1,000 a month.
But then he got fired.
He wrote about it.
He wrote about all the ups and downs he was facing trying to build something from scratch on the internet in 2013 and people connected to the raw and unfiltered way he wrote about his struggles and his ideas about art.
His audience grew and the positive responses he got every time he wrote a new post made him wonder:
What would happen if I just threw them together in a book?
He hired an editor, asked a friend to design a book cover, and self-published The Art of Being Unmistakable in 2013.
It became a Wall Street Journal Bestseller.
He made tens of thousands of dollars from that book.
He was invited to interview on national television.
But a few years later, he felt like his life was falling apart.
Now, he had something to lose.
Despite the burst of success from the book, the money wasn’t enough to keep the business going. Things were tight.
Sponsors from the podcast weren’t renewing their contracts.
“It's so hard to disconnect your identity from your work.”
Srini had to cancel a conference he’d put on the year before that was wildly successful because it wasn’t going to be financially feasible to put on this year.
But this time, he didn’t feel like sharing his raw failures online.
He was no longer the scrappy creator learning and failing up. He’d reached the “top.” He'd been on a bestsellers list. He’d been on national TV. Now, he had an identity to uphold.
Now, he had something to lose.
And he was losing it.
And it hurt.
It's so hard to disconnect your identity from your work. So when the work isn't going well, it's a reflection on you as a person, unfortunately. At least, you see it that way.
My self-esteem in that moment, my sense of confidence, my sense of belief in myself was built entirely on external validation from the fact that I was now on the Wall Street Journal Best Sellers list, from the fact that we sold out for the event…that is a house of cards.
I think that we all have this idea in our head that ‘When I get to this level,’ whatever it is, ‘I'm going to have all my problems solved.’
As Srini’s house of cards started to fall, he wanted to fall too: “Most nights I went to sleep hoping I wouldn't wake up the next day.”
He felt like the last five years had been wasted.
He felt like his work was pointless.
On his worst days, he felt like his work had done more harm than good.
Here I am, the person who is supposed to be this guiding light and I can't find my way out of this darkness.
I wish that we wouldn't sugar coat the reality of how hard some of this is and what a number it can do on your life and your self-esteem and your sense of self-worth.
Being a public figure in a world of social media basically means that you put on a face for your audience 24/7.
They have an expectation of who you are and what you're supposed to be like based on having consumed your content.
And when you do not meet that expectation, which inevitably you won't because you're human, it's like the most hellish thing. And that is one of the ugly parts of this that nobody ever sees.
No matter how bright it gets, it will always go away.
I ask Srini what got him out of that dark period, and I’m surprised when the first thing he mentions is getting rid of books.
He went through all his books Marie-Kondo-style and got rid of every one he didn’t find inspiring anymore.
When he finished, he looked at his “donate” pile and realized every book there was about social media and marketing.
I was like, ‘Okay, this is no longer a reflection of who I am.’
Often, on the other side of what feels like overwhelming failure, is transition – the kind of growth that is less about upward movement and more about bending toward the light.
Srini remembered who he was outside of his online persona.
He remembered he was more than his business or marketing success.
He remembered not everything is in his control: “the journey of [being a creator] is literally a series of ups and downs, constantly.”
He also learned to be wary of moments in the spotlight; no matter how bright it gets, it will always go away.
Life is going to go back to normal at some point. It doesn't matter who you are. And that is something I lost sight of.
A friend, after listening to Srini lament about his “failures,” said once: “Don't forget the guy who’s happy to sell 300 copies of his book.”
That woke him up.
He’d gotten caught up in other people’s metrics, other people’s expectations. He never wanted to let that happen again.
He wanted to be the guy happy to sell 300 copies of his book, thankful to have learned how to catch any wave, not just the giants.
Sometimes it’s releasing that grip that leads to the biggest breakthroughs.
Two years after Srini self-published The Art of Being Unmistakable, an editor from Penguin reached out and offered him a book deal. Penguin published Unmistakable: Why Only is Better Than Best in 2016.
“One for them, one for you.”
Srini knew that having a publisher didn’t mean he didn’t have to work to sell books. He decided to focus on building an audience (instead of an ego), and one that he’d own; he started an email list.
He loved focusing on his direct connection to his audience again.
But this time, instead of building a persona, he built a community.
He also started selling online courses on creativity and learned how to launch a product using email.
The biggest mistake you want to avoid is to be like, ‘Hey, I've been sitting around working on this,’ and you tell your audience the day it comes out.
You need to build anticipation.
A lot of authors freak out because they're like, ‘I don't want to send all these emails.’ It's like, wait a minute, these people have been waiting for this. They're on your list for a reason.
Srini sold his books via email too. (“Email is the biggest driver of book sales to this day.”)
In 2018, Penguin also published his next book, An Audience of One. This time he wrote about the importance of not letting audience-building strategies drown out the very thing that may draw your audience to you – your own voice.
I ask Srini what he thinks about the tension between pleasing an audience and pleasing yourself with your creative work, and how he’s reconciled it in his own creative life and business:
I think that you have to have this balancing act. I was re-watching [the HBO show] Entourage, and in the second season, Vince, [a famous actor in the show], comes back from New York after doing this indie film and his agent says, ‘One for them, one for you,’ and that stuck with me.
So when Srini had an idea to write his next book and publishers kept rejecting it, saying over and over again, “Nobody's going to buy this,” he had an epiphany:
I was like, wait a minute. Why am I concerning myself with the opinions of gatekeepers, whereas the people that matter here are my readers.
You know what? I'm going to write the book anyways, and I'm going to go back to self-publishing.
“Email is the biggest driver of book sales to this day.”
He was so grateful for his first book deals and what they did for his career, but he didn’t want to be reliant on gatekeepers to keep moving forward.
I realized I couldn't sit around any longer waiting for that opportunity. I have something to say, so I'm going to say it.
Srini still creates based on his audiences’ needs to keep his business afloat, but he also creates for himself, like one of his latest books called The Scenic Route:
I didn't write this for anybody. I wrote this for myself. I was like, ‘I don't care if this sells any copies.’ It was so much fun to write. It was just fun to create.
“We use their yardsticks to measure our lives.”
Srini doesn’t care anymore about having (or building) the biggest audience – instead, he cares about having an engaged audience.
One of his favorite email strategies is deleting cold subscribers; he doesn’t care about building an audience that doesn’t actually find value from his art.
He started to let go of all the pressure and define creative success for himself:
We live in this world that is so heavily informed by the content that we're consuming.
You look through your Instagram feed and you’ll see, ‘Hey, so-and-so has a million followers’ and this person is on the New York Times best seller list.’
So we end up setting our goals based on other people's metrics. We use their yardsticks to measure our lives.
Srini set down other people’s yardsticks and started asking himself what he thought was enough.
He actually made a list.
It was a list of what he wanted – but more importantly – why he wanted it. When the why wasn’t strong enough – “so often we want status because other people have it” – he cut it from the list.
What ended up staying?
I want to basically be able to surf and snowboard consistently, travel at least once a month. I want to be able to have enough money to start a family and to basically pay off my student loans, and that's it.
So much of the pressure he put on himself was financial, and yet he realized he didn’t need as much money as he thought he did.
“I have something to say, so I'm going to say it.”
His version of “enough” was a lot less than the world’s.
But the world’s voice is loud, relentless, ever-present.
It’s easy to feel like you’re drowning in the information, the status markers, confusing knowing how to do it all with wanting to do it all – becoming so overwhelmed that you can’t find space for yourself, for your version of “all”.
The great paradox is that while being a creator and putting your work “out” there garners opinions that are easy to drown in, the very perk of being a creator is that you are the one who first gets to decide what’s important.
Srini noticed a shift when he started focusing his attention more on art and connection and less on opinions, and even advice:
The irony is, my audience started to grow when I stopped reading things about how to grow an audience.
Instead of worrying so much about how big his audience was or how successful he seemed on the outside, Srini shifted his attention to four things (that now make up the pillars of his membership community for creatives):
- The ability to manage your attention and focus on what matters most to you.
- Developing a creative practice.
- Building systems for sustainability (something Srini says a lot of people overlook or don’t talk about when it comes to how professional creators make a living; systems free up more time to create).
- “And then the final one,” Srini says, “is community. You need other people.”
Srini may never have been able to finish his “100 Reasons You Should Hire Me” list, and that is precisely the point. Everything changed for him when he stopped making it about himself and instead started creating for himself.
The audience followed, and while he’s learned and tried many tactics, he’s no longer interested in viral success or big flashy moments: for him, the real success came when he started narrowing his attention on focus, craft, systems, and community: “Behavior lasts; tactics have a shelf life.”