Not Your Typical 9 to 5 Job

In the blossoming businesses of famous Instagrammers, freelance artists and entrepreneurs, millennials and recent college grads have begun to carve their own interesting paths in the "real world” — paths that reflect more opportunity than the typical 9-to-5.

Story by Gentry Railsback

John Montesi - Freelance writer and Managing Editor, TERASU Magazine

John Montesi has carved his path into the freelance world with an unexpected amount of freedom. Montesi says he can hardly believe the flexibility it has allowed him to have. “I get to be that guy that sits in a coffee shop for five hours and writes. Then I maybe go for a bike ride, then sit at another coffee shop wondering how I get to be there all day,” Montesi says. “It varies so much every day and every week. I tell some of my friends what my life looks like and they’re like, ‘That sounds so scary, I could never handle the uncertainty.’ But I like it.”

In the midst of that exciting uncertainty, Montesi says he has seen tremendous and sometimes surprising growth in the opportunities presented to him as a writer. “Early on in my career I thought, ‘Why not try this?’ and I’ve maintained a few of my clients since day one as a source of income,” Montesi says. “The fact that I’m getting flown to California to cover a bike race and people are asking my shoe size and what kind of tent I want because I’m getting that stuff for free… That’s the kind of thing that, a year ago, I would’ve said, ‘Is that a real job? And how do I get it?’”

Photo courtesy of Dani Austin

Dani Austin - YouTuber and Style Blogger

Similarly, Dani Austin has seen growth in her YouTube career by the thousands of fan-girling subscribers. And each user that subscribes to her page is the reason Austin kick-started her career as a YouTuber.

“I didn’t have a sister growing up, and it can be pretty difficult navigating your life as a girl without another female influence,” Austin says. “I just want to encourage, inspire and help [viewers] see some parts of their lives in a different way by sharing my own personal experiences or opinions. YouTube is a perfect platform for that. It’s a blessing to be able to relate to girls all over the world through a YouTube video.”

Throughout her time developing her name and brand in the YouTube community, Austin has experienced some unforgettable moments. “I remember walking into this massive Google office. It looked like a huge grown up playground. There was a massive screen covering the whole wall playing my video. It was surreal,” Austin says. “I was chosen to participate in a project YouTube hosted one summer at YT Space in LA, and for three months they provided full crews to help me film videos, editing suites, dinner every night, a graphic designer for my branding and partnerships with Seventeen Magazine, bebe and Target, all for free. I was in heaven!”

Even with the perks, Austin’s days as a YouTube personality aren’t easy — she is always under a time crunch. She spends countless hours communicating with her manager, researching trends, shooting and editing videos, maintaining all of her thriving social media accounts and requesting post approvals. “I have left in the middle of class, birthday parties and even my internship to have enough time to edit a change brands have requested, export the video, and get the link to the brand in time,” Austin says.

Will Ko and Winston Tri - Ping Social

Within the realm of entrepreneurialism, hard work always pays off, especially in the case of Will Ko and Winston Tri. Ko and Tri are respectively the co-founder and CEO and lead iOS developer of the social meetup app Ping Social. “People don’t realize that starting something like this and really wanting it to succeed can just suck everything away,” Tri says. “It can suck away things that you want to do, time that you want to spend with other people. You really sacrifice a lot, knowingly and unknowingly.”

To keep steady progress with Ping Social, the team has dedicated countless hours to iOS coding and marketing strategy, but they always return to the driving idea that keeps them moving forward: their passion for the success of Ping. “In the end, it’s something we’re so passionate about. That’s why we have the perseverance to keep going and keep developing,” Ko says. “Since the beginning of this process, the idea of Ping has been refined and polished. It changes over time and always ends up better than what it was originally.”

As Ping Social continues to develop, and downloads rise, so do the responsibilities of the Ping Social team. But that certainly doesn’t stop them from taking joy rides time to time on their motorcycle steeds.

From freelance writers to YouTubers and app-developing entrepreneurs, opportunities for growth, adventure, hard work and pursuit of passions reveal themselves in all forms. One common piece of advice from creatives with non-traditional jobs? Always be self-disciplined in order to work hard day and night, be prepared for surprises good and bad and stay true to your work’s true purpose.

“To jump into something big, you have to care about it so much and want to solve a problem so badly, that you lose sleep at night,” Tri says. “That’s what makes the hard work worth it.”