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‘Focus on unsexy problems’: 3 millennial freelancers on how to build a successful career

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PowerPoint presentation designer Courtney Allen.
Courtesy Courtney Allen, graphic design by Gene Kim

Graduating college can be terrifying. It means leaving those familiar safety nets like home and school and diving into unchartered waters like living alone and the job market.

The latter can be especially scary. Do you prioritize a role you want to do? Or whatever is available at the moment? How much you're getting paid? Or the team you're potentially going to be joining? What if you don't get hired anywhere at all?

The truth is, there's no telling where your work life's going to take you. Along the way, you could encounter unique opportunities you never thought were possible. And with the advent of the internet and work platforms like Fiverr and TaskRabbit, people worldwide are offering niche services and making a pretty good living doing something they enjoy. As a recent grad and with the skills you picked up during college, it's fairly easy to dive in.

Here are three pieces of career advice from freelancers with unconventional jobs.

'Whatever it is that you do, look at where it's used'

Mike Burton, 38, always loved rapping, he just didn't think he could ever do it as a job unless he nabbed some sort of record deal. Even as he worked at call centers and fast-food joints, he found time to make music on the side.

Eventually, Burton learned people were offering their rapping skills for hire on Fiverr and decided to give the freelance platform a shot himself. He now makes up to $9,000 per month writing original raps from parents to their kids, DJs to their cheerleading squads, Norwegian confirmations and so on.

"Whatever it is that you do, look at where it's used and how it's used," he says. Even before he started his profile on Fiverr, he saw that people wanted songs for TV shows. He'd buy books to figure out how he could get in on it, like an almanac for musicians with information about how to send songs to record labels.

"There's always resources," he says. "As long as you keep asking questions, you'll find an answer" and maybe some creative way to get paid doing what you love.

Ask yourself, what 'personality skills' do you have?

In 2015, Jen Glantz, now 35, posted an ad as a bridesmaid for hire on Craigslist. She received more than 300 inquiries — some from people whose friends couldn't make it, others from people who needed help planning logistics. That's how she started her Bridesmaid for Hire business, which now offers a range of services including help on the maid of honor speech and hiring a bridesmaid like Glantz.

She's also expanded the brand to blogging about wedding planning, online courses about public speaking and writing books, all of which bring in more than $5,000 per month.

When it comes to career advice, figure out what skills you already have and how you can optimize them. And "not just skills related to your degree," she says, "but also personality skills, character skills, hobbies."

"I was asked to be a bridesmaid so many times by so many people," says Glantz about her 20s. "Even people who I wasn't close with, and a lot of why they were asking me was because I was a good friend, I was also reliable and somebody who took that role pretty seriously." So she built a business around that.

'Focus on unsexy problems'

Courtney Allen, 33, found her love of PowerPoint presentations in college while designing one for the National Student Advertising Competition. After getting her degree in graphic design she decided presentations were going to be her focus and began freelancing as a dedicated PowerPoint creator for executives at companies like Cisco.

In 2015, she buckled down on finding projects through work marketplace Upwork and ultimately founded her presentation-making company, 16X9, to help field her many requests. Together, she and her company have brought in more than $2 million on Upwork.

"Focus on unsexy problems or unsexy ideas," she says, adding that, in the graphic design world, "there's a lot of flashier things like advertising and branding and stuff like that. But I decided to focus on something that I personally enjoyed that a lot of people did not." As a result, she's been able to a serve a much-needed demand for many employers.

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Making $82,000 a year as a rapper on Fiverr
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Making $82,000 a year as a rapper on Fiverr