How a Creative TikTok Landed a New Grad Her First Freelance Gig

Industry

UpNext: Fresh Grad, First Client contest

In May 2024, Upwork launched UpNext, a campaign designed to help Gen Z find fulfilling work on their own terms and to educate businesses on how to attract and retain this new generation of talent. Upwork partnered with Keeper, a popular tax-filing service for freelancers, to launch the Fresh Grad, First Client contest. The prize? Winning a short-term freelance contract with Keeper to work as a social media content creator through Upwork.

Rather than submitting a proposal on Upwork, new grads were encouraged to create a video on Instagram or TikTok explaining why they deserved to win the contest.

Harris’s creative take on “Espresso” by Sabrina Carpenter, declared the “song of the summer” by Billboard, showed Keeper that she had the content creation skills and personality they were looking for.

Keeper’s creative strategist, Kristal Chan, shares what about Harris and her submission stood out.

“I think she was just the most engaging. It was a fun video to watch. Madelyn brought her personality and her energy to the piece of content that she created. And because we were looking for someone who wasn't just going to be programming the feeds and making graphics, but we wanted someone who could be on camera, she seemed the perfect fit because she had that on-camera personality.”

Freelancing as a first job

Today, the job market is highly competitive, and many employers are looking for experience. Graduates often find themselves in the tough position of not having had enough prior work experience to land a full-time job, and unsure about how to gain it.

Fortunately, businesses from Fortune 500 companies to startups and entrepreneurs are embracing freelancers to support their teams and meet their deadlines. Freelancing success is judged based on skills and performance rather than length of experience. Clients typically care about your abilities, reviews, and past work samples more than how many years you’ve been working.

Freelancing is a way for new graduates to gain that experience and build their resumes and portfolios while exploring an alternative to working nine-to-five.

Harris explains some benefits of freelancing as a Gen Zer and new grad.

“Freelancing offers so much flexibility and opportunity, no matter what your specialty is. So whether it's social media, marketing, graphic design, or coding, there are so many opportunities. And while it's less structured than a university or maybe a corporate life would be, it also allows you to create your own schedule and work from anywhere.”

When you’re job hunting right out of college, standing out among other applicants with just a resume and cover letter can be challenging. Having a portfolio can help showcase your talents, and freelancing is a great way to build your portfolio while earning an income.

As a freelancer on Upwork, your profile has everything that clients need to get to know you and assess your skills quickly. On your profile, clients can see your work history, feedback, and portfolio. You can even add an optional introduction video to show off your personality and make a personal connection with clients.

Harris encourages companies to think outside of the box and go beyond the traditional cover letter and resume format when hiring, especially in creative roles. She had experienced difficulty in getting her resume past the applicant tracking system and into the inbox of an actual recruiter or hiring manager, but the video introduction helped her to shine.

“I actually think that more creatives and companies looking for creatives should offer this sort of job application instead of a traditional style of resume.”

Freelance talent is Keeper’s secret sauce

Social media is incredibly fast-paced. Blink, and you’ll miss a trend—most likely set by Gen Z. If a brand wants to stay relevant on social media, it needs to be actively trendspotting and creating memorable content.

This is one of the reasons Chan and her team choose to work with freelancers, especially Gen Zers.

“If you're a company that has an audience of Gen Z consumers, I think it's really valuable to have that demographic represented on your team, especially for roles like social media and content creation. I think that demographic brings a finger on the pulse of all things that are trending and viral, but also a digital savviness that can really help a lot of companies stay relevant in a fast-evolving digital landscape.”

Filing taxes in the U.S. can be complicated, stressful, and costly. Being self-employed makes taxes even more complex.

Taxes aren’t withheld from your earnings when you're self-employed. You have to pay taxes either quarterly or annually. This process can be expensive and confusing for many professionals, making them wonder if freelancing or contracting is even worth it.

Keeper is a tax filing and expense tracking software designed for freelancers and independent contractors. They aim to make tax filing and expense tracking simpler and more accessible through their software and free resources. Worrying about how to file taxes shouldn’t hold you back from pursuing a career as an independent professional.

Keeper uses freelancers on Upwork to create educational content at scale that is relatable and easy to understand. On Instagram and TikTok, they break down tax codes, deductions, credits, and other helpful information–all while keeping it engaging and entertaining.

“We don't have to rely on one full-time or two full-time content creators to create all of this content for us. We like working with a lot of different content creators because it diversifies our content mix and it also helps us reach that output goal faster.”

Tapping into freelance talent is one of Keeper’s secrets to success. The brand has been hiring freelancers on Upwork for the past five years.

“Freelancers are our bread and butter at this point. It really helps us reach our goals, especially with content creation. It's a system that works for us.”

Keeper is also Upwork’s tax partner in the U.S. to help make filing taxes on the platform easier for freelancers on the platform. This made Keeper a natural fit for the UpNext campaign.

“The UpNext partnership came at a perfect time because we needed a dedicated person to figure out off-tax season, can we drive impact there for on-tax season? And because it's a social role, ideally, we would want to hire someone who was social media and digital tech-savvy, which is why Gen Z made sense for us. And then, luckily Madelyn came along.”

In Harris’s first month working for Keeper creating social content, the Instagram account saw a 13x increase in engagement, and after three months impressions had doubled.

Harris’s experience freelancing

Before freelancing, Harris always imagined herself entering the corporate world. While in college, she worked as a brand social media intern at T-Mobile and a public relations associate for the University of Washington.

“I honestly always saw myself as a corporate person in terms of being in an office and being around people, kind of things like that, but once I tried freelancing, I just loved the fact that I could create my own schedule.”

Harris comes from a family of creatives, many of them independent professionals. Her sister is currently freelancing in Switzerland and her mom is a graphic designer. Being a single mother, freelancing allowed Harris’s mom to work from home and spend more time with Harris and her sister while they were growing up.

Harris didn’t feel the pressure to find the first full-time job that she could. Instead, her mom encouraged her to create her own path and explore her options.

“She was like, you do you. You find your career that fits your personality, that fits your dreams and desires. That’s something that I really appreciate now after going through school with some kids who didn't have that. My mom was always home with us growing up. She was able to drive us to those activities that she wouldn't have if she was working a nine-to-five.”

As a freelancer, you can typically jump right into a project. During Harris’s first week with Keeper, Chan gave her time to get comfortable with the tools and join the content team meetings. Then, once she was ready, it was time to start creating.

“And we immediately started crafting scripts and then filming,” said Harris. “And the editing process—I learned a lot about the type of editing that Keeper prefers.”

During her time at Keeper, Harris was able to dive deeper into social media and broaden her skill sets. Chan knew what it was like to be an eager and excited new grad and was more than willing to show her the ropes.

“Kristal was open to anything in the social media realm that I wanted to learn about. When it came to talking about UGC creators and influencers and pairing with them, I was like, that really interests me. I've never worked on that before, but I'd like to. And then, when it came time to interview them, I’d never interviewed anyone before. So, I got to sit and watch Kristal interview an influencer to make sure she was a good fit. So that's been a really great addition to my skills that I've carried on with one of my upcoming clients.”

Gen Zers entering the workforce

Harris is from Gen Z, a generation that is more likely to embrace the new ways of working and is often misunderstood. Gen Z has the digitally native trendspotters who can learn new tech and tools lighting fast. They’re also open to rethinking the outdated “grind mentality” with unnecessarily long hours and unfair pay. Gen Zers aren’t lazy. They’re willing to work hard but may be less likely to compromise on their values and what they want out of life—who can blame them?

The Upwork Research Institute found that 53% of Gen Zers freelanced full-time, working as independent professionals instead of traditional nine-to-five employees.

Gen Zers reported that they choose freelancing because they want to:

Have flexibility in their schedule
Work in an environment not restricted by the limitations of age, race, or gender expectations
Work from the location of their choosing
Be able to pursue work they are passionate about or find meaningful
Take more control over their personal development and career path

Chan advises companies not to believe the stigmas around Gen Z, especially freelancers. Rather than seeing a lack of traditional experience as a negative, Chan and Keeper see it as a positive. They find that Gen Z freelancers are eager to learn, which gives them an advantage.

“One of the nice things about working with a Gen Z employee like Madelyn is that you are like a sponge. I was in your same position not that long ago, and it's really refreshing to work with someone who really wants to learn and absorbs information quickly.”

Gen Z is a tech-savvy generation. For as long as they can remember, they’ve been creating content, editing videos, and downloading new trending apps to try out. Gen Z isn’t intimidated by having to learn new software or tools. Give them a little bit of time, and they’ll figure it out.

“When Madelyn joined our team, she didn't know how to use some of the tools that we were using, like Figma or Later. But it took her a day, maybe a couple of days, and she learned it, and I didn't really have to do anything. So to those people I would say those are all myths. Don't be afraid. Don't lean with judgment. A lot of great fruitful working relationships can come out of working with a Gen Z freelancer.”

Advice for new grads

After graduating from college, many new grads ask, “What’s next?” Before the days of being able to work anywhere with a laptop and Wi-Fi, the traditional career path after graduation was landing a nine-to-five full-time job in an office. Freelancing can be an alternative that lets you work remotely and create a schedule that fits your lifestyle.

Figuring out what you want to do after graduation can be challenging. Many new grads don’t walk across the stage and grab their diplomas knowing they have their dream jobs lined up. Harris has experienced the frustration of spending time applying for a job only to get automatically rejected in an hour.

“I only have one friend post-grad who has a full-time job, and most that I know either have part-time jobs or things like that they're not in love with, but they do to get by. One of my friends is a web designer, and I'm like, you should just start freelancing because your skills are needed, and you don't like your current job, so why not try something else?”

Consider freelancing

Even if your long-term goal is to land a full-time role, freelancing can be a stepping stone to help build your resume and gain work experience while making money. You can also always come back to freelancing if you’re between jobs or decide to make a career change. Freelancing allows you to learn new skills and gain immediate real-world experience by taking on small client projects while working toward financial independence.

Upwork makes it easier to get started as a freelancer. Instead of having to send cold emails pitching your services to clients, you can apply to jobs posted by companies actively looking to hire freelancers like you.

“The way that the platform works is you can put in your skills, your expertise, and things like that, and you essentially have a For You page. It's going to be jobs that fit your skills and hourly rate. Upwork really takes a lot of the hard work out of it for you and makes it so much easier. And then additionally, just like there are specific milestones, which are helpful in that both you and your client know that you're staying on track. A lot of that communication that sometimes gets warped is just simplified, which is important.”

Being a freelancer means you’re running your own business. You have to submit proposals to jobs and market your skills. You may not win every contract. Working on building a great profile and spending time personalizing your proposals can help you get off to a strong start.

Leverage your personal network

Checking job boards and submitting your resume may not be enough to land the job you want. Chan recommends networking to find opportunities and explore different careers. Just having a personal connection or referral can go a long way and help you stand out from other candidates. You can learn about new roles or projects before the company posts about them and be one of the first applicants.

“It's a really, really tough market right now. So, a lot of companies are undergoing layoffs. The applicant pool is supersaturated with highly qualified people. That said, those are things you can't control, but there are a ton of things that you can control to get your foot in the door and land the right gig for you, like leveraging your network. If you have professors or advisors or your peers or mentors that you admire or resonate with in college, they can help you find career paths and opportunities.”

Be open to different opportunities

You may want the financial and job security of working as a full-time employee, and that’s OK. Try not to let the idea of landing a full-time role keep you from looking at other working arrangements that have the potential to become employee positions. During the interview process, you can ask questions to see if the role has long-term potential.

Chan advises new grads to be open to different opportunities. There’s no harm in applying and taking an interview; it’s all experience. Freelancing and contract jobs can help you figure out exactly what you want to do.

“A piece of advice I could offer is not to be afraid of freelance or contract work. A lot of companies are contract-to-hire, especially for junior roles. That's how I landed my first gig out of college. I contracted for a couple of months, and then I was just like a sponge that just wanted to learn everything. And I think for college students, college is hard; it's really easy in that you have a routine and a schedule, and you just put one foot in front of the other to get to graduation. But after college, there's just this big unknown of “I don't know what I want to do” or you might not know how to get started. Having that time to contract, at least for me, out of college helped me figure out, OK, these are the types of things that I actually really like to do that will help me intentionally apply for future roles.”

Many companies use contract positions as trial runs for full-time roles. At the end of the contract, you may be able to convert to a full-time employee. The same can go with part-time positions and internships. Making connections and getting introductions can help expand your professional network.

On Upwork, you can add to your profile that you’re open to contract-to-hire positions and specifically search for these kinds of roles. This lets clients know that you’re open to eventually working full-time as an employee.

Find your passion through freelancing

Whether you know exactly what you want to do after graduation or are still figuring it out, freelancing can be a great career move. As a freelancer, you can get real-world experience using the skills that you learned in college and use that experience to develop your portfolio. You can freelance instead of getting a part-time job to make ends meet or build a career that gives you the flexibility to work from anywhere and choose your schedule. Freelancing can be your side hustle or your main source of income, and it’s always something you can fall back on. Create an Upwork account today and see what jobs fit your skillset.