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The Ins & Outs of Starting a Freelance Career

Posted December 29, 2021
Morissa Schwartz

Freelancing: The Good & The Ugly

Morissa is the Founder and Owner of Dr. Rissy’s Writing & Marketing. She and her team offer a full suite of marketing solutions, including SEO, PR, social media, and paid search. Morissa also owns Gen Z Publishing, a book publishing firm, which caters primarily to indie (independent) authors. She is a regular contributor to leading magazines like Entrepreneur and Forbes, and she currently sits on Forbes’ Young Entrepreneur Council.

She is an absolute dynamo, and we were so impressed with her accomplishments (including her Guinness World Record for the longest bracelet chain).

We invited Morissa to be a guest on the Revenue Marketing Report podcast because of her wealth of experience as an entrepreneur. A lot of people are reevaluating their careers. Marketing operations skillsets are in extremely high demand, and it’s important to weigh the benefits and risks of starting an entrepreneurial adventure before ruling it out.

“I started freelancing in high school. I grew up in my parent’s mom & pop carpet shop. Growing up around entrepreneurs, I saw they were very involved in the local community and helping other small businesses. I loved that.

“When I was in school, I saw that friends were getting jobs in medical offices or the mall. They hated their jobs. I wanted a job I enjoy, and my mom suggested freelancing.

“I didn’t go to a traditional high school; it was a biomedical science academy. I’d take regular classes by day and college courses by night. However, I’d rush through my biomedical studies to work on my freelancing writing.

freelance pros cons

“That’s when I realized I had more of a passion for writing than science.”

Major life events are natural inflection points, and with a pandemic still causing havoc, people are reevaluating their careers. Some people are naturally drawn to the prospect of not reporting to a manager, but the responsibilities of running your own business are nothing to sneeze at.

“I learned the hard way with many different things. I believed, and still do believe, that people are inherently good. I was very trusting, and that’s dangerous. I fell victim to scammers a good dozen times in my first few years as a freelancer. It still happens sometimes.

“I was 19 and naive, so when an employee asked for my driving license and personal information, I thought it was normal. Also, I had clients who said they’d pay after the work was done and then disappear. That happened at least once a month in the beginning.

“I learned the hard way that you need contracts and systems in place. You need to set boundaries. Now that I’ve matured a bit more, I probably wouldn’t have fallen for 90% of those things.”

Morissa didn’t share the warning to scare anyone away from starting a business. There are steps you can take to insulate yourself. For example, when contracting with a business, they will require sensitive documents like a W-9. Forming an LLC and applying for an EIN helps insulate your personal information (because you won’t have to supply your social security number).

Outsourcing & Building a Team

No one knows the ins and outs of starting a business on day one. Many experts make a living coaching small business owners. Lawyers should be consulted before forming a company and can help point you in the right direction when filling out paperwork with your city and state. Accountants, digital marketers, and virtual assistants are all great people to lean on when getting a newly established business off the ground.

“Outsourcing can be a very scary part of freelancing. I’d been doing things independently and was apprehensive about letting others do things for me. Nevertheless, I eventually realized that you can make more money by outsourcing because you have time to focus on the things you enjoy and are better at. The first thing I outsourced was graphics. Writing is my thing. Still, people asked for graphics to accompany my social media posts. While working on books, people would ask, “can you help me with my book cover?” I would try my best, but it just wasn’t my strength.

“So, I met Maria, and she still works with me. I hired her to do my graphics. When we do social media posts, Maria provides the graphics. She also makes graphics for all our clients. Since then, I’ve hired about a hundred other people. Many of them have come and gone because that’s how the freelancing space is. But folks like Maria have stuck with me since starting my business.”

outsource or hire

Another big thing to consider is whether you want to run a single-person business or expand to include additional people on your team. Morissa ran through her decision-making process before expanding her agency.

“I had a lot of clients who were requesting different things. At first, it was SEO, so I took some SEO courses. But then, people started asking for ads and other things. I thought, ‘I can only wear so many hats!’ Then I decided to hire some experts and let them do the things they’re good at and enjoy. I’ll focus on the things I’m good at.

“I hired my first team member when I was getting my master’s degree. I had only a few people at the beginning of grad school, but by the time I got my doctorate, I had 25 people on my team. It really made a difference.”

When you hire more people to join your team, there’s a lot of risks and rewards. You risk your reputation with each new hire since each teammate is an extension of your business, but you gain camaraderie and the ability to expand your client base rapidly.

“So many of my first people are still with me because they were right there at the starting line. They feel like they helped build the company. It’s as much their baby as it is mine.”

Don’t Neglect Lead Generation

Morissa offered her insights on why freelancers must build and nurture a professional network and her strategies for doing so.

“I think nowadays if I were to start afresh, I’d build my social media presence. This is how I get my clients now. I create marketing videos every day on TikTok. I also post on YouTube Shorts and Instagram Reels talking about marketing, writing, and all those things. It solidifies my thought leadership and authority. The beautiful thing about these platforms is you’ll establish amazing organic reach. Every month, I get a few million people who see my videos simply because I use the right hashtags to get the right amount of organic reach.

“I also optimize my website. When you Google, ‘writing and marketing in New Jersey,’ we’re the first company on the SERPs. I do a lot of social media marketing too on platforms like Linkedin, Facebook, Twitter, Instagram, and Pinterest every day. My team and I also do PR, appear on podcasts, and guest-write articles on Forbes and Entrepreneur. It all helps.”

running a small business

We know it sounds like a lot, but you don’t need to adopt every social media platform at once. Start where you’re comfortable and (more importantly) where your audience spends time. For example, you may find people looking to outsource talent on MOPs community Slack forums or on LinkedIn. If a company is looking to hire a full-time marketing operations professional, it’s okay to reach out and ask if they would be open to a contractor.

Once you have a few established clients, Morissa also offered her thoughts on engaging and nurturing them.

“We send out email newsletters. Some people believe email is dead, but it isn’t. It’s actually great because organic reach can be difficult, especially with Facebook, as they’re only showing your post to a small percentage of people. You risk landing in spam with email, but we have decent open rates. l also connect with a lot of clients on social media.”


For more details about starting your own business with Dr. Rissy, listen to the full Revenue Marketing Report episode at the top of the article or anywhere you podcast.