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Interview with Janjay Sherman


Freelancing is intimidating because working without an established company’s resources behind you requires more time and effort. We spoke with Janjay Sherman—a Brand Strategist with experience at Square, Estée Lauder Companies Inc, and Paper Communications—about her experience freelancing. She gave us her best tips on how to start and build a freelancing business.


Janjay started doing freelancing before it was as popular as it has been recently. She was looking for flexibility but that doesn’t mean freelancing was easy. It came with a lot of work, including taking care of the customer.

You’re the client handler, you’re HR, you’re the assistant, you’re doing a lot of things to make sure that your clients are taken care of.”

If you are thinking about starting, make sure you get the foundational experience in an actual role first because a lot of people just start without realizing what it entails.


Before you start freelancing, start taking some side projects throughout the month. Get a few clients to bill some hours to, so you get a feel for it. This will help you learn some of the pitfalls and help you determine whether this is a good path for you before you give up your paycheck.

Here are some ways to get clients:

🤝 Networking


👏 Show off your work

👀 Apply to jobs where you could be a good fit

Be creative in seeing opportunities to gain a client. Don’t be intimidated when you see a full-time position where you would be a perfect fit for freelancing.

“If you see a role that you’re interested in, it’s worth messaging the recruiter. Asking if there is flexibility with this position to potentially have it be a short-term role at least opens up the conversation. Now, you’ve put yourself in front of someone who could potentially be a client.”

Janjay saw a lot of success doing this, but also many failures. Because, understandably, many organizations are looking for someone who will grow in the company.


“You don’t just want to be book smart, right? If everyone learns how to do marketing by the book, what would make somebody special? People need your point of view. They need your perspective because it’s unique.”