Ask an Expert·5 min read

What You Need to Know to Build a Successful Freelance Career

woman sitting at couch with laptop
January 24, 2024

Stories of layoffs, hiring freezes, and mandatory return-to-office policies can make it tempting to consider ditching traditional employment in favor of being your own boss. And there’s a lot of benefits when you’re the one in charge of office policies. Here, Chelsea Winstead, cofounder of HerHQ, an organization that helps female entrepreneurs maximize their business, shares how to maximize your own freelancing success. 


Chelsea Winstead

Chelsea Winstead - Cofounder and co-CEO of HerHQ

I’m a freelancer. How can I achieve financial stability?

Many of us are taught that you secure income by working full-time. That can be the case, but when you’re only getting paid by one employer, you’re only making money through that one income stream. By freelancing, you can diversify your income by working with a variety of clients at one time. This way, you’re shielding your pocketbook and you’re allowing yourself to make money through a variety of streams. I recommend really homing in and becoming an expert at one thing and then offering that as a service to multiple clients. A lot of people get started on platforms, like Upwork or MarketerHire. I’d say that’s the easiest way to get in front of clients who are ready to hire now.

What are three common money mistakes freelancers make?

First is downplaying the value of your skills. At a corporate job, you’re often doing a hundred things. But with freelancing, you can be the expert at one thing and charge a higher price for it. It’s like going to the doctor: If you have a specific problem, you want to go to a specialist. You want to be a specialist. That way, your rates can reflect your specific value.

Number two is having the overall fear that freelancing is risky. There are many more opportunities for freelancers to work with clients on an ongoing basis than you might think — not everything is a project. Most of the students that we work with at HerHQ work with clients for anywhere from six to 12 months, minimum. 

The third people don’t realize is that while you don’t get some of the benefits or the 401(k) of a full-time job, you can charge anywhere from 25% to 50% more than your hourly rate at a full-time job. You're not trading an apple for an apple. Employers are often willing to pay more per hour for fewer hours than they would be for someone working in that job as a full-time position.

How can I plan for retirement as a freelancer?

It’s scary and stressful, and the best way to prepare is by having a personal plan for you. At HerHQ, we lean on SCORE, a small business nonprofit, and we recommend that our students take advantage of it, too. It’s a free resource and you're able to walk away knowing how much you need to set aside for a 401(k) and knowing what your health insurance would look like given your circumstances. Tap into free resources that can help you make a personal decision. 

Advice for balancing my work life and personal life as my own boss?

You might want to burn your whole house down at first, right? You're like, ‘I don't want to follow any rules. I'm gonna wake up at two in the afternoon. Don't tell me what to do.’ But once you get over those first three months and that freedom high, you crave a little bit of stability. So I'd say, it’s really about building a routine. For example, maybe you don’t open any client communication until 9 am. It's about setting personal boundaries and knowing that there's always more work to be done. It's more about having more control over your time day-to-day and less about the extremes. Build a schedule that works for you. Sometimes you don't want to work a Wednesday or a Thursday and you prefer working on a Saturday because you feel the most creative. 

I want to improve my freelance rates. What’s a script I can use?

When you’re first setting a rate for yourself, it's scary. You don't know what to expect. When I first started freelancing, I think I started at $20 an hour. By the time I moved into mentorship, I was charging upwards of $120 an hour. 

Sometimes, a client will ask if you can do it for less or say they have a certain budget. If that’s the case, you can negotiate in a kind way: “This is out of your current budget. I totally understand that. I totally respect that there are going to be other people out there that you may want to work with that have maybe a lower rate. But as of today, this is the rate that I have based on my experience and what I'm going to bring to the table for you.”

As long as you deliver that in a kind but firm way, you'll see that most people are accepting. They may choose someone cheaper, and that’s totally fine. You can then say, “I’m here for when you’re ready for the next level of support.” Most of the time, they will come back and say, “I actually think I want that.”

It’s really easy to get a little combative or defensive when somebody's questioning how much you're going to get paid. But if you can remain calm and positive and give a nice explanation as to why your rate is what it is, it may actually go in your favor. This interview has been edited and condensed for clarity.

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