3 Women on the Highs and Lows of Going Freelance

From left: Jillian Vieria, Sharla Farrell and Serena Lalani.

Maybe you love your colleagues, maybe you enjoy the structure of an office, maybe you love knowing exactly when you’ll get paid. And yet, the pull to go freelance is strong. Maybe you want to be your own boss, maybe you want to set your own hours and maybe you want to make more money. This week on Girlboss, we’re taking the leap into the world of freelancing with helpful tips, inspiration and stories of real women who did the thing. Freelance, baby!

The time has come. You’ve read our tips for first-time freelancers, bookmarked our financial guide and learned how to build a community and beat loneliness. You’re 99.9% sure you’re ready to make the jump to freelancing full-time but one thing is holding you back: the unknown. “What if it doesn’t work?” “What if I completely fail?” These three women have made it to the other side—and haven’t looked back since. Here are their freelancing success stories. You’re next.

Sharla Farrell, PR pro and founder of Easy Consulting

“I studied communications and I did a post-grad in corporate comms and public relations. I’ve always been in the industry and I’ve seen it change dramatically. I was consistently working for companies where I was hired on to be ‘the voice.’ That’s what they tell you Oh, we trust your creativity and your instincts.’ You get sold this dream of coming on at a company. Then, as soon as you start speaking up it’s, ‘Oh, that’s not what we want. We need to go back to the drawing board.’ You get hit with all these restrictions instead of opportunities. And then you realize that these companies don’t even really want to make change. It sucks. I should probably take my own ideas and operate my business the way I want to operate.

In the PR industry in particular, it changes so frequently that you have to adapt to new technologies, understand TikTok, etc. In my past experiences, it was like, ‘Why aren’t we doing new things and adapting?’ You feel so stifled. For me, being an entrepreneur means that I get to advise my clients to take on new opportunities instead of feeling like the owners of the agency didn’t want to make changes.

I always knew I wanted to start my own business, but I didn’t know exactly what it was going to be. I had toyed around with selling vintage clothes. Then I got let go from the agency I worked at and a week later, I just decided to start freelancing. It took me about a month to get situated and start my website. I needed that moment, I needed that push. I was so caught up in my 9-5 and staying home and laying on the couch and watching TV after work and not being able to process anything. I needed that kick.

I made this crazy Excel spreadsheet and went on Instagram and I listed my 20-30 top clients. I put together these personalized pitches (hey, I had the time). I would go to a coffee shop and email five of them a day. ‘I really want to work with you, here’s my website, here are my credentials.’ Two people got back to me and became my first two clients. I also reached out to others who had started freelancing and it was so helpful. I had a little support system with someone who was going through what I went through.

It took about a year to feel like this was the right decision. In that year I went to Mexico City and worked remotely and I realized that this is what I always wanted. What I’m doing in terms of creating change is being a bit more honest about the industry. I’m straight up with my clients—PR is not a way to make sales. I don’t know where people got that from.

And being one of very few Black women in this industry. I’m very proud to say that I’m here and I’m doing the damn thing, I guess!

For me, it’s all about honesty. I’ve been in the room where a senior director has literally lied to a client about sales. That’s one of my favorite things about working for myself. And being one of very few Black women in this industry. I’m very proud to say that I’m here and I’m doing the damn thing, I guess!

This past year we’re really understanding the idea of rest. I have specifically scheduled my days so that I’m online at 7am and I’ll log off at noon and I’ll go on TikTok for three hours. It’s not because I’m wasting time. It’s because I genuinely need to know what’s going on in the world. What songs are trending? What’s happening? What can I take back to my clients? Technically I’m working, but I’m on the couch.

The biggest lesson was setting boundaries. It goes back to being online for 24 hours. As a new freelancer you want to be like, ‘I will respond to this email at 10pm.’ But that doesn’t make sense. That was a bad habit that I picked up from working at an agency and I don’t do it anymore.

Finances is a big one, and it’s something that I’m still learning. Not getting paid on time, or if people don’t pay you if they don’t feel like they received the services laid out in the contract even though they did. And as women, we tend to lowball ourselves. I will build up another freelancer and encourage them to charge more, and then I’ll go back to a client and lowball myself. Plus, it takes a long time to find the right person to say yes. A lot of people will say, ‘that’s not in my budget right now.’

90 percent of my job is admin work. You don’t think about that when you start freelancing. I remember the first time I did taxes, I realized I wasn’t saving 30% of my pay. It’s about knowing and identifying that you don’t have certain strengths. Finances are not my strength so I hired an accountant. I send all my receipts, she balances my books and I don’t have to think about it.

My advice would be, if you’re thinking about freelancing and you’re at a job and you’re unfulfilled, just do it. What people get so scared of is losing that security. If you’re working at a job that you hate, the paycheck is still amazing and I totally understand and I miss it. But if you feel that itch, take the leap and do it. Even if you can do it on the side. If your job allows you to freelance on the side, it’s an easier way in.

Overall, it was harder than I thought. You have all this flexibility, but you are your own boss. And you need to push yourself. You have total control of your earning potential.”

Serena Lalani, freelance writer and content creator

“I studied journalism, but I always knew that news journalism wasn’t the path I wanted to take. I tried to freelance write here and there but it wasn’t something we were taught in the classroom. We were pushed to take jobs at mainstream publications. I took an internship at a national newspaper. I actually tried to become a full-time freelancer once that internship ended, but I found it so difficult to make a full-time income while pitching stories. And didn’t have as much information or skills as I do now. I felt super lost through the entire process. But we weren’t taught those things in school. Even finding a mentor proved difficult.

I ended up getting a job as a web producer at a daytime television show. I picked up so many skills while working in the digital and lifestyle space. It was more in the direction of things I wanted to do. But I also had to sacrifice a lot of my passions and the things that I genuinely cared about in order to be working at this company and on this show. Eventually it got to the point where I knew I wanted to explore something outside of my 9-5 job. I gave my notice in December of 2020, so it’s been about a year. In the last few months of my job I started to pick up some freelance work to get things rolling. If I wanted to leave this job, I needed to at least start networking to see where my place would be in the freelance market. I got my first two clients at that time, and though it wasn’t enough money yet, it was enough for me to take that leap of faith and leave my job and lean into it fully.

I was told a lot, ‘why are you leaving this job? Are you insane?’ We’re told in school that once you get that gig in the industry, you’re set. But once you’re in it, you do not feel that way at all. It actually feels a bit limiting. When I wasn’t laid off during the pandemic, I was actually pretty surprised. And when I wasn’t, I really took that as a sign to rethink my career.

Not everyone works well in a 9-5. I work best at night! My weeks are better when I have meetings on Mondays and Tuesdays, and then no more for the rest of the week. I wanted to create a routine that would work with me, not against me.

I knew that I needed a mental-health break, and I knew that flexibility would play a big role in that. I really wanted to structure my days how I wanted to work when I’m most productive. Not everyone works well in a 9-5. I work best at night! My weeks are better when I have meetings on Mondays and Tuesdays, and then no more for the rest of the week. I wanted to create a routine that would work with me, not against me.

Once I was getting ready to leave my job, I mentioned to my clients that I already had what my plan was. The beauty of having even one person in your corner is that they can refer you to someone else who might need your services. So I made sure that the people I was working with knew what my goals and plans were. I was not even ready for how many clients I got just based on referrals! Don’t underestimate the power of even one connection.

Ask for what you want, and say what you need. The answer is not always going to be ‘no.’ It’s not always going to be ‘yes.’ But that’s ok! The more straightforward you are, the more inclined others will be to help you. Even going as far back as my professors and the director who managed me during my internship, I thought back to certain spaces, even if I felt like I outgrew them, it doesn’t hurt to reconnect.

I had to get really clear on what types of work I wanted to do. You don’t have to pick one thing necessarily and scale that. It has been a year of freelance, and my website is still not up! It’s something that I said I was going to have done. I realized that the reason it’s not up is because I don’t 100% know what services I want to continue to offer. This last year has been really about experimenting to see what kind of freelance work I like to do. In a job, you’re not always given that choice.

I was seeing all this stuff online, ‘These are the things you need to scale your business. You need to have a website, you need to brand yourself.’ I have done none of them. I still think I had a very successful first year of freelancing. And honestly, it’s because I didn’t do those things. If I had put myself into a box, I would have limited myself.

It’s not how much money I made at the end of the year, or how many clients I’ve had on my roster. It’s the fact that with each client I have genuinely been all-in and I’ve cared about it. And I know that it’s going to make an impact. That’s what I view as success.”

Jillian Vieira, freelance fashion stylist and writer

“In 2009 I was interning at a magazine that was called Glow, and then I graduated and became an editorial assistant. Essentially, the long-story-short of my career is that I would go to a magazine or a brand, and it would either shutter or close after 2 and a half years. That was my cycle. The gears started turning when I felt like I had done everything I could do within my position and I didn’t see opportunities to go bigger, higher or to do new things. What is the answer to that? And I thought of freelance. When you’re at a brand or a position, you’re in a box. They’re not generally just going to make a new position for you if you’ve outgrown yours.

I felt like I needed a new challenge. But I’m very risk-averse so it was a big decision, but it was the right time and I had the right opportunities to get myself started. I left in February of 2019, and I started thinking about it that fall. I started saving pretty aggressively, but I saved a couple months’ rent. I started putting feelers out, and doing my research and seeing what other brands were using freelancers for. In a lot of ways though, it was a pretty big leap.

I also signed with an agency. Not because I couldn’t get enough clients on my own, but because it gave me a buffer when it comes to negotiation—money, how long something would take. That’s something that’s really hard when you start, especially if it’s not in your nature, you tend to undersell yourself. I wanted someone on that side of my business to be my voice for me. I never had to be the person to put a number in an email or in a call.

There is always room to negotiate. And, to be honest, if they agree too early, that’s when my bell goes off that I undersold myself.

It always feels so scary to press ‘send’ on an email on what your rate is, or how long it’s going to take you. But I’ve yet to encounter a project where someone said, ‘no absolutely not, we will not be working with you based on the number you just gave.’ There is always room to negotiate. And, to be honest, if they agree too early, that’s when my bell goes off that I undersold myself.

The one thing that I found challenging was getting used to not having a paycheck every two weeks. I really planned my life to a tee around that. The thing with styling, and it’s something I still don’t do but that I should do, is that I don’t keep track of how much I get paid on styling (the agency does that all for me). So it’s always a surprise at the end of the year. I was getting paid and once I started realizing, ‘oh, I’m putting away even more money than I was before when I was on staff,’ that’s when I thought I was making on my own and feeling good about it.

The biggest learning has been figuring out, based on how much you’re getting paid, to really only allocate a certain amount of time. I think of my time as how much I get paid per hour. I was taking on writing jobs that would take me so much longer than my hourly threshold. Part of that was me being inefficient, but it was also about taking on work that wasn’t worth my time. I did not yet have a good grasp on how to manage myself.

Every time I get a project, and I see the number, I divide that by what I consider to be my ‘hourly rate’ and if I can’t do it in that amount of time, then I’ll decline. Being able to say no is a really big lesson that you have to learn. If you overload yourself, there’s no one to reassign tasks to.

I also became a mother last year. Initially, I took some work six weeks after he was born and I was like, ‘I am even writing sentences?’ I started taking on some small projects the summer after he was born. The mat leave that I had envisioned, where I could meet friends and go to the mall and have relaxing lunches wasn’t a reality because of the pandemic. And your identity becomes fully wrapped up in your child, so freelancing again was a great outlet to regain the other elements of my life that I had put aside for good reason.

It’s a challenge. When he puts his head down on the pillow for his hour-and-a-half morning nap, that’s when I’m on my laptop squeezing in every minute. In the last year I’ve gotten really efficient with my time because I don’t have the luxuries of an open schedule anymore.

Taking a full maternity leave did not feel super feasible for me and for my little family because I bring in a good chunk of the money that goes towards our life and our lifestyle. You don’t get a top-up when you’re self-employed. As much as I believe in saying no to things, I didn’t want to step away. I wanted to stay relevant and still be in front of clients. It has definitely pushed me in ways I haven’t been pushed. And while having a baby, I made pretty close to what I made in my first year of freelancing, which to me is a good sign.

I don’t know if others feel this way, but for me, the idea of how I approach my work, and what work means to me has really been redefined in the last year. This year it’s about balance. People keep reaching out for bigger projects and I’ve had to turn them down. I’ve managed to have a pretty solid career, and a solid paycheck while working a measured amount. I like it that way. I’m interested in getting challenging work but I want to keep it manageable and be able to enjoy my life. Ultimately, that’s the biggest benefit of going freelance. I have my life back and I’m making considerably more money than when I was with a brand.”