The Truth About Full-Time Freelancing


The concept of freelancing for a living is a shifty, shadowy mystery to me. In fact, I regard it the same way I do celebrity. As in: it’s probably super amazing but maybe it’s horrible and awful and I probably don’t want it but also maybe I’m kind of down? In other words I’m ignorant. Minus bliss, plus confusion.

So I found five women who are either living the full-time freelance lifestyle or have in the past and asked them if they’d be willing to pull the dusty curtain off of it once and for all. They said yes, because they’re cool, and then they let me prod them, figuratively. Evidence is below!

If you’re considering a switch away from full-time employment, already did it or are intrigued by the concept of freelancing in general, read on for trove of entrepreneurial wisdom that will make you want to hustle.



1. What surprised you most about freelancing when you started doing it full-time?

Ashley Ford | Freelance Writer: When I started freelancing, the biggest surprise was how hard it became to take a break. Part of the reason I went freelance was to have more time to deal with physical and emotional health issues, but I learned very quickly that it was harder to differentiate between Working Ashley and Not Working Ashley. All my time still felt like it should be work time. Freelancing helped me become something I’d never considered myself capable of being: a workaholic.

Jacqueline Harriet Freelance Photographer: The seasons really can affect the flow of assignments coming in. For example, the winter can be quite slow when everybody takes extended holiday breaks around the beginning of the year….and the weather makes it more difficult to shoot anywhere comfortably besides in studio! For me, I really like the up and down of it all, it’s kind of like running a marathon where you’re so busy shooting and editing and planning every waking minute for weeks and then all of a sudden you cross the finish line and have this time to catch your breath before the next one.

Jamie Bartolacci Freelance Digital Art Director: The thing that surprised me most was how seamless it was in my industry. I was and have been able to move around from magazine to magazine fairly easily. At first, I thought I would be at a disadvantage being freelance — that potential employers would look down on the fact that there were so many jobs on my resume — but, after doing it for a while, I realized I was almost in a better position because of it. Magazines always need freelancers. I took a small break and went full-time at Women’s Health two years ago but I surprised myself and ended up going back to freelance after six months. There is something really appealing about the freedom of it. And it gives me the opportunity to work on my passion project(@lilbrowngoat) with my sister and aunt.

Lacy Wittman Video Director/Producer: The most surprising aspect of freelancing for me is how much better of an employee I became. Knowing I’m being paid per day to complete a job has helped me focus on the tasks at hand and do them as best as I can. Especially because my reputation and future employment is at stake. The belief that the better I do leads to future gigs is an incredible motivation. Another surprising aspect is adjusting to having random weekdays be your weekend days. Sleeping in and running errands on a Tuesday is a great change of pace.

Laura Killberg | Freelance Brand Strategist: Two things come to mind. First, I didn’t realize how much I really knew or the value I was able to provide until I went freelance. I had been working in full-time roles for nearly seven years and had amassed a lot of skills. In a full-time role, everything I did was just my job. In a freelance role, it’s the additional value that I can bring to a company. That’s really empowering. Second, every company is different and I have to adapt to how they work. I have to be super comfortable with shifting goals, expectations and work hours. For example: some companies want me to be part of the team and I have to be okay with spending some of my down time getting to know them. Other companies are happy to have to work on a discrete project or two and never show my face in the office.



2. What advice would you give to someone who isn’t sure if they should go full freelance or not?

Ashley: I would encourage them to write down all the reasons they think they want to be a freelancer and see if there is any way they can get most of those things without becoming a freelancer. I feel like people often go freelance for reasons that could easily be discussed and acquired in their current position. If that’s the case, I’d stick with the company. However, if you need to take the risk and build the career or life you need to be happy, then by all means, leap.

Jacqueline: The ideal situation when making that transition is to hopefully have a few repeat clients lined up. “Bread and butter” jobs, so to speak. Those are the kinds of projects you can count on to help ease the transition from a steady paycheck to a more project-based one. But even if you don’t have clients lined up, it’s definitely doable, as long as you’re willing to put the time in to get on clients’ radars, which, in the beginning and always, will be more time-consuming than a 9 to 5!

Jamie: When other people ask me about going freelance, I always ask them: is this freelance job something that is going to further your career? Is it an opportunity to do something that you would not been able to do at your full-time job? If so, the risk is worth if. Even if you crash and burn, you will walk away with more knowledge than you started with and a greater appreciation for what you want to do.

The other bit of advice that I give is to make sure you always have some money to fall back on. Freelancing can be stressful and there are times you will be living paycheck to paycheck. Make sure you can cover your rent and expenses for a month or two, and be sure to stay on top of your invoices. (My friend actually developed a great app to help with this!)

Lacy: Go for it! Force the hand. It’ll never feel like you’re ready or it’s the right time. You just have to make the leap. Once you’re in it, it’ll create the energy and momentum you need to put yourself out there and let everyone know you’re available for hire! Also, remember (industry depending, of course) companies are always looking for temp or freelance help. After you get your first couple gigs and do well, you’re in!

Laura: I originally went freelance more out of necessity than choice. I was laid off due to downsizing after three years at a start-up and was both too burnt out and too unsure of my next steps to jump into another full-time role. However, it’s obvious to me now that being at a start-up– where roles, priorities and timelines are shifting every day — was a good bootcamp for freelance. You need to be really comfortable with risk and uncertainty.



3. What tips do you have for someone who is just getting started?

Ashley: Hire an accountant, they are more than worth the money. Keep all of your receipts. Protect your reputation. Schedule real work breaks. And don’t let any company convince you that you need them more than they need you. Oh! And only work for free if you really want to get something out of it that is valuable to you.

Jacqueline: Create a routine or schedule for the days when you aren’t working specifically on a project or assignment. Even though I might only shoot 2-3 days out of the week, I try and wake up around 7 or 8 a.m. on most weekdays and go about sending emails and photo researching for a few hours. And make sure you’re open to wearing a lot of different hats! Sometimes I feel like an accountant on days where I’m chasing checks or writing out budgets. When you’re not backed by a team with various departments, you have to learn how to do some of the nitty gritty yourself.

Jamie: My best tip is this: you never know until you ask. Ask if there is more you can do. Ask if there are more hours available. Ask if you can take on a bigger role or take on more responsibility. You will make yourself irreplaceable and make a great impression. If there is one thing I have learned from being a freelancer my whole career, it is that it doesn’t matter where you went to school or what your G.P.A. was. What matters is the connections you make and the impressions you leave on people. Word of mouth is everything and the connections you make, plus your reputation, will always lead to your next gig.

Lacy: Have patience. It’ll likely take a year to feel like you have a consistent set of clients who call. Have a social media presence! Post what you’re working on Instagram, update the old LinkedIn profile and create a personal webpage. It’s okay to be terrified. My first year of freelancing I embraced knowing I would be outside my comfort zone A LOT. So I declared it the year of fear. But after a while things stopped being so intimidating. I love getting the chance every day to learn something knew, meet new people and work from different offices.

1. Take every meeting. Reach out to anyone you’ve ever found interesting. Ask for what you want. Think of networking as a series of conversations where you get to learn a lot about interesting businesses and new roles. All of my first freelance roles came from asking someone for additional connections and just getting hired by them instead.
2. Help other people you meet along the way (connect them, review a proposal for them, etc.). It builds good karma and you’ll also be top of their mind when they are asked to recommend a freelancer.
3. Continue to learn. Take classes. Find a mentor. Ask for stretch projects. Learning is incredibly important to professional growth and you can’t take on bigger, more interesting projects if you just coast.
4. Be diligent about not working 24-7. When I started, I thought I would finally have time to go art exhibits and matinees. Instead, I worked twice as much. I quickly learned that I had to schedule in a gym class like I would a meeting.
5. Know yourself and create the work environment that helps you be productive. I found that when I work from home, I stay in my PJs and do dishes instead of cranking out that marketing strategy that needed a lot of thought. Now I get up at the same time every day and get out of the house as if I was working full-time.

Photographed by Krista Anna Lewis. Collaged by Ana Tellez.


Haley Nahman

Haley Nahman

Haley Nahman is the Features Director at Man Repeller.

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