What I Wish I’d Known Before I Went Freelance

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I wish I’d known: Not to put all my energy into one thing.

Sarah Blesener

Sarah Blesener, 27, Freelance Photographer (Documentary & Photojournalism):

How long have you been freelancing for?“Around seven years now.”

What kind of work do you do?“Now, I freelance primarily for the New York Times and the Wall Street Journal, doing documentary stories and news. I also spend a lot of time working on personal, long-term projects.

“For my personal projects, I have worked mostly with National Geographic and TIME. The themes I focus my photography projects on are adolescent identity and youth movements.”

What was your biggest challenge? “My biggest challenge was making the frightening first step decisions to become a freelancer: Committing to move to New York City, leaving more stable work behind, and facing many months of anxiety and lack of work was the biggest challenge to face — and one that all freelancers go through.

“Those challenges will always exist, but the first year is the most difficult. At times, I wasn’t sure if I had made the right decision, or if I could ever make it in NYC as a freelancer. It’s undeniably a terrifying transition.”

What has been your biggest learning lesson?“How to be strategic with my passion versus survival. For my industry, the jobs that pay my rent and keep me stable are not necessarily the jobs that I feel most passionate in.

“So, for example, learning to pitch for and take jobs that are commercial portraits and advertising do not lie in the realm of what I pictured myself doing as a journalist. However, these are the jobs that support my income throughout the year, while the editorial jobs pay far less while being more in line with what I want from my career.”

What do you wish you’d known before you started freelancing?“It would have been helpful to know, before starting this industry, not to put all of my effort in the same category. It’s helpful, for both your sanity and checkbook, to offer a variety of services and skills.

“For example, working in the editorial world is extremely complicated, and the paychecks are very low. Having a commercial job now and then, or advertising work, often completely saves my year and allows me to work on other aspects of photography that may pay less, but that I enjoy more. I wish I would have known to invest in those other areas of my career that are crucial to my success, not necessarily the ones that are the most exciting.”

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I wish I’d known: To save 30-40% of my earnings for taxes.

Roxanne Ravago

Roxanne Ravago, 29, Independent Product Designer (UX/UI/Interaction) & Creative Technologist:

How long have you been freelancing for?Since March 2016, so almost three years.”

What kind of work do you do?“I provide all kinds of design services because I love touching different parts of the design process — and because a client will usually need more than one of my service offerings to launch a product or experience.

“Mostly I work in product design, UX/UI/interaction design, branding and visual identity, information architecture, illustration, branding and icon design, and learning design for creative computing.”

What was your biggest challenge? “My biggest challenge, especially in the beginning, was believing and owning my worth, understanding that I had something of value to offer someone, and that I needed to negotiate my rates commensurate to the value I knew I offered.

“Should a potential client not believe or agree that my value was worth the rate I asked for, I needed to have the courage — time and time again — to walk away. It’s easier said than done but this practice, over time, helped me to understand how to create value and own it.”

What has been your biggest learning lesson?“I’ve also learned (and am still learning) to not take my independence for granted, but to reclaim and own it. Going freelance comes with great responsibility because, for the first time, you — not anyone else — own your time and energy and what you choose to put it towards. You determine how your days, weeks, months and years look, so that’s a lot of decisions to make compared to a 9-to-5 in a corporate career ladder where a lot has already been structured for you!

“I’ve reached a point after three years where I’m looking over a plateau, and no manager or HR person is going to be there to advise me where and how to grow. I feel there aren’t many visible and vocal female role models who’ve gone independent, and are years ahead of me, that I could look to for some guidance and mentorship.

“I’m learning that when the path isn’t clear or there isn’t one yet, I must create it. I’ve been conditioned from working in a 9-to-5 to ask for permission from my seniors, but I’m learning that I don’t need to ask for permission anymore to try something, fail, then try something else. Finally, I’m learning that no person could give me the answer on where and how to grow. That answer can only come from within.”

In hindsight, what do you wish you’d known before you started freelancing?“I wish I’d known to never underestimate how much money I could make from the beginning, so that I’d start developing a system for saving 30-40% to pay taxes on every income I make. That was a $14,000 mistake that I owed to the IRS after my first year freelancing — and am still paying off in installments.”

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I wish I’d known: How to navigate the creative industry.

Nick Francis

Nick Francis, 24, Creative Director in Visual Media: Illustration, Animation, Film:

How long have you been freelancing for? “I have been freelancing since 2013 while I was still in school at California College of the Arts, but I’ve been working full time as a freelancer since 2016 when I graduated.”

What kind of work do you do?“My works is pretty fluid, with my emphasis being in collage art and illustration, though I have been working more heavily as an animator, director, creative director for the last year. I started professionally with Fantastic Negrito’s 2016 Grammy Winning “The Last Days of Oakland” album and now have several music videos and a short film coming out in the next few months.”

What has been your biggest challenge?“The biggest problem for me as a freelancer is always navigating my health. I have several chronic illnesses that require 24/7 management, which can be difficult to juggle while working, in particular when dealing with rush deadlines.”

What has been your biggest learning lesson?“Learning the rules, codes, of navigating the industries, and then relearning them every few months.

“It has been my experience that the creative industries are far more fluid now than people understand, and require constant relearning and adjusting — not just to maintain your current status, but more importantly to advance. Understanding that the gears are moving around you constantly is a critical element to my survival tactics and planning for the future.”

What do you wish you’d known before you started freelancing?“A lot of the rules I was personally taught around working as a freelancer were all based in outdated modes of the publishing industries, many of which are less applicable now (for the type of work I do). The fluidity of this new world brings many advantages and disadvantages.”

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I wish I’d known: To protect my energy.

Brittney Oliver

Brittney Oliver, 30, Freelance Career & Lifestyle Writer, Founder of Lemons 2 Lemonade:

How long have you been freelancing for?“I’ve been a freelancer since 2015 while holding down a full-time job and building a networking event series. It wasn’t until this year that I freelanced full-time.”

What kind of work do you do?“I am a freelance writer who’s work has been featured in Fast Company, ESSENCE, Teen Vogue, Time, Revolt, Business Insider and xoNecole. As a freelance writer, I pitch content ideas under the career and lifestyle niche to editors or media outlets who may be interested in my content.

“I am also the founder of Lemons 2 Lemonade, a networking event series and online platform offering career and lifestyle content.”

What was your biggest challenge? “As a freelancer, there are periods of time where you can feel like your editors are ghosting you. You don’t have a front row seat to what is happening internally at the corporate offices. All you can do is wait to hear back from someone and don’t take the lack of communication personally.

“Following my editors on social media also helped me navigate a slow response from them. A quick look on my editors Instagram page sometimes showed me when they were traveling for work and so pitching them via text message for a timely article will be better than sending an email.”

What has been your biggest learning lesson?“Media is ever-evolving, and outlets are folding and downsizing at rapid speed. Because of this, I learned early on to work for multiple outlets. You really can’t keep all of your eggs in one basket because there will be times that an outlet does not have the budget for new articles or they may be going through an internal reorganization the will limit the opportunities for work.

“I also learned more of the business of media by the content that I pitched. Understanding the impact of SEO helped my pitching and helped me to diversify the opportunities to write for other outlets. Once I had conversations with my editors and took an inventory of what was trending online, it helped me to target and finesse my pitches to ensure more ‘yes’s’ and fewer ‘no’s.'”

What do you wish you’d known before you started freelancing?“I wish I had known that many publicists and entrepreneurs don’t understand the media landscape. My inbox is always inundated with bad pitches with my name misspelled. If the pitch is not good, you simply decline. If it has potential, I tell them to rework it, but most of them never do and that’s their loss — never do the work for them. Protect your energy, spend less time complaining about it, and move on.

“I also discovered that I was doing a lot more work for less. As a freelancer, you want to keep the money coming in and often times you don’t realize that you are doing more than it’s worth. I realized early on that I spent way too much time on articles that weren’t worth much and time is a precious thing that you don’t get back.”

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I wish I’d known: My work has value.

Kate Quinn

Kate Quinn, 29, Freelance Voiceover Artist:

How long have you been freelancing? “I’ve been freelancing as a voiceover artist for nearly three years.”

What kind of work do you do?I record and edit the voiceovers for many commercials on TV and radio, podcast intros and outros, explainer videos, smart home devices, corporate voicemails, animated series, audiobooks, etc. I’ve worked for large companies like Disney, Kodak, GM, Raymour and Flanigan, JP Morgan, and AirBnb and many startups and smaller businesses.”

What has been your biggest challenge?“Keeping up with messages and orders at all hours each day (Fiverr allows me to have clients all over the world, meaning it’s always working hours somewhere!) can be a challenge. Without a human boss, I do my best to please the algorithm of the site. This can be demanding.”

What has been your biggest learning lesson?“In the beginning, I was pretty vague about my requirements and initial communication with clients; I learned this is not the best way to achieve what the client wants.

“In an online medium, details are everything. I have a fairly comprehensive set of requirements my clients fill out regarding the work they expect (policies, tonal direction, etc.). This ensures that everyone is on the same page and that I can deliver exactly what the client wants the first time I deliver.”

What do you wish you’d known before you started freelancing?“Your work has value! Yes, the premise of Fiverr is providing affordable freelance work, but clients are willing to pay a bit more for excellent customer service, quick turnaround, and a high quality product.”

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I wish I’d known: I am a problem-solver.

Lina Ortega

Lina Ortega, 25, Freelance Videographer & Motion Graphics Editor:

How long have you been freelancing for?“I’ve been freelancing for seven months.”

What kind of work do you do?“I create stop motion content on Fiverr for different brands.”

What was your biggest challenge?“My biggest challenge thus far has been ensuring that I’m organized at all times, but also able to be honest and open with clients and myself.

“At times, I can be very busy and all of a sudden a new client comes along. There comes the combination of a new opportunity, money, and actually being able to do the job. It also has to do with organization because anything is achievable, but one has to make decisions such as how to distribute the workload while also making sure I still have a personal life.”

What has been your biggest learning lesson?“My biggest learning has been the importance of specifying to the client what they’re paying for and setting expectations appropriately. If I’m not clear about what my ‘package’ includes, things can get messy.

“The most important thing is to always be on the same page. I used to think I would love it when I got a vague client because then I was able to do the work exactly the way I wanted. Not the case! This only means that the client doesn’t know what they want, but need help and guidance. If I don’t offer that, it will be a wasted opportunity because they might not get the results they were hoping for. Which, consequently, is not good for either of us in the long run.”

What do you wish you’d known before you started freelancing?“I’m not merely producing something for a client, I am helping them solve a problem and hopefully contributing to the success of their business. When I started freelancing I saw it more of like ‘Wow, they’re paying me to do what I love to do!’ — which is true in a certain aspect, but I really needed to focus on becoming a supporting tool for the client and their business. After all, it is a marketing strategy and they choose me to do the work.”

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I wish I’d known: Freelancing can mean having many bosses.

Dara Avenius

Dara Avenius, Founder & Freelance Publicist at Fascinate Media:

How long have you been freelancing for?“I’ve had my public relations company, Fascinate Media, since 2011. In addition to that, I also sometimes take on contract work for other public relations and event planning firms.”

What kind of work do you do?“I’m a publicist. Many people hear ‘publicist’ and don’t know what it is. I’ve been asked what books I publish or what clubs I promote. The simple explanation is that I bring awareness of your brand, personage or company to the public.

What was your biggest challenge?“The biggest challenge is the lack of respect that people have for freelancers and small business owners. I can’t tell you how many times someone’s been interested in hiring me, asked for a proposal and then ghosted.

“Other issues are when clients sign a contract then decide halfway through they don’t need to honor it. The worst, of course, for a freelancer or small business owner is when a client doesn’t pay. We don’t have the benefit of a corporation behind us to protect us or absorb those costs, so it can have a huge impact. If you have any employees or interns, this can not only affect us but those who work for us.”

What has been your biggest learning lesson?“The biggest lesson I’ve learned is that not every potential client should become a client. As a woman, I think many of us struggle with this — freelancer or not — so another lesson I’ve also learned is to value my work and charge appropriately.”

What do you wish you’d known before you started freelancing?“If you have several contracts, you end up having several bosses and not just one. I also wish I’d known that freelancers are often not respected — and not paid.”