Illustration/Animation by Jake Foreman

In medieval times, a 'free lance' was a mercenary who was sworn to no kingdom or lord. No oaths. No masters. Just their weapon and their reputation for getting s**t  done. Today's creative mercenaries may have traded swords for styluses, but they're still hired guns with no client allegiances or masters of coin to pay the rent. Just their tools, their reputation, and the ability to deliver when the brief drops.

If you’re ready to swap a steady paycheck for creative freedom, here's a guide from some of our favorite creatives on how they learned to thrive on the freelance battlefield.

No Lord, No Limits, No Safety Net

Every mercenary knows the deal: maximum freedom, minimum guarantees. You choose your battles, set your own hours, and bow to no boss. But it's not all swashbuckling adventures and creative freedom. It also means no guaranteed income, no cushy perks, and more admin and spreadsheets than you probably signed up for. 

Andreas Pederson understands the importance of balancing client work with the personal projects and experiments that help drive his practice forward.  

“The absolute most positive thing about being freelance is the sense of freedom,” says Art Director Andreas Pedersen. “From the hours you want to work, to which products you decide to use in your workflow, all the way down to which kind of projects and clients you want to work with. You're free to choose.”

Sounds great, right? Honestly, it is, but freelancing is not without its challenges, the obvious ones being irregular paychecks, creative isolation, and no perks such as health insurance (what up, America!), paid leave, or boozy Christmas parties on the boss's dime. 

"I started doing music posters for friends just for fun, then I started charging for it. When I realized I could make a living with this, I started studying graphic design." — Marte Galarza.

Brand Designer and Creative Director Alex Rinker rattles off a laundry list of non-creative responsibilities, saying you have to be “more than just a designer. You have to take on roles you may not want to do or be good at, such as business development, marketing, accounting, project management and customer service... It can also be hard to step away or detach yourself, especially when you need a break or are burnt out.” Bronx-based Designer and Illustrator Pope Phoenix adds, “it can't be overstated how much you have to learn about contracts and taxes. These are important factors that can save or destroy your freelance career. I can't stress how organized you have to be. Not only with your artwork, but also with your paperwork. Freelance is 50% creative and 50% administrative.”

While that might be daunting for some people, many freelancers thrive with a little variety in their workload. Illustrator and True Grit founder Andrew Fairclough says, "Creatively speaking, you can't be 'on' all the time. I often use admin to recharge from the (self-imposed) pressure of trying to create the best work I can. It's all about the attitude you bring to those tasks." 

Whatever your tolerance and talents for numbers and time management, the absolute worst thing you can do is ignore that side of things because you prefer the creative stuff. It’s much wiser to just allocate a little bit of time each day or week to the ‘boring stuff’ or you risk it turning into an unmanageable mountain of admin, or worse, serious problems that will drain your cash flow. 

The good and bad news is that it can (and has) happened to the best of us. You might assume that an industry powerhouse like Aaron Draplin would be immune to such administrative dumb-fuckery but success rarely comes without hard lessons. "Tax riff raff. Just simple miscommunication with my accountant that dinged me BIG TIME. Stay on top of that shit! I learned QUICK".

When he's not creating highly tactile branding for boutique hotels and cannabis brands, Alex Rinker is likely staying on top of business development, project management, and accounting. 

For Marte Galarza, a NYC-based graphic designer and lettering artist, “the hardest part of being a freelancer is being your own union. Sometimes it's hard to say no to projects and prioritize your health, your sleep and your free time.” In many ways, when you have a full-time gig, it’s easier to plan your day-to-day life and keep a healthier separation between life and work. Once you leave the office, that’s it. Come back to it tomorrow. Going on vacation? Nice. See you in two weeks! As a freelancer, it’s harder to find that healthy separation. The pressure of missing opportunities or not having a team to refer clients to means that work starts to dominate every minute of your day. 

It’s inevitable that you’ll have periods, particularly when you’re starting out, when work will be a priority over self care. But that isn’t sustainable longterm. If you are prone to being a workaholic, try to reframe what downtime is in your mind. Taking time out for a massage, for example, is ‘work’, because it’s ultimately a tool to help you manage stress, which is vital to your actual work. The same goes for exercise, staring at a TV, and eating healthily. Think of them as being extensions of your worklife, not in conflict with it.

Leaving the Castle: From Full-Time to Free Agent

There's no blueprint for going freelance. Some people plan their exit for months, others get laid off and figure it out. Some quit their insufferable day job cold, while others moonlight until the side hustle pays more than the salary. The timing's different, the reasons vary, but one thing's consistent: going freelance requires a shift in how you think about work, money, and risk.

"Make the kinds of personal projects you want to be hired for, and you'll get hired for those kinds of projects." — Aley Wild

Illustrator Aley Wild met artists while travelling, who opened her eyes to the possibilities of a freer lifestyle. Creative Director Jon Contino became a freelancer right out of high school because that’s just what made sense to him. After being laid off from her full-time role, Jennifer Hood, co-founder of Hoodzpah, started her own studio with her sister, Amy. Martina Galarza never had any plans to become a freelance designer and just kinda fell into it by making music posters for friends. And after more than 10 years working for the man, creative director Alex Rinker simply quit his job to set up on his own.

“AS SOON AS YOU TIE YOUR INCOME IN WITH A PASSION, IT CREATES A TENSION BETWEEN CREATIVE FREEDOM AND PROFIT.” 

Jake Foreman

There’s a fundamental ‘mental’ difference between being full-time and freelance. Suddenly, what you love has a price tag; the stakes become higher; your entire life becomes dependent on you performing consistently well. Whether you’re feeling hungover or heartbroken, there’s nowhere to hide.

Personality type also plays a vital role when it comes to those who manage to set themselves up for long-term freelance success. “You have to be extremely disciplined,” says Contino, “you can't just sit back and collect a paycheck when you're not working and don't even think about the words health insurance without having a major panic attack.” 

What were you doing with your spare time in highschool? Acclaimed lettering artist and creative director Jon Contino started freelancing simply because he "didn't know there was any other way to make art for a living."

Timing is important, too. One of the most common causes of failure among new freelancers is cash-flow issues. No matter how much work you have been promised, only make the leap if you have a little bit of money saved up or a part time job that will help you ride out the dry patches. Jobs get pushed back or cancelled and invoices get ‘misplaced’. This is a fact of freelance life. Ideally, you’ll have about three months of living expenses stashed away just in case, but if you want to live life on the edge, make sure you can live for at least a month without pay when you’re starting out.

Being ok with not knowing when or where your next paycheck might be coming from is certainly something that successful freelancers can handle. No one loves that uncertainty, of course, but if having a sporadic income is going to consume your thoughts and make you unwell, then freelance life might not be for you. That said, a little anxiety about what’s coming next can push you to be more assertive and proactive when it comes to building relationships and following through. Just be honest about what kind of personality type you are because the truth of the matter is, no one becomes a freelancer because they want to be more stressed out.

Recent brand work by Jon Contino for the New York Giants to celebrate the team's 100th anniversary. 

As Foreman points out, “if things aren't working out, I can't point the finger at anyone. It’s up to me to choose what areas I work on, then be accountable for those decisions." This is another aspect of freelance life that can make or break you. On the one hand, knowing that you’re totally responsible for your own success is empowering. On the other hand, this can lead you to place so much pressure on yourself that you can’t free yourself up to be creative.

Battle-Tested Wisdom For Newbs

Ask any freelancer what they'd do differently and the answers are surprisingly consistent. Network earlier. Don't work in isolation. Protect your energy. Learn the boring stuff before it becomes a crisis. The good news? You don't have to learn everything the hard way. 

“I would have connected with the creative community more and sooner,” says Wild. “I got used to working in isolation during the pandemic, and eventually I felt like my creative world was caving in on itself. I've been a part of a vibrant shared studio in Sydney for the last couple of years, and my practice and life has become so much richer since.” Hood adds, “My sister and I were very spongey. We'd go to meetups and reach out to other creatives and just compare notes and try to learn as much as we could from them. We were really hungry for advice and guidance, and were very aware that we didn't know anything.”

"Be strategic about your style and what you want to be doing. In my experience, merch and gig posters offer opportunities for cool work, but unless you're fast it's hard to earn a living. I found developing a style I enjoy making, but larger brands can also embrace, help attract (higher paying) advertising projects." — Jake Foreman.

“When I started doing freelance the second time, I learnt that skill isn't as important as the strength of your network and reputation,” says Phoenix. That might not be music to introverted ears, but it’s definitely a fact of life. "I was so green, and I'm also quite an introverted person,” says Pedersen, “so it was difficult for me to talk to new potential leads and clients." No matter how good you are, if you’re not making connections with people who will commission and champion you, then you’re going to struggle to survive.

“ADAPTABILITY AND POSITIVITY ARE ESSENTIAL. EVEN WHEN YOU DO EVERYTHING RIGHT, A CLIENT, ECONOMIC SHIFT, OR UNEXPECTED EVENT COULD THROW THE BEST PLANS OFF. SO BE  PREPARED TO PIVOT, AND LOOK FOR SILVER LININGS.”

Jennifer Hood

Hoodzpah Design are proof that you don't get to work on branding projects for Nike without learning a few lessons along the way. 

And then there’s self-care, and we don’t mean just mean taking the odd yoga class and eating something green regularly, you also need to manage your emotions and energy levels. The last thing you want to do is put everything into building an amazing roster of clients and a killer portfolio only to burn yourself out. “Notice which projects energize you and which ones drain you,” advises Galarza. “You’ll be doing this for a while, so try to keep it fun. Pushing yourself to be great can help at the start, but over time it’s more valuable to find the balance and territory that feels sustainable.”

Putting A Value On Your Sword Arm

Talking about money is uncomfortable. Asking for what you're worth feels greedy. Negotiating feels downright confrontational. And when you're starting out, you're so grateful for any work that charging properly seems almost impossible. But here's the truth: undercharging doesn't just hurt you—it sets the bar for every freelancer who comes after you. So let's talk numbers. One of the hardest aspects of making the jump to freelance is knowing how much your time and talent is worth.

"The more experience you get in winning clients over and troubleshooting their hangups, the better. Those are not skills taught in art school." — Jennifer Hood 

“A great place to start is reminding yourself that your creativity has value and you deserve to make a living from it,” says Fairclough. Wild adds “Learn how to self-advocate. Art school fails to teach about licensing, contracts, or tax, which you definitely need to know about if you're working for yourself.” Nonetheless, there’s plenty of published guidance available from reputable sources. “The Graphic Artists Guild Handbook of Pricing & Ethical Guidelines and Jessica Hische's The Dark Art of Pricing are excellent resources.” 

It helps to know how much you need to make to cover rent, equipment, software, and other expenses. Calculate that each month and divide it by the number of days you realistically expect to work, and then boom–you’re not too far off your reasonable minimum day rate.

“Asking the client straight up what their budget is can prevent a lot of back and forth,” continues Fairclough. “If you’re still drawing a blank, ask your creative friends and community to get a sense of what they are charging. You’ll be surprised how forthcoming other creatives are in helping each other out because the truth is, none of us ever truly know the answer to what we should or could charge.”

Pricing concerns aside, clients aren't the only source of income for freelancers. "Part of my income is from licensing my personal art, where I get to follow my creative whims and make the work I want." — Aley Wild.

So, as much we’d love to provide a one-size-fits-all pricing formula here, that’s a much deeper discussion for a much longer article (coming soon). There are too many variables based on your professional experience, the specific client, what the licensing terms might be, and how urgent the deadline is. But if you really, really want to press us for a figure, generally speaking, a freelance artist working in a major city should not charge less than 80 USD per hour. Hourly rates are only one way to calculate your pricing, but it's important to feel out each job and do what feels right for you and your clients. 

"Bronx born and raised Pope Phoenix knows what it takes to make it as a freelancer in The Big Apple. 

Just remember, when you quote for a job, don’t only think about your own needs, think about how you’re shaping the industry going forward. Beware of clients who ask for a discount on the first job with the promise of bigger budgets or future work that may or may not ever materialise. For every job you undercharge, you’re lowering the bar for every future project with that client. As freelancers, we all have a responsibility to set pricing expectations that help keep the industry sustainable. 

So You're Ready To Start Freelancing. Now What?

Freelancing isn't a test you pass or fail—it's a lifestyle that either fits your personality and circumstances, or it doesn't. If you've been dreaming of owning your own business and having the freedom to shape your creative future, then there's no better time than now to start working towards that goal. 

"THERE'S NEVER A PERFECT TIME TO MAKE THE LEAP"

Every Freelancer Ever

Jen Hood emphasises that it won’t happen instantly, but you also don’t have to go all-in from day one.  “Just try freelancing on the side if you can. Keep your 9-5 until you're sure it's right for you. Once you start, give yourself a solid 2 years to give it your best effort. It will not happen overnight. It just won't. It takes months, years, to build up a client roster and start fostering word-of-mouth referrals and reputation. All the while, share your work and (share your) process as much as you can publicly to get eyes on the job. You have to remind someone of what you do hundreds of times before they actually need what you're offering.

Build up your savings before you go full-time freelance. And find a community that you can learn form and be transparent with, so you can share your struggles and learn from peers already navigating the same things. A community you trust will be invaluable. They will encourage you, send you referrals, and save you from making the same mistakes they did.”

"I definitely fucked up a few projects and paychecks in the first few years. But looking back, those mistakes are what has made me grow, learn and develop." — Andreas Pederson.

Living Your Best Freelance life.

Ask any freelancer who's made it through those first couple of years, and they'll tell you that despite the challenges, the freedom, creativity, and potential earning capacity far outweigh any downsides. Fairclough reflects, "My first two years freelancing had a steep learning curve, but it was exciting and wildly creative. The freedom and sense of being in control, even when I was totally out of control, was so energizing and exactly what I needed after a few punishing years of full-time employment in an agency. I could never go back. After 20 years of freelancing, I'm basically unemployable. Not because I'm useless, but because I'm spoiled by the freedom and lifestyle that freelancing has afforded me.

Galarza adds that freelancing has given her so much. "I love being a freelancer. During my 20s, I was able to travel a lot thanks to the flexibility of freelancing. I’d say I’m living close to my dream freelance life. My main goal now is to work fewer hours and maintain a good work–life balance. I always try to take at least a month off in the summer, and working on weekends is a strong no for me. I let myself sleep in if I need it, do something fun in the mornings, and I never work past 6 p.m.

“I COULD NEVER GO BACK. AFTER 20 YEARS OF FREELANCING, I’M BASICALLY UNEMPLOYABLE”

Andrew Fairclough

Of course thriving as a freelancer takes discipline and hard work, expecially at the start, but if you're ready to take control of your creativity and your work/life balance (and not afraid of a bit of admin), it might just be the path for you. 

So here's your final slice of reality. Just like those medieval mercenaries before us, there's no one true freelance roadmap to follow. And when most of us start, we're just making it up as we go. “I had no clue what I was doing and was basically feeling around in the dark trying to find the light switch,” says Contino. “To this day, there's still a certain amount of that in my career. But then again, the exciting part is not knowing what's next.”

Thank you to the freelance creatives who contributed their years of experience and wisdom to help create this article:

Alex Rinker | Aley Wild | Andreas Pedersen | Andrew Fairclough | Hoodzpah | Jake Foreman | Jon Contino | Marté Galarza | Pope Phoenix