Freelancing has a certain glamour to it from the outside. No commute, no boss, no fixed hours, just you, your talent and a laptop. For a lot of creatives, that glamour is exactly what draws them away from agency or studio life, even if you do need to invest in some freelance kit of your own.
But talk to anyone who's made the leap to freelance, and a more complex picture emerges. One with genuine highs, but also some hard-won lessons. To look past the social highlight reel, I asked five working creatives to talk honestly about what freelancing has really given them, and what it's taken away.
Their answers cover career control, financial uncertainty, isolation and the mistakes they'd rather you didn't repeat.
You get extra time, freedom and control
Perhaps the most obvious benefit of freelancing is the extra time you save from not having to travel. As designer Jade Douglas says: "Instead of commuting, I'm able to curate my own morning, walk my dog and start the day on my terms rather than in someone's armpit in a packed train or bus."
But that's by no means all. For Ollie Hirst, an illustrator who's worked with New Scientist, The Washington Post and The Lancet, the biggest pro is the sense he can be himself. "I used to work in advertising as a creative and it felt very much like I wasn't in control of my career," he recalls. "I was being put in a box I didn't really fit inside or want to be inside."
In the best-case scenario, freelancing can open new doors and provide you with fresh options that simply weren't available to you before. That's exactly what happened to Priscilla Tey, an illustrator and picture book author. "What I didn't expect was how diverse some of these projects could be, and the variety of people I'd be working with and learning from," she enthuses. "In allowing myself to work with a diverse group of people, I learnt so much, which is a liberating experience in its own way."
Senior designer Alex Hill, who went freelance this January after eight years in agency life, has had a similar experience. "The biggest difference between working agency side vs freelance is now I get to choose who I want to work with, and what I want to do," she reports. "I’ve been able to focus on working with brands that really interest me, and have had much more opportunity to get involved in leading larger campaigns."
Discipline is hard, and income unpredictable
Jade, however, cautions that freedom is a double-edged sword, with anxiety potentially lurking on the opposite side. "I have ADHD, so it's good being able to jump around chase fun projects," she begins. "But then I need to push through a lot of boring things that I either delay or ignore. I have no-one to push me but myself. Discipline is hard when you don't have any external factors maintaining consistency, and it's taken lots of trial and error to find what helps."
Alex, meanwhile, points to another flipside to all that creative freedom: the loss of a financial safety net. "The scariest part of freelance for me has been the thought of giving up security," she says. "Security of a regular income, holiday pay, sick pay, a pension." That said, she's learned to see this in context. "If you consider yourself as your own employer and put money aside for these circumstances, the anxiety of taking a break or being ill isn’t as daunting."
Meanwhile the paperwork has also caught her off guard. "The admin side of things will take up more time than you realise," she warns. "Scheduling emails outside of the usual nine to five, creating invoices, doing your tax return, time spent reviewing contracts, should all be considered as work time. It's important to consider this when first calculating your day rate."
How to cope with unpredictability
The unpredictability of your income is perhaps the most universal 'con' about freelancing, and Ollie – who's been freelance for seven years now – is candid about how it never gets any easier.
"The uncertainty never goes away," he admits. "There'll be months where I'm living out of savings. The important thing is to simply accept that your income will fluctuate as a freelancer. It's normal. It's okay."
Priscilla's approach was to build a cushion before she needed one, spending seven years as a full-time teacher while running a studio practice on the side. "Holding a full-time job before entering the freelance world can be a good strategy for some," she says. "It gives you time to hone your skills, observe the industry, learn how things work in your city and, more importantly, a space to build a network that you can leverage when you become a freelancer."
Jade offers similar advice. "I tell everyone to have at least six months of savings to cover a dry spell," she says. "It came in handy the last two years when I had practically no work, but was able still get married and have a honeymoon because we had saved enough from the ‘feast' years before."
Loneliness and isolation are real
Working alone is another recurring thread through every conversation. "It's the mental side of it, as 99% of us are remote WFH," says Ollie. "I've put big efforts into using my online platforms to freely share advice and build community. So I essentially have colleagues I can call on when crises strike."
Brand designer Chloe Doyle, founder of The Chatty Freelancer podcast, tells a similar story. "When I first went freelance, I certainly felt the cons of isolation," she relates. "I'm very much a people-person, so being at home with only my laptop really impacted my mental health. I'd overthink my creative work, then imposter syndrome would settle in. Not having anyone there to say: 'This looks great, have you thought about this?' or 'You're being too tough on yourself, you've nailed it' was something I was really missing."
To counter this, she made concrete efforts to find her community. "Genuinely what saved me was going to creative events and meetups," she recalls. "It's taken years of showing up outside of my home office to really build those creative relationships, but now I have such a strong community around me, to the point where I was able to bring them all together in my own community group called Creative Pals."
Her top tip? "Go to as many different events and meetups as you can until you find the one that you love, then become a regular and make an effort to chat and get to know the people there. Because who knows, you might make a new bunch of friends who will save you from that feeling of isolation."
Lessons to pass on
Most seasoned freelancers will warn against a common early mistake: trying to please everyone. Ollie outlines the problem. "Trying to make your work for everyone, rather than a target audience, only leads to a portfolio that feels weak, superficial and, in an ocean of talent, that's a big problem," he says. "You need identity and a point of view to stand out. Find the meeting points between your interests and what conversations are happening in the world we live in. The overlap is your opportunity."
Priscilla makes a related point. "What works for another freelancer doesn't necessarily work for you," she explains. "So be mindful and critical about what you read online, and avoid comparing yourself to others."
Ultimately, none of the freelancers I spoke to would trade independence for a full-time role. But none of them pretend it's easy either. As Alex puts it: "Both working in an agency and as a freelancer have their pros and cons, but I still wish I'd gone freelance sooner."
And that, perhaps, is the honest summary. The freedom is real, so is the risk, and the creatives who make it work are the ones who plan for both.
