Dear Boom, the fifth installment of our advice series. We’re tackling one of the toughest decisions that a creative has to make: whether or not they should give up on their self-employment.
A reader wrote: “I’ve been freelancing for three years, but it feels like I’m constantly hustling for scraps. I love the freedom, but I’m exhausted and broke. Every job feels like survival mode. Is it time to admit freelancing isn’t for me?”
You’re not alone if you nod along. Over the past couple of years, freelancers in creative industries have had to endure a lot. Many freelancers have been left wondering if the struggle to be independent is worth it because of AI, budget cuts, uncertainty and intense competition.
You don’t have to quit just because you’re struggling. You may need to refine your strategy, pivot or give yourself some more time. We asked creatives who have been in your shoes to help answer this question.
More time is needed
Three years is not a long time. This may be something that many people do not want to hear, but it’s important to know. As illustrator Ollie Hirst puts it: “This isn’t enough time to establish yourself fully. Freelancing is always the tough route, but as this person says, the freedom and potential payoff are huge.”
Keith Dodds is a graphic designer who has some first-hand experience. “I was almost here myself after an awful 2024, but this year I’m on course to be my best financially since I went freelance 12 years ago,” He reveals. “There’s definitely something to be said for just riding it out and not giving up.”
He admits it’s hard. Desperation kills creativity. It’s difficult to produce your best work when every inquiry feels like it is a survival issue.
“I worked in advertising full-time for four years alongside building a freelance illustration career,” He explains. “Having that day job took the financial pressure off me and gave me space to explore and find my freelance feet. When freelancing is your only income initially, it creates nothing but desperation.”
Tim Easley, the director of art at Easley Studios in New York City, agrees. “If you’re ‘hustling for scraps’, it sounds like full-time freelancing might not be for you,” He says. “Remember, you can always take smaller gigs on the side of a PAYE job, and there’s no shame in working part-time to pay the bills and allow you to cherry-pick the freelance bits.”
Mel Langton, an artist from Australia: “Never be afraid to take a side job to keep you afloat. It’s not failure, it’s just all part of self-preservation and keeping your dream afloat.”
Consider yourself a businessman
Another uncomfortable truth is that being good at a craft does not automatically translate into success in business. Many creatives find it difficult to freelance because they lack the skills required.
Amy Slatem, an illustrator and designer, urges us to change our mindset. “Think of yourself more as a business owner than a freelancer,” She says “Actively network, market, outreach, and position yourself as an expert who solves a specific problem.”
This will allow you to avoid the vicious cycle of feast or famine, which is one of the cruelest aspects about freelancing. Ellie Foster, an illustrator and animator notes that balancing work while looking for work can be a difficult balance. “Often when you’re caught in the hustle, it can be hard to find time for outreach,” She says “But then, when the project ends, you’re in panic mode, looking for the next. When freelancing works well for me, it’s because I work cold emails, batching content, etc, into my routine, and the next project is queued up before I finish.”
Maryam El Sada, a brand and packaging designer says that finding new customers is not the only goal. “Invest time and energy with your existing ones, so they’ll always be eager to work with you on next projects or recommend you for others.”
Richie Meldrum, a brand strategy consultant at Meldrum Brand Strategy believes that the terminology is important. “I’d recommend moving away from positioning yourself as a freelancer,” He suggests. “Makes people think fast, cheap and disposable. ‘Independent designer’ is a better option.”
Diversify Your Income
No matter how gifted you may be, it’s risky to put all of your eggs into one basket. Luis-Manuel Lambrechts, an illustrator and artist, recommends that you spread the workload. “You can create illustrations, books, murals, give art courses and workshops, make art and sell it in shows, create prints, etc.”
Mel discovered it through his own experience. “I’ve really had to learn to pivot, evaluate what’s working, what isn’t, what I want to do more of, and what’s absolutely not bringing me joy or serving my business,” She reflects. “Most of the work I’ve done over the past five years is work I’d never have dreamt of, and often out of my comfort zone.”
Priscilla Téy, an illustrator from Singapore, has also found refuge in the education system. “When I hit a dry spell, I hop back into conducting workshops and lessons in schools,” She explains. “It’s not glamorous work, but it can be fulfilling, provide some income and inject perspective into your freelance career.”
Why you began
It’s easy, when you’re tired and broke to forget why you started freelancing. Lennart Menkhaus, an illustrator from Germany, believes that the answer comes down to purpose. “I think you shouldn’t freelance just for the sake of freelancing, but because of the job you truly want to do,” He says. “In the end, I believe it all comes down to one question: how much do you really want to pursue this profession, and how important is freedom to you?”
Jack William Martindale, illustrator and designer Jack William Martindale gives a different perspective. “It’s always worth remembering that we never created as kids to get paid, we did it because it makes us happy inside,” He reflects. “Whilst putting food on the table is important, keeping the love for the craft going is too.”
When times are tough, what do you do? Steve Krentz, a brand designer, frames the test as one of character. “If you don’t enjoy the challenge, or the freedom, of doing things your own way, freelancing might not be for you,” He acknowledges. “And that’s okay; it’s hard. But when things are finally going well, sustainably so, it’ll be the best decision you’ve ever made.”
What is the answer to this question?
Should you quit? Answer: Maybe. It’s not likely to happen.
You need to make changes if you are constantly worried about your finances after three years. It doesn’t mean you have to give up freelancing. You might need to find part-time jobs in order to reduce the stress. It might mean diversifying your income streams. You might need to refine your portfolio, or be more strategic in the way you work.
What direction should you take? Priscilla gives some wise advice. “It’s important to be flexible in this day and age, but pivoting too much or too frequently can read as chaotic,” She observes. “The trick is to know where the anchors in your practice are. What is the heart and soul of your practice that doesn’t flinch? And where are areas you’re willing to be flexible with?”
Truthfully, the road ahead isn’t always the same. Freelancing can be a great way to earn money. Some people find that the security of a regular salary is more conducive for their wellbeing and creativity. Either choice is fine.
It’s important to be honest about your needs, both emotionally and practically. It’s okay to choose a new path if freelancing makes you miserable, despite all your efforts. It’s not failure if you choose to work; it is just another way of using your talent.
If you feel the spark, if giving up would make your stomach turn then don’t. You can adjust your approach and seek help. Give yourself the permission to try something different. Freelancing doesn’t fit all, so if you struggle it’s not a sign that you are doing something wrong.
It can also mean that you are still learning. It’s OK.