Interview: Matt Dowling On Being A Freelance Photographer And The Importance Of Finding A Mentor


Why do most freelancers fail? What can they do to fix it? Do freelancers need mentors?

In this interview, I talk about these burning questions and more with Matt Dowling, co-founder and director of The Freelancer Club and the director of Freelance Academy.

Matt freelanced for over 12 years before starting The Freelancer Club. You can learn a thing or two about becoming a successful freelancer from him. So, go ahead and start reading.

Did freelance before starting The Freelancer Club and what was that experience like?

Matt: Yes, I was a freelance fashion photographer for more than 12 years.

Why did you pursue your career as a freelancer instead of finding a job at a company?

Matt: Initially, I started shooting because I couldn’t get a job after uni. I wanted to work in the media but after a few months of rejection, had to start making money so I picked up my camera and offered my services to a few friends.

Is it difficult to find freelance work in the fashion industry?

Matt: The fashion industry is tough because so many people want to work in it and brands take advantage of that. The majority of freelancers will work for very little or nothing at all to get ahead in fashion and many brands exploit that fact. The irony is most of those freelancers fail due to selling themselves short and it’s a vicious cycle that needs to be addressed.

What do you think is the most challenging aspect of freelancing?

Matt: Freelancers need to know a little about a lot. From accounts and taxes to marketing and sales, the business side of freelancing is often an afterthought.

Have you ever encountered any conflicts with your clients and how did you manage to fix it?

Matt: When I was freelancing, there were challenges. The big conflict was with a fashion brand that neglected to pay me for a number of months which resulted in near bankruptcy and personal anguish. The big positive that came from that experience was the idea of The Freelancer Club.

Now you have several big titles under your belt, and you’re the director of several companies, do you still freelance and how do you manage so much work without burnout?

Matt: I don’t freelance although I do consult a select number of clients in addition to running my businesses. It took a long time to realize but actually taking a break, switching off the devices, and detaching from business a few times each year really does revitalize one’s enthusiasm for the business.

Let’s talk about The Freelancer Club. There are way too many freelancing platforms out there. What makes The Freelancer Club different from the rest?

Matt: The vast majority of ‘freelancing’ platforms are glorified jobs boards that don’t address the real issues freelancers experience. We’re a community that has been set up by freelancers and we like to think that shows. We know our members, meet them at our events, listen to their story and share in their journey.

In addition to applying to jobs, we host hiring events, masterclasses, offer free legal advice, downloadable contracts, industry discounts, access to mentors, online and offline networking, and lots more. The Freelancer Club has a heart that we think separates us from the others.

Why do you think so many freelancers fail to succeed and have difficulties finding work?

Matt: Simply put, they run out of money. The main reason why this happens is a lack of business acumen. Creative freelancers, in particular, don’t start their career thinking about business until reality hits and often it’s too late. We launched our sister company Freelance Academy to teach freelancers the business essentials for this exact reason.

If you could give one piece of advice to a freelancer who’s just starting out, what would it be?

Matt: Get a mentor. When I started freelancing, I had no clue what I was doing. Even the basics like registering my business and paying tax were alien to me. A mentor who has been there and done it can not only guide you on the business basics but offer tips on the industry that a business book could never tell you.

Most freelancers starting out are happy to spend money on the tangible things like a new kit or tech but good advice can make you thousands.

What are your plans for the future of your career?

Matt: We’re planning to roll The Freelancer Club out in New York next year so that should be fun. The site is constantly evolving too and we’re keen to make it more tailored for our members. We also have a few new cutting-edge features that nobody else offers due to launch in the next 2 months.

In addition, we’re making great inroads with our campaign #NOFREEWORK in our attempt to stop brands asking freelancers to work for experience, exposure, or prestige and the fight against unpaid work.

Are there any apps or services that you can’t live without?

Matt: We love Slack. We work with a lot of freelancers all over the world and communication is paramount. Asana is good for project management too.

In conclusion, is there anything else you would like to add?

Matt: Freelancing is growing at an alarming rate but more and more businesses opting to use a flexible model. In theory this is great, however, it also means higher competition in a crowded marketplace. Don’t forget, you have a value and should never sell yourself short.

I’d like to thank Matt for taking the time to answer my questions and also for sharing his experience and advice with us.

Did you find this article useful? Then you should check out my book Freelance Like A Pro. It includes 21 lessons and 5 secrets from my freelance career to help you supercharge your journey as a freelancer. Click here to learn more.

Roshan Perera
Roshan Jerad Perera is a freelance writer, blogger, and founder of His main goal is to help others get started in freelancing and guide them toward a successful career and financial freedom.
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  • Simone Crane Mar 11,2021 at 10:20 AM

    Some pearls of wisdom in this interview. Matt is a pioneer in the freelance world and continues to be the voice for so many of us. I’ve had the pleasure of seeing him live on 2 occasions and been blown away both times.

    Freelancer Club’s latest campaign on Ethical Hiring is worth reading up on too – the benefits of paying fairly, diversity and inclusion when using freelance talent.

  • Tanya Feb 25,2020 at 5:45 PM

    Great interview. I got a ticket to hear Matt speak at the Financial Times Next Gen event last year and he was inspirational. With so much emphasis on ‘startups’ and ‘founders’ these days, freelancers don’t have too many people they can look up to – Matt is leading the way and arguably the most important voice in the freelance community at the moment. Check out their campaign on unpaid work and the Freelancer Club’s focus on mental health.

  • Lucy Tones Jul 15,2019 at 3:24 PM

    Excellent read. Got the chance to see Matt speak at an event early this year and he was massively inspirational. As a freelance designer myself, we need more leaders who know what it’s like to freelance to speak up. Keep up the good work.

  • Tony Feb 25,2019 at 2:49 PM

    I’d like to note that though freelancing seems easy, every job requires growth and self-improvement. Just take a look at all freelance photographers – they create their own blogs and constantly apply for courses to improve their skills. And they have to seek inspiration! For all photographers, there are a few blogs that can help with that –

  • James Jul 9,2018 at 3:07 PM

    I’ve been a member of Freelancer Club for 3 years and it’s massively helped me build my freelance career. I’ve met so many people on their site and learned about the business side of freelancing. If you’re creative and a freelancer, check them out.

  • James May 18,2017 at 10:09 AM

    Great article. I’ve been a member of The Freelancer Club for over a year and love what they do. They are one of the very few companies supporting creative freelancers and should be commended.

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