20 Freelance Writers Share What They Would Do Differently: Expert Roundup

There’s a well-known saying that hindsight is perfect. No matter the journey we’re on, there’s always the tendency to look back and say, “if I’d only done (insert incredibly clever tactical move here), I would have found success sooner, or made more money, or…you get the point.

But mistakes are an important part of the learning process, and no one gets everything right the first time.

Here at ZTF, I have the opportunity to interact with a lot of successful freelancers. And one of the things I’m always interested in finding out is what advice they would give to aspiring freelancers who are just getting started.

Over the past few months, I posed the following question to 20 top freelance writers:  

Name ONE thing you would do differently if you were starting over today?

Here’s what they had to say.

Taylor Medine

“I would have asked for help when I needed it. Early in my career, I thought to ask for help or pointers from other writers was a sign that I was a failure. That couldn’t be farther from the truth. Networking and masterminding with other freelancers have had the most positive impact on my career. I’ve been able to ask what other people charge and increase my prices based on their advice. I’ve also gotten job referrals and introductions from other writers that have been invaluable.”

Ben Luthi

“Nothing. I have a unique journey with freelancing, having worked full-time as a writer for a couple of big websites, but I think that path has been a big reason for my success now.”

Emily Guy Birken  

“I would ask for more money earlier. I fell into the freelancer trap of thinking I was lucky to land any paid gigs. But I undersold myself for quite some time. It does take time to build up your portfolio so that you can request more money. However, you can increase your rates incrementally, even early on. I wish I had done that because I earned less than I was worth for a few years.” 

Miranda Marquit 

“ I would have started my own blog from the get-go. I had been freelancing for six years (and writing about money for five) before I started my own blog.” 

Kevin Payne 

“If I were starting over today, I’d set up systems and documentation to track assignments, clients, invoices, and even sourcing better than I have. Like most things, it’s easier to implement those steps early on instead of having to go back later and do it.”

Kyle Kroeger 

“Start my personal brand website immediately. Then, everything I do should route to that website. I became a freelance writer as a result of my blogging efforts. The sooner you create your brand, the sooner you build more credibility. Credibility leads to more job opportunities and more revenue for your efforts. It’s the best way to create a business based on your terms.” 

Sandra Parsons 

“I would have spent less time on job boards and more time building real relationships within the writing community.”

Chhavi Agarwal 

“If I were to start over today, I would spend more time networking with online business owners and bloggers on Facebook groups. As a freelance writer, I always relied on job boards and pitching clients directly, but what I missed (a very profitable part) was to network with business owners online. I realized it pretty late, and when I started, I gained clients and referrals quickly.

The best way to do it is to join active Facebook groups and provide value in conversations. Don’t just pitch your services everywhere. Instead, help business owners, answer their questions, and nurture a relationship.” 

Melanie Lockert

“Go after higher-paying clients sooner.”

Related Post: How to Find Freelance Writing Jobs for Beginners

Amanda Kruse 

“At the beginning of my freelancing work, I had a nice balance and stuck to a schedule. I set limits on my hours and how much I was willing to work. And felt like I was compensated adequately for my efforts. Six months in, more opportunities came my way. I felt like some were just too good to pass up. So I added those opportunities, even though I suspected I would be undervaluing and overworking myself. And my work-life balance became lopsided. 

I worked too much and dealt with a lot of unnecessary stress as a result. All that to say, that if I were to start over, I would respect my time by saying “no” to some (hard to pass up) opportunities. It would be clear that taking on more work means letting go of some current work. And I wouldn’t try to prove myself with opportunities that undervalued my time and efforts.”

Catherine Alford 

“#NoRegrets – Every lesson, every mistake, was part of the journey and helped me become the entrepreneur I am now.”

Eric Rosenberg

“I would invest more in my business faster. When I started, I was hesitant to pay $7 for a domain name and $50 per year for website hosting. If you are serious about online business, you should be willing to invest at least $100 per year to make it a success.”

Sarah Li-Cain

“I would be a lot kinder to myself when I would get rejection emails. It’s not useful to do that at all.”

Laura Gariepy 

“I would’ve gotten serious sooner! Despite being a natural, published writer before quitting my job to be self-employed, fate had to hit me on the head with a shovel for me to see freelance writing as a viable option. It took getting a surprise payment for a guest blog post for me to have that revelation. Had I stepped back to reflect on my talents from the get-go, I probably could’ve started freelance writing sooner. But, ultimately, I regret nothing. Everything happens for a reason.”

Sa El 

“I would get even more education before starting.  The more certifications you have the more you can niche down and charge more for writing your content.  I would also have taken some sort of writing or grammar course to become a better writer much faster than It took me to do it “on the job” per se.”  

Clint Proctor

“I would have taken Holly Johnson’s writing course sooner. Once I completed that course, I started landing clients fairly quickly.”

Kate Braun 

“I’d value my work higher. I started freelance writing in college and definitely spent too much time writing for 3 cents a word. Good writing is a valuable professional skill, and it’s worth more than ramen-noodle rates! If you need to start out with some cheaper work to get established and prove your value, that’s fine–but don’t assume that your starter rate is a true representation of what your work is worth. 

Freelance rates also need to be higher than traditional employee hourly pay to account for the higher taxes and lack of benefits. I’d tell my past self (and new freelancers) not to be afraid of asking for rate increases and always to have an eye open for the next gig or client that can help you scale.”

Bobby Warren

“I would not do anything differently. I say this not because I did everything right, but I learned from everything I have done.”

Choncé Maddox 

“I would have worked on my confidence, charged more and sooner.”

Tom Blake 

“If I could do one thing differently when starting over, it would be to ask my existing clients for additional work. I’m currently a full-time freelance writer, but it took me about a year and a half of hustling on the side and blogging to acquire clients before I felt comfortable quitting my job. In reality, I could have fast-tracked this process if I had simply asked my first few clients for more assignments per month. 

Clients want to work with writers who make their life easy, meet deadlines, and produce quality work. If you check those boxes, there’s no reason for a client to hesitate if you ask for more work, provided they have the budget.”

Final Thoughts on Hindsight and Starting Over 

There you have it, twenty top freelance writers sharing what they would change if they had a chance to start over. Of course, I have a feeling that if we were to dig a bit deeper, many would say that they wouldn’t change a thing. After all, we learn so much from our mistakes. Reflection can be very helpful, and if the advice these talented writers have shared here makes the journey a bit easier for someone else, it’s a good thing. ♥️

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