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Every freelance writer is different. But that doesn’t mean that the challenges we face are. I caught up with some of the most successful freelance writers who didn’t have restraining orders on me and asked them what their biggest challenges were when they were just starting out.

They were kind enough to share the secrets to their success, which involved everything from leaps of faith to changes of gender. What follows are some of the best pieces of advice that the web’s best writers have to give. Make sure you take notes.


For me, the biggest barrier was that first client/clip. I started by volunteering for a local publication that served a population and cause that I care about deeply (Latino/immigration issues). As the publisher saw that I was dedicated and reliable, he started giving me more responsibilities, including writing articles, which eventually served as my first clip. I was hired on within a year, and I’ve been with the magazine ever since (almost 7 years now).


The biggest obstacle that I had when I started out was a lack of self-confidence. I had worked as a technical writer and a marketing writer for many years. I had been told that I was very good at what I did. (One person actually stated that they thought I had the ideal skills to be an independent contractor.) Despite that, I didn’t have much confidence in my own abilities. I also had no idea how many opportunities there really are.

Becoming a freelancer was a huge change for me. Looking back, I wish I had done it sooner.


When I went freelance, the biggest obstacle I faced was the lack of contacts. I’d been teaching journalism for five years and only doing the occasional piece, so it was like starting from scratch when I was ready to find freelance work. I adopted a ‘try-every thing’ approach. That meant setting up a website, creating some clips on blogs and article sites, signing up for some freelance marketplaces, and generally getting the word out. Of those, blogging was the most successful, because I made contact with a network of writers and publishers that helped me get my first gigs. And while I’ve not had much success with freelance marketplaces, I landed one blogging contract that ran for more than four years – that was a big help in finding other freelance work.


In 2004, I was working for an international nonprofit organization working on things like volunteer recruitment, event organization, and donations. I knew for years that I eventually wanted to work for myself, but ultimately it was a sudden decision to make that move to self employment (starting my PR and social media consulting firm — I moved into writing full-time officially in 2008 although I did this on the side for years in addition to PR writing through my company). I simply got fed up with the politics of the nonprofit world, and I wanted out.

I already had contacts in my specialty area, so that helped. But my biggest obstacle was time. Everything felt rushed to me — putting together a business plan, the aggressive marketing to bring in intial clients, and trying to establish my brand. It was my network that really made things happen for me. Music PR was my initial emphasis until I later branched out. So I tapped local connections immediately. As I got to know more artists in the region, they introduced me to others. Networking religiously opened a lot of doors for me, and the network I built through my PR work also established my freelance writing business as many of those clients came with me.

That’s something new freelancers sometimes don’t think about. They might have more (and better) connections than they realize, even when they’re just starting out. They know people who can spread the word for them. We all “know somebody who knows somebody,” so to speak. They just have to be willing to talk to people and ask for help. Chances are good someone can open doors for other new freelancers just like family members and those early local artists did for me.