Surprising Lessons About Freelancing

If You Want Four-Part Harmony You Have to Go Where They’re Singing
(and other surprising lessons about freelance writing)

By Glenn A. Hascall

We each have personally held assumptions about everything – even things we know very little about. That could be books, movies, politics or parenting. Let me just say that assumptions always tend to end badly – or at the very least encourage us to move forward after the humiliation brought on by wrong assumptions. Thus it has ever been so.

When I first started writing I had absolutely no clue that I could be paid for what I did. I gave away my writing for four years without receiving anything other than a byline. My assumption was that if my work was good enough someone was going to call me and sing my praises in four-part harmony possibly accompanied by a kazoo. In that fairytale phone call I would be told my work had value and that I should expect a life changing check by Friday.

I never verbalized it that way, but I absolutely assumed that one-day someone would notice my work and that would be the turning point in my writing career. My wife apparently was not as convinced.

Indeed, the phone never rang and I was never ‘discovered’ the way I thought I would. No four-part harmony, no kazoo, just the regular requests for free writing.

My own personal tipping point came when my wife looked at me and gently said, “Are you always going to write for free? Do you think anyone outside this area would even think about buying your work?”

She had seen me stay up late at night writing and sending articles to people who were very happy to receive content, but had either no ability or intention of paying for it. My wife’s not a writer, but she saw that exercise as a bit insane.

In that moment I wasn’t angry. I was however startled to find myself considering whether I truly felt my work had worth. I took my wife’s questions as the encouragement I needed and began to actively look for paying work. I tried some freelance websites and came away with slave wages. I wrote a story about a cooking disaster in my home and sent it to a recipe website and they actually paid me $40. I became a member of a content delivery team and made enough money to pay for Christmas one year. I sent manuscripts to a few publishers and came away with three book deals. The successes continued and the learning curve straightened out.

In some ways I don’t regret writing for free for so long. I’ve been told a writer needs to pen at least a million words before they write something really good. Maybe that time was the proverbial paying of dues for me.

If you assume freelance writing is easy – you’re wrong.

If you assume someone will discover you – they probably won’t.

If you think a publisher will love your work – you might be right, but don’t hope for too much.

If you think that you can quit your day job – don’t expect that day to come soon.

If you think that you know everything there is to know – you don’t.

I’ll be honest. I don’t know everything there is to know, but I get emails almost daily from other writers looking for direction on how and where to take that next step. I have made it my goal to learn something new everyday and I’ve taken lots of steps. I have learned it is not in my best interest to assume I know how everything will work. Writing is a trip up a mountain with lots of divergent trails. Stop treating freelancing writing like it’s a recipe. There’s no pinch of this and dash of that to make the process successful. It’s as individualized as DNA.

Think of it a bit like parenting. Your children are born completely unique. They will not act the same as other children. They will not like the same food other children like and they think that bodily noises are a form of high comedy. Read all the parenting books you want, but I bet they won’t be able to perfectly describe your child.

This is the best picture I can create when it comes to freelance writing. It is a unique experience for every writer and no one arrives at a point of success in the exact same way.

I have found a few ways to take some of the overall guesswork out of the process and that has been something I try to share with others along the way.

Here are just a few takeaway points…

1. Research is your friend. Don’t always think you need a website with all the answers. Travel down publishing trails that interest you. It’s possible you will find a gem.

2. Sometimes you are your own worst enemy. We often look for stumbling blocks that others place in the way of our success. Sometimes we put those barriers up ourselves.

3. Freelancing is never easy. No matter how gifted you are as a writer there will always be a client who is never satisfied or there will be times when it takes you much longer to complete a project than you anticipated.

Last, but not least let me say that the only person that really has the power to say you can’t do this thing called freelance is you. So, what is your answer?


Glenn Hascall has been a professional writer since 1995 and has been published every month for the past 13 years. He is a former mayor and the writer of more than 300 stage presentations. He has participated in the writing of more than 50 books and is the author of a new ebook entitled The Ultimate Guide to a Successful Freelance Writing Career. In fact this article was adapted from this new resource. He publishes a weekly advice column for writers and has produced his own clean comedy CD.

Hascall is also a veteran broadcaster who recently gained top honors as his state’s Personality of the Year. He has won numerous other prestigious awards for his voice work and can be heard on television and radio stations around the globe. He is the father of two and the husband of one and as it turns out these are his most cherished achievements.

You can order The Ultimate Guide to a Successful Freelance Writing Career here.