A reader named Elizabeth asked me the following question:
I am a writer and have two areas of expertise from about six years of combined experience as a copywriter and grant writer. My ultimate dream is to freelance. I have done tons of reading on becoming a freelancer and am talking to dozens of people. I have also joined several relevant professional associations, and am volunteering my time as a writer.
The key issue that I'm grappling with is TIMING! When do I know if I'm ready to go out on my own? How do I or should I measure if I am "good enough" to freelance now? Would love to know your thoughts/advice on the matter.
Elizabeth, you and I were cut from the same cloth! Sixteen years ago, I recall having exactly the same feelings. I had a senior job with a large, metropolitan newspaper, and I anguished over whether I should leave to freelance.
I did and it turns out to be one of the best decisions I ever made. BUT -- and this is a big "but" -- you need to be prepared.
Funnily enough, this preparation has little to do with writing and more to do with selling and marketing. I trust you when you say you are a writer but do you have the skill and training to sell your work? Sadly, that is often the far more important skill for freelancing success.
"But, wait," you say. "Shouldn't the best writers get the most work?" I agree, but the sales engine is what runs the world. People who know how to know how to make clients feel "cared for" get the most work. People who are good listeners get the most work. People who have thick skins and don't seem to feel the sting of rejection get the most work.
Don't worry about your writing -- it sounds fine and you sound competent. More than competent, actually. But what you need is a business plan.
When I started, I landed a very big contract fairly quickly. It represented more than 75% of my income. This was good for me, at the time, because I was a new mom with young children. Not having to make a lot of sales calls was a benefit to me. But as a business strategy, it sucked.
After a few years, PFFT, the company was sold and I was suddenly without 75% of my income. I scrambled like heck and became a "traditional" freelancer for a full 13 months before I was able to find another "anchor" client. During the year, I was able to match my income, but it was stressful.
During that same year, I also launched my website so I'd never have to depend so much on a single client ever again.
You didn't say whether you have a job now (I'm going to assume you do). I suggest you start your "freelance" life during your off hours -- you know, by working evenings and weekends. Yes, it will be demanding doing two jobs at once, but it will allow you to have a taste of freelance work without jeopardizing your full-paying job. Furthermore, it will allow to you develop some clients and save some money.
You should have at least three month's of income in the bank and some paid-freelance experience under your belt before you start. If you don't feel comfortable "selling" then take a course or get a coach. I took a bit of sales coaching and found it extraordinarily helpful. One book my coach recommended that I really enjoyed is: Action Selling: How to Sell Like a Professional Even if You Think You Are One by Duane Sparks.
The freelancing life is invigorating. But too many writers tend fret about their writing skills -- when what they really need to worry about is their sales acumen. Good luck to you, Elizabeth, and happy selling!