This Author Has 101 Tips For Becoming a $100,000-a-Year Freelance Writer

By Charlie Kasov September 12th, 2014

For freelance writers, $100,000 per year seems to be the golden number.

Dawn Josephson, a writer and writing coach based in Jacksonville, is one of the few who has climbed the mountaintop to a six-figure salary. And in August, she released 101 Tips For Becoming A 100,000-a-Year Freelance Writer, a pamphlet-sized book that dishes out tips freelancers of all skill levels can benefit from.

I had the opportunity to chat with Josephson about hiring accountants, drawing up contracts, taking breaks, and other finer points that helped her reach that magic threshold.

Why did you decide to publish such a short book?

There’s so much stuff out there for writers because writers are starving for information about how to be successful. I didn’t want them to have to wade through yet another full-length book when they should just be out there writing. If it takes them more than ten minutes to read, then they’re slow readers.

I wanted to give bite-sized tips of what it takes to be successful as a writer. I also wanted them short because I believe in affirmations and that you should have short, little messages you can program into your mind. If there’s something that someone’s really struggling with, they could just take that one tip and put it on an index card and look at it every day to remind themselves how to do it.

Some of the tips feel like great jumping-off points for freelancers. Do you have any recommended reading or follow-up advice about self-promotion?

I would say emulate and learn from people who are successful in your niche. Don’t copy their materials, but look at what they’re doing that makes them successful. They probably have a website, a blog, and marketing materials, and you should have them as well.

Also, look at the market you want to penetrate. If a company I’d like to write for uses flashy marketing language and colors, that company will respond to the same style from freelancers. So make your marketing materials match the market you want to break into.

You have one tip about contracts. Is it ever worth it for freelancers to retain a lawyer to handle contracts?

When I first started, I hired a lawyer to draft a non-specific contract I could modify depending on the situation. It was a big investment, about $500 in 1998, but it’s definitely money well spent. You’re going to use that contract over and over, unless the client you’re working with provides you with a contract.

You should remind clients that your contract isn’t just there to protect you; it’s to protect them as well. You want the contract to put the client at ease. For example, mine contains a provision for what happens if the client is not satisfied, that way they can better expect to get a quality piece of writing from me.

How long did it take you to reach $100K?

I started in 1998, and I reached it around 2002. As you get your name out there, you charge more and work less.

In the beginning, I didn’t charge a lot. I worked an easy 60+ hours a week between writing and marketing myself. I didn’t have kids at the time, so I was able to travel to every conference and networking event. Once the momentum built and I surpassed my goal, I was slowly able to wind down hours.

Today, realistically, I work about 20 hours a week and maintain my income. My name is out there, and I’m entrenched and in-demand in my niche, so I can charge higher rates.

$100,000 divided by 101 tips equals $990.10 per tip. Is each tip in the book worth $990.10 in freelance income?

Well, I never looked at it that way, but kind of, yes. The way I see it is, if you’re making $70,000 a year, you’re already following most of the tips, but there are still several tips in the book that could help you over the $100,000 mark.

On the other hand, I’ll coach people who are just starting out and are only making $200 a month from freelance writing income. Across a few months of coaching, I end up teaching them most of the tips, but they’ll see results.

Tips No. 49 and No. 50 are advice about voicemail and email etiquette. What are your rules about texting and social media messaging? Is it professional?

It’s up to the client. I won’t text first unless it’s an emergency. If they’ve never texted me before, or if they’ve never messaged me on Facebook before, then that’s my cue that’s not their preferred means of communication.

I do have some clients who will text me all the time, and I’ll text them back. I have a rule in which I’ll text a little outside of traditional office hours, but if a client texts me at 11 p.m., they’re not hearing back from me until the morning.

You mention delegation in a few tips and handling taxes in others. Is hiring an accountant a worthwhile delegation?

Definitely, unless you love numbers. Maybe you’re writing in the financial sector, and all those numbers make you giddy. Me, not so much.

The thing with delegation is you have to look at it in two ways. First, ask yourself, by doing this task, are you being kept from making real money? If I could be making more money writing while I pay someone else to stuff envelopes or clean my house, then those tasks were worth delegating. Second, ask yourself if the task is something you enjoy doing. If that’s the case, then maybe it’ll help clear your mind, which is also valuable.

Tip No. 63 is about taking breaks from writing. What do you find to be the most rejuvenating break-time activity?

I like to walk out in nature. No headphones. Just me and silence. Another thing is folding laundry. It depends on what recharges you. I’m an introvert, so going into quiet places recharges me. For extroverts—there are extroverted writers out there—I’m sure spending an hour at a coffee shop excites them. Find what works for your personality. Whatever it is, do something to recharge yourself.

What would you consider the three most important tips in the book?

I would lump tips No. 3 [“Think of writing as a business”], No. 4 [“Do the things businesses do”], and No. 5 [“Remind yourself to view your freelance writing as a business”] together as one of the most important messages. You can’t treat this as a fun little hobby if you’d like to be successful at it.

A second important tip is about networking and marketing. As much as I hate networking, you need to do it. You’re not going to make the same connections sitting around on social media. You have to actually get out there and meet people and hand out business cards.

The third one—I know there’s a lot of controversy around this—when you’re still a nobody making $100 a month from your writing, I say you work for free for a little bit. I know there’s people out there who want to shoot me for that. But when you’re trying to get your portfolio together and gain some credibility, you want to get published any way you can. So I say write for free maybe two or three times, and do your best work. You shouldn’t need to do it any more, because now you should have a good portfolio that will get you paid work.

What’s your next project?

I’m going to write an e-book, a bit longer than 101 Tips, about how to succeed as a ghostwriter. It’s an untapped freelance market, and it’s extremely niche. In the United States, there’s only a few hundred people who are making their entire living off of ghostwriting. There are so many companies who need freelance ghostwriters. You don’t get the fame and glory because you don’t get your name out there, but it’s lucrative.

Can you just give me $100,000?

Umm, sure, if you earn it!

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