How I Added Coaching to My Writing Business

Photo by Mathilda Khoo on Unsplash

Back in the day of typewriters I began to make my way into freelance writing. I’d been sneaking into bookstores to buy Writer’s Market for yearssneaking because I didn’t want anyone to know I truly wanted to write professionally — and eventually began to actually put words on paper and submit to magazines. I posted my first two rejection slips on my bedroom wall because I dimly understood that I had accomplished something important by actually writing and submitting.

I kept at it and began to sell some, and then more of my pieces. Computers arrived and because they’d check my still highly creative spelling I became what we later called an ‘early adopter.’

Off and on I cut my teeth on a few actual writing jobs — that is I showed up at an office five days a week, wrote and got paid. For example I worked in for a small newspaper, and I took a tech writing job for a long-gone computer company who used me to write first manuals then for their magazine.

When the ‘net arrived I recognized the web as a publishing platform and before long was making a decent living writing online by writing for others and by creating a blog about freelance writing for a blogging network. That morphed into which is just over 15 years old now.

I noticed I was answering a ton of questions

Several years ago I noticed I was answering a lot of questions asked in comments section of my blog. Life coaching was getting popular, and people were beginning to branch out into specialties. I realized I could probably coach writers. I bought a book on life coaching to help me figure out how to set it up and market it, and announced my new side hustle (although that term wasn’t in use yet) on my blog. Gradually I found paying clients, many of them who either referred me or stuck with me for several years or both. It was around that time that I also developed what is now known as the Five Bucks Writing Forum — yep, it costs $5 a month.

The key to either business, and both are businesses, is deciding to do them, then following up on that decision.

I was approached by a successful life coach who offered to help me expand into life coaching. It worked, and so it is I write, I coach writers and I coach others about their life. I’m also heavily involved in a nonprofit non-partisan high tech startup called Democracy Counts which is a whole other story I’ll tell someday.

My secret is that I decided to write, then decided to coach, and I followed up on each one. Decisions can be incredibly important.

My biggest lessons

The biggest lessons I’ve learned in starting a coaching business in addition to my writing business is just that — each is a business. If I don’t treat them like a business nothing much happens.

By that, is just as I have to market my writing, I have to market my coaching. Much as I’d rather skip the marketing, it simply doesn’t work that way.

My secret is that I decided to write, then decided to coach, and I followed up on each one. Decisions can be incredibly important.

I also have to figure how much I charge, how to keep track of my income and outgo, file taxes, and do all the other things an entrepreneur really must do in addition to the coaching and the writing.

My biggest problems

In one way, my biggest problem is what I call my laziness. I’m not sure that’s totally fair, but I’d rather read a novel, go to the beach (with a novel) or sailing or… well do almost anything but the businesses side of my two businesses. I

Another is my love for what I’ve come to call ‘bright shiny objects.’ You know, the brand new idea to chase.

do love to write most of the time which is a real blessing and has allowed me to establish (gasp) good writing habits. Coaching is also a blast. I mean who wouldn’t like getting paid for helping others figure out how to do their lives?

Another problem is my love for what I’ve come to call ‘bright shiny objects.’ You know, the brand new idea to chase. I sometimes have to slap my hands to keep myself for starting a new business that probably isn’t right for me but sure sounds good when I first hear of it. Usually, what it is is a total distraction from what I’ve set out to do. Fun and exciting for a bit, then either suddenly or slowly I realize I’ve allowed myself to be pulled away from what I really want to do, which over and over again is the writing and the coaching. Learning to recognize and turn down these distractions has been key to my success.


Yes, you can learn from this article. You could, for example, use it to encourage you to start an additional side hustle, or to recognize you need to pay more attention to the business side of your writing business. Or you might use it as a cautionary tale to avoid falling for the next bright shiny object. And if you’re clever you’ll recognize this as an example of turning life experience into a publishable piece of writing.

Write well and often,

Anne Wayman —

Writer, life and writing coach, book ghostwriter, Grandmother, Buddhist. Liberal who listens to the other side, political

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