How to Find the Perfect Writing Coach for You

2021.06.03 - Me and Justine Pic

A shower. That is what I needed after this email from a potential coach. 

What is it about being hard sold that makes us want to wash our skin? It doesn’t seem to make intellectual sense, and yet, everyone to whom I read the email had the same reaction. Ewwww. As if it were gross.

In a way, it was. 

If you’re shopping for a writing coach, you will encounter people who make you feel this way. In sales, (which is not essentially a bad thing in itself), there is the sizzle — the promise, the excitement, the salesmanship — and then there is the steak — the outcomes, the details, the real-life value. Some people who provide services focus way too much on the sizzle, the selling. I had encountered one of those people. 

Though I was, in this instance, shopping for a business coach, the lessons I learned while finding my perfect coach can help you in your hunt for a writing coach. 

Why I Use Coaches

The last year of working with my client Kirsten Jordan has cemented my belief that building big things out of your life requires personal development. It can take many forms. For a long time, the only “coaches” I could afford were the books from the library and YouTube videos. 

In the post-recession darkness of 2011, I called a career coach and said, “Hello, I have no money but I was wondering if you could give me one piece of advice.” She recommended I read The Overnight Resume. I did, as well as other books on job hunting. When I finally got offered a job, even though I was desperate, I knew from the books I’d read that I should negotiate. I asked for $5,000 more on top of my salary, even though I would have accepted $5,000 less because I was tired of crying onto the cheese boards at my waitressing job.

They countered with 1% commission. Over the next three years I worked for the company, that made a $100,000 difference. It paid off my student loans.

Personal development pays. The cheapest forms can lead you to be able to afford its more powerful forms. For example, once I was making better money, I could buy classes at Hugo House, the Seattle writing center. 

The most powerful form of personal development is the coach. This person gets to know you and your challenges, and applies their knowledge and experience in a customized way. 

Seeing how much Kirsten invests in coaches convinced me I should be getting as much coaching as I can afford.

But it doesn’t all have to be as pricey as coaching. I still use a mix of free and paid personal development. 

The personal development habits I’m using right now:

  1. Reading a business book 30 minutes a day: free
  2. Weekly hour-long business mastermind with a friend: free
  3. Weekly team growth meeting watching a class on LinkedIn Learning: free through my library
  4. Bi-weekly writing workshop with writers in my fellowship cohort: free
  5. Personal trainer/Spanish tutor: $200/month
  6. Weekly financial coach: bartering with one of my coaching students
  7. Classes at Hugo House: $100 – $400
  8. Daily meditations and writing sessions with A Very Important Meeting: +$15/session as the host

My mantra is: I need a lot of help and I give it to myself. 

What a writing coach (or any kind of coach) does

Previously, I’d hired a writer who I really liked to do some editing for me. But, she kind of just does it as I come to her. She doesn’t email me and say, “Hey lady, where are your pages!” She’s not invested in my overall progress. She’s not a coach. 

A coach learns about you and roots for you. They keep you accountable. They call you on your B.S. They should also have about a decade more knowledge than you in the area in which you’re trying to push yourself. This combination of experience and personal attention is the magic formula. 

What a writing coach does that other accountability measures can’t 

  • Helps you spot your mindset hurdles
  • Points out your particular gifts
  • Speaks from a more experienced perspective
  • Finds your particular patterns of mistakes

Shopping for a coach

In my weekly mastermind with my friend Ryan, we’ve been talking about getting coaches for a while. His partner had spent $5,000 on a career coach and landed a job at twice his salary. We adult dared each other to contact three coaches each to see how we felt about it.

I ended up contacting a total of five coaches, and I encountered some troubling behavior along the way. 

🚩Red flags when shopping for a writing coach 😬 

They don’t follow up. 

If someone is charging you more than $1,000 for a service, they’d better be on their shit. The first people I called didn’t call me back. They finally emailed two weeks later with a “Whoops we missed your email.” By then, they’d missed the chance to work with me, too. 

They rush you to make a decision.

“My goal is to get you to a hell yes or a hell no on this call,” said one coach.

One of the joys of studying sales is that you can spot one of its tactics right away. This sentence is called time pressure. Yawn. What else you got?

If someone doesn’t want to give you time to think about your decision, they’re trying to catch you in the hot emotional state they’ve worked you into during the call. In a hot state, you’re not thinking as clearly and rationally as you might after a night’s sleep. You might go over your budget or sign onto something you’re not really ready for. If you need time to think about a decision, someone who’s really giving you value shouldn’t have a problem with that.

They make it look easy. 

This is a power move. “Making it look easy” is literally a rule in the 48 Laws of Power.

But here’s the thing: it does you a disservice. Because being a writer or a freelancer is not easy. It’s worth it, but it’s tough. (I try to show this side of things as much as possible, which is why I post all my rejections on my Instagram.)

If pursuing a goal feels hard, but someone has told you it’s as easy as following their three-step formula, you start to think there’s something wrong with you.

No one has a secret formula. Anyone who tells you they do is BS-ing.

They encourage you to put it on a credit card.

Um, no. Especially not for writing. I put Amanda Abella’s course on my credit card years ago now. Is that credit card paid off? No, though I have earned many multiples on what I spent with what she taught me. I don’t have regrets about taking her course, just that I charged it.

I went to Amanda exactly because she was the salesiest person I’d ever met. I will never be half as salesy as she is, but her program got me over the hump of thinking just because I’m an artist I’m not allowed to make money. You can learn from people at the extremes without going extreme yourself. 

But do NOT put coaching on a credit card. 

I often offer people who can’t afford coaching or who want to continue after purchasing a program to barter for services. Ask if a barter is possible!

You feel like you need a shower after talking with them

The second I started talking to the aforementioned gross coach, she made me feel like a mouse who had entered her maze of hard sales. Like no matter what I said, she had a counter to it. I could tell that it wasn’t about helping me. It was about making the sale. 

I couldn’t wait to get off the call.

When I said I couldn’t afford more than $500 a month on coaching, she scoffed and said that’s what she charges for a group with her assistant. Um, ok…

Then she sent me an email saying she didn’t think that with my “level of commitment” I was the right person to work with her. HA! Math is not a level of commitment.

That email was designed to make me feel like I should come crawling back to her saying, “No, please take me as your pupil!” Gross.

What to look for in a writing coach

After that first round of failure, I wanted to quit, like a sad online dater after a date with someone who showed up smelling like Patchouli and trying to get them to invest in Bitcoin. But the promise of the perfect coach out there for me still called to me. After another mastermind with Ryan to vent, I got back to searching, remembering what I was actually looking for.

They’ve accomplished what you want to accomplish

One coach I looked at had an “accomplishment” on her page that really just meant she was good at SEO. Testimonials are nice, but they can be faked. We all have siblings or friends or hell even stock photos and low moral standards. Even mentions like this can be the result of a PR investment, (though mine wasn’t), just so they can forevermore say “As seen in the New York Times!”

Look for what the person has actually done. 

  • Have they been published where you want to be published?
  • Have they done the kinds of projects you want to do?
  • Do they have the network you want to be connected to?

You “align”

This can be a kind of eye-rolly coach jargon, but it really just means you’re going the same way and believe in the same things.

  • Does this person look up to the people you look up to?
  • Are they inspired by the same books?
  • Do you have the same values?

You like them as a person

You’re going to be spending a lot of time talking with this person, and your conversations are going to get real personal. If this person is a dirty interrupter or belittles what you say, move on.

  • Do you actually enjoy the “discovery call”?
  • Did they make you smile or, god forbid, even laugh?
  • Do you want to have a business relationship with this person?

Finally finding my coach

I decided to give it one more shot. I found a website with a woman who looked professional but not fake. I liked what she had to say. When we talked, she’d done her research on my business and seemed like she’d be excited to work with me. She also had a British accent, which I didn’t know was one of my requirements, but immediately got added to the top of the list.

When she sent a list of book recommendations, not only had I read quite a few, but she had included Eckhart Tolle and Tara Brach, two of my favorite spiritual teachers. We ✨aligned✨. 

She has a decade more experience than I do, listened when I talked, and gave me great ideas. When it came time to close the sale, she didn’t even have to convince me. Because I truly valued what she had to offer and felt it was offered with caring and respect, I didn’t feel like I was being sold. I felt like it was a mutual exchange of value. And that’s what makes business beautiful. 

If you’re looking for a writing coach and think I might be the perfect one for you, let’s have a free 15-minute chat that won’t make you feel like you need a shower.

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