Should You Hire a Writing Coach?

A year and a half ago, I found myself in a rut. I had a steady stream of freelance assignments, but I felt uninspired brainstorming ideas for my regular editors and couldn’t seem to break into new markets.

So I wound up hiring Jodi Helmer, a freelance journalist and writing coach in Charlotte. At that point, I’d taken plenty of online writing classes, but most were too general. What I needed was one-on-one attention.

Now, whenever I feel stuck for more than a day or two, I email Helmer to set up a coaching call. I still post the occasional question on freelance forums like ASJA or Freelance Success, and consult freelance friends, but sometimes I find that seeking advice from one person I trust is better than getting a chorus of conflicting opinions, especially when it’s a more personal or complicated issue.

With Helmer’s help, I’ve gotten better at honing my ideas for older clients while also landing several new ones, including a trade magazine and a major financial news outlet.

But when is the right time to hire a coach? And if there is a right time, how do you know who to choose? I talked to several coaches (including mine) to find out.

Who benefits from coaching?

Rochelle Melander, a Milwaukee-based writing coach and author of Write-A-Thon: Write Your Book in 26 Days (And Live to Tell About It), said there are a couple key times when a writer might want to hire a coach:

1. When they’re tackling new and unfamiliar goals like transitioning from journalism to content marketing or writing a book for the first time.
2. When they’re dealing with a persistent issue like writer’s block or time management problems.

“Think about what you want to achieve from coaching before you interview a coach and see if they can help you do it,” Melander said.

Also make sure you can set aside the time to prepare for coaching sessions and follow through on their advice. If you’re looking for a quick fix but don’t put in the time to execute, you won’t get much out of it.

Choosing a coach

Besides cost, which can vary wildly depending on what you need and who you’re hiring, there are plenty of other factors to consider when hiring a coach.

Luckily, most coaches offer trial runs. Melander said it’s common for coaches to offer a complementary 20-minute session so you can both decide if it’s a good fit. She encourages writers to interview two or three before choosing one.

But before you take on the commitment of a trial session, make sure you consider these questions.

Do you prefer group or individual coaching?

While I enjoy the personalized attention of one-on-one coaching, other writers like getting multiple points of view with group coaching. Group coaching is led by a coach, but participants also get feedback and insights from each other much like they would in a group therapy setting.

“People have told me they just learn so much from [group coaching] and get so much emotionally from hearing that other people are going through the same things that they’re going through,” said Carol Tice, who runs a mastermind (a concept similar to group couching in which a group, sans an official coach, shares wisdom and brainstorms together) for freelance writers and group coaching programs.

Nida Sea, a B2B copywriter based in central Texas, signed up for Tice’s Den 2x Income Accelerator last spring. The group coaching program was designed to help freelancers double their income—and Sea has since quadrupled her income after working on her letters of introduction and honing her approach to writing copy.

“We were all on a single chat on Skype, so you could just jump into the conversation,” she said. “You get feedback not just from Carol, but from everyone.”

What kind of commitment is required?

Tice favors a structured coaching program that takes you through a set of actionable steps so you’re not tempted to simply shoot the breeze with your coach. Other coaches, however, offer more flexible coaching where you can schedule calls when you need them.

Helmer said she used to use a specific six-month program that included a certain number of calls and critiques because that’s what her coach (Helmer has a coach of her own) recommended. After a while, she realized the format wasn’t for her; plus, she didn’t want people to feel locked into a long-term commitment that wasn’t right for them.

“I would strongly suggest that you have at least a couple of session individually before you sign on to any long-term agreement so that you don’t feel stuck,” she said.

Personally, I always send Helmer a list of things I want to discuss before our sessions to keep us focused and give her a chance to brainstorm in advance.

Have they accomplished what you want to accomplish?

Many newer freelancers call themselves coaches, so look carefully at a potential coach’s credentials.

Have they gone through formal coaching certification? Have they achieved the writing milestones you’re aiming for? Without real experience, you may find yourself regretting committing to a coach with flashy promises but underwhelming results.

“Read their about pages carefully,” Tice said. “How long have they been doing this thing? Anyone can hang out a shingle and call themselves a coach, so look at their portfolio. Who have they written for? Does it bare a relationship to the folks you’d like to write for? Have they run their business through at least one major economic downturn?”

Do your personalities match?

Just because someone has published best-selling books or written for all the glossy magazines you want to pitch doesn’t mean they’re the right coach for you.

“Sometimes someone can be super successful, but personality-wise it’s not a love connection,” Helmer said. “Personality match is important.”

You’ll want to feel comfortable sharing your income goals, insecurities and other details of your freelance life, so during that initial call, look for someone who puts you at ease and understands your point of view. Because if you’re lucky enough to find that perfect coach for your needs, you may find it’s one of the best investments a freelancer could make.