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Coaching: How to Get Ahead

I have to admit- I love coaching people. I’ve always been a natural at teaching others. When I was really little, I would always want to play “classroom” with my sister. I was the teacher, she was my student.

In the professional space, I became the designated trainee. I even helped develop a mentorship program at one of my facilities. Early on, I was scarred when I was barely trained at a job. I decided that I didn’t want anyone to feel as uncomfortable as I did. Everyone deserves to be trained.

So it just makes sense that I now coach new writers. I offer a few different coaching packages to accommodate different time restraints and budgets. I’ve also played around with group coaching.

This article goes over why coaching is the ideal strategy for anyone looking to get ahead with some individualized support.


Most of my clients come to me asking for a step-by-step strategy. When you’re starting out as a new writer, you have a mountain of tasks. You’re told you need a website, a robust portfolio, and that you need to be networking on LinkedIn. On top of all that, you need to be sending out letters of introduction and doing discovery calls. It’s easy to get lost and forget what’s really important.

One of the most profound ways we can use our time together is to create a strategy so you can tackle what you need to, in an appropriate order. If we work together for multiple weeks, I may give light homework or suggestions for the upcoming week. Then, we talk about how the strategies worked in the next session. That way, we can address any questions together.

Sometimes, strategizing focuses on a particular hurdle. Some writers have a hard time getting their first few clients. So we may come up with some ways to facilitate client acquisition. Other clients struggle with prioritization, writer’s block, LinkedIn optimization, or finding appropriate resources.

During these sessions, I go over my step-by-step recommendations to give them actionable advice they can put into use immediately. With me, it’s as easy as 1,2,3.

Questions Answered

During these sessions, this is your time. Ask all the questions you need. And make sure you have a pen and paper ready, because I want to make it as informative as possible.

When I first started writing, I had a million questions. What’s a PO? What’s an invoice? How do I set one up? What the heck is a discovery call? The list literally went on and on.

And I didn’t want to bother anyone because I had no one I was comfortable rattling off my questions to. Well, this is your chance. Ask whatever you want to know, but you’ve been too hesitant to ask someone.

Follow-up Period

I always offer a brief follow-up period with my sessions. I’m the type of person that internalizes everything. So, when I go to bed, I’m replaying my day and processing what happened. And usually that means questions pop up.

I let my mentees shoot me emails or message me on LinkedIn in between sessions. If something quick comes up, I’m all ears. If our session sparks another question or two, I can help you chat it out. When we have sessions together, we’re not just in contact for our specific set time. I want to make sure you’re satisfied with the subjects we cover.


We all need a little bit of support and encouragement every once in a while. Writing can be a bit lonely. You may have gone from having coworkers you can bounce questions on to not really having that same level of support.

How do you know if your progression is normal? Did you make a mistake, or is that situation the type of thing that happens to everyone? Did you have a weird experience with a client, recruiter, or publication? We can chat it out together.


You can succeed without a mentor. I did it. But it’s going to take longer. And you won’t have any industry insights or step-by-step advice to guide you. Mentor sessions can help you overcome individual hurdles, get encouragement, and find the motivation you need to drive forward.

Freelancing is a bit tough at first. It comes with a lot of rejection and a lot of personal decisions that you need to make. But you don’t have to do it alone. Mentoring is a great way to bridge that gap.

Curious about mentor programs? You can find mine here.

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