A few days ago I shared the story of hiring my 18-year-old sister-in-law, Cailee, to do a proofreading job for me.

And today I want to give an update on this because it looks like I may start coaching her on how to start a freelance writing business.

Here’s what happened…

Cailee came over last night (Sunday) to hang out with my wife Lacie and I. I asked how the proofreading project was going I gave her on Friday. It was a big project so I expected her to maybe get done Tuesday or Wednesday this week. So when she said, “oh I’m done,” I was impressed!

After commending her on a job well done I asked if she’d be interested in doing this in the future.

Come to find out my wife had already been talking to her about this and was encouraging her to pursue not just freelance editing, but also freelance writing.

“You’re a good writer and if you wanted to figure out how to get clients and do freelance work then Josh would be a great resource for you,” Lacie said.

Cailee said she would like to pursue this and seemed excited to learn how to get started as a freelance writer.

I did my best to answer her questions like, “So what type of things do you write about?” and “How do you get started?

The three of us ended up talking until almost 1:00 a.m. last night, which is unusual because I’m usually in bed by around 10:30. But the hours flew by because I love talking about stuff like this!

By the end of the night I let Cailee know that if she was serious about doing this then I’d be happy to start coaching her. Sounds like she is, so my next step is to take some time to reflect on the lessons I’ve learned during the last six years as a freelancer and organize those into a “coaching course.”

I’ve coached a few other aspiring freelancers in the past but I’ve never formalized my process. We’d usually just meet for coffee and they’d pick my brain about how to get clients and how to grow a freelance business.

So I’m looking forward to putting together a curriculum for this. Like I told Cailee last night, I love the lifestyle that freelancing has allowed me to live. I get to see my wife and kids throughout the day and I can work from anywhere. So I love it and would love to see others enjoy that same kind of lifestyle.

I was honest too and told her that it’s not easy. It’s hard work but it’s worth it.

So anyway, that’s the latest and greatest from my life. I’ll do my best to keep you posted on how this unfolds. I’d love to one day launch an online course to show others how to start and grow a freelance writing business.

But for now I’m content to simply do my best to coach Cailee! If she can learn and develop a skill that will benefit her for the rest of her life, then it’ll all be worth it!