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Sample Business Coaching Session

I thought it’d be useful to see an example of a business coaching session for freelance writers. This is an approximation of how it usually goes, whether we chat online or over the phone. If you want to read a bit more about how this “sample” session came to be, I wrote a Medium article about it.

I’ve taken a few months to get my own websites up and running. They’re not generating income yet, but I’m working on it.

First of all, congratulations. That’s AWESOME. A lot of people have the idea of building a website and writing what makes them happy but then never do it. It’s a huge undertaking to create a website (let alone two!) and even braver to put your own writing out there, regardless of the topic. So, bravo. Take a minute to pat yourself on the back for that because you deserve it.

The savings I’ve been living off is running out. I know I have to earn money again soon, probably by getting more clients.

There are A LOT of ways to earn money. Do you absolutely have to get more clients, or at least the kind of clients you’re dreading?

I wonder if there are clients that are more aligned with what you’re focused on now — and who are also willing and able to pay, of course.

My advice is to sit with that for a bit. Take out a pen and paper and write down the smaller details of what it is you’re doing with your sites. Not just the niches and sub-niches, but also the skills you’re using or developing.

There are probably a lot of money-making and client-acquiring ideas in there that you haven’t thought of or explored before. Going back to client work doesn’t mean you have to do exactly what you were doing before, especially if you’re dreading it as much as you say.

For example, if you’re using a certain tool to research SEO, can you write about that tool? Maybe reach out to the company or similar companies (like publications that write about that tool) and pitch a few ideas.

Also, if you move forward in a new client direction buoyed by topics and ideas you’re passionate about, everything is going to come out better and easier — the cold emails, the writing you turn in, etc. Actually, if you think about it like that, it would be a BAD business decision to do anything else — I’d be afraid you’re setting yourself up for failure if you try to go back to something you know you hate.

I’m dying to veer away from client work completely, but I realize I’m not in a position to live off my websites yet.

We’ve already talked about the first part of this, so I’d like to address something that stood out to me that’s separate from that.

“I’m not in a position to live off my websites YET.” This makes me think that you (a) know you can live off them and (b) know you WILL live off them. That’s incredible. There’s a lot of confidence there and a lot of drive. Even if you don’t quite know how you’re going to monetize your sites, you know you are, and it’s only a matter of time, effort and probably experimentation until that dream comes true.

Again, bravo. Even in this mud you feel stuck in, there’s a lot you’re looking forward to. I suggest you hold that close, especially right now. Because “I have to get client work and I’m miserable” can become “I have to get client work so I can support myself while I realize this dream.” Same path, two very different outlooks — and the one that’s more helpful than the other is obvious, yeah?

I’m not sure what to focus on, and I’m overwhelmed knowing how much work everything is going to take.

Here’s the time when I get a little tough love-y on you, if that’s OK. Look — this is not the career to get into if you don’t want to have a lot of work. There are going to be a lot of times when you’re completely overwhelmed with work. Dare I say DROWNING in work. It’s what happens. It’s one of the drawbacks of this job — it’s what you get when you trade in all the things you hate about traditional work.

This may be a time when you have to work longer hours, get up earlier, do more of what you don’t like and then also figure out how to do enough of what you do like, etc.

That also makes it the time to take care of yourself even more than before. Sleeping, taking short and long breaks from work, disconnecting from work (because even during breaks, you could be thinking about work), getting into hobbies even if you only have a tiny amount of time to devote to them, etc. is so, SO important right now.

And I can’t not mention all of the things you do to take care of your health. I’m by no means a doctor or able to offer health advice for you, but whatever the basics are for you — 7 hours of sleep, 100 ounces of water a day, an hour at the track every afternoon, stretching before bed, meditation, more green in your diet, whatever — this is the time. It’s going to help you both during work and when you’re separating from work. If you neglect your health, it’s going to be nearly impossible to feel OK while trying to keep up with this workload that’s coming.

If you’re struggling with freelance writing and want to talk about it, get in touch or fill out my Business Coaching Inquiry form.