Every month we run through a series of questions to help you run your freelance business like a bigger business—“self-coaching” your way to better results and a better life. 

Hey!

Checkups with a doctor help you catch physical issues before they become a bigger problem. Your freelance business works the same way. 

That’s why, twice a year, we dedicate a round of CEO Month to Income and Assessment. If you don’t have your spreadsheet, you can download that here.

I just finished mine and I’ll be honest…while I’ve made some good progress in the first half of 2025, I’ve suffered some blows in my niche that have slowed down career and financial growth that I thought was in progress. But…

Since I’ve been filling this out since 2016, I can look back and see that the ups and downs are normal. I’ve come out of valleys before. I can also see what I did to make that progress. 

So take a little time to go through yours this month. Some of the questions are uncomfortable, but I promise the self-reflection is more than worth it.  

#2 Income and assessment: Clients 

This is my absolute favorite section to look back on, especially my favorite and least favorite clients. I forgot a lot of these people! (…especially how some of them frustrated me)

This section is great for giving you perspective on things that can feel like the biggest challenges ever in your freelance life, even if they’re just bumps in the road in the big picture. 

Spend a little time on this section this week, and don’t be scared to be honest about how you feel about any clients you’re working with. 

Got any fun client stories to share? Stop by the BlackFreelance Mastermind Discord.

Megan