Two Ashleys Talk About Freelance Work [078]

I remember the first tax bill I got as a freelancer. I remember being so proud of myself for having this side hustle, and finally being able to save money, and then I got my tax bill—and there went all my savings. I told a friend of mine about it, and they laughed, and asked why I didn’t know that the IRS would claim almost a third of my income. 

Freelancing is fucking hard. It sounds fun and exciting—I don’t have to report to a boss everyday, I get to work from home, I get to make my own schedule—but there have been times where I’ve really considered if this is something I’m cut out for. 

I see more of my friends and colleagues take up creative pursuits, and dabble in the world of side hustles and part time consulting work, and I think there’s still a lot to the freelance world that still feels clouded in mystery. 

How do you pitch an idea? How do you know how much money to charge for a project? The government is taking what in taxes? There’s no easy guide—especially in the coffee world—to how to navigate setting a rate for yourself, or how to balance your work and your life, or how to get paid when people are avoiding the fuck out of you. 

I wanted to talk more about these things, so I invited my friend, Ashley Elander, to sit and swap stories about what it means to be a freelancer and how to truly advocate for yourself and your worth as a creative professional. Ashley is a freelance illustrator, and we try to be as candid as possible with both the ups—and the downs—of working for yourself.