Workday Structure & Time Management as a Freelancer w/ Ashley Cummings

Treyton DeVore
August 13, 2022

Ashley Cummings began her freelance career in 2011 after leaving her 9-5 job as a corporate trainer/instructional designer and gig at a university as a Russian instructor.

She was an English major and previously worked in marketing, so the transition into writing was a familiar next step. Since then, she's established herself as a content marketing expert and her work has appeared in Shopify and Salesforce amongst many other publications.

This week's Money Matters:

How do you structure your days as a freelancer?

I’ve been freelancing for 11 years, and I find it’s incredibly important to prioritize balancing my personal time and time I spend growing my business.

I usually schedule my work a month in advance. I try and front-load my months so I am doing the majority of my writing at the beginning of the month. I also leave some flexibility in my schedule to plan for the unknown—writer’s block, getting sick, doctor’s appointments, sick kids, unplanned fun, etc.

Last year, I was facing a ton of burnout and made it a priority to take a week off every month. I accomplished this by front-loading my months, hiring subcontractors for help with outreach, research, and editing. And, I also worked hard to fine-tune my processes to cut down on time it takes to do manual and mundane tasks.

In terms of my daily schedule, I usually reserve mornings for exercise and my family, and then dive into work around 8:30 am. I start by answering emails and catching up on newsletters and trends. Then, I dive into writing. I work until 2:30 and then put work away.

What’s the best investment you’ve made in your freelance business?

The best investment I’ve made in my freelance business is relationships with peers. I’m constantly amazed at how smart my colleagues are and how willing they are to share their expertise. I’ve learned a lot from my freelance and content marketing friends.

If you could give one piece of financial advice to a growing freelancer, what would it be?

Raise your prices quickly and incrementally and invest in tools that help you save time. Learning how to manage your time is the best way to grow your business.

(Bonus) What’s your favorite thing to spend money on?

Travel and food

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