S1:E3 Life is Expensive! Balancing Contracting Work in your Business
Meet your Season One Co-Host: Caitie Cupples
Caitie is a copywriter who bravely volunteered to be the first cohost and come with me in my messy journey to launch a podcast without overthinking it (too much).
We're using a Thread as a jumping-off point for today's conversation. Caitie and Erin go deeper into the realities of running a business and why doing consulting work might be THE thing that keeps your business afloat, not something to be ashamed of.
Back in February of 2026 we came across a Thread by KP of Jupiter Content Co that we wanted to discuss and share our personal experience.
Here is the Thread if you’d like to review the original conversation starter
I’m not sure who thinks contract work is problematic, but it certainly isn’t either of our beliefs.
Caitie has done several bouts of contracting gigs throughout her journey and at the time of recording was considering another. This provides project-based businesses a way to keep their income stable during the dips of business.
Erin spent quite a bit of time contracting as a project manager in corporate settings during the first couple years of her business until she found her footing. As Lunimae is primarily retainer-based, there is more consistency with income than a project-based business.
The biggest issue is that the online space has coaches/marketing “experts” making it seem like you’re failing if you aren’t immediately hitting 10k months. That’s not the reality of most businesses and we need to keep this conversation open and flowing so no one feels less-than for a slowdown in business or picking up a stable income gig that doesn’t fall into the standard scope of business.
To learn more about Caitie:
Website: www.caitiecupplescreative.com
Newsletter: www.caitiecupplescreative.com/subscribe
Instagram: www.instagram.com/caitiecupplescreative
CHAPTERS
00:00 Vacation Preferences: Beach vs. Adventure
01:43 Jobs you wish you knew about
03:07 Looking forward to in 2026
03:35 What's for Dinner?
04:59 Caitie Intro
05:27 Business Realities: Contract Work and Retainers
16:01 Weighing Your Options with a Contract Opportunity
20:21 Summer Schedules
25:23 Corporate vs. Business Owner Risks
Mentioned in the Episode:
KP is a Certified 9-grid freak | Social Media + content strategy for weirdo small business owners feeling lost on social - learn more here
The massive Chicken Pot Pie
I’m your host, Erin!
Systems pro, avid fiction reader, and new Portugal resident
It takes a minute to get to know the real me. So when I decided to start a podcast, I knew it had to be different than your usual show. While most guest-led episodes limit us to just one conversation, I wanted Two Desks Down to be more than that.
Here, you’ll learn you aren’t the only one having that problem, business advice from experts, and what books to add to your TBR.
two desks down
This is the small business podcast where you can drop in - just two desks down - to get advice from people who get it, make a new friend, and have some fun. Every season’s a new guest. Every episode is less than an hour. And every single one’s a good listen.
