EPISODE · Oct 20, 2025 · 14 MIN
Did I Just Lose Money?
from Freelance to Founder · host Millo
Have you ever sent a proposal, completed extra work, and then panicked about sending the invoice? Laura did exactly that—and she's convinced she's about to lose a valuable client. But here's the thing: the disaster she's imagining might only exist in her head. In this episode, Clay and Preston tackle the all-too-common problem of freelancers building up worst-case scenarios before anything bad actually happens. They break down why you should send that invoice, how to handle pushback if it comes, and why the story you're telling yourself is probably far worse than reality. If you've ever hesitated to bill a client for work you've done, this episode will give you the confidence to stop panicking and start acting. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask Learn more about your ad choices. Visit megaphone.fm/adchoices
What this episode covers
Have you ever sent a proposal, completed extra work, and then panicked about sending the invoice? Laura did exactly that—and she's convinced she's about to lose a valuable client. But here's the thing: the disaster she's imagining might only exist in her head. In this episode, Clay and Preston tackle the all-too-common problem of freelancers building up worst-case scenarios before anything bad actually happens. They break down why you should send that invoice, how to handle pushback if it comes, and why the story you're telling yourself is probably far worse than reality. If you've ever hesitated to bill a client for work you've done, this episode will give you the confidence to stop panicking and start acting. Support our show sponsors → https://freelancetofounder.com/sponsors Submit your own question → https://freelancetofounder.com/ask Learn more about your ad choices. Visit megaphone.fm/adchoices
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Did I Just Lose Money?
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