Is Freelancing Freedom a Lie? episode artwork

EPISODE · Feb 27, 2026 · 20 MIN

Is Freelancing Freedom a Lie?

from Freelance to Founder · host Millo

Dana in Seattle went freelance for the freedom—and now she's drowning in deadlines and client expectations she can barely keep straight. Sound familiar? Preston and Austin Church unpack the promise that draws most people into freelancing in the first place, and whether the "no boss, no calendar" dream was ever really the point. Along the way, they share three dead-simple systems for keeping projects organized without the suffocation—including a one-page brief that replaces a hundred scattered emails and a counterintuitive trick involving more deadlines that actually sets you free. Support our show sponsors -> ⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠ Join Austin's Community for Advanced Freelancers -> ⁠⁠Freelance Cake Community Learn more about your ad choices. Visit megaphone.fm/adchoices

Episode metadata supplied by the publisher feed · Published Feb 27, 2026

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Is Freelancing Freedom a Lie?

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