freelancing is not for everyone (i learned this the hard way) episode artwork

EPISODE · Mar 29, 2026 · 21 MIN

freelancing is not for everyone (i learned this the hard way)

from Pretty Philosophical · host Pretty Philosophical with Denée Seaton

Freelancing is often marketed as the ultimate freedom, but it demands much more than just talent. In this episode, discover the hidden challenges of freelancing as I share personal experiences and insights from my career, built from the ground up. Learn why freelancing requires mastering uncertainty, time management, and self-regulation, especially when things don't go your way. I've collaborated with seven and eight-figure brands, faced client losses, and secured new opportunities. Find out what differentiates successful freelancers from those who burn out. If you're considering freelancing or are already on this path but feel something's missing, this episode will provide clarity. 0:00: Intro1:45: Why most freelancers burn out3:48: My first client and what it taught me5:21: Losing a client and what happened next7:57: Freelancing is a leverage game11:30: Why discipline isn’t enough14:20: The trap of feeling “not good enough”17:12: The truth about freedom and responsibility #freelancing #career #self-regulation #timemanagement #uncertainty #burnout #freedom #discipline See show notes: https://inlet.fm/denee/episodes/69c968ee101f55619a6e64e9 Learn more about your ad choices. Visit podcastchoices.com/adchoices

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freelancing is not for everyone (i learned this the hard way)

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