Being Boss with Emily + Kathleen #4 - How to Be Boss When You're Afraid of Failing
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Jan 27, 2015 They talk about leaping from a day job to a self-made career and how to bridge the gap to your goals. They cover building street-smarts through messy trial and error and gaining real experience while employed. They discuss finding mentors, partners, and a supportive community. They outline practical tactics like selective freelancing and tracking dream contacts to build confidence and momentum.
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Agency Experience Before Going Solo
- Kathleen spent years gaining agency experience, moving up to senior art director before launching her business.
- That agency time taught her client relationships, project trafficking, and admin skills, which let her scale to six figures quickly once she left.
Day Job Versus Owning Your Business
- Kathleen compares a day job to renting and entrepreneurship to owning, showing tradeoffs between safety and creative control.
- Renting (a job) lets you learn mistakes on someone else's dime; owning forces responsibility but enables full creative ownership.
Turn Naysayers Into Supporters
- Share your vision and ask for specific help to turn well-meaning naysayers into supporters.
- Kathleen asks her husband to build spreadsheets and regularly shares small wins with her parents to make them invested in the business.
