Everyone loves the idea of being their own boss. But what happens when your side gig becomes a real business?

In this episode of Biz, Lisa Lie chats with Cherie Clonan, CEO of The Digital Picnic, about what it actually takes to make the leap from employee or freelancer to business owner.

Cherie gets brutally honest about the reality of building a business with bub in tow: three years without a salary, the pressure of making payroll, the temptation to quit, and why business ownership isn't necessarily the freedom fantasy we're sold.

She explains how she knew The Digital Picnic had "legs", what changes when you go from selling your own time to building a team, and why the biggest leap might actually come after becoming a freelancer.

Plus, Cherie shares her simple "horizons of growth" framework to balance the day-to-day work of keeping a business alive with the bigger ideas that drove you to start it all.

In this episode you'll also learn:

• How to tell if your side hustle actually has legs
• Why you don't necessarily need to quit your job to start a business
• The reality of going years without paying yourself
• The moment Cherie realised she had become the bottleneck in her own business
• What changes when you hire your first employees

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Got a work life dilemma? Send us all the questions you definitely can't ask your boss for our Biz Inbox episodes - send us a voice note or email us at podcast@mamamia.com.au. You can remain anon! 

HOST: Lisa Lie

GUEST: Cherie Clonan - The Digital Picnic 

EXECUTIVE PRODUCER: Courtney Ammenhauser

SENIOR PRODUCER: Thom Lion
VIDEO PRODUCER: Marlena Cacciotti

Mamamia acknowledges the Traditional Owners of the Land we have recorded this podcast on, the Gadigal people of the Eora Nation. We pay our respects to their Elders past and present, and extend that respect to all Aboriginal and Torres Strait Islander cultures.