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

THE END BITS

Support independent women's media.
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.

<ul data-start="1876" data-end="2336"></ul>
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:
<ul data-start="2672" data-end="3171">
<li data-section-id="1n321dk" data-start="2672" data-end="2723">How to tell if your side hustle actually has legs</li>
<li data-section-id="y9apej" data-start="2724" data-end="2797">Why you don't necessarily need to quit your job to start a business</li>
<li data-section-id="13o2t6j" data-start="2798" data-end="2850">The reality of going years without paying yourself</li>
<li data-section-id="h6i46" data-start="2965" data-end="3043">The moment Cherie realised she had become the bottleneck in her own business</li>
<li data-section-id="8deib0" data-start="3044" data-end="3093">What changes when you hire your first employees</li>
</ul>
THE END BITS
<a href="https://mamamia.com.au/subscribe/?utm_source=shownotes&amp;utm_medium=podcast&amp;utm_campaign=quicky&amp;utm_content=mm-birthday&amp;code=TQBIRTHDAY">Support independent women's media</a>. Got a work life dilemma? Send us all the questions you definitely can't ask your boss for our Biz Inbox episodes -<a href="https://help.mamamia.com.au/en-US/send-a-podcast-voice-note-467960"> send us a voice note</a> or email us at podcast@mamamia.com.au. You can remain anon!&nbsp;
HOST:&nbsp;<a href="https://www.instagram.com/lisa.lie_learna/?hl=en">Lisa Lie</a>
GUEST: <a href="https://www.linkedin.com/in/cherie-clonan/">Cherie Clonan</a> - <a href="https://www.thedigitalpicnic.com.au/">The Digital Picnic</a>&nbsp;
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.

BIZ is a podcast about work and how to make it work for you.

This season, we're promising new wisdom, fresh energy, and zero fluff. Co-hosts Em Vernem (ambitious but efficient) and Lisa Lie (founder of Learna) bring real talk, real hacks, and real experience. No vague inspo, no recycled advice—just smart, straight-up strategies that actually work. Because work is hard enough without having to figure it all out yourself.

Because work is hard enough without having to figure it all out yourself.

BIZ is a podcast about work and how to make it work for you.
This season, we're promising new wisdom, fresh energy, and zero fluff. Co-hosts Em Vernem (ambitious but efficient) and Lisa Lie (founder of Learna) bring real talk, real hacks, and real experience. No vague inspo, no recycled advice&mdash;just smart, straight-up strategies that actually work. Because work is hard enough without having to figure it all out yourself.
Because work is hard enough without having to figure it all out yourself.

Biz 

Grit Or Quit? How To Know When To Go All In On Your Freelance Gig 

https://api.omny.fm/orgs/3ea926be-9be7-482a-8ac3-a44f016e43d1/clips/98b14fc5-3170-4654-8b0b-b4aa0067087a/transcript