Have you ever done something meaningful and kept it to yourself because talking about it felt like bragging?

Lynn Harris is the founder of Gold Comedy, the online school and community helping women and non-binary creators build comedy careers, side hustles, and creative confidence — but this conversation goes way beyond comedy. Lynn and I talk about the real difference between bragging and simply letting people know what you do, and why staying quiet about your gifts isn't humility, it's a habit that keeps you small.

In this episode:

- Why staying quiet about what you do isn't humility, it's a habit
- How two of Lynn's students changed their careers in midlife by no longer keeping quiet
- The real difference between an anecdote and a story worth telling
- Why being specific, not broad, is what actually makes people relate to you

More from Lynn Harris & Gold Comedy:

- Gold Comedy: https://www.goldcomedy.com/
- Explore classes & community: https://club.goldcomedy.com/
- Build and Pitch Any Idea with Ryan Cunningham (starts Sept 28): [ INSERT YOUR ROOTABL AFFILIATE LINK ]
- Use code GOLD10PERCENTOFF for 10% off any Gold Comedy class or membership
- Book a free comedy consult with Lynn: https://calendly.com/chat-with-lynn-harris/chat-about-your-comedy-goals-w-lynn-harris-gold-comedy

Also mentioned in this episode

- Dead Moms Club: It'll Be Funny, We Promise: https://youtu.be/vYwpnawcC1M

Wine Camp is laughter, adventure, girlfriend connection—shared over some very good wine and cocktails.

We're heading to Temecula, CA, July 15–18, 2027, for brand-new experiences centered around women, community, connection, and a whole lot of fun.

Registration is limited to the first 40 women. Learn more and save your spot at https://winecamp.info.

Want support growing your business? Book a free Discovery Call with Penny: https://tidycal.com/pennyforyourshots/call

Wine Camp 2027 - Join the list or save your spot:
https://www.pennyforyourshots.com/winecamp

Become an Insider for weekly updates, tips, inspiration, and episode extras:
https://www.pennyforyourshots.com/insider

Love cocktails + community? Join the Sipper Club:
https://www.pennyforyourshots.com/sip

Explore all things Penny: coaching, podcast, events, & more:
https://www.pennyforyourshots.com

Follow Penny on Instagram: @penny4yourshots
Or on Facebook: Penny (Kuhlers) Fitzgerald

Ever caught yourself wondering if the "safe" job is actually the risky one?

This week I'm sitting down with Melissa Broughton, owner of Busy Bee Advisors and creator of the One Hour Bookkeeper training system, to talk about what it really takes to leave corporate behind and build something that's actually yours. Ten years into her own business, Melissa's found a rhythm most corporate jobs could never offer — the freedom to fly out for her son's college football games every weekend, fire a client who isn't a fit, and build an income on her own terms.

We talk about:

- Why corporate "job security" isn't what it used to be

- A simple exercise for facing the fear that keeps women stuck ("what's the worst that could happen?")

- The real story behind a $90,000 fraud catch — and why the human touch still matters even with AI in the mix

- What to actually plan for before you take the leap

Melissa's sharing a free 3-step guide to work-life balance with our listeners: https://gift.1hourbookkeeper.com/penny

Wine Camp is laughter, adventure, girlfriend connection—shared over some very good wine and cocktails.

We're heading to Temecula, CA, July 15–18, 2027, for brand-new experiences centered around women, community, connection, and a whole lot of fun.

Registration is limited to the first 40 women. Learn more and save your spot at https://winecamp.info.

Want support growing your business? Book a free Discovery Call with Penny: https://tidycal.com/pennyforyourshots/call

Wine Camp 2027 - Join the list or save your spot:
https://www.pennyforyourshots.com/winecamp

Become an Insider for weekly updates, tips, inspiration, and episode extras:
https://www.pennyforyourshots.com/insider

Love cocktails + community? Join the Sipper Club:
https://www.pennyforyourshots.com/sip

Explore all things Penny: coaching, podcast, events, & more:
https://www.pennyforyourshots.com

Follow Penny on Instagram: @penny4yourshots
Or on Facebook: Penny (Kuhlers) Fitzgerald

Have you ever looked at your own past (a job, a business, twenty years of running a household) and quietly decided that none of it counts toward what you want to do next?

This week I'm sitting down with Sarah Noked, a 20-year Online Business Manager (OBM) and the founder of OBM School, who admits she believed exactly that when she started her own business, even though she'd already run a landscaping company from the ground up.

In this episode, you'll hear:

• What an OBM actually does, and why it's different from hiring a VA
• Why Sarah calls the idea of "having no transferable skills" a total farce
• How to know if your "why" is strong enough to carry you through the hard days
• Why documenting your systems (yes, even the ones in your head right now) might be the single biggest thing missing from your business
• What quality of life actually looks like on the other side of twenty years of building something real

Sarah's free resources for our community:

OBM Starter Kit: https://www.obmschool.com/penny-starter

SOP Kit: https://www.obmschool.com/penny-sop-kit

Find Sarah at https://www.sarahnoked.com/, on Instagram (https://www.instagram.com/sarahnoked/), LinkedIn (https://www.linkedin.com/in/sarahnoked/), and on YouTube at The OBM Show with Sarah Noked.

Read the full blog post: https://www.pennyforyourshots.com/blog/you-already-have-the-skills

Wine Camp is laughter, adventure, girlfriend connection—shared over some very good wine and cocktails.

We're heading to Temecula, CA, July 15–18, 2027, for brand-new experiences centered around women, community, connection, and a whole lot of fun.

Registration is limited to the first 40 women. Learn more and save your spot at https://winecamp.info.

Want support growing your business? Book a free Discovery Call with Penny: https://tidycal.com/pennyforyourshots/call

Wine Camp 2027 - Join the list or save your spot:
https://www.pennyforyourshots.com/winecamp

Become an Insider for weekly updates, tips, inspiration, and episode extras:
https://www.pennyforyourshots.com/insider

Love cocktails + community? Join the Sipper Club:
https://www.pennyforyourshots.com/sip

Explore all things Penny: coaching, podcast, events, & more:
https://www.pennyforyourshots.com

Follow Penny on Instagram: @penny4yourshots
Or on Facebook: Penny (Kuhlers) Fitzgerald