"I started thinking about having a kid as it related to my career long before I even started my business. And actually it was really the impetus to start my business."

What do you do when you're self-employed and need to take four months off for maternity leave? If you're Sara Royf, you get ridiculously strategic about it.

Most of us panic at the thought of stepping away from our consulting businesses for any extended period. What happens to our clients? Our income? Will anyone remember we exist when we come back? Sara faced all these fears when she got pregnant, and instead of spiraling, she created a plan that actually worked.

Well, mostly worked. Because this is Confessions, and we're gonna talk about the stuff that didn't go as expected, too.

Sara breaks down exactly how she pre-scheduled four months of content (yes, four months), managed client expectations, and kept her audience warm while she was away. She also gets real about the maternity leave waitlist that converted exactly zero clients and why she'd completely flip her communication strategy if she did it again.

But here's what makes this conversation especially valuable—Sara's not just sharing theory. As a LinkedIn coach who teaches consultants how to get clients through authentic relationship-building, she literally practices what she preaches. Her approach to LinkedIn DMs is the opposite of gross sales tactics, and it works so well that clients book discovery calls with her while simultaneously telling her they hate DMs.

Plus, she drops a confession that'll surprise anyone who follows her work: she's actually not that fond of LinkedIn. Plot twist, right?

Highlights:

• Stop trying to optimize for everything when planning extended leave. Sara chose creative outlet and audience warmth over maximum revenue, and that clarity shaped every other decision she made.
• The 30-person waitlist that converted zero people immediately taught her that timing in business is everything. Sometimes your best-laid plans flop, and that's totally okay if you've layered your strategies.
• Make more noise about coming back than going away. Sara wishes she'd spent less energy announcing her departure and more energy announcing her return—your audience cares about when you're available, not why you're not.
• LinkedIn DMs work when you treat them like in-person conversations. The "would you say this at a conference?" test transforms how people respond to your outreach and makes it feel authentic instead of sales-y.
• Even the experts doubt themselves. Sara had to constantly remind herself she'd achieved exactly what she optimized for, proving that mindset challenges hit all of us—and why having good business friends matters.

Don’t miss the end of the episode to find out how you can connect with Sara and get expert feedback on your LinkedIn profile—completely free.

Connect with Sara:

• Linkedin: https://www.linkedin.com/in/sara-royf/

Find Us Online: https://www.confessionswithjessandcindy.com

Connect with Cindy:

• Cindy Wagman Coaching: cindywagman.com
• Fractional Fundraising Network: fractionalfundraising.co/
• LinkedIn: ca.linkedin.com/in/cindywagman

Connect with Jess:

• Out In the Boons: outintheboons.me
• LinkedIn: linkedin.com/in/jesscampbelloutntiheboons/

"I'm not gonna do it like everybody else. I'm very stubborn. I'm very competitive. I do believe that differentiation is stronger than competition."

That's Trevor Nelson from HGA Fundraising, and he's built something pretty incredible by completely ignoring what his competitors were doing. While everyone else was chasing the luxury market at the "tip of the pyramid," Trevor went straight for the base – working with smaller nonprofits that everyone else was overlooking.

The result? A 7-figure consignment business with 24 employees, serving thousands of events.

And they're just getting started.

In this episode, Trevor pulls back the curtain on his anti-competition strategy and shares why trying to beat everyone else at their own game is a losing battle. Instead, he chose to be the best at something completely different, and it's working.

Highlights:

• Stop trying to out-compete everyone else. Trevor looked at what his competitors were doing and deliberately chose the opposite path. Sometimes the best strategy is not to play the same game.
• Volume can be your friend if you're not afraid of it. With thin margins and a "make a little off of a lot" model, Trevor embraces scale instead of running from it. His mindset: "All I have to do is exactly what we're doing right now, just more of it."
• Family business isn't a dirty word. Against all conventional wisdom, Trevor built his company by hiring his sister, brother-in-law, and best friends. His take: "Those are the people you can trust and roll with."
• Relationships are your real equity. Trevor's entire business model is built on genuine connections – even talking prospects out of using their services if it's not the right fit. The long game always wins.

Ready to stop competing and start differentiating? This conversation will shift how you think about positioning your consulting business in a crowded market.

Connect with Trevor:

• LinkedIn: Trevor Nelson
• Company website: hgafundraising.com
• Podcast: "Hey Nonprofits" (YouTube, Apple, Spotify)

Find Us Online: https://www.confessionswithjessandcindy.com

Connect with Cindy:

• Cindy Wagman Coaching: cindywagman.com
• Fractional Fundraising Network: fractionalfundraising.co/
• LinkedIn: ca.linkedin.com/in/cindywagman

Connect with Jess:

• Out In the Boons: outintheboons.me
• LinkedIn: linkedin.com/in/jesscampbelloutntiheboons/

Ever roll your eyes when someone tells you AI will "revolutionize your business"? Yeah, our guest Brooke Richie-Babbage felt the same way. She was firmly in the "I don't need some tool to write weird poems" camp until one conversation completely shifted her perspective.

Now? Brooke has built an AI-powered business advisory system that's replaced expensive professional services, streamlined her financial reporting, and gives her marketing insights that used to take days to compile. And she's doing it all without becoming a tech guru or spending hours crafting perfect prompts.

In this candid conversation, Brooke pulls back the curtain on exactly how she went from AI skeptic to power user, sharing her specific systems for training custom GPTs that actually know her business, understand her clients, and deliver actionable insights she can trust.

Whether you're curious about AI but haven't found your use case yet (hi, Jess!) or you're ready to move beyond basic content creation, this episode breaks down practical applications that can actually transform how you run your consulting practice.

Highlights:

• Stop starting from scratch every time. Brooke's custom "Business Advisor" GPT is trained on 15+ business frameworks, her specific goals, and detailed customer insights—so it gives advice that's actually relevant to her business model.
• Turn raw data into actionable insights. Those monthly P&L reports and Google Analytics downloads you avoid? Brooke uploads them to AI and gets comprehensive business analysis in 15 minutes instead of spending three days doing it herself.
• Your clients need this too. The same AI systems Brooke uses for her own business are helping the nonprofit leaders she works with get strategic insights without hiring expensive consultants or drowning in spreadsheets.
• Training matters more than prompts. Forget perfect prompt architecture—the real game-changer is giving AI the right knowledge base to draw from, whether that's business frameworks, customer feedback, or your own proven methods.

Resources Mentioned:

Connect with Brooke

• LinkedIn: https://www.linkedin.com/in/brookerichiebabbage
• Brooke’s website: https://brookerichiebabbage.com/

Find Us Online: https://www.confessionswithjessandcindy.com

Connect with Cindy:

Cindy Wagman Coaching: cindywagman.com

Fractional Fundraising Network: fractionalfundraising.co/

LinkedIn: ca.linkedin.com/in/cindywagman

Connect with Jess:

Out In the Boons: outintheboons.me

LinkedIn: linkedin.com/in/jesscampbelloutntiheboons/