Confessions with Jess and Cindy

It's a Wrap! Why Sometimes You Have To Kill What You Love

After hundreds of episodes and countless conversations, Jess and Cindy are making one of the hardest business decisions: ending Confessions (for now). But this isn't just a goodbye episode - it's a masterclass in strategic decision-making and knowing when to let go of something you love for the sake of your business. In this candid conversation, they pull back the curtain on how they made this decision, why "it's fun" isn't always enough of a business reason, and how regular business evaluations led them to this crossroads. From Cindy's pivot to fractional work to the reality that successful consultants still face doubt and struggle, this episode is packed with real talk about business evolution. Whether you're holding onto something in your business that's no longer serving you or wondering how to make tough strategic decisions, this conversation will give you permission to choose growth over comfort. Highlights: * Regular business audits are non-negotiable. What worked 12 months ago might not align with where your business is headed today. * "It's fun" isn't always enough. If something doesn't serve your business goals, it might be time to let it go - even if you love it. * Your business should evolve with you. Cindy's shift from general nonprofit consulting to fractional specialization shows how niching down can clarify everything. * Everyone struggles, even the "successful" people. Comparison truly is the thief of joy, and behind every confident consultant is someone who still has moments of doubt. Thanks for being part of this journey with us. Keep doing the important work - the sector needs you. ❤️ 🎧 What's next? Connect with Jess at Building Better Together (buildingbettertogether.co [https://buildingbettertogether.co/]) and follow Cindy's fractional work at nonprofitfractionals.com/fracture [https://www.nonprofitfractionals.com/fracture] Connect with Cindy: * Cindy Wagman Coaching: cindywagman.com [http://cindywagman.com] * Fractional Work: nonprofitfractionals.com/fracture [https://www.nonprofitfractionals.com/fracture] * LinkedIn: ca.linkedin.com/in/cindywagman [http://ca.linkedin.com/in/cindywagman] Connect with Jess: * Out In the Boons: outintheboons.me [http://outintheboons.me] * Building Better Together buildingbettertogether.co  [http://buildingbettertogether.co] * LinkedIn: linkedin.com/in/jesscampbelloutntiheboons/ [https://www.linkedin.com/in/jess-campbell-outintheboons/]

Stop Doing What You 'Should' Do: How Rachel Muir Built a Membership Business Model Around What She Loves

"I was so grossed out. I would send an email and want to go hide under my bed." That's how Rachel Muir, founder of League of Extraordinary Fundraisers, describes her old high-pressure launch strategy. Now? She's built a thriving membership business around the things she actually loves doing: monthly webinars and writing emails that people think are newsletters (spoiler: they're sales emails, just really good ones). In this episode, Rachel pulls back the curtain on her complete business model transformation during COVID, when her speaking revenue disappeared overnight and she had to choose: adapt or fail. Her choice? Build around what energizes her, not what she "should" be doing. Highlights: * Stop forcing yourself into marketing channels that drain you. Rachel admits she barely posts on LinkedIn and doesn't have a VA—and her business is thriving anyway. * The 80/20 split that works. Rachel spends 80% of her time marketing her membership and 20% delivering—and why that ratio makes sense. * How to handle the "commitment issues" of subscription pricing. People assume they're locked in for a year. Rachel's messaging strategy addresses this head-on. * Why scaling isn't always the goal. With twins heading to college, Rachel's choosing travel and flexibility over aggressive growth—and that's perfectly fine. Listen to discover how letting go of the "shoulds" and building around your natural strengths can create a business that actually works for your life. Ready to ditch some business "shoulds" of your own? Subscribe to Confessions for more real talk on building a thriving consulting business. Connect with Rachel: * Rachel’s website: https://www.rachelmuir.com/ [https://www.rachelmuir.com/]  * Membership website: https://www.leagueofextraordinaryfundraisers.com/ [https://www.leagueofextraordinaryfundraisers.com/]  Find Us Online: https://www.confessionswithjessandcindy.com [https://www.confessionswithjessandcindy.com] Connect with Cindy: * Nonprofit Fractionals Network: https://www.nonprofitfractionals.com/ [https://www.nonprofitfractionals.com/]  * LinkedIn: ca.linkedin.com/in/cindywagman [http://ca.linkedin.com/in/cindywagman] Connect with Jess: * Out In the Boons: outintheboons.me [http://outintheboons.me] * LinkedIn: linkedin.com/in/jesscampbelloutntiheboons/ [https://www.linkedin.com/in/jess-campbell-outintheboons/]

Self-Employed Maternity Leave Strategy: How to Take 4 Months Off Without Losing Your Consulting Business

"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/ [https://www.linkedin.com/in/sara-royf/]  Find Us Online: https://www.confessionswithjessandcindy.com [https://www.confessionswithjessandcindy.com] Connect with Cindy: * Cindy Wagman Coaching: cindywagman.com [http://cindywagman.com] * Fractional Fundraising Network: fractionalfundraising.co [http://fractionalfundraising.co]/ * LinkedIn: ca.linkedin.com/in/cindywagman [http://ca.linkedin.com/in/cindywagman] Connect with Jess: * Out In the Boons: outintheboons.me [http://outintheboons.me] * LinkedIn: linkedin.com/in/jesscampbelloutntiheboons/ [https://www.linkedin.com/in/jess-campbell-outintheboons/]

Stop Competing, Start Differentiating: Trevor Nelson's 7-Figure Strategy

"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 [https://www.linkedin.com/in/trevor-nelson-b8922a167/] * Company website: hgafundraising.com [http://hgafundraising.com] * Podcast: "Hey Nonprofits" (YouTube [https://www.youtube.com/@RaiseMoreMoney], Apple [https://podcasts.apple.com/us/podcast/hey-nonprofits/id1612837149], Spotify [https://open.spotify.com/show/6VuQF5foIAjhjkWrmDKuDB]) Find Us Online: https://www.confessionswithjessandcindy.com [https://www.confessionswithjessandcindy.com] Connect with Cindy: * Cindy Wagman Coaching: cindywagman.com [http://cindywagman.com] * Fractional Fundraising Network: fractionalfundraising.co [http://fractionalfundraising.co]/ * LinkedIn: ca.linkedin.com/in/cindywagman [http://ca.linkedin.com/in/cindywagman] Connect with Jess: * Out In the Boons: outintheboons.me [http://outintheboons.me] * LinkedIn: linkedin.com/in/jesscampbelloutntiheboons/ [https://www.linkedin.com/in/jess-campbell-outintheboons/]

The "Oh Shit" Moment: When AI Finally Clicks for Nonprofit Consultants

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 [https://www.linkedin.com/in/brookerichiebabbage] * Brooke’s website: https://brookerichiebabbage.com/ Find Us Online:  https://www.confessionswithjessandcindy.com [https://www.confessionswithjessandcindy.com/] Connect with Cindy: Cindy Wagman Coaching: cindywagman.com [http://cindywagman.com/] Fractional Fundraising Network: fractionalfundraising.co/ [http://fractionalfundraising.co/] LinkedIn: ca.linkedin.com/in/cindywagman [http://ca.linkedin.com/in/cindywagman] Connect with Jess: Out In the Boons: outintheboons.me [https://www.outintheboons.me/] LinkedIn: linkedin.com/in/jesscampbelloutntiheboons/ [http://linkedin.com/in/jess-campbell-outintheboons/]