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) and follow Cindy's fractional work at nonprofitfractionals.com/fracture

Connect with Cindy:

• Cindy Wagman Coaching: cindywagman.com
• Fractional Work: nonprofitfractional.com/fracture
• LinkedIn: ca.linkedin.com/in/cindywagman

Connect with Jess:

• Out In the Boons: outintheboons.me
• Building Better Together buildingbettertogether.co
• LinkedIn: linkedin.com/in/jesscampbelloutntiheboons/

"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/
• Membership website: https://www.leagueofextraordinaryfundraisers.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/

"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/