Confessions with Jess and Cindy

Ever feel like you're working harder but not necessarily smarter? In this candid conversation, Jess and Cindy pull back the curtain on the simple but game-changing strategies they use to stay productive, focused, and sane while building six-figure consulting businesses.From Cindy's "CEO weeks" that give her massive chunks of uninterrupted deep work time to Jess's 90-minute screen detox that flattened her afternoon energy crashes, this episode is packed with practical hacks you can implement immediately.Whether you're struggling with boundaries around your time, looking for ways to generate content ideas effortlessly, or just need permission to throw money at problems (hello, summer childcare!), this episode will give you the permission slip to experiment with what actually works for your life and business.Highlights:Stop living in meetings if you want to grow your business. Cindy's CEO weeks—alternating between meeting-heavy weeks and deep work weeks—has been a game-changer for actually getting needle-moving work doneThe first 90 minutes of your day set the tone for everything. Jess's screen detox (no screens, no caffeine before food) eliminated her afternoon energy crashes and helped with adrenal fatigueChange your environment to change your energy. Sometimes the simple act of getting out of your house and walking to a different workspace can make you feel human againYour best business ideas won't come at your desk. Jess generates weeks of content ideas during weighted vest walks—combining exercise, inspiration, and productivity in one efficient packageThrow money at the problems you can solve with money. From hiring summer babysitters to getting salads delivered, sometimes the best productivity hack is just paying someone else to handle itReady to try CEO weeks? Start with just one protected week and see what happens.Resources Mentioned:Brick: https://getbrick.app/?srsltid=AfmBOoo4tU7sTn04-E9A8rU8cxTkCwCBZoPF5OLMltu9ysX44DM3F_Jc Diary of a CEO: https://www.youtube.com/TheDiaryOfACEO IFC Conference: https://www.resource-alliance.org/event/ifc-2025/ Find Us Online:  https://www.confessionswithjessandcindy.comConnect with Cindy:Cindy Wagman Coaching: cindywagman.comFractional Fundraising Network: fractionalfundraising.co/LinkedIn: ca.linkedin.com/in/cindywagmanConnect with Jess:Out In the Boons: outintheboons.meLinkedIn: linkedin.com/in/jesscampbelloutntiheboons/

In this episode, Dr. Tiffany shares how her "faith walk" led her from feeling defeated in her corporate role to building HR Tailormade, a thriving consultancy serving as the virtual HR department for nonprofit organizations. She pulls back the curtain on her seven-year journey to clarity, how health challenges became the catalyst for entrepreneurship, and why it took finding the right marketing partner to finally get her messaging right.From structuring retainer relationships that make HR expertise accessible to small nonprofits to building strategic partnerships through intentional LinkedIn outreach, Dr. Tiffany offers a masterclass in building a consulting business that aligns with both your strengths and preferences (hello, fellow introverts!) while delivering exceptional value to clients.Highlights:Define clear service boundaries in your virtual practice. Tiffany is so beautifully clear about what her virtual HR department doesn't do (recruiting and payroll) and instead builds partnerships with others who excel at those services. What a relief to know you don't have to do it all!Simplify your marketing as a virtual consultant. After trying ALL the platforms, Tiffany realized her nonprofit clients were primarily finding her through LinkedIn and word-of-mouth. Sometimes less really is more when it comes to marketing your virtual services!Ask for what you need, always. As Tiffany wisely says, "a closed mouth doesn't get fed." She shows us how to request testimonials and website mentions in ways that feel comfortable and authentic - essential skills for growing a virtual practice.Be patient with your niche journey. It took Tiffany seven years to get completely clear on serving nonprofits as a virtual HR consultant. Business clarity emerges through experience, not perfect planning from day one.Build a virtual support community. I love how Tiffany intentionally reaches out to 10 LinkedIn contacts weekly, resulting in quarterly meetings with trusted peers. This business journey is too hard to do alone, especially when you're working virtually!Resources Mentioned:HR Tailor Made: https://hrtailormade.com/ Canva: https://www.canva.com/ LinkedIn: https://www.linkedin.com/Women's Business Center (St. Louis area) https://www.wbdc.org/en/event/getting-to-know-the-womens-business-center-st-louis/ Find Us Online:  https://www.confessionswithjessandcindy.comConnect with Dr. Tiffany:Website :https://hrtailormade.com/ LinkedIn: https://www.linkedin.com/in/tiffany-e-slater Connect with Cindy:Cindy Wagman Coaching: cindywagman.comFractional Fundraising Network: fractionalfundraising.co/LinkedIn: ca.linkedin.com/in/cindywagmanConnect with Jess:Out In the Boons: outintheboons.meLinkedIn: linke

"I'm gunning this year to get to double digit millions."That's not something you hear every day. But Shannon Brome-Ward isn't just any financial coach. As a money mindset coach and financial educator, Shannon is on a mission to help consultants move from middle class to millions, and she's not shy about her own financial goals.In this candid conversation, Shannon opens up about the mindset shifts required for consultants to build real wealth. She challenges the scarcity thinking that keeps so many of us (especially women) playing small with our pricing and financial goals. From explaining why "getting by" is no way to live, to breaking down exactly how to start investing with as little as $25 a month, Shannon brings practical strategies any consultant can implement immediately.If you've ever caught yourself whispering about wanting more money or felt guilty about charging premium rates while serving nonprofits, this episode is your permission slip to think bigger. Shannon walks us through how creating multiple revenue streams can provide the freedom to weather economic storms, and why having millions isn't about luxury—it's about options.Highlights:Women and money shame is real. Shannon reveals why female consultants often whisper about wanting more money, while men never express concern about being "too greedy"—and how to overcome this limiting belief.Millionaires have multiple paychecks. Learn why diversifying your income beyond your consulting business is critical for building generational wealth, and practical examples of revenue streams to consider.Starting expert to build wealth.Charge more, live on less. The simplest wealth-building equation: increase your consulting rates while becoming comfortable living on less than you make, and invest the difference.Resources Mentioned:Podcast - From Middle Class to Millions: https://podcasts.apple.com/ca/podcast/from-middle-class-to-millions/id1781017144 Website: https://www.thewholebudget.com/ Find Us Online:  https://www.confessionswithjessandcindy.comConnect with Shannon:Instagram: https://www.instagram.com/thewholebudget/reels/ TikTok: https://www.tiktok.com/@thewholebudget Facebook: https://www.facebook.com/TheWholeBudget/ Website: https://www.thewholebudget.com/ Connect with Cindy:Cindy Wagman Coaching: cindywagman.comFractional Fundraising Network: fractionalfundraising.co/LinkedIn: ca.linkedin.com/in/cindywagmanConnect with Jess:Out In the Boons: outintheboons.meLinkedIn: linkedin.com/in/jesscampbelloutntiheboons/

Rachel Bearbower, founder of the Nonprofit Automation Agency, shares her inspiring journey from running a struggling membership model to commanding $30,000 for her automation services. She candidly discusses the emotional challenges of letting go of her previous business and how a website crash spurred new opportunities. Rachel emphasizes the importance of understanding client needs, offering premium services, and strategically following up — even if it takes 109 days! Her transformation is a testament to resilience and growth in the nonprofit sector.

Marc Pitman is a DELIGHT. The CEO of Concord Leadership Group joined us to spill all the tea on what it actually takes to keep a consulting practice alive and thriving for over two decades.Marc took us on his journey from bow-tie-wearing "Fundraising Coach" to running multiple brands under his company umbrella. And yes, we finally got him to admit the truth about "passive income" (spoiler alert: it's completely made up!).If you've ever felt like everyone else has it figured out while you're still flying by the seat of your pants, this episode will make you feel SO MUCH BETTER. Marc's old-school approach to marketing (dude literally picks up the phone and calls people every day) combined with his willingness to evolve makes for a masterclass in consulting longevity.Highlights:The "Jeremy Bearimy" approach to marketing: Marc focuses on activities he can control (like making daily phone calls) and trusts that business will come—but not in the linear, trackable way modern marketing promisesAudience building then and now: From early blogging in 2003 to navigating today's "walled-off" social platforms, Marc shares how he's consistently adapted his approach while maintaining his core focus on serving firstOvercoming the comparison trap: Marc explains how he stops himself from second-guessing content when he sees others covering similar topics, and how finding your unique voice matters more than originalityThe consulting long game: Even with multiple revenue streams (speaking, coaching, books, etc.), Marc shares that the goal isn't to sell the business but to be "used up" when he dies—living up to all the potential entrusted to himResources Mentioned:Fundraising Coach - Marc's blog since 2003Concord Leadership Group - Umbrella company for Marc's brandsThe Nonprofit Academy - Low-cost, CFRE-accredited training programAsk Without Fear - Marc's first book on fundraising"The Surprising Gift of Doubt" - Marc's book on leadershipGallup Strengths Finder - Marc mentioned having "Maximizer" as one of his strengthsQuadrant Three Leadership Coach Certification - Program that Marc and his wife runFind Us Online:  https://www.confessionswithjessandcindy.comConnect with Marc:Website: https://marcpitman.com/ Linkedin: https://www.linkedin.com/in/marcapitman/ Connect with Cindy:Cindy Wagman Coaching: cindywagman.comFractional Fundraising Network: fractionalfundraising.co/LinkedIn: ca.linkedin.com/in/cindywagmanConnect with Jess:Out In the Boons: outintheboons.meLinkedIn: linkedin.com/in/jesscampbelloutntiheboons/

Ever find yourself doing work you swore you'd never do? You're not alone! When Brittny Wilson launched her consulting business in 2021, she quickly found herself saying yes to everything – especially event planning, which was literally on her "absolutely not" list.In this chat with our friend Brittny, she opens up about her journey from reluctant event planner to confident recruitment agency owner. The turning point? When her kids flat-out told her she wasn't "nice" during event season (ouch!) and when looking at her actual numbers showed her that what felt risky – walking away from steady event clients – was actually more profitable.Brittny gets real about the emotional rollercoaster of pivoting her business, the game-changing moment at Jess's conference when she started introducing herself differently, and how she's navigating the feast-or-famine nature of client work. Plus, she shares the exact pricing structure that's working for her now.Whether you're feeling stuck in work that drains you or trying to find the courage to specialize, Brittny's journey will remind you that sometimes the scariest business decisions lead to the most aligned (and profitable!) outcomes.Highlights:Your gut knows when something isn't working. When Brittny's kids pointed out how stressed she became before events, it confirmed what she already felt – this work wasn't sustainable for her wellbeing.Saying something out loud makes it real. The confidence to call herself a "recruitment agency" came before she felt 100% ready – and that declaration helped others see her differently.Your pricing can protect your mission. Brittny's three-phase approach ensures clients don't skip critical elements like onboarding support – the key to her mission of keeping good people in the sector.Systems save sanity. Working with a systems-focused contractor and implementing Airtable automations allowed Brittny to create a repeatable process that doesn't depend solely on her.Seasons are normal. Six clients in fall, crickets in January – Brittny reminds us that business ebbs and flows are totally normal (even when they're nerve-wracking!).Resources Mentioned:Airtable - https://www.airtable.com/ Ashley (Airtable expert) - https://systemsoverstress.co/about LinkedIn - https://www.linkedin.com/login Shannon Bowen - https://monsoonleadership.com/about/ Find Us Online:  https://www.confessionswithjessandcindy.comConnect with Brittny:Website: https://www.brittnywilson.com/ Linkedin: https://www.linkedin.com/in/brittnywilson/ Connect with Cindy:Cindy Wagman Coaching: cindywagman.comFractional Fundraising Network: fractionalfundraising.co/LinkedIn: ca.linkedin.com/in/cindywagmanConnect with Jess:Out In the Boons: outintheboons.meLinkedIn: linkedin.com/in/jesscampbelloutntiheboons/

In this high-energy replay of the finale to our Fractional/Shift summit, entrepreneur Vivian Kaye (founder of KinkyCurlyYaki and operations coach) introduces us to "The Chadacity" – a mindset framework that teaches nonprofit consultants how to show up with bold confidence in their businesses.After bootstrapping a multi-million dollar business as an immigrant, college dropout, and single mother, Vivian shares how adopting just a fraction of the unapologetic confidence that mediocre “Chads” often display can transform your consulting practice. This isn't about being someone you're not – it's about stepping into the fullest, most confident version of yourself.From imposter syndrome to pricing strategy, Vivian challenges nonprofit consultants to stop playing small and start demanding what their expertise is worth. Through hilarious examples and practical advice, she demonstrates how confidence isn't something you wait for – it's something you build by taking bold action, even when (especially when) it feels uncomfortable.Highlights:Stop Questioning, Start Claiming Your Worth: Your expertise isn't a luxury – it's valuable. Vivian demonstrates how mindset shifts around money and worth are essential to scaling past six figures. "Common sense is not common – there are people who will gladly pay for what you think is simple."Take Bold Action Before You Feel Ready: The confidence muscle only develops through practice. Start with one bold move today (not tomorrow), whether that's raising your rates, adding a client even when you feel at capacity, or launching a service you've been hesitating on.The "What Would Chad Do?" Framework: When facing decisions or opportunities, ask yourself what an overconfident person would do in your situation – then do it (minus the jerk behavior). This simple reframe helps bypass self-limiting beliefs that keep consultants stuck.Take Up Space Unapologetically: Whether through your personal brand, communication style, or physical presence at events, stop minimizing yourself. Vivian notes how she intentionally wears bright colors and makes direct eye contact to be memorable in professional settings.Confidence Without Compromise: True confidence isn't about stepping on others to get ahead – it's about showing up authentically while uplifting those around you. Use your "Chadacity" to create positive impact and inspire the nonprofit community.Resources Mentioned:Connect with Vivian Kaye on Instagram: @VivianKayeVivian's website: VivianKaye.comFractional Fundraising Network: https://www.fractionalfundraising.co/ Vivian's business coaching: Operations coaching for entrepreneursFind Us Online:  https://www.confessionswithjessandcindy.comConnect with Cindy:Cindy Wagman Coaching: cindywagman.comFractional Fundraising Network: fractionalfundraising.co/LinkedIn: ca.linkedin.com/in/cindywagmanConnect with Jess:Out In the Boons: outintheboons.meLinkedIn: linkedin.com/in/jesscampbelloutntiheboons/

Okay, so you know how Jess has been bugging Cindy FOREVER to host a summit? Well, she finally did it! In this fun behind-the-scenes chat, Cindy spills all the tea on her first-ever Fractional Shift Summit that absolutely crushed it with 1,400+ registrations and $24K in revenue (and yes, she's got the Airtable data to prove it — you should see how happy spreadsheet data makes her!).Cindy opens up about why she finally felt ready to "take up space" as THE fractional expert, how she convinced practically every sponsor she approached to say yes (only three said no!), and why she thinks the nonprofit world needs way more time to make decisions than those "launch in 3 days" gurus will tell you.If you've been on the fence about hosting your own signature event, this episode is your permission slip to either go all-in or wait until it feels right. As Cindy says, it's definitely a "high effort, high reward" project — but now that she's built it once, she can rinse and repeat next year with half the stress.Highlights:The moment Cindy knew she was ready to claim her spot as THE thought leader on fractional roles (and why she's glad she waited)How she crafted a "curated approach" to partnerships that made sponsors feel like they were getting the golden ticket (and they funded all her speaker fees!)Why she started promoting a full two months before launch (and why LinkedIn delivered even better than her email list)The hilarious reality of launching her Academy right when the nonprofit world was in crisis mode (and what she'll do differently next time)Her secret weapon named Christine who made the whole thing possible (because let's be real, no one does this alone!)Breaking News Alert! Jess and Cindy also drop the bomb that they're hosting in-person masterminds this year in Toronto (May 21), Boulder (August), and possibly Atlanta (October). Listen to the end for details!Find Us Online:  https://www.confessionswithjessandcindy.comConnect with Cindy:Cindy Wagman Coaching: cindywagman.comFractional Fundraising Network: fractionalfundraising.co/LinkedIn: ca.linkedin.com/in/cindywagmanConnect with Jess:Out In the Boons: outintheboons.meLinkedIn: linkedin.com/in/jesscampbelloutntiheboons/

In this episode of Confessions, Jess and Cindy chat with Caroline Danks, a UK-based fundraising consultant who runs Lark Owl with her partner. Caroline shares her journey from traditional consulting to developing multiple revenue streams, most recently transitioning her email newsletter to a monetized Substack publication called The Nest Egg.Caroline discusses how she began as a freelancer in 2016 after being made redundant, then discovered the potential of online business beyond selling time for money. After initially creating and selling online courses for several years, she faced email deliverability challenges in 2023 that prompted her to rethink her business model. This led her to Substack, where she now monetizes her weekly newsletter directly, charging £6/month or £60/year.Caroline shares her marketing strategy, focusing on LinkedIn for discovery, Substack's recommendation feature for cross-promotion with other writers, and consistently producing high-quality content that people naturally share. She also discusses her decision to retire her online courses and workshops in favor of a simpler business model that prioritizes what she truly enjoys.Key Takeaways:Monetize What You Already Love Doing: Caroline found success by turning her passion for writing emails—something she was already doing weekly—into a revenue stream. As she puts it, "there's a simplicity in being able to monetize a thing that you would be doing anyway and a thing that you probably would do if nobody paid you for it because you love it so much."Quality Content Is Your Best Marketing Tool: Caroline emphasizes that creating genuinely valuable content is central to her strategy. Each piece helps her clarify her own thinking on important topics while providing tactical advice to readers, which naturally encourages sharing and word-of-mouth growth.Simplify for Sustainability: By retiring her online courses and reducing workshops and affiliate marketing, Caroline created a more streamlined business model that reduces overwhelm and focuses on her strengths. This intentional simplification helps maintain quality while preventing burnout.Alternative Revenue Models Require Patience: Caroline is transparent about the "slow burn" nature of subscription models, noting that a low-cost product requires higher volume to be significant financially. She's comfortable with this gradual growth because it aligns with her lifestyle needs and desire for business simplicity.There's Power in a Weekly Commitment: For five years, Caroline has consistently published content every Tuesday at 10am without fail (except for planned breaks in August and December). This consistency has been crucial to building trust and a loyal audience that's willing to pay for her expertiseFind Us Online:  https://www.confessionswithjessandcindy.comConnect with Caroline:LinkedIn: Caroline Danks: https://uk.linkedin.com/in/caroline-danks-ab54b921 Substack: The Nest Egg: https://larkowl.uk/newsletter/ Connect with Cindy:Cindy Wagman Coaching: cindywagman.comFractional Fundraising Network: fractionalfundraising.co/LinkedIn: ca.linkedin.com/in/cindywagmanConnect with Jess:Out In the Boons: outintheboons.meLinkedIn: linkedin.com/in/jesscampbelloutntiheboons/

Ashley Rose, a systems expert and ADHD advocate, shares her journey in scaling a consulting practice using just Airtable and automation. She reveals how her ADHD diagnosis inspired her to develop systems that enhance efficiency. Ashley discusses the financial realities of entrepreneurship, including her experiences with debt and decision-making. Listeners can expect practical tips on using Airtable to manage everything from client experiences to sales tracking, highlighting the importance of having a system as your first hire.