The Other Side – Details, episodes & analysis

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The Other Side

Jane Curtis

Business

Frequency: 1 episode/13d. Total Eps: 15

The Charity Freelancer's Podcast | Where Charity Experience meets Freelance Success

The Other Side: The Charity Freelancer's Podcast explores the journey from charity professional to thriving freelancer. Join us for practical tips, real stories, and community connection for anyone considering or already on their freelance journey in the sector.

Jane Curtis chats with individuals who've made the leap to freelance or self employment from the charity sector and in doing so uncovers invaluable practical tips and incredible insights first-hand.

Whether you're considering making the move or you're already on your freelance journey, or you’re just nosey and want to know what goes on behind the scenes of well known freelance businesses… you're in the right place.

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https://www.janecurtisevents.com/mega-money-march
26 shares
https://janecurtisevents.com
15 shares
https://thecharityeventspecialists.lpages.co/the-charity-freelance-course-list/
8 shares

https://www.linkedin.com/in/fromfundraisertofreelancer/
15 shares

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Score global : 53%

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Rosie Milsom - Building A Joyful Portfolio Career With Purpose And Self-Worth

Tuesday, November 11, 2025 • Duration 38:32

Ready to trade a single job title for a life that actually fits? Jane sits down with former grants fundraiser Rosie Milsom to map her rewarding shift from sector employment to a flexible, purpose-led portfolio career. It starts with side projects and a LinkedIn post, winds through a deeply personal fertility journey, and lands on a simple insight with big consequences: self-worth powers everything.

Rosie shares the practical moves that made her transition stick: taking on training, launching coaching while employed, and negotiating part-time hours to create space for clients. We unpack the way she uses joy and values to filter opportunities, and the systems she leans on when forecasts wobble. Expect real talk on pricing with confidence, setting boundaries, and building resilience without pretending everything is fine.

We also dig into the engine of sustainable growth: relationships. From sector groups to conferences, follow-ups to case studies, Rosie shows how thoughtful outreach compounds into referrals and a reputation. She explains why many purpose-driven women stall despite credentials, and how to rebuild that self-worth foundation so your marketing, offers, and money mindset finally click.

You can connect with Rosie on LinkedIn or visit her website.

You can also check out her free confidence block quiz - https://rosiemilsom.scoreapp.com

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Jane Curtis, founder of The Charity Freelancing Course, host of The Other Side Podcast and Co-founder of The Rich & Restored Movement.

Jane has spent 26 years in the charity sector, is a former events fundraiser, and now supports over 100 charity sector freelancers to build businesses that make more money with joy and integrity.

Connect here:

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Rob Woods - From Charity Job To Bright Spot Business

Tuesday, October 28, 2025 • Duration 44:54

Ready to trade one-off wins for lasting momentum? Bright Spot founder Rob Woods joins us to unpack how charity professionals can build a sustainable, values-led business without burning out or getting lost in feast-or-famine cycles. Rob shares the pivotal moment he moved from training days to the Bright Spot Members Club, creating an environment where fundraisers stay inspired, practise proven techniques, and follow through long after the workshop buzz fades.

We talk strategy and structure: how to test offers by teaching, why consistency outperforms talent, and the daily habits that protect deep work. Rob describes the power of choosing one channel, and showing up reliably so trust compounds. He also offers practical guidance for a safer leap: reduce hours before resigning, calculate your financial runway, and treat your new venture as a business from day one.

Community is at the core of Rob’s success. From early accountability groups to long-term learning cohorts, he shows how the right relationships shorten the learning curve, normalise ambition, and facilitate decision-making. If you want a clear, human blueprint for moving from charity role to thriving freelancer, built on generous marketing, practical tools, and steady consistency, this conversation delivers.

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Check out his website where you can find out more about Corporate Partnerships Mastery, Major Gifts Mastery programs, and Brightspot Members Club, and also listen to his Fundraising Bright Spots Show podcast.

If this resonates, please follow the show, share it with a colleague, and leave a quick review to help more charity professionals find it.

Send us Fan Mail

Jane Curtis, founder of The Charity Freelancing Course, host of The Other Side Podcast and Co-founder of The Rich & Restored Movement.

Jane has spent 26 years in the charity sector, is a former events fundraiser, and now supports over 100 charity sector freelancers to build businesses that make more money with joy and integrity.

Vic Hancock Fell - From Charity CEO to Collective Consultancy

Wednesday, October 22, 2025 • Duration 45:16

This week Jane sits down with former small charity chief exec turned consultant, trainer, and social enterprise co-founder, Vic Hancock Fell. They unpack the power of a long runway, a clear offer, and a values-led business model.

Vic shares how a master’s degree exposed the gap in sector support for small charities, and how that insight grew into two distinct paths: a personal consultancy of one-to-many leadership training, and Fair Collective, a not-for-profit matchmaking service connecting social good organisations with trusted freelancers.

We dive into the nuts and bolts of the associate model at Fair Collective and we chat about her income mix of front-loaded course enrolments, evergreen e-learning, speaking, and one-to-one work, that creates stability without a 60-hour week.

This conversation covers the school-run, ADHD-aware planning, the constant pull to overcommit, and the skill of saying no.

You’ll hear practical tactics for building a supportive community, publishing fair prices, and designing a work week where you can thrive not just survive.

You can connect with Vic on:

LinkedIn - https://www.linkedin.com/in/vichancockfell/
Insta - https://www.instagram.com/vichancockfell/

Enjoyed this chat? Subscribe, share it with a colleague planning their own freelance journey, and leave a review so more purpose-led charity professionals can find it.

Send us Fan Mail

Jane Curtis, founder of The Charity Freelancing Course, host of The Other Side Podcast and Co-founder of The Rich & Restored Movement.

Jane has spent 26 years in the charity sector, is a former events fundraiser, and now supports over 100 charity sector freelancers to build businesses that make more money with joy and integrity.

Lesley Pinder - Finding Your Compass in Freelance Life

Tuesday, October 14, 2025 • Duration 32:59

Jane sits down with Lesley Pinder, founder of Compass, her start up company that explores how charities can make generosity feel great by designing experiences that reflect human behaviour, not tidy funnels.

We unpack the moment Lesley chose to leave the 9-5, why specialisation is key, and how “you don’t need a map, you need a compass” became the north star for her consultancy.

We talk practicalities too, from shaping consultancy offers from live demand, to carving out routines to protect deep work.

Expect honest reflections on recovery after busy roles, the slow path from first chat to signed contract, and the money mindset required to hold your rate without flinching.

You’ll take away actionable ideas on donor retention, supporter journeys, and human-centred design. You’ll also hear how mentors and community can accelerate the leap, plus the unglamorous moves that matter early: choosing a clear niche, having a memorable brand, hiring a good accountant, and keeping a savings runway.

If you're looking for support with supporter experience - Lesley's happy to chat even if you're not sure what that means yet.

You can connect with Lesley on LinkedIn, head to her website or drop her an email.

Enjoyed the conversation? Subscribe, share with a freelance friend, and leave a quick review so more charity professionals can find the show.

Send us Fan Mail

Jane Curtis, founder of The Charity Freelancing Course, host of The Other Side Podcast and Co-founder of The Rich & Restored Movement.

Jane has spent 26 years in the charity sector, is a former events fundraiser, and now supports over 100 charity sector freelancers to build businesses that make more money with joy and integrity.

Richard Berks - Turning Charity Comms Into a Sustainable Freelance Career

Tuesday, October 7, 2025 • Duration 27:51

What happens when a scientist trades lab notes for writing stories that move donors to act? Richard Berks traces his path from research to charity communications to a sustainable freelance career, and the surprising tweet that sparked a community trusted by thousands for connection and clarity.

Richard shares the lesson many of us learn too late: offering everything is not a strategy. He breaks down how he narrowed his services to what medical research charities actually buy, offering donor-friendly content that shows how funding changes lives. We talk through shaping a niche without boxing yourself in, validating offers by listening to what clients repeatedly ask for, and setting boundaries that protect family time instead of burning it at conferences and events.

There’s practical marketing throughout: simple LinkedIn visibility, a “I’m now freelance” post, nudging ex-colleagues, joining sector directories, and sending respectful cold emails when you have a defined audience. We also explore the human side of freelancing- loneliness, winter slumps, and the mental load of working from home- and how small habits like a 20-minute walk, focus-friendly background audio, and a personal “energy playlist” can turn a slow afternoon into a productive one.

You’ll also hear how Charity Freelancer Chat began with a casual coffee invite, and became a monthly anchor for freelancers across the sector.

You can connect with Richard and follow Charity Freelancer Chat on LinkedIn.

If this episode resonates with you, please subscribe, leave a review, and share it with a colleague who’s thinking about their own freelance leap.

Send us Fan Mail

Jane Curtis, founder of The Charity Freelancing Course, host of The Other Side Podcast and Co-founder of The Rich & Restored Movement.

Jane has spent 26 years in the charity sector, is a former events fundraiser, and now supports over 100 charity sector freelancers to build businesses that make more money with joy and integrity.

Cindy Wagman - From Accidental Consultant to Fractional Business Coach

Tuesday, September 30, 2025 • Duration 41:42

What if you could build a six-figure consulting business while still having time for the life you want? Cindy Wagman takes us on her fascinating journey from charity professional to thriving business coach who's helped over 100 nonprofit consultants create profitable, values-driven practices.

Cindy shares how she became an "accidental consultant" during maternity leave when her mentor suggested negotiating a contract instead of accepting a traditional job offer. With remarkable candour, she reveals the moment she shifted from feeling like she needed to "beg" for opportunities to confidently stating her terms—and how this fundamental mindset change transformed her career.

The conversation explores Cindy's evolution from running a six-person consultancy to developing her Fractional Fundraiser Academy (soon to be rebranded as the Non-Profit Fractional Operating System). Rather than continuing to grow her team when demand increased, she chose a different path: teaching experienced professionals how to deliver the same services independently. This pivot allowed her to scale her impact without sacrificing the quality of life she'd built.

Cindy's practical approach to work-life balance truly stands out. She details her strategy of alternating "CEO weeks" dedicated to deep work with client-facing weeks for meetings and connections. For those struggling with the "always available" mentality common in the charity sector, her framework offers an alternative that prioritises both productivity and personal wellbeing.

Cindy's advice on warming up your network, understanding your numbers, and letting go of the "workaholic" identity provides a roadmap for building a sustainable business aligned with your values. As she wisely notes, "focus on what you want, what you need right now out of consulting, and try to quiet the rest of the noise out there."

Cindy's always happy to chat with people exploring fractional consulting
Connect with her on LinkedIn and check out her private podcast Fracture.

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Jenny Perez - How A Fundraising Leader Rebuilt A Career On Her Terms

Tuesday, November 18, 2025 • Duration 42:00

What if the top job isn’t the right job? Jenny Perez spent 30 years in the charity sector, rose to a national CEO role, and discovered that the work she loved most had been buried under daily operations and admin. Her path back to energising work runs through redundancy, a freelance contract in mentoring, and a master’s degree completed while solo parenting. The lesson is not about grit for its own sake, it’s about designing your days around the work that makes you come alive.

Jenny shares how she blended PAYE stability with freelance contracts to de-risk the transition, then went fully independent with structure and intention. If you think trust fundraising is just form-filling, think again. Jenny explains how the field has shifted to relationships, clear decision-ready proposals, and smart use of digital touchpoints. Her Think Like A Funder approach helps teams mirror assessment criteria, surface evidence, and tell stories that cut through crowded rounds and early-closing funds.

We also get honest about boundaries, pricing, and the urge to say yes to everything. Jenny maps how investing in herself through coaching, communities and a restorative retreat have helped to fast-track confidence, pricing clarity and networks. For anyone curious about a career pivot later in life, her message is clear: experience compounds when you work on your terms, and it’s never too late to choose meaningful work over job titles.

Subscribe for more candid journeys from charity professional to thriving freelancer, share this episode with someone planning their leap, and tell us: what would you redesign first: your offer, your routine, or your pricing?

You can connect with Jenny on LinkedIn

Send us Fan Mail

Jane Curtis, founder of The Charity Freelancing Course, host of The Other Side Podcast and Co-founder of The Rich & Restored Movement.

Jane has spent 26 years in the charity sector, is a former events fundraiser, and now supports over 100 charity sector freelancers to build businesses that make more money with joy and integrity.

Simon Scriver - How A Charity Fundraiser Built An Inclusive Training Community Online

Tuesday, November 25, 2025 • Duration 44:17

In Episode 8 of The Other Side, Simon Scriver shares how two failed ventures shaped a thriving, accessible training community for fundraisers. From street fundraising to global virtual events, Simon breaks down luck vs grit, why boring work matters and how to stop under-pricing your services.

We also discuss hiring fears, building a supportive community without burning out and whether the charity sector is ready for the growth in freelance and consultant services.

One of my fave episodes to date, listen on all your usual platforms and at the link below.

You can connect with Simon on LinkedIn and at https://www.fundraisingeverywhere.com/

Send us Fan Mail

Jane Curtis, founder of The Charity Freelancing Course, host of The Other Side Podcast and Co-founder of The Rich & Restored Movement.

Jane has spent 26 years in the charity sector, is a former events fundraiser, and now supports over 100 charity sector freelancers to build businesses that make more money with joy and integrity.

Connect here:

Instagram

Facebook

Website