Money Confident Podcast: Finance Tips, Budgeting, and Cash Flow for Small Business Owners

What happens when the business you've worked so hard to build isn't actually giving you the life you want?

Welcome back to Happy Hour, the bonus series where Jillian sits down with fellow creative entrepreneurs for honest conversations about business, money, creativity, and building a life you actually enjoy.

In this episode, Jillian is joined by Katie Costa, an Atlanta-based freelance designer and former owner of Blynk Social, a social media and creative agency she spent six years building.

After growing her agency, hiring a team, and finding herself spending more time managing people and invoices than actually designing, Katie realized something had to change.

So she made a big decision: she closed her agency and went back to being an independent designer.

Now she's creating bold, colorful work for nonprofits and community organizations, enjoying more creative freedom, and building a freelance business that supports her lifestyle instead of draining her energy.

And she's sharing what that transition taught her about burnout, money, pricing, and redefining success on her own terms.

Inside This Episode, You'll Learn:

• Why Katie decided to close her successful creative agency and return to freelancing

• How growing a business can sometimes pull you further away from the work you actually love

• Why scaling and hiring a team aren't the only definitions of business success

• How Katie learned to price her creative services around her lifestyle, values, and financial needs

• The importance of setting client boundaries, enforcing contracts, and charging appropriately for your work

• Why creating your own freelance schedule doesn't mean you're working any less

• How long-term contracts and recurring income can create more financial stability for freelancers

• Why consistently marketing your creative business helps keep new clients coming

• How building a portfolio around the work you want to do can attract more aligned projects

• Why community, flexibility, and creative fulfillment matter just as much as revenue

Your Happy Hour Reminder

You don't have to keep growing a business in a direction you don't actually want to go.

Sometimes the next level isn't a bigger team, more clients, or a million-dollar agency.

Sometimes it's simplifying your business, protecting your creative energy, and making enough money to enjoy the life you've built.

Connect with Katie Costa
Want to see Katie's colorful design work or collaborate on your next creative project?

Find Katie at @KatieCostaDesign on Instagram and TikTok.

She specializes in branding, logos, websites, packaging, and creative campaigns for businesses and community-centered organizations, including projects in Atlanta's Virginia Highland District and Oakland Cemetery.

Join Jillian at Happy Hour

Love conversations about money, business, and building a creative career on your own terms?

Jillian hosts in-person Happy Hours in Atlanta, bringing creative entrepreneurs together to connect, talk business, and build community.

Follow @_JillianTodd on Instagram for upcoming events, more Money Confident Podcast episodes, and your regular dose of Money Mom encouragement.

Episode 16: How to Rebuild Your Savings After an Emergency (Without Panicking)

You worked hard to build your savings…and then life happened.

Maybe you had to move, cover an emergency, deal with an unexpected expense, or lean on your savings during a slow season in your business. Now the balance that once made you feel safe is looking a lot smaller, and you're wondering how the hell you're going to rebuild it.

Inside This Episode, You'll Learn:

In this episode, we're talking about how to rebuild your savings after an emergency without letting fear, guilt, or scarcity take over.

• Why using your emergency fund means your savings did exactly what they were supposed to do

• How to move from guilt and financial anxiety into gratitude for what past-you built

• Why Jillian recommends calming your nervous system before making a new financial plan

• The "financial pendulum" that can send you from panic into extreme restriction

• Why trying to rebuild your entire savings account immediately can backfire

• How to use your past savings habits to create a realistic rebuilding timeline

• Why $5K or $10K milestones can feel much more achievable than jumping straight back to $50K

• How to rebuild your savings without giving up everything that makes your life enjoyable

  
  

Your Money Mom Reminder

Your savings weren't wasted. Past you gave current you a gift.

You put that money aside so that when something unexpected happened, you had options. Instead of beating yourself up for using it, take a second to appreciate the financial security you created for yourself.

Then take the next baby step.

You built your savings before. You can build it again.

Need Help Rebuilding Your Savings?

If you're staring at a lower savings balance and aren't sure what your next move should be, send Jillian a DM on Instagram @JillianTodd.

She'd love to help you create a realistic strategy for rebuilding your savings—and if you have a question you'd love a future Money Mom pep talk about, send that her way, too.

Welcome back to Happy Hour, the bonus series where Jillian sits down with fellow creative entrepreneurs for honest conversations about business, money, creativity, and building a life that actually feels good.

In this episode, Jillian is joined by award-winning photographer, creative director, and marketing strategist Annie Caplan. Together, they explore everything from finding your unique creative voice to navigating chronic illness as an entrepreneur, embracing mindset shifts around money, and building a business that's rooted in your values instead of hustle culture.

Inside This Episode

• How Annie transitioned from a successful corporate career into full-time entrepreneurship

• Why following your curiosity can lead to the career you're truly meant to build

• The story behind Jillian and Annie's unforgettable Joshua Tree branding and boudoir session

• How living with endometriosis shaped Annie's business, creative process, and mission

• Why representation, inclusivity, and the female gaze are central to Annie's photography

• The importance of advocating for yourself and building supportive community when navigating chronic illness

• How mindset, boundaries, and pricing helped Annie move beyond scarcity and burnout

• Why investing in yourself and your business often creates opportunities you can't predict

• Annie's experience working with Jillian to organize her business finances and find more confidence in her numbers

• A candid conversation about balancing strategy, intuition, and the energetics of running a creative business

  
  

One of Jillian's Favorite Takeaways

"Sometimes the biggest business growth doesn't come from working harder, it comes from slowing down enough to build a business that's actually aligned with your life."

Whether it's choosing clients who respect your value, protecting your energy, or creating systems that support your health, this conversation is a reminder that success doesn't have to come at the expense of your well-being.

Connect with Annie

Follow Annie on Instagram at @annie.caplan.photography, or learn more about her photography, branding, and coaching services at AnnieCaplanPhotography.com.

Join Jillian at Happy Hour IRL

If you're an Atlanta-area creative entrepreneur, come join Jillian's monthly Happy Hour meetups! They're a chance to connect with fellow creatives over drinks while talking about business, money, marketing, and all the beautifully messy parts of entrepreneurship.

Follow Jillian on Instagram for upcoming Happy Hour dates, and if there's a creative entrepreneur you'd love to hear on a future bonus episode, send her a DM!

The Money Confident Podcast with Jillian Todd

Episode 15: Values-Based Budgeting: Build a Budget That Reflects the Life You Want

When you hear the word budget, what comes to mind?

Restriction? Guilt? Cutting out your daily latte?

In this episode, Jillian challenges everything you've been taught about budgeting and introduces a different approach: values-based budgeting.

Instead of obsessing over every dollar, you'll learn how to use your budget as a tool to invest your money, time, energy, and creativity into the people, experiences, and opportunities that matter most to you. Because a budget shouldn't just help you save money—it should help you build a life you're excited to live.

Inside This Episode, You'll Learn:

• Why traditional budgeting advice often doesn't work for creatives and small business owners

• How to use your values as a filter for financial decisions

• Why budgeting isn't just about money—it's also about your time, energy, and creativity

• Jillian's simple framework for deciding when to say "yes" or "no" to a purchase or opportunity

• How supporting artists, small businesses, and your community can be part of your financial plan

• Why a more expensive purchase can actually be the right financial decision when it aligns with your values

• How to stop making money decisions out of guilt and start making them with intention

Jillian's Values-Based Budget Framework:

✔️ Does this fit within my financial means?

✔️ Does it support the goals or priorities of this season?

✔️ Does it align with my personal values?

✔️ Is this the best use of my time, energy, and resources right now?

When you run your decisions through these questions, budgeting becomes less about restriction and more about creating a life that's aligned with what matters most.

Jillian's Favorite Reminder:

"Your budget isn't just about where your money goes. It's about where your time, energy, creativity, and resources go, too."

Ready to Build a Budget That Actually Works for You?

If you've ever felt like traditional budgeting advice just doesn't fit the way you live or work, Jillian would love to help.

Whether you're navigating inconsistent income, trying to spend more intentionally, or simply want your finances to reflect your values, you don't have to figure it out alone.

Send Jillian a DM on Instagram to chat about creating a values-based budget that supports your creative business, your financial goals, and the life you're building.

The Money Confident Podcast with Jillian Todd

Happy Hour with Sabrina of Seriously Sabrina Photography: Building a Sustainable Creative Career

Welcome back to Happy Hour, the bonus series where Jillian sits down with fellow creative entrepreneurs for honest conversations about business, money, creativity, and building a life you actually enjoy.

In this episode, Jillian chats with her friend and client Sabrina of Seriously Sabrina Photography, a longtime wedding photographer whose career has evolved to include commercial photography, interiors, agricultural photography, and a full-time role at the University of Kentucky.

Together, they talk about what it looks like to grow beyond the business you first built, balancing multiple income streams, learning to invest as a self-employed creative, and why sometimes the biggest goal is finally enjoying the life you've created.

Inside This Episode

• How Sabrina built a photography business that's evolved far beyond weddings

• Why diversifying your income can create more flexibility and stability

• The realities of balancing self-employment with a full-time creative job

• Setting clear boundaries when new opportunities come your way

• How Jillian and Sabrina met through a creative business retreat and how that friendship eventually led to financial coaching

• What it felt like to start investing and saving for retirement as a self-employed creative

• Why financial confidence isn't about knowing everything—it's about having someone to help you navigate the next step

• The joy of missing out (JOMO) and learning to enjoy the business you've already built

One of Jillian's Favorite Takeaways

"Sometimes success isn't about chasing the next goal. Sometimes it's about realizing you've built a business that finally lets you breathe."

After years of working toward bigger milestones, Sabrina shares why she's intentionally embracing a season of stability, trusting the systems she's built and giving herself permission to simply enjoy them.

Connect with Sabrina

You can follow Sabrina's photography work on Instagram at @SeriouslySabrina, where she shares weddings, commercial photography, portraits, and creative projects.

You can also find her agriculture photography work through Craft and Calling, highlighting stories from farms, food, and the agricultural community.

Join Jillian at Happy Hour IRL

If you're an Atlanta-based creative entrepreneur, come join Jillian's monthly Happy Hour meetups! Grab a drink, meet other creatives, and chat about money, marketing, business, and all the beautifully messy parts of running a creative business.

Follow Jillian on Instagram for upcoming Happy Hour dates, and if there's a creative entrepreneur you'd love to hear on a future bonus episode, send her a DM!

The Money Confident Podcast with Jillian Todd

Episode 14: Why Group Coaching Is Better Than 1:1 

When you think about getting support with your finances, your first instinct might be to look for one-on-one coaching.

But what if the fastest path to financial confidence isn't going it alone?

In this episode, Jillian shares her hot take on why group coaching can be even more powerful than private coaching when it comes to reaching your biggest financial goals. From learning alongside other creatives to finding accountability, community, and fresh perspectives, she explains why the people sitting next to you might be just as valuable as the coach leading the room.

If you've ever wondered whether group coaching is "enough" support, this episode might just change your mind.

Inside This Episode, You'll Learn:

• Why community can accelerate your financial growth
• How group coaching creates a safe space to ask the questions you're afraid to ask
• Why hearing someone else's coaching often leads to your biggest breakthroughs
• The surprising advantages of learning from creatives in completely different industries
• How Jillian's first mastermind changed the way she thinks about coaching
• Why accountability feels different when you're working toward a goal alongside others
• The Pilates analogy that perfectly explains why group coaching works

Why Jillian Loves Group Coaching:

✔️ You don't have to figure everything out by yourself.

✔️ You learn from other creatives' experiences—not just your own.

✔️ You gain fresh ideas from people with different business models and perspectives.

✔️ You build relationships with people who understand what it's like to run a creative business.

✔️ You stay accountable because your community is cheering you on every step of the way.

Jillian's Favorite Reminder:

"Sometimes you don't need to hear it from your Money Mom—you need to hear it from someone who's walking the path right beside you."

Ready to Build Your Financial Goal Alongside Other Creatives?

Breadwinner is Jillian's 12-month group coaching program designed to help creative entrepreneurs set—and actually achieve—their biggest financial goals.

Whether you want to pay yourself more, build your savings, invest for retirement, or finally feel confident with your money, you'll do it with expert coaching and a community of creatives cheering you on every step of the way.

Learn more and apply at:👉 jilliantodd.com/breadwinner

Have questions about whether Breadwinner is the right fit? Send Jillian a DM on Instagram—she'd love to chat and help you decide if it's the right next step.

The Money Confident Podcast with Jillian Todd

Money Happy Hour with with Jeannene of Intentionally Tabled: Building a Values Based Business

Welcome to the very first Happy Hour bonus episode! 🍸

In this new series, Jillian sits down with fellow creative entrepreneurs for honest conversations about business, money, creativity, and the beautifully messy journey of building a life you actually love.

For the inaugural episode, Jillian is joined by wedding planner and creative community builder Jeannene, founder of Intentionally Tabled. Together, they chat about meeting at a retreat in the French countryside, finding your people as a creative entrepreneur, rebranding your business to better reflect your values, and why community can change everything.

It's like grabbing a drink with two creative business owners who can't stop talking shop—in the best way.

Inside This Episode, You'll Hear About:

• How Jillian and Jeannene met while attending a creative retreat in France
• Why creative community is so important when running a solo business
• The story behind Jeannene's rebrand from Jeannene Lillie Events to Intentionally Tabled
• How leading with your values can transform your business (and make marketing feel more authentic)
• Why separating yourself from your business can create healthier boundaries
• The role that mentorship and creative friendships play in business growth
• A behind-the-scenes look at Jillian's wedding planning experience and why shared values mattered more than aesthetics
• How honoring clients' privacy and experiences can become part of your brand values

One of Jillian's Favorite Moments:

"Sometimes the people in your community can see something in you before you can see it yourself."

Whether it's a business rebrand, a new offer, or simply taking the next brave step, this conversation is a beautiful reminder that you don't have to build your business alone.

Connect with Jeannene:

Learn more about Jeannene's wedding planning business, Intentionally Tabled, and her Creative Collective events designed to bring creative entrepreneurs together for intentional connection and community.

Want to Join Jillian in Person?

If you're an Atlanta-based creative entrepreneur, don't miss Jillian's monthly Happy Hour meetups! Grab a drink, meet other creatives, and chat about money, marketing, business, and everything in between. Follow Jillian on Instagram for upcoming dates and details.

Have someone you'd love to hear on a future Happy Hour episode? Send Jillian a DM—she'd love to hear your ideas!

The Money Confident Podcast with Jillian Todd

Episode 13: Real Breadwinner Success Stories: Retirement, Cash Flow & Big Life Goals

What does financial confidence actually look like?

In this episode, Jillian is taking her mentor's advice and bragging a little—in the best way possible. She shares three real client stories from inside Breadwinner to show what happens when creatives stop running their money on vibes and start building a financial plan that supports the life they actually want.

Whether you're feeling behind on retirement, stuck on the cash flow rollercoaster, or simply know you could be more strategic with your money, these stories will help you see what's possible.

Featured Success Stories:

✔️ Client S: Went from $1,500 invested to $25,000 invested while creating a retirement strategy that also reduced her tax bill

✔️ Client T: Escaped the cash flow rollercoaster and successfully made it through the slow season without using credit cards

✔️ Client J: Went from "running my business on vibes" to creating a strategic financial plan that gave her the confidence to pursue a move and grow her family

Jillian's Favorite Reminder:

"Sometimes you don't need a rags-to-riches story. You just need to know that someone like you has done the thing you're hoping to do."

Thinking About Breadwinner?

If you're ready to feel more strategic, more confident, and more powerful with your finances, Breadwinner is currently open for enrollment.

Inside, you'll build a financial plan that works for your life, your business, and your brain—with support every step of the way.

Apply Now

Have a big financial goal but aren't sure how to get there?

Every application comes directly to Jillian. You can text with her, ask questions, or schedule a free call to talk through what's going on in your business and how she can help.

Got questions? Send Jillian a DM on Instagram @_jilliantodd. She'd love to hear from you.

The Money Confident Podcast with Jillian Todd

Episode 12: The Artist’s Guide to Building Long-Term Wealth

When most people hear "financial planning," they picture spreadsheets, retirement calculators, and people with traditional 9-to-5 jobs.

But what does financial planning look like when you're an artist, creative, or small business owner with inconsistent income?

In this episode, Jillian breaks down the six essential areas every creative needs to understand to build a sustainable, profitable business and create long-term financial stability without giving up the work they love. Whether you're currently "checking your bank account and vibing" or you're ready to get more strategic with your money, this episode will help you take the next step.

Inside This Episode, You'll Learn:

• How to manage inconsistent income with a simple cash flow planning system
• Why understanding your pricing is the key to building a profitable business
• The biggest tax mistake creatives make (and how to avoid it)
• How retirement planning actually works when you're self-employed
• Why your money mindset may be impacting your financial results more than you realize
• How to use your financial data to grow your business intentionally and sustainably

Jillian's Favorite Reminder:

"You don't have to choose between being creative and being financially secure. You can build a life you love using your art, your creativity, and your gifts while also creating stability, peace of mind, and a plan for the future."

Want More Support?

Breadwinner is Jillian's 12-month group coaching program designed to help creatives build money confidence, pay themselves well, and create a sustainable business that supports the life they want.

Learn more at:👉 jilliantoddcoaching.com/breadwinner

If this episode resonated with you, send Jillian a DM on Instagram @_jilliantodd and let her know what stood out most.

The Money Confident Podcast with Jillian Todd

Episode 11: Pay Yourself More Without Earning More (Webinar Replay)

You’re making money in your business… but somehow not feeling paid?

In this replay of Jillian’s live training, she breaks down exactly how creatives can pay themselves more—without taking on more clients, working more hours, or burning out.

If your income feels inconsistent, your savings feel confusing, or you’re just “checking your bank account and vibing”… this episode will give you a real plan.

Inside This Episode, You’ll Learn:

• Why earning more doesn’t automatically mean taking home more

• The 3-step framework to pay yourself more without increasing revenue

• How to predict your income (even if it feels inconsistent)

• Why raising your prices isn’t just about money—it’s about your life

• The truth about saving too much (and why it might be holding you back)

• How to stop avoiding your numbers and actually feel confident with them

The 3 Steps Jillian Teaches:

✔️ Predict your income so you can trust what’s coming in

✔️ Keep more of what you earn by focusing on profit (not just revenue)

✔️ Save less (strategically) so you can actually enjoy your money

Real Client Wins from This Episode:

✔️ A seasonal business owner who turned 4 months of income into year-round stability

✔️ A photographer who raised her prices, worked less, and paid herself more

✔️ An author who stopped hoarding money and started spending in alignment with her values

Jillian’s Favorite Reminder: “You don’t need to hustle harder to feel financially secure. You just need a plan—and the confidence to trust yourself with money.”

Want Support With This?

Jillian’s 12-month program, Breadwinner, walks you through this work step-by-step—so you can build real money confidence (not just more income).

Doors are open April 6th - 30th. Apply now: 👉 jilliantoddcoaching.com/breadwinner

Got questions? DM Jillian on Instagram—she’d love to help you figure out your next step 💛