Kicking off the second week of January, we continue the financial planning conversation with a practical, no-shame approach to setting yourself up for the year ahead. From improving financial literacy and knowing your numbers to spending with intention, paying down debt without guilt, and building flexibility into your plans, this episode is about creating stability without rigidity. We also revisit the power of building the right financial team and intentionally growing your drip, trickle, flow, and flood income streams — so your money supports your life, not the other way around.

We discuss:

1. Financial literacy is an ongoing practice, not a finish line.
2. Whether it’s podcasts, books, conversations, or using AI to break things down in your own learning style, consistently investing in understanding money builds confidence and clarity over time.
3. Knowing your numbers creates freedom, not restriction.
4. Understanding what’s coming in, what’s going out, and what’s left applies to both personal and business finances. Simple systems and regular money check-ins make everything easier to manage.
5. Spend with intention, not guilt.
6. Reviewing subscriptions, travel choices, and education investments helps ensure your money aligns with what actually matters to you without cutting joy or shaming yourself.
7. Pay down debt without emotional baggage.
8. Not all debt is bad, and carrying shame only adds an unnecessary emotional cost. Owning where you are, learning from it, and moving forward is progress.
9. Plan for change and diversify your income streams.
10. Financial plans are never perfect. Flexibility, a strong support team, and intentionally growing your drip, trickle, flow, and flood income streams help you stay steady when life shifts.

Our Links

Tony’s website

Melissa’s website

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Rate and Review

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Disclaimer:

The information provided in this podcast is for informational and entertainment purposes only and should not be considered financial, investment, tax, or legal advice. The opinions expressed by the hosts and guests are solely their own and do not reflect the views of any companies or organizations they may be affiliated with.

Listeners should conduct their own research and consult with a qualified financial professional before making any investment or financial decisions. While we strive for accuracy, we do not guarantee that the information presented is complete, current, or applicable to your specific situation. Investing involves risk, including potential loss of principal.

By listening to this podcast, you acknowledge and agree that the hosts, guests, and producers are not responsible for any financial decisions you make based on the content discussed.

Money decisions are rarely just about math. They’re about fear, confidence, trust, and timing. In this episode of Drip Trickle Flow Flood, we’re joined by Cheryl Hirss, owner of Sagewater Financial, to demystify what financial advisors actually do, who benefits most from working with one, and how taking emotion out of investing can dramatically change long-term outcomes. From navigating retirement transitions to managing family dynamics and building a true “financial team,” Cheryl brings a calm, grounded perspective to a world that often feels overwhelming and reactive.

We discuss:

1. A financial advisor’s real value is removing emotion from money decisions.
2. Fear and greed drive most poor financial outcomes, and having a disciplined plan helps prevent reactive buying, selling, or freezing.
3. There’s no “too late” — only unrealistic goals and lack of discipline.
4. People start working with advisors at every life stage, and progress is still possible with clear expectations and consistency.
5. Wealth is a system of pillars.
6. Investments, real estate, entrepreneurship, taxes, insurance, and estate planning all work together, not in isolation.
7. Couples don’t need identical money personalities, just a shared plan.
8. Objective risk assessments and data-driven tools can help partners find common ground without emotional conflict.
9. A good advisor thinks about the gaps you don’t know to look for.
10. From estate planning oversights to life transitions, real financial planning goes far beyond picking investments.

Learn more about Cheryl at her website: https://www.sagewaterfinancial.com/team/cheryl-hirss

Our Links

Tony’s website

Melissa’s website

Drip Trickle Flow Flood T-Shirts

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Rate and Review

If you loved this episode, please take a moment to rate and review Drip Trickle Flow Flood on your favorite podcast platform. It helps new listeners discover the show and it makes our day. Thanks for listening!

Subscribe to this newsletter for income ideas that drip, trickle, flow, and flood into your life.

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Disclaimer:

The information provided in this podcast is for informational and entertainment purposes only and should not be considered financial, investment, tax, or legal advice. The opinions expressed by the hosts and guests are solely their own and do not reflect the views of any companies or organizations they may be affiliated with.

Listeners should conduct their own research and consult with a qualified financial professional before making any investment or financial decisions. While we strive for accuracy, we do not guarantee that the information presented is complete, current, or applicable to your specific situation. Investing involves risk, including potential loss of principal.

By listening to this podcast, you acknowledge and agree that the hosts, guests, and producers are not responsible for any financial decisions you make based on the...

What does it look like to build a creative life over decades and make it deeply satisfying and sustainable?

In this episode, we sit down with cartoonist, illustrator, musician, and writer Todd Webb, creator of the daily comic strip The Poet. Todd shares how a project that started as a short book quietly turned into a six-year daily practice, how Substack, book collections, and pop culture art prints support his work, and why he’s more interested in enjoying the act of creation than chasing a single “big break.”

We discuss:

1. You don’t need one big income stream. Small creative trickles add up.
2. Todd’s work is supported by a mix of Substack subscriptions, book sales, art prints, conventions, and commissions. None of them are floods, but together they create enough space to keep making what he loves.
3. Make the thing you want to exist, not the thing you think will sell.
4. The Poet wasn’t designed to be a daily strip or a long-running project. It became one because Todd followed the work instead of forcing an outcome.
5. Giving your work away can be a powerful long-term strategy.
6. From mailing mini-comics to artists he admired to offering a mostly free Substack, Todd shows how generosity builds real connection over time.
7. Creative success doesn’t have to mean constant escalation.
8. Not every project needs to become a TV show, a franchise, or a brand empire. Sometimes success is simply having the time and energy to keep creating.
9. You get more than one chance every single day.
10. Missed opportunities, rejected pitches, and projects that don’t pan out aren’t dead ends. They’re material. Ideas can be reused, reshaped, and reborn when the timing is right.

About Todd

Todd Webb has been drawing the daily comic strip The Poet for the past six years. Prior to that he did a lot of other stuff like comic books and graphic novels, music, illustration, screenwriting, and animation. Find info on all of it (and subscribe to The Poet) by visiting TODDBOT.COM

Follow Todd on Instagram

Our Links

Tony’s website

Melissa’s website

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Rate and Review

If you loved this episode, please take a moment to rate and review Drip Trickle Flow Flood on your favorite podcast platform. It helps new listeners discover the show and it makes our day. Thanks for listening!

Subscribe to this newsletter for income ideas that drip, trickle, flow, and flood into your life.

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Disclaimer:

The information provided in this podcast is for informational and entertainment purposes only and should not be considered financial, investment, tax, or legal advice. The opinions expressed by the hosts and guests are solely their own and do not reflect the views of any companies or organizations they may be affiliated with.

Listeners should conduct their own research and consult with a qualified financial...

What does Home Alone have to do with inflation, buying power, and why your money can’t just sit still anymore? A lot more than you’d think. In this episode, we kick things off with a nostalgic look at Kevin McCallister’s $19 grocery run and use it as a lens to unpack how inflation quietly reshapes everything from groceries and housing to creative businesses, side hustles, and long-term financial security. Along the way, we connect the dots between rising costs, shifting industries, and why having multiple income streams is essential.

We discuss:

• That $19 grocery bill from Home Alone would cost roughly $72 today, an easy way to see how steady inflation compounds over time.
• Inflation quietly erodes buying power by 3–4% a year, which means money sitting still is effectively losing value.
• Different industries feel inflation differently: digital products and subscription models often absorb it better than physical goods and service-based businesses.
• Small businesses that survive economic pressure tend to adapt by reducing costs, changing models, or creating new revenue streams.

Our Links

Tony’s website

Melissa’s website

Drip Trickle Flow Flood T-Shirts

We’ve got merch! That’s right, Drip Trickle Flow Flood t-shirts are officially here and they’re as comfy as they are conversation-starting.

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Rate and Review

If you loved this episode, please take a moment to rate and review Drip Trickle Flow Flood on your favorite podcast platform. It helps new listeners discover the show and it makes our day. Thanks for listening!

Subscribe to this newsletter for income ideas that drip, trickle, flow, and flood into your life.

https://driptrickleflowflood.substack.com/

Disclaimer:

The information provided in this podcast is for informational and entertainment purposes only and should not be considered financial, investment, tax, or legal advice. The opinions expressed by the hosts and guests are solely their own and do not reflect the views of any companies or organizations they may be affiliated with.

Listeners should conduct their own research and consult with a qualified financial professional before making any investment or financial decisions. While we strive for accuracy, we do not guarantee that the information presented is complete, current, or applicable to your specific situation. Investing involves risk, including potential loss of principal.

By listening to this podcast, you acknowledge and agree that the hosts, guests, and producers are not responsible for any financial decisions you make based on the content discussed.

Having multiple streams of income sounds smart in theory… until it starts feeling chaotic, exhausting, and completely unsustainable.

In this episode, we dig into the real question behind “multiple income streams”: how do you do it without burning out?

We unpack why not all income streams should be treated the same, how energy (not time) is often the real constraint, and why seasons of earning matter just as much as strategy. From life-giving work to draining-but-lucrative opportunities, this conversation reframes how to think about side hustles, creative work, and capacity in a way that actually works long-term.

If you’ve ever felt overwhelmed by the idea of adding “just one more thing,” this episode is for you.

We discuss:

1. Not all income streams should feel the same

Some streams are life-giving, others are life-taking, and that matters. A stream that energizes you can often fit more easily into your life than one that drains you, even if it takes more time.

2. Expectation misalignment is a fast track to burnout

Trying to turn every idea into a high-performing “flow” immediately is exhausting. Some streams are meant to be drips or trickles for a long time, and that’s not failure, it’s strategy.

3. Think in seasons, not forever

Income doesn’t have to be evenly distributed year-round. Short, intentional seasons of earning—whether it’s the holidays, a launch window, or a contract-heavy month—are often more sustainable than constant pressure.

4. Capacity matters more than productivity

Your emotional and mental bandwidth is finite. Understanding when you’re best suited for certain types of work (creative, physical, on-camera, administrative) helps you design income streams that fit your real life.

5. Use “capacity math” to make better decisions

Assigning a simple capacity score to each income stream can clarify what belongs in your Drip, Trickle, Flow, or Flood, and what might not belong at all. If the energy cost outweighs the return, it’s worth rethinking.

Our Links

Tony’s website

Melissa’s website

Drip Trickle Flow Flood T-Shirts

We’ve got merch! That’s right, Drip Trickle Flow Flood t-shirts are officially here and they’re as comfy as they are conversation-starting.

Grab yours!

Rate and Review

If you loved this episode, please take a moment to rate and review Drip Trickle Flow Flood on your favorite podcast platform. It helps new listeners discover the show and it makes our day. Thanks for listening!

Subscribe to this newsletter for income ideas that drip, trickle, flow, and flood into your life.

https://driptrickleflowflood.substack.com/

Disclaimer:

The information provided in this podcast is for informational and entertainment purposes only and should not be considered financial, investment, tax, or legal advice. The opinions expressed by the hosts and guests are solely their own and do not reflect the views of any companies or organizations they may be affiliated with.

Listeners should conduct their own research and consult with a qualified financial professional before making any investment or financial decisions. While we strive for accuracy, we do not guarantee that the information presented is complete, current, or applicable to your specific situation. Investing involves risk, including potential loss of principal.

By listening to...

In this episode of Drip Trickle Flow Flood, we sit down with intuitive coach, strategist, and podcaster Elena Lipson to talk about using intuition to craft your income streams.

Elena walks us through her evolution from corporate trainer to coach, copywriter, employee, creator, and multi–income stream entrepreneur, and how intuition guided every shift. If you’ve ever stuck with something because you’re good at it, even when your body is screaming no, this one will feel uncomfortably, beautifully familiar.

We discuss:

Why your identity is not your job title.

Elena shares how being “the coach” or “the copywriter” became her whole identity, and what it took to separate who she is from what she does, especially during big life and career pivots.

Intuition is quiet… but persistent.

Elena breaks down how intuition actually shows up (the “little voice,” sensations in your body, quick answers that bubble up before your brain talks you out of them) and simple ways to start hearing it again.

You’re allowed to change tracks more than once.

From tech to training to coaching to copywriting to content creation and podcasting, Elena shows that you can keep evolving as your seasons, values, and capacity shift, without throwing away your past experience.

Money decisions are deeply emotional and deeply practical.

Elena talks about making uncomfortable investments, unpacking old money stories, and using both intuition and logic when deciding where your money goes.

Designing your next chapter starts with one question: “What do I want?”

Whether you’re entering an “open stretch” season or just feeling the itch to change, Elena offers a gentle framework for designing a life and income that reflect your current values.

Connect with Elena

Elena’s website

Take Elena’s Intuition Quiz

Listen to Elena’s podcast: An Intuitive Life

Follow Elena on Instagram

Our Links

Tony’s website

Melissa’s website

Drip Trickle Flow Flood T-Shirts

We’ve got merch! That’s right, Drip Trickle Flow Flood t-shirts are officially here and they’re as comfy as they are conversation-starting.

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Rate and Review

If you loved this episode, please take a moment to rate and review Drip Trickle Flow Flood on your favorite podcast platform. It helps new listeners discover the show and it makes our day. Thanks for listening!

Subscribe to this newsletter for income ideas that drip, trickle, flow, and flood into your life.

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Disclaimer:

The information provided in this podcast is for informational and entertainment purposes only and should not be considered financial, investment, tax, or legal advice. The opinions...

In this episode of Drip Trickle Flow Flood, we dive into the real cost of the holidays. Not just the dollars, but the emotions, expectations, and financial landmines that show up between November and January. From family pressure to overspending guilt to creative alternatives that keep the joy (and ditch the debt), we share honest personal stories, practical scripts, and a few hilarious holiday fails. This is your permission slip to celebrate intentionally, spend mindfully, and ditch the holiday perfection myth once and for all.

We discuss:

1. “Perfect holidays” are expensive — but meaningful ones don’t have to be.

Social expectations and family pressure can lead to overspending, but simple traditions, thoughtful gifts, or inexpensive games can create even more joy.

2. Boundaries are the ultimate financial wellness tool.

Scripts like “I love you, and I’m being mindful of my budget this year…” help you honor both your wallet and your energy without guilt.

3. Creativity beats consumerism.

Story bowls, side-dish-only dinners, and “favorite foods night” prove you don’t need a big budget to make big memories.

4. Avoid the December debt hangover with ‘joy dollars.’

Budget for holiday fun with intention — spend on what genuinely lights you up, not on obligation, pressure, or last-minute panic.

5. Holiday seasons can be abundance seasons.

For creatives, makers, side-hustlers, and small businesses, November–December can become a strategic earning opportunity, from markets to seasonal offerings to smart holiday sale upgrades.

Our Links

Tony’s website

Melissa’s website

Drip Trickle Flow Flood T-Shirts

We’ve got merch! That’s right, Drip Trickle Flow Flood t-shirts are officially here and they’re as comfy as they are conversation-starting.

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Rate and Review

If you loved this episode, please take a moment to rate and review Drip Trickle Flow Flood on your favorite podcast platform. It helps new listeners discover the show and it makes our day. Thanks for listening!

Subscribe to this newsletter for income ideas that drip, trickle, flow, and flood into your life.

https://driptrickleflowflood.substack.com/

Disclaimer:

The information provided in this podcast is for informational and entertainment purposes only and should not be considered financial, investment, tax, or legal advice. The opinions expressed by the hosts and guests are solely their own and do not reflect the views of any companies or organizations they may be affiliated with.

Listeners should conduct their own research and consult with a qualified financial professional before making any investment or financial decisions. While we strive for accuracy, we do not guarantee that the information presented is complete, current, or applicable to your specific situation. Investing involves risk, including potential loss of principal.

By listening to this podcast, you acknowledge and agree that the hosts, guests, and producers are not responsible for any financial decisions you make based on the content discussed.

In this episode we’re talking to Eric, the creator of Ducktown Weekly—a nostalgia-packed print publication that brings back everything you loved about the funny pages. If you were the kid who raced to the comics before anyone else touched the newspaper, this episode is your warm hug. We dive into how Eric revived a nearly extinct format, why print can still feel magical, what it takes to start a newspaper in 2025, and why hundreds of people are rediscovering the joy of comics, puzzles, national park features, and more.

We discuss:

• Why holding a physical paper, looking forward to the mail, and escaping screens for a few minutes still gives people real joy.
• Comics are a multigenerational love language. Whether you connect with classics or discover new favorites, comics hit an emotional sweet spot.
• Starting a “newspaper” today is shockingly accessible. With modern software, syndicate licensing, and outsourced printing, one person can build something that used to take a whole newsroom.
• Side hustles can be passion projects. Eric runs Ducktown Weekly while also working full-time as an economist, proving that joy-driven projects can still thrive.
• The value of analog connection is rising. People crave real mail, quiet moments, and screen-free experiences, making Ducktown Weekly a refreshing alternative to algorithm-driven everything.

Our Links

Tony’s website

Melissa’s website

Drip Trickle Flow Flood T-Shirts

We’ve got merch! That’s right, Drip Trickle Flow Flood t-shirts are officially here and they’re as comfy as they are conversation-starting.

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Rate and Review

If you loved this episode, please take a moment to rate and review Drip Trickle Flow Flood on your favorite podcast platform. It helps new listeners discover the show and it makes our day. Thanks for listening!

Subscribe to this newsletter for income ideas that drip, trickle, flow, and flood into your life.

https://driptrickleflowflood.substack.com/

Disclaimer:

The information provided in this podcast is for informational and entertainment purposes only and should not be considered financial, investment, tax, or legal advice. The opinions expressed by the hosts and guests are solely their own and do not reflect the views of any companies or organizations they may be affiliated with.

Listeners should conduct their own research and consult with a qualified financial professional before making any investment or financial decisions. While we strive for accuracy, we do not guarantee that the information presented is complete, current, or applicable to your specific situation. Investing involves risk, including potential loss of principal.

By listening to this podcast, you acknowledge and agree that the hosts, guests, and producers are not responsible for any financial decisions you make based on the content discussed.