The holiday season brings moments of joy, connection, and generosity — but also brings with it a host of financial decisions where we must balance spending and saving. The season highlights the challenge of balancing celebrations with protecting our financial well-being. Spending on gifts, experiences, and travel can create a conflict between enjoying the moment and focusing on our future. This tension is natural. It often grows stronger as the year ends and our values, priorities, and self-care come into focus.
In this episode, Danielle Town shares a mental model to help reframe how we think about money during these times. Drawing from her own experiences, she explores how we can honor both joy and responsibility. She introduces her “Either Way, I Win” mindset. This empowering shift turns financial decisions into opportunities for growth, rather than sources of stress.
With this perspective, both spending and saving become choices that add value to our lives. It’s a kinder, more mindful way to approach money, reducing guilt and keeping long-term investing in view. Tune in to discover how this simple shift can help you navigate the season with clarity and renewed financial purpose.
Here are three reasons why you should listen to this episode:
Discover a practical mindset that helps you make financial decisions with confidence, not guilt.
Learn simple strategies for balancing everyday spending with your long-term investing goals.
See how embracing emotional honesty and self-acceptance can lead to healthier, more mindful money habits.
Resources
Rule #1s "InvestED" Podcast and Website: Website | Apple Podcast | YouTube
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Danielle Town: Website | LinkedIn | Instagram | Facebook | YouTube | X (Twitter)
Setting the Stage for Holiday Spending & Mindful Investing
The holiday season brings warmth, tradition, and connection. It’s also one of the busiest times for spending. The warm and bright decor, coupled with gift lists, is certainly exciting!
However, they also carry a financial weight that lingers after the celebrations end. The joy of the season often comes with a price tag that stretches far beyond December.
As expenses pile up, many of us feel torn between enjoying the season and protecting our financial future. The desire to give generously while staying disciplined can feel overwhelming.
As Danielle shares, “I always love getting gifts for people. It’s one of my love languages. It’s one of my great joys. I also love not having my savings account go down and down and down. And I think we all balance that in different ways every year at the end of the year.” Her words capture the search for balance between heartfelt moments and responsible money choices. It’s a feeling many of us know well.
The Holiday Spending Dilemma: Joy vs. Savings
The holidays highlight the joy of giving and celebrating with loved ones. However, they can also drain our bank accounts faster than we’d like. From plane tickets to special gifts, every purchase sparks the question: Is this worth it?
This tension between joy and savings is something everyone faces. It’s not just about budgeting, it’s about making sure our spending — and saving — reflects our values. The real challenge is learning how to honor both: enjoying the present while keeping our future in mind.
The "Either Way I Win" Mental Model
Financial decisions are already weighty when it comes to everyday life. During the holidays, that pressure grows as expenses seem to multiply overnight.
The “Either Way, I Win” is a refreshing mental model that helps reframe these choices. We all make these tiny or big decisions over and over, probably 100 times a day. It's the ones where we stand there and think about it, where this mental model can help us. We can then think either way, we win.
This mindset shift transforms financial decisions from sources of stress into opportunities for growth and enjoyment.
Imagining Two Buckets: Investing vs. Life Expenses
Visualize your finances in two distinct buckets. One bucket is dedicated to investing for the future. The other bucket covers everyday and optional expenses, from rent and bills to special gifts or travel.
Separating money this way makes it easier to see where each dollar belongs. It also empowers more intentional and thoughtful decisions. This simple structure can bring a sense of control, even during busy seasons.
The Win-Win Decision Process
With this “Either Way I Win” model, every choice becomes a win. If money goes into investing, it builds potential for the future. If it is spent, it creates meaningful experiences in the present. Either way, there is value gained, and the stress of “losing out” disappears.
Instead of thinking we are doing such a bad job of managing our money... let’s shift it to, how do we win either way? This simple shift encourages a more positive, empowering approach to each financial decision.
Real-Life Examples: Applying the Model
We are often faced with decisions that many people can relate to. For example, we might choose between a more convenient but pricier plane ticket. Or, we could choose a cheaper option at a less ideal time.
Sometimes, we also consider whether a small treat like a morning latte is worth the cost. These everyday choices show how the “Either Way I Win” model works in real life. Each decision becomes an opportunity for self-compassion and growth.
Here’s how to apply the “Either Way I Win” model
Pause and reflect: Take a moment to pause and reflect when you face a tough spending choice.
Ask two questions: What future gain comes from saving? What present joy comes from spending?
Value both paths: See both saving and spending as meaningful wins.
Think positively: Replace guilt with self-compassion.
Practice daily: Small shifts build lasting, healthy money habits.
If you’re ready to strengthen your investing foundation, explore Phil Town’s free online course on the basics of Rule #1. Sign up to gain access to practical lessons, tools, and exercises. They are designed to help you build both skill and confidence as an investor.
Shifting from Guilt to Empowerment in Money Decisions
Money guilt often shows up during seasons of higher spending. It’s easy to believe that every dollar spent should have been saved or invested instead. But always putting off happiness for the sake of future gains can lead to frustration and burnout. True empowerment comes when we view spending as a natural and healthy part of a balanced financial life.
We can use this “Either Way I Win” model to help turn guilt into confidence. We can start to develop this mindset that spending is an act of self-care, not a mistake. Responsible investing and thoughtful spending can work together. This mindset makes it possible to enjoy the present while still preparing for the future.
Move beyond guilt with these principles:
Accept natural guilt: It’s normal to feel uneasy when spending.
Enjoy the present: Happiness matters now, not just in the future.
Reframe spending: See it as caring for yourself and your loved ones.
Balance is possible: Smart investing and spending can go hand in hand.
Use kind words: Replace negative money thoughts with compassion.
Making Financial Models Your Own
The most effective financial models are personal. Adapting ideas to fit your own values and lifestyle makes them more meaningful and lasting. When your approach feels authentic, it’s more likely to stick.
Small luxuries, like a daily coffee or a thoughtful holiday gift, are often more than just expenses. They can be moments of joy and connection. Recognizing this helps build a money mindset that values both financial growth and personal well-being.
If you’re interested in taking the next step, consider joining the Rule #1 Virtual Investing Workshop. It’s a great way to deepen your understanding of core investing principles. Gain practical experience, all with support from expert coaches.
Expert Advice & Powerful Quotes
“I always love getting gifts for people. It's one of my love languages. It's one of my great joys. I also love not having my savings account go down and down and down. And I think we all balance that in different ways every year at the end of the year.”
“We all make these tiny or big decisions over and over, probably 100 times a day. It's the ones where I sort of stand there and think about it, where this mental model helps me. I think either way I win.”
“Instead of thinking I'm doing such a bad job of managing my money... I've shifted it to, how do I win either way?.”
“I would suggest to you try it out. Maybe it helps, maybe it doesn't. Maybe you have your own different shift to it, in which case, go for it. Because I think when we take these ideas and turn them into our own words, our own models, they stick.”
“Go and have a great holiday season. Enjoy your investing practice.”
Danielle Town – Attorney, Author & Investing Advocate
Danielle Town is a best-selling author, attorney, and passionate advocate for empowering new investors. She has a background in law and a deep curiosity about financial independence. Danielle is dedicated to demystifying investing for anyone seeking financial control. She co-authored Invested, sharing her journey learning value investing with her father, Phil Town. Danielle believes anyone can build confidence in investing by focusing on clarity, patience, and wisdom.
Through her writing, podcasting, and teaching, Danielle helps others cut through the noise of the market. She guides people in developing sound investing habits that last. Her approach encourages aligning money choices with personal values and long-term goals. Danielle shows that investing is a lifelong practice, built on steady learning and self-awareness. She inspires anyone to take the first step and make smart, values-driven decisions.
📌 Expertise: Value Investing · Financial Education · Personal Finance · Mindful Money Management
🔗 Connect: Website | LinkedIn | Instagram | Facebook | YouTube | X (Twitter)
Finding Joy and Balance in Your Investing Practice
During the holidays and throughout the year, it’s easy to feel pulled in many directions with your money. Investing doesn’t have to mean sacrificing all present joys for future gains. Instead, it’s about creating space for both. Enjoy meaningful moments today while keeping your long-term goals in view.
Listen to the Full Episode: In this episode of the InvestED Podcast, Danielle Town shares her personal approach to navigating spending and saving, especially during high-expense seasons. She introduces her “Either Way, I Win” mental model. This shows how thoughtful choices can support both your happiness now and your financial future.
Reflect on Your Own Process: Consider how you approach money decisions during the holidays. Are you able to find value in both saving and spending? Danielle encourages you to adopt a perspective that honors your unique needs and values. By practicing self-awareness and compassion, you can make choices that support your well-being today and tomorrow.
Explore More: Visit Rule #1 for more episodes and resources on building your investing discipline. Discover workshops, tools, and stories that support your journey to becoming a mindful and successful Rule #1 investor.
With a balanced mindset and a willingness to grow, investing becomes more than just numbers. It becomes a path to self-discovery, resilience, and lasting wealth. One thoughtful decision at a time.
