Most people don't fail at life because they weren't smart enough or talented enough. They struggle because no one ever gave them the ground rules. Twelve years of school, and rarely does anyone sit you down and say: here is how you build a life that doesn't quietly fall apart on you. That's what this episode is about.

**The Foundations: Money That Doesn't Wreck You**

The first two ground rules are financial, and they're not complicated — they're just unpopular. Don't carry consumer debt, and live below your means. Consumer debt is a quiet life-wrecker: invisible in the moment, compounding in the background. The gap between what you earn and what you spend is where real freedom lives. It's not about being cheap — it's about being intentional. Lifestyle inflation is real, and resisting it is how you actually get ahead.

**Protect Your Health Before It Drifts**

Your body is the vehicle for everything you do — your energy, your relationships, your ability to show up. And most people don't feel the consequences of their health decisions until they're deep into them. Maintaining your health is dramatically easier than rebuilding it. The ground rule is simple: don't be perfect, but don't let things get too far gone. Move, sleep, eat real food, get checkups.

**The Drift Principle**

Most of life's biggest problems aren't sudden events — they're slow drifts that go unnoticed until they become a crisis. You don't wake up $40,000 in debt one day. You don't suddenly have a broken marriage. You drift there, one small decision at a time. Understanding the drift principle changes how you read your own life. Small corrections are cheap. Big corrections are expensive — in time, money, and sometimes relationships you can't fully recover.

**Audits, Compasses & Enough**

Doing regular life audits — even a simple one with coffee and a journal twice a year — keeps the drift visible before it becomes irreversible. Having a compass (knowing where you actually want to go and what's non-negotiable) protects you from ending up wherever the wind takes you. And knowing what "enough" looks like for you personally keeps you from trading things that actually matter for things that won't satisfy.

**Personal Principles & the Long Game**

Three to five personal principles — not a long list, just a short one that you genuinely live by — become the needle on your compass when everything else is uncertain. And underneath all of it is the long game: small steps, done consistently, that compound over time. The person who exercises three times a week for twenty years is a different physical being than the person who does it sporadically. Consistency beats intensity every time.

Pick one area today and ask yourself honestly: am I drifting? You don't have to fix everything. You just need to notice it.

Jill’s Links

http://jillfromthenorthwoods.com

https://www.youtube.com/@startwithsmallsteps

https://www.buymeacoffee.com/startwithsmallsteps

https://twitter.com/schmern

Email the podcast at jill@startwithsmallsteps.com

By choosing to watch this video or listen to this podcast, you acknowledge that you are doing so of your own free will. The content shared here reflects personal experiences and opinions and is intended for informational and inspirational purposes only. I am not a licensed healthcare provider, psychiatrist, or counselor. Any advice or suggestions offered should not be considered a substitute for professional medical or mental health advice. You are solely responsible for any decisions or actions you take based on this content.

What does it actually mean to use AI and still feel like yourself? In this episode, Jill breaks down her personal approach to AI — not the flashy, let-it-do-everything version, but a quieter, more honest one. If you've ever felt uneasy about AI but couldn't quite explain why, this one's for you.

Top Topics Covered:

1. Why AI Makes So Many of Us Uncomfortable It's usually not about being afraid of technology. Most people are really worried about three things: taking jobs from others, getting fed fake information, or pretending to be someone they're not. Naming that discomfort is the first step.

2. The "Jill Method" of Using AI Three simple rules for using AI without losing yourself: use it as a mirror, not a mask. Let it reflect your thinking back to you — not replace it. The moment it starts covering for you instead of clarifying you, that's the line.

3. AI Isn't New — We Just Didn't Call It That Remember when Amazon started suggesting books you might like? That was AI. It's been woven into our lives for a long time. What's changed is how smart and conversational it's become — not what it fundamentally is.

4. The Job Question Nobody Wants to Answer Yes, AI will change some jobs. The internet did too. But the internet also created millions of jobs no one could have imagined in 1990. History gives us reason to be cautious — and reason not to panic.

5. Using AI to Think Better, Not Less The best use of AI isn't outsourcing your ideas — it's sharpening them. Use it to find holes in your thinking, practice hard conversations, organize your thoughts, or understand something confusing. It's the assistant you could never afford to hire.

Takeaway: This episode isn't anti-AI or blindly pro-AI. It's about finding your own honest middle ground. Tools don't steal your authorship — abdicating your thinking does. When AI helps you become a clearer, stronger version of yourself, that's exactly what it's for. And when it starts to feel like a mask? That's when Jill puts it down.

Jill’s Links

http://jillfromthenorthwoods.com

https://www.youtube.com/@startwithsmallsteps

https://www.buymeacoffee.com/startwithsmallsteps

https://twitter.com/schmern

Email the podcast at jill@startwithsmallsteps.com

By choosing to watch this video or listen to this podcast, you acknowledge that you are doing so of your own free will. The content shared here reflects personal experiences and opinions and is intended for informational and inspirational purposes only. I am not a licensed healthcare provider, psychiatrist, or counselor. Any advice or suggestions offered should not be considered a substitute for professional medical or mental health advice. You are solely responsible for any decisions or actions you take based on this content.

What if the problem isn’t your budget—but your income? When cutting expenses isn’t enough, it’s time to rethink how money actually works. This episode breaks down practical, realistic ways to earn more without burning out.

When Budgeting Isn’t Enough: How to Earn More Without Working Yourself to Death

This episode wraps up a multi-part series on money by shifting the focus from cutting expenses to increasing income. After learning how to budget, categorize spending, and manage money responsibly, the conversation turns to a hard truth: sometimes the math simply doesn’t work without earning more. Drawing from personal experience and insights inspired by Tiffany Aliche and How to Get Good with Money, the episode explores why income is tied to value, replaceability, and visibility—not effort alone. It reframes earning more money as a strategic, skill-based process rather than a moral judgment or measure of self-worth.

Why Working Harder Isn’t the Answer

The episode explains why long hours and exhaustion don’t automatically translate into higher pay. Income is connected to market value, how specialized a role is, and how easily someone can be replaced. Understanding this removes shame and helps people think more clearly about their options.

Asking for a Raise—With Evidence

Rather than emotional appeals, raises should be approached with data. A “brag folder” becomes a powerful tool for tracking accomplishments, customer impact, time saved, and problems solved. This evidence makes performance visible and reduces anxiety during reviews and salary conversations.

Becoming Harder to Replace

Learning one critical skill deeply can change an entire career trajectory. Specialization, not job titles or degrees, often creates leverage. The episode highlights how focusing on overlooked problems or difficult tasks can dramatically increase stability and income.

Recognizing Hidden Skills

Skills aren’t just technical. Teaching, organizing, calming upset people, troubleshooting, and managing projects all carry real value. Personal life experiences—like leading volunteers or handling conflict—count and can be translated into paid work.

Side Hustles That Don’t Drain Your Life

Side income doesn’t have to mean building an empire. The episode explores low-setup, low-stress options that align with existing strengths, from short-term projects to platform-based work that fits into real life.

Making more money isn’t mysterious—it’s strategic. Income grows when skills, needs, and visibility align. The most powerful step is taking responsibility for understanding personal value and learning how to place it wisely. Whether through negotiating pay, building expertise, changing roles, or adding a small side income, progress comes from intentional, realistic action. When expenses can’t shrink further, increasing income becomes the other half of the equation—and it’s one that can be approached one small step at a time.

Money doesn’t just live in your bank account—it lives in your gut, your sleep, and your sense of safety. What if saving wasn’t about restriction, but about relief? This episode breaks down how emergency savings can completely change your relationship with money.

In this episode, the conversation explores how deeply emotional money can be and how fear, panic, and avoidance often shape financial decisions more than logic ever does. Drawing from lived experience and insights from Get Good With Money by Tiffany Aliche, the discussion walks through practical, realistic ways to build emergency savings, reduce anxiety, and regain control. The focus isn’t on becoming wealthy overnight, but on creating stability, resilience, and peace of mind through intentional saving and smarter systems.

Money problems often show up as panic, dread, and sleepless nights. When bills arrive or emergencies hit, the lack of savings can trigger fear and avoidance. Understanding that money is emotional—not just mathematical—is the first step toward change.

Emergency savings are framed as protection, not deprivation. Using the analogy of squirrels storing acorns during good times, the episode emphasizes saving when life is calm so emergencies don’t lead straight to debt and chaos.

Building even a small emergency fund can break the cycle of constant debt. Once there’s a buffer, unexpected expenses no longer require credit cards, and financial momentum finally begins to shift.

A “noodle budget” identifies the bare minimum needed to survive if everything goes wrong. Knowing this number removes fear and clarifies how much flexibility actually exists in everyday spending.

Automating savings and separating money into purpose-driven accounts removes decision fatigue and emotional stress. Bills get paid, savings grow quietly, and spending money becomes clear and guilt-free.

Emergency savings create calm, not limitation. Having money set aside reduces panic, improves sleep, and allows better decisions during crises. Over time, savings transform money from a source of fear into a tool for freedom.

Priorities matter more than appearances. By focusing on what truly brings value—rather than constant small purchases—long-term goals like security, retirement, and meaningful experiences become possible.

Money works best when it’s intentional and invisible. Systems that move money automatically make consistency easier than willpower ever could.

Money doesn’t have to feel scary, confusing, or overwhelming. It can become calm, clear, and even empowering. This is where learning to get good with money really begins.

This episode begins a new series focused on building a healthier, calmer relationship with money. It explores how fear, avoidance, and past experiences shape financial behavior, and how learning simple, practical systems can replace panic with clarity. Drawing inspiration from the book Get Good With Money by Tiffany Aliche, the episode focuses on understanding money emotionally first, then practically, so long-term change can actually stick.

Money and Emotional Stress

Money is rarely just about numbers. Anxiety, fear, and avoidance often come from early life experiences and repeated financial struggles. This episode explores how recognizing those emotional patterns is the first step toward changing them.

Budgeting Without Panic

Budgeting is reframed as awareness, not restriction. Instead of obsessing over every dollar, the focus is on simply understanding what comes in, what goes out, and where money actually lives. Knowledge replaces fear when money stops being a mystery.

Simple Categories That Create Control

Expenses are broken into clear groups—fixed bills, usage-based bills, and flexible spending. Seeing money this way makes it easier to identify where change is possible without feeling deprived or overwhelmed.

Systems That Support Real Life

Automation, multiple accounts, and separating bill money from spending money help reduce stress and protect progress. These systems aren’t about perfection—they’re about creating guardrails that make consistency easier.

Getting good with money starts by removing shame. Past mistakes don’t need to be relived or punished—they just need to be acknowledged and left behind. Progress comes from moving forward with better information, not perfect behavior.

Money improves when it becomes neutral. Like cleaning up a spill with a towel, financial missteps don’t require panic or self-judgment. They require calm action and follow-through.

A healthy relationship with money creates stability, confidence, and peace of mind. Wealth isn’t the first goal—emotional safety is. When fear is removed, better financial decisions naturally follow.

We explore the power of listening to tough life stories—not to compare pain, but to understand human endurance, build compassion, and rediscover resilience. From personal family history to generational trauma and wisdom, the episode invites us to step beyond our own moment and tap into the deep well of human experience. By hearing how others have navigated impossible situations, we gain perspective—and a path forward.

Top Topics Covered:

1. The Story That Sparked It All

A reflection on the host’s grandmother who lived through extraordinary hardship—from immigration to loss, poverty, and displacement. Discovering her story through research led to a deeper appreciation of what past generations survived and why those stories matter.

2. Why Our Struggles Feel So Heavy

Our suffering often feels unique and overwhelming, not because it’s worse—but because it’s all we know. Without knowledge of the past, we miss out on the wisdom and perspective of those who lived through hardship with far fewer resources.

3. Pain Is Not a Competition

Acknowledging the suffering of others doesn’t erase our own. Instead, it grounds us in shared human experience and helps us carry our own burdens with more context and humility.

4. Generational Resilience and Lessons

Each generation faced its own form of chaos, danger, and uncertainty—from the Great Depression to nuclear war anxiety, to Gen Z’s digital saturation. Understanding this helps bridge divides and connects us through shared struggle, not blame.

5. Where to Find Real Stories

If you didn’t grow up hearing these stories firsthand, they’re still out there: in your community, your church, libraries, senior centers, volunteer work, or even through memoirs and biographies. Real people, real wisdom.

Takeaways:

This episode isn’t about dismissing modern pain—it’s about expanding our lens. The quiet strength of people who had no roadmap, no information, and no guarantees is deeply instructive. We aren’t the first to face hard times, and we don’t have to figure it out alone. When we connect with others—across generations, cultures, and stories—we discover that human resilience is not extraordinary; it's ordinary people doing the next right thing.

We learn to act even when we’re afraid. To take small steps, like those before us. And to remember that strength doesn’t come from avoiding pressure—it comes from walking through it. Their stories shape our own, if we choose to listen.

265: The Power of Pretending: How Psychological Halloweenism Can Improve Your Life

In this episode, we explore a fascinating and unexpected idea: pretending your way into better choices. It might sound counterintuitive, especially in a culture that champions authenticity. But what if tapping into a different persona, even temporarily, could make you braver, healthier, and more productive? Welcome to the concept of psychological Halloweenism—the practice of stepping outside your own identity to access traits you need in the moment.

Inspired by a quote from Jim Henson—“Life’s like a movie. Write your own ending. Keep believing. Keep pretending.”—this episode dives into how adopting a different mindset or character can push us toward growth and better decision-making.

Top Topics in This Episode

1. The Science of Pretending and the Brain's Role

Pretending isn’t about being fake—it’s about gaining perspective. When we imagine how someone else would approach a problem, the brain pulls from our own experiences and merges them with that imagined personality. This creates mental distance from our usual behavior patterns, helping us think and act in new, more productive ways.

2. Lessons from Childhood: Halloween and Beyond

Kids know this intuitively—put on a superhero costume and suddenly they’re bold and unstoppable. That confidence boost doesn’t have to be limited to childhood. Adults can benefit from stepping into different roles too, whether it’s through visualization, intentional behavior changes, or playful role-play.

3. Psychological Halloweenism in Action

We look at a 2016 study that showed how pretending to be someone else—like a narrow-minded librarian or a creative poet—helped people think more creatively. The specific persona didn’t matter; what mattered was getting outside their default mindset.

4. Real-Life Role Models and Borrowed Traits

From imagining a friend who’s super organized to channeling a bold, assertive personality in tough situations, you’ll hear practical stories about using alter egos to face challenges. Whether it’s Grocery Shopping Jill, a fictional rule-setter who keeps spending in check, or a fitness-minded adventurer friend, these personas offer clarity and motivation.

5. Power Poses and the Missed Message

We revisit the infamous “power pose” concept, not as a failed body language trick, but as an example of missing the point. It wasn’t the pose that created confidence—it was the story and persona behind it that mattered. Without imagination and internal narrative, the magic falls flat.

6. Odysseus and Rule-Based Self-Control

Drawing inspiration from Greek mythology, the episode illustrates how we can create systems to protect ourselves from our own impulses. Just as Odysseus tied himself to the mast to resist the sirens, we can adopt personas that follow pre-set rules to avoid self-sabotage.

Key Takeaways

Sometimes, we need to borrow courage, discipline, or creativity. Pretending to be someone who already has the traits we lack in the moment can help us overcome inertia, make better choices, and reach our goals. This doesn’t fracture your identity—it builds a bridge to the person you want to become. Whether it's Grocery Shopping Jill, a fearless adventurer, or a highly organized roommate, those alter egos can be powerful guides.

Using psychological Halloweenism gives us a break from self-judgment, allowing action and growth where there might otherwise be resistance. Pretending, far from being fake, can be one of the most authentic steps toward change. So the next time you're stuck, ask: Who would handle this better? Then, pretend you’re them—just long enough to take the next right step.

This episode is your invitation to explore what it means to grow through imagination and intentional identity-shifting. Who might you become—if only for a moment—to move forward in your...