Complete Financial Fresh Start Planning Collection

261 planning questions and 14 expert readings across 6 guides.

Planning Questions

• Think about the last time you felt stressed about money. What specific purchase or bill triggered it? What did you tell yourself in that moment?
• Write about your earliest money memory from childhood. What were you told about money? What did you observe about how adults handled it?
• Recall 3 times in the past year when you felt great about a money decision. What made those moments different from your usual spending?
• Document times when you've tried to budget or "be better with money" before. What did you try? How long did it last? What made you stop?
• Think about someone you know who seems to handle money well. What specifically do they do differently? What have you noticed about their habits?
• Write about a purchase in the past month that you regret. Walk through the decision: What were you feeling? What did you tell yourself? What would you do differently?
• Reflect on your relationship with checking your bank balance. Do you avoid it? Check obsessively? Feel neutral? When did this pattern start?
• Think about the moments when you're most likely to overspend. What time of day? What emotional state? What situations? List specific patterns you've noticed.
• Write about what financial security would feel like for you. Not a dollar amount, but what would be different in your daily life? What would you stop worrying about?
• List every source of income you received last month. For each: How reliable is it? Could it disappear? What's the actual take-home after taxes?
• Think about the last 3 times in your life when something unexpected happened that cost you money. What were they? How did you handle paying for them? What feelings came up when you realized you needed that money?
• Write about your earliest memory of financial stress in your life - either yours or someone close to you. What happened? How did people react? How do you think this shapes how you think about emergency funds today?
• List 5 times in the past year when you said "I should be saving more" or felt guilty about not having savings. What triggered each thought? What did you do (or not do) after each moment?
• Document your current relationship with the idea of "safety" and money. When you think about having 6 months of expenses saved, what emotion comes first? Excitement? Anxiety? Doubt? Why do you think that is?
• Reflect on someone you know who has financial security. What do you notice about how they talk about money? How they make spending decisions? What's different from your current approach?
• Think about the last time you had $500+ in your checking account that wasn't earmarked for anything. What happened to it? Did you spend it? Save it? How did it feel having that cushion?
• Write down 3 financial decisions you made in the past 6 months that you'd change if you could. What would you do differently? What pattern do you notice across these decisions?
• Document what "enough" means to you. If someone said "you have enough savings," what number pops into your head? Where does that number come from? Your parents? Media? A specific experience?
• Reflect on the difference between how you spend when you're stressed vs. calm. Think of specific examples from the past month. What does this tell you about building savings during different emotional states?
• Document your true monthly expenses: Go through your last 3 months of transactions and categorize every expense over $20. What's your actual average monthly spending? What surprises you about this number?
• Write about the moment you realized your financial situation had become a crisis. What specific event or realization triggered this awareness? What were you doing when it hit you?
• Document 3 financial decisions from the past 2 years that felt uncomfortable or risky at the time. For each: What pressure were you under? Who influenced the decision? Looking back, what was the real driver?
• Reflect on your earliest money memory from childhood. What did your family teach you about money - through words or actions? How does that show up in your current situation?
• List the last 5 times in the past year you avoided looking at your bank balance or credit card statement. What were you afraid you'd find? What does this pattern tell you?
• Think about the conversations you had (or avoided) with your partner, family, or close friends about money in the 6 months before the crisis. What didn't you say? Why?
• Write about a time before this crisis when you felt financially secure or in control. What was different then? What specific habits or systems did you have that you've lost?
• Document the physical and emotional sensations that come up when you think about money now. Where do you feel it in your body? When during the day is it worst?
• Reflect on 3 purchases or financial commitments from the past year that you justified to yourself but deep down knew were risky. What were you actually seeking or avoiding?
• List the money advice you've given other people in the past. What's one piece of advice you gave others but didn't follow yourself? Why the disconnect?
• Think about Sunday nights over the past 3 months. What specific thoughts about money keep you awake? When did this pattern start?
• Think about the last time you had extra money (a bonus, tax refund, or unexpected windfall). What did you do with it? How did you feel about that decision 3 months later?
• Write about a time in the past 2 years when money felt tight or stressful. What was happening? How long did that feeling last? What did you learn about yourself?
• Recall 3 specific moments when you checked your bank account or credit card balance. What prompted you to check? What emotion came up? What does this pattern tell you about your relationship with money?
• Think about someone in your life who manages money in a way you admire. What specifically do they do? When did you first notice this? What makes their approach different from yours?
• Document your most recent impulse purchase over $100. What were you feeling right before you bought it? Do you still value it? What would you do differently now?
• Write about what your parents or caregivers taught you about money—both what they said explicitly and what you absorbed from watching them. Which of these lessons still influences you today?
• Think about a time in the past year when you almost invested or started investing but didn't. What stopped you? What were you afraid might happen? Is that fear still present?
• Imagine your bank account loses 20% of its value overnight. Write down the first three thoughts that come to mind. What would you actually DO in that moment? Be honest—not what you think you should do.
• List 3 times in your life when you delayed a financial decision. What were you waiting for? Did waiting help or hurt? What pattern do you notice?
• Research and document: What is your current savings account interest rate? When did you open it? How does it compare to current high-yield savings accounts (list 3 specific rates you find)?
• Think about the moment you realized your debt was a real problem. What triggered that realization? What did you feel? What did you tell yourself?
• Write about your earliest memories of debt - either your own or watching family members deal with it. What messages did you absorb? What patterns do you recognize now?
• Recall 3 specific purchases or decisions that led to your current debt. For each: What were you feeling at the time? What were you hoping would happen? What actually happened?
• Reflect on times you've tried to pay down debt before. What strategies did you try? How long did they last? What made you stop or give up?
• Think about how you feel when you see the balance on your highest debt. Describe the physical sensation. When did you start feeling this way? What does it remind you of?
• Document the stories you tell yourself about your debt. 'I'm bad with money,' 'It's not that much,' 'Everyone has debt' - what narratives run through your mind? Where did they come from?
• Write about someone you know who successfully paid off debt. What did they do? What do you imagine was different about their situation or personality? What assumptions are you making?
• Recall the last time you added to your debt. Walk through that decision minute by minute: What happened right before? What were you telling yourself? What would you do differently now?
• Think about what life would feel like without this debt. Not just 'I'd have more money' but specifically - what would you do on a Tuesday morning? What would stop worrying you?
• Reflect on the relationship between your debt and your self-worth. When do you feel shame about it? When do you justify it? What does this debt mean about you in your own mind?

Expert Readings

• Beyond the Basics: Emergency Funds for Freelancers, Parents, and High Earners

  The standard advice assumes W-2 employment and stable income. Here's what changes when you're self-employed, raising kids, or making $200k+.

• Emergency Fund vs Debt vs Investing: The Priority Matrix

  You have $1,000 to allocate. Should it go to your emergency fund, credit card debt, or index funds? Here's the math that changes everything.

• The Emergency Decision Tree: When to Tap Your Fund (and When Not To)

  Your furnace died. Is that an emergency? Here's the framework that separates true emergencies from expensive wants—and why it matters.

• Building $10K in 10 Months: The Tactics That Actually Work

  Forget "skip the latte." Here are the seven proven strategies that move the needle, ranked by dollar impact per hour of effort.

• The Three-Bucket System: Where to Actually Keep Your Emergency Fund

  Most people lose thousands in potential earnings by keeping everything in checking. Here's the liquidity-optimized system banks don't want you to know.

• Why 3-6 Months is Wrong for Most People

  Financial advisors push the same formula for everyone. Here's the risk-adjusted calculation method that actually fits your life.

• When Standard Advice Fails: Bankruptcy, Settlement, and the Nuclear Options

  Most debt advice assumes you can pay it back. Here's the roadmap for when you can't—bankruptcy vs settlement math, what happens to your life, and the 5-year rebuild plan.

• Credit Score Recovery: What Actually Rebuilds Credit During Payoff

  Paying off debt tanks your credit before it helps. Here's the timeline of what happens to your score, which actions help vs hurt, and the 18-month recovery roadmap.

• The Emergency Fund Paradox: Should You Save While Drowning in 22% APR?

  Financial advisors say "build emergency fund first." Math says "pay off 22% debt first." Here's the framework that splits the difference and saves $4,800 in interest.

• Negotiating with Creditors: The Scripts That Saved $847,000

  Most people are terrified to call creditors. Here are the exact scripts debt negotiators use—one conversation can save $3,200 in interest or get $8,000 settled for $2,400.

• The Consolidation Math: When $15,000 in Fees Makes Sense

  Everyone says "avoid fees!" Sometimes paying $15,000 upfront saves $31,000 long-term. Here's the break-even analysis credit counselors use to decide if consolidation helps or hurts.

• The First 90 Days: Actions That Create $500/Month in Momentum

  Most people waste the first 90 days "getting organized." Here are the five moves that find an extra $500/month and build unstoppable momentum—starting this week.

Available Guides

• Building an Emergency Fund

  Save 3-6 months of expenses for security

• Financial Recovery

  Rebuild after bankruptcy or financial crisis

• Investing for Beginners

  Start investing with confidence

• Mastering Your Budget

  Take control of your spending and saving

• Paying Off Debt

  Create a debt payoff strategy that works

• Retirement Planning

  Build a retirement strategy at any age