Decision Guides for Life's Big Moments
Life is full of pivotal moments that define our future path. From choosing a career to making a significant investment, these big decisions can feel overwhelming. Our guides provide a structured, calm space to think through these common scenarios. Each one is equipped with tailored questions, proven mental models, and key considerations to help you navigate complexity and choose with confidence and clarity.
How to use this page
- 1Find a guide that resonates with your current challenge. Don't worry if it's not a perfect match; the underlying principles are universal.
- 2Engage with the recommended framework. These aren't just checklists; they are powerful tools for structured thinking.
- 3Be honest and thorough in your answers. The more thoughtful your input, the more profound your insights will be.
- 4Use your completed decision as a reference. Your decision log becomes a personal knowledge base, helping you make better choices in the future.
- 5Notice the patterns. Over time, you'll see how you approach different types of decisions, giving you a unique insight into your own mind.
Browse all decision guides for life's big moments
Should I Quit My Job or Stay?
Feeling stuck? This guide uses powerful mental models like Second-Order Thinking and the Dichotomy of Control to help you decide whether to quit your job or stay.
Should I Accept This Job Offer?
Deciding on a job offer? This guide uses mental models like Opportunity Cost and the Regret Minimization Framework to help you look beyond the salary and make the best choice.
Should I Ask for a Raise?
Thinking of asking for a raise? This guide helps you determine your market value, build a compelling case, and navigate the conversation with confidence.
Should I Switch Careers?
A career change is a major life decision. This guide uses mental models to help you explore your options, test new paths, and make the leap with confidence.
Should I Negotiate My Salary?
Salary negotiation can be stressful. This guide provides a clear framework for how to research your value, anchor the conversation, and negotiate with confidence.
Should I Start a Side Business?
Thinking about starting a side business? This guide helps you validate your idea, manage your time, and decide if it's the right path for you.
Should I Freelance or Work Full-Time?
Deciding between freelancing and a full-time job? This guide explores the trade-offs in stability, freedom, and growth to help you make a conscious choice.
Should I Take a Sabbatical?
Considering a sabbatical? This guide helps you weigh the financial, professional, and personal factors to decide if a career break is a wise move.
Should I Go Back to School?
Thinking about more school? This guide uses mental models like Opportunity Cost and Inversion to help you decide if a degree or bootcamp is the right investment for you.
Should I Buy a House or Keep Renting?
Deciding whether to buy a house or rent? This guide uses mental models to help you look past the myths and calculate the true cost and benefit of each.
Should I Pay Off Debt or Invest?
Confused about whether to pay off debt or invest? This guide provides a clear, step-by-step framework to help you make the optimal choice for your financial future.
Should I Buy a New or Used Car?
This guide breaks down the new vs. used car debate, focusing on depreciation, total cost of ownership, and the 20/4/10 rule to help you make a wise financial choice.
Should I Get a Financial Advisor?
This guide helps you decide if you need a financial advisor by explaining what they do, how much they cost, and how to find a trustworthy, fee-only fiduciary.
Should I Start Investing in Stocks?
Intimidated by the stock market? This guide breaks down the simple, proven steps to start investing, from financial prerequisites to choosing your first index fund.
Should I Lend Money to Family or Friends?
This guide helps you navigate the difficult decision of lending money to family, with frameworks for saying "no" and for protecting yourself if you say "yes."
Should I File for Bankruptcy?
Considering bankruptcy? This guide explains when it makes sense, the difference between Chapter 7 and 13, and the long-term consequences for your credit.
Should I Take Out a Loan?
This guide helps you decide when taking on debt is a smart financial move and when it's a trap, using the concepts of Good Debt vs. Bad Debt and Opportunity Cost.
Should I Buy Life Insurance?
This guide demystifies life insurance, explaining who needs it, why term life is almost always the right answer, and how to calculate your coverage.
Should I Contribute to my 401(k) or Pay Off Debt?
This guide provides a clear, step-by-step framework for deciding between 401(k) contributions and paying down debt to maximize your long-term wealth.
Should I Break Up with My Partner?
Feeling stuck in your relationship? This guide uses mental models to help you distinguish between a rough patch and a true incompatibility, and decide on your next steps.
Should I Move In with My Partner?
Thinking of moving in with your partner? This guide helps you ask the right questions about finances, expectations, and compatibility before you sign the lease.
Should I Get Married?
Thinking about marriage? This guide provides a framework for the critical conversations you need to have about values, money, and life goals before you commit.
Should I Have Kids?
Deciding whether to have kids is a monumental choice. This guide uses mental models to help you explore your motivations, readiness, and the true costs.
Should I Set Boundaries with Family?
Struggling with family dynamics? This guide provides a clear framework for why, when, and how to set healthy boundaries to protect your peace.
Should I End This Friendship?
Friendship breakups are painful. This guide helps you decide when a friendship is over and how to end it in a way that honors your history and protects your peace.
Should I Apologize or Let It Go?
Struggling with whether to apologize? This guide helps you decide when an apology is needed and how to deliver one that actually repairs the relationship.
Should I Forgive This Person?
This guide explores the difficult decision of forgiveness, helping you understand what it is (and isn't) and whether it's the right choice for you.
Should I Pursue This Relationship?
This guide helps you decide whether to pursue a new romantic interest by evaluating green flags, red flags, and long-term compatibility.
Should I Give Them a Second Chance?
Deciding whether to give someone a second chance is a difficult emotional choice. This guide helps you distinguish genuine change from empty promises.
Ready to make better decisions?
Start using these frameworks in your own decision log. Track your thinking, build better habits, and make choices you'll feel confident about.