How to Fail at Almost Everything and Still Win Big

July 01, 2025

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How to Fail at Almost Everything and Still Win Big

My notes from "How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life" by Scott Adam's

Success is the result of building effective systems, managing your personal energy, and stacking complementary skills.

Part 1: The Core Philosophy

Before adopting new tactics, one must adopt a new philosophy. Adams argues for a fundamental shift away from emotional, outcome-based thinking toward a more durable, process-oriented approach.

1. Passion is Overrated

The common narrative is that passion fuels success. Adams argues the reverse is more often true: success causes passion.

  • Passion as a By-Product: It’s easy to be passionate about something that’s working out.
  • The Passionate and the Broke: Passionate people are often willing to take enormous risks for unlikely goals which leads to survivorship bias. Rare, spectacular successes shine through and the much vaster number of passionate failures is unseen. A banker's best loan customer is someone with a solid plan and a desire to work hard on something that looks good on a spreadsheet, not a dreamer.

2. Goals vs Systems

  • Goal: A specific, finite objective you either achieve or don't (e.g., "lose 20 pounds," "run a marathon in under four hours"). Satisfaction is fleeting and comes from achievement.
  • System: A process to increase odds of success (e.g., "eat right every day," "exercise daily"). Systems have no deadline and must provide satisfaction from regular feedback and small wins.

Adams's Personal System as a Writer: Instead of aiming for one specific successful venture (a goal), his system was to continuously create things the public might want and find a way to reproduce them easily. This system guaranteed a string of failures but, by playing the odds repeatedly, dramatically increased the chances of an eventual big win (Dilbert).

3. Commitment, Grit, Discipline

  • "If you want success, figure out the price, then pay it." In terms of money, time, effort, and forsaken alternatives.
  • The Price is Negotiable: While success always has a price, choosing the right system can dramatically lower that price. A good system makes the required effort feel sustainable and even enjoyable, rather than like a grueling sacrifice.

Part 2: Managing Personal Energy

Instead of juggling dozens of life priorities, you should focus on one master metric: your personal energy. Maximizing this makes every other goal easier.

Pillars of Energy

  1. Eat Right: Fuel your body correctly.
  2. Exercise: Create more energy and improve your mood.
  3. Get Enough Sleep: Essential for mental and physical recovery.
  4. Have Excitement: Work on something that makes you eager to wake up.

Tactics for Energy Management

  • Match Task to the Mental State:
    • Morning (High Creativity): Do your most creative work (writing, brainstorming). Adams used 4 AM for his side projects.
    • Mid-day (Energy Dip): Perfect for physical activity like going to the gym or running errands.
    • Afternoon/Evening (Low Creativity): Ideal for simple, mechanical tasks (paying bills, final art for Dilbert, responding to simple emails).
  • Simplify, Not Optimize:
    • Optimization is about tuning until you have the absolute best solution.
    • Simplification is about removing what does not work, finding an easy, effective, "good enough" solution. This principle reduces decision fatigue.
  • Design Your Environment:
    • Setting: Dedicate locations to specific activities (e.g., desk for work, couch for relaxing). This creates powerful mental triggers that help you focus or relax on command.
    • Tidiness: A tidy space reduces cognitive load and removes background stress.
  • No Asshole Behaviors:
    • Dominating conversations, changing subject to oneself.
    • Bragging, cheating, or lying.
    • Disagreeing with every trivial suggestion.
    • Using honesty as excuse for cruelty.

Part 3: Mastering Mindset

Humans are "wet computers" that can be programmed for happiness and success. If you control the inputs, you can reliably influence the outputs.

  • Smiling: Smiling, even faking, triggers the release of dopamine. Smiling at strangers does the same in another person's brain — mind control.
  • Affirmations: Verbalizing what you want to achieve repeatedly.
  • Delusions That Work: Choose a perception of reality that serves you. Believing in your success generates energy, motivation, and creates a self-fulfilling prophecy.
  • Success Spillover: Success in one area, even a hobby or sport, builds a "habit of success" that carries over into more important quests. "Winners"
  • Success By Association: You are heavily influenced by the people you spend time with. Actively spend time with people who embody the traits you want.
  • Invert Happiness: Avoid the major contributors to a bad mood: inflexible schedule, not imagining a positive future, no sleep, bad diet, no exercise

Part 4: Systems For Diet and Fitness

Do not rely on willpower, build systems.

Diet

  1. Find Patterns: Pay close attention to how you feel after eating certain foods to find what drains your energy. When tired or craving food, try high-fat healthy snacks (nuts, cheese, avocado)
  2. Remove Choice: Replace unhealthy, energy-draining foods in your home for convenient healthy foods (apples, pre-cut vegetables, nuts, protein bars).
  3. Make It Taste Good: Use seasonings — salt, pepper, butter, soy sauce, cilantro, lemon, garlic, curry, hot sauce, tomato sauce, balsamic vinegar, black bean sauce.

Fitness

Be active every day, without fail.

  1. Avoid Soreness: Soreness is a penalty that discourages habit formation. NOTE(MC): I strongly disagree with this one. Instead reframe your brain to like the pain. David Goggins shit.
  2. Make It A Habit: Create a habit loop (Cue > Routine > Reward). Have a consistent time (cue) to exercise (routine) and give yourself treat afterward — healthy snack, time to read, etc (reward).

Part 5: Skills

Become very good (top 25%) at a combination of 2-3 valuable skills.

Key Skills to Develop:

  • Public Speaking
  • Business Writing (Clarity and persuasion are key)
  • Psychology / Persuasion
  • Basic Technology Concepts
  • Proper Voice Technique
  • Social Skills (including small talk)
  • Good Grammar
  • Basic Accounting

Summary: The Unifying Principles

  1. Forget Goals, Build Systems: Focus on your daily process, not a distant finish line.
  2. Failure is the Raw Material of Success: Every failure is a data point. Invite it, learn from it, and use it to refine your systems.
  3. Manage Your Energy, Not Your Time: Prioritize diet, exercise, and sleep to maximize your personal energy, which will improve everything else.
  4. Program Your "Wet Computer": Understand that you can control your outputs (mood, productivity) by managing your inputs (food, exercise, thoughts, environment).
  5. Develop a Skill Stack: Become very good at a few complementary skills to make yourself uniquely valuable.
  6. Simplify: Reduce complexity in your life to conserve mental energy for what truly matters.
  7. Happiness is the Ultimate Goal: True happiness comes from having good health, a flexible schedule, and an optimistic view of the future. Build systems that deliver these.