Big Decisions

Frameworks for life's major choices: career, relationships, location, and major commitments.

What Makes a Decision "Big"

Big decisions share these characteristics:

1. Irreversible or costly to reverse - You can't easily undo them
2. Long-lasting consequences - Effects play out over years or decades
3. High stakes - Significant impact on happiness, wealth, or identity
4. Uncertainty - Hard to predict outcomes in advance

The General Framework

Step 1: Clarify What You're Actually Deciding

Often we think we're deciding one thing but we're really deciding another.

Surface: Should I take this job? Real question: What kind of life do I want? What do I value? What am I optimizing for?

Write down the actual decision and underlying questions.

Step 2: Generate Options

Most people compare two options. Better decisions come from considering more.

• What are the obvious options?
• What would I do if Option A didn't exist?
• What would a creative person do?
• What's the opposite of what I'm considering?
• What would I do if I had to decide in 5 minutes?

Step 3: Gather Information

• What would change my mind?
• Who has made this decision before?
• What's the base rate of success for each option?
• What am I assuming that might be wrong?

Step 4: Decide

• Use appropriate frameworks (see 01-frameworks.md)
• Check for biases (see 02-cognitive-biases.md)
• Consider risk appropriately (see 03-risk-uncertainty.md)
• Make the decision

Step 5: Commit and Execute

• Stop second-guessing after deciding
• Execute fully
• Set review points

Career Decisions

Choosing a Career Path

Long-term considerations:

• What's the trajectory of this field? (Growing, stable, declining)
• What skills will I build? (Transferable or narrow)
• What's the optionality? (Can I pivot later)
• What's the income ceiling?
• Does it align with my values and interests?

The explore/exploit tradeoff:

• Early career: Bias toward exploration (try things, learn what you like)
• Later career: Bias toward exploitation (go deep on what works)

Key question: "If I stay on this path for 10 years, where does it lead?"

Job Offers

Beyond salary, evaluate:

Red flags:

• High turnover
• Negative Glassdoor reviews about management
• Unclear expectations
• Pressure to decide immediately
• Inconsistent information from interviewers

Leaving a Job

When to leave:

• You've stopped learning
• You're being treated poorly
• The company's trajectory is negative
• A significantly better opportunity appears
• You're staying only from fear or inertia

When to stay:

• You're still learning and growing
• You haven't given it a fair chance (minimum 18-24 months)
• You're running away from something, not toward something
• You'd be burning bridges unnecessarily

Starting a Business

Key questions:

• Can I survive 2 years of no income?
• Do I have relevant skills and experience?
• Am I solving a real problem?
• Can I tolerate the uncertainty?
• What's my exit plan if it fails?

The regret test: At 80, would I regret not trying this?

Relationship Decisions

Commitment Decisions

Marriage, moving in, major commitment.

The 80% rule: Are you confident this person has 80%+ of what matters to you? No one is 100%.

Key questions:

• Do I respect this person?
• Do we want compatible futures? (kids, location, lifestyle)
• How do we handle conflict?
• Do they bring out the best in me?
• Am I excited about this, or just comfortable?

Warning signs:

• Hoping they'll change
• Ignoring repeated patterns
• External pressure to commit
• Fear of being alone driving the decision

Ending Relationships

When to leave:

• Fundamental incompatibility on major values
• Repeated broken trust
• You've tried sincerely to fix things and they haven't improved
• The relationship makes you worse, not better

When to stay:

• Problems are solvable with effort
• You haven't communicated your needs clearly
• You're reacting to a temporary situation
• You're running from discomfort rather than real incompatibility

The fresh start question: If you weren't currently in this relationship, would you choose to start it?

Location Decisions

Where to Live

Major factors:

The test visit: Spend 2-4 weeks living like a local before committing.

Common mistakes:

• Visiting during the best season only
• Not considering career trajectory
• Underweighting existing relationships
• Overweighting short-term excitement

Moving for a Job/Relationship

Key questions:

• Would I want to live there independent of this job/person?
• What happens if the job/relationship ends?
• What am I giving up by moving?
• Can I build a life there beyond the immediate reason?

Financial Decisions

Major Purchases

House:

• Can I afford the total cost? (Mortgage + taxes + insurance + maintenance + opportunity cost)
• Am I staying 5+ years?
• Am I buying for lifestyle or investment? (Different criteria)
• What happens if my income drops?

Car:

• Total cost of ownership (not just sticker price)
• Do I need this status/features, or do I want them?
• What's the opportunity cost of this money?

The 24-hour rule: Wait at least 24 hours before any purchase over $1,000.

Education Decisions

Questions:

• What's the expected salary increase?
• What's the total cost (tuition + opportunity cost)?
• How long to break even?
• Are there cheaper ways to get the same outcome?
• Will this actually change my trajectory?

The ROI calculation:

Salary increase × Years of work remaining
─────────────────────────────────────────── = Education ROI
           Total cost of education

The Pre-Decision Checklist

Before any major decision:

□ Have I clearly defined what I'm deciding?
□ Have I generated multiple options?
□ Have I talked to people who've made this decision?
□ Have I considered what the outside view says?
□ Have I checked for major biases?
□ Have I slept on it?
□ Would I advise a friend to do this?
□ Am I deciding from hope or fear?
□ What would I need to see to change my mind?
□ What's my plan if I'm wrong?

Post-Decision Practices

Commit Fully

• Once decided, stop evaluating
• Execute with full energy
• Don't waste mental cycles on "what if"

Set Review Points

• "I'll evaluate this decision in 6 months"
• Pre-determine what success looks like
• Create tripwires for when to reconsider

Accept Uncertainty

• You'll never have full information
• Some decisions that turn out badly were still good decisions
• Some decisions that turn out well were still bad decisions
• Judge the process, not just the outcome

Common Big Decision Traps

1. Paralysis by analysis

• More information has diminishing returns
• At some point, you need to decide

2. Deciding by not deciding

• Inaction is also a choice
• Time passing often closes options

3. Following the crowd

• What's right for others may not be right for you
• Conventional paths aren't always optimal

4. Over-weighting current emotions

• How will you feel in 10 years, not 10 minutes?
• Make decisions from your best self, not your current state

5. Ignoring opportunity cost

• Every "yes" is a "no" to something else
• Consider what you're giving up