The central rule
Protect your future ability to choose.
Pressure narrows attention to immediate relief. When I am angry, afraid, excited, or uncertain, I replace the first question in my head with a better one.
Six months from now. Tap either question above.
Immediate comfort does not tell me whether a decision is sound. I judge a choice by its consequences. The relief or excitement it creates today is not enough.
My rule is direct: never sacrifice long-term freedom for short-term relief, ego, money, approval, anger, excitement or fear.
I wrote this guide for moments when pressure weakens my judgment. Search for the situation you face and start there.
Start here
What is happening right now?
01 Read reality through six questions
Before any important decision, answer these. A clear answer matters more than a strong opinion.
Checklist
Can you answer all six?
I pay special attention to question five. Avoiding a necessary conversation often keeps a solvable problem in place.
02 Reversibility sets the speed
Many bad decisions begin at the wrong pace. Even the right choice can go badly when made too quickly or too slowly.
Make reversible decisions quickly because acting gives you the information you need. Take more time with irreversible decisions because the evidence bar should rise with the cost of being wrong. Drag the dial, or tap an example.
Tool
How hard is this to undo?
The dial is a rule of thumb. Its only job is to make you name the cost of being wrong before you decide how fast to move.
03 Find the situation you are in
These are situations worth preparing for. Use the filters or describe the situation in your own words with the search box above.
Hover a glyph to name it. Tap to open it.
- Send the message now
- Resign now
- Threaten or retaliate
- Embarrass someone publicly
- Make a permanent decision to solve a temporary feeling
- Stop communicating for now.
- Write down exactly what happened.
- Separate the actual offence from your interpretation of it.
- Name the boundary that was crossed.
- Decide what outcome you actually want.
- Communicate the boundary once you are calm.
- Escalate only if the behaviour continues.
Anger provides information. Decide your response separately.
Fear produces two bad reflexes. Avoid everything, or control everything. Do neither automatically.
Classify the fear as probable, possible, unlikely, imagined, or preventable. Protect against the realistic downside and stop there.
Manage risk. Do not worship safety.
Do not solve ten problems at once. Write down what you know, what you do not know, what information would genuinely change the decision, and what information is merely comforting to collect.
Set a deadline. When enough evidence exists, decide.
More thinking helps only while it can still change the decision.
- Physical safety
- Health
- Sleep
- Essential money
- Legal obligations
- Important relationships
- The next necessary action
Reduce the time horizon. You are not solving your whole life this week.
Under overload, protect the foundation before optimising the future.
I do not trust major conclusions reached while exhausted. I restore sleep, food, movement, quiet and basic routine first, then reconsider.
Do not redesign your life while depleted.
- Stabilise.
- Understand.
- Decide.
- Act.
Never reverse that order. Do not make a major decision merely to stop an uncomfortable feeling.
Stabilise first. Understand second. Decide third. Act fourth.
Never evaluate a role on salary and title alone. Ask whether it increases at least two of capability, judgement, network, ownership, reputation, autonomy, or future earning power.
Be careful with more money plus more responsibility plus no new leverage. That combination is a golden cage.
Do not confuse being needed with progressing.
Before asking whether to quit, name the component. Manager, role, company, industry, pay, workload, autonomy, values, geography, or your own expectations.
Do not demolish the whole structure if one part can be repaired. Do not keep repairing something whose basic architecture is wrong.
Fix the component when possible. Leave the system when necessary.
Responsibility without authority is dangerous. Responsibility without compensation is exploitation. Authority without competence is dangerous.
Authority with competence, resources and accountability is the version worth having.
Never accept importance merely because it flatters your identity.
- Start because you hate your boss
- Start merely because you want freedom
Work through the real questions. Is there a real customer? A real problem? Will someone pay? Can the economics work? What is your unfair advantage? How long can you survive if growth is slow?
Experiment cheaply before believing expensively.
Brilliance alone is insufficient. Evaluate ethics, emotional stability, incentives, financial discipline, communication, reliability and reputation.
Before you begin, agree ownership, responsibilities, decision rights, compensation, how disagreements get settled, and exit terms.
Trust people emotionally. Structure agreements professionally.
- Invest because everyone else is making money
- Invest because you fear missing out
- Invest because someone sounds confident
- Invest because you need a large return
- Invest to recover a previous loss
Understand how money is made here, how it can be lost, the liquidity, the concentration, the leverage, and the worst case.
Never risk something essential to obtain something nonessential.
Do not raise your lifestyle to match the new number straight away. Put the increase into safety, freedom, assets, knowledge and bargaining power first.
Avoid building a life that forces you to keep doing work you will eventually hate.
Use money to build freedom from bad choices.
Cut unnecessary fixed costs, status spending, ego spending, and commitments that return little.
Preserve housing, health, food, essential insurance, productive tools, critical relationships, and your capacity to earn again.
During contraction, protect the machine that can rebuild.
Wait when excitement is unusually high. Then ask what freedom you are exchanging for it.
The real price includes maintenance, debt, attention, storage, insurance, and sometimes an inability to leave a job.
Count the full price, including the freedom you give up.
Know your preferred outcome, your minimum acceptable outcome, your alternatives, and what you are willing to walk away from.
The strongest person in the room is rarely the loudest. It is the one who can leave.
Options create bargaining power.
Chemistry begins the connection. Judge its long-term potential through reliability, honesty, conflict behaviour, accountability, financial behaviour, treatment of people with less power, respect for boundaries, apologies, and consistency between words and actions.
Attraction tells you to approach. Character tells you whether to stay.
Choose long-term partners by their repeated behaviour.
Stay curious about who they actually are. Do not explain away repeated bad behaviour because the connection feels exceptional.
Compatibility requires evidence beyond emotional intensity.
- Say what happened.
- Say how it affected you.
- Say what you need.
- Ask what they need.
Do not silently accumulate evidence against someone.
Early honesty is cheaper than late resentment.
Ignore one unusually good day. Ignore one unusually bad day. Look at the pattern.
Then ask whether the problem is painful but repairable, or structural and repeatedly denied.
Do not stay on sunk cost alone. Do not leave merely because intimacy takes effort.
Judge the full pattern across many conversations.
Respect does not require unlimited access. Love does not require permanent obedience.
Help people without becoming responsible for every consequence of their decisions.
Compassion without boundaries eventually becomes resentment.
It does not need to be equal every week. Over a year there should be mutual concern, effort, honesty, respect and goodwill.
Do not stay loyal to people who punish your growth. Do not drop good people because your circumstances improved.
Protect relationships that want both your wellbeing and your growth.
Do not become submissive because they have status. Do not become rebellious because they have authority.
Study their incentives and find where your interests genuinely overlap. Stay respectful without surrendering judgement.
Understand power without becoming psychologically owned by it.
Take the useful information and discard the hostility. If it is accurate, improve. If it is inaccurate but consequential, clarify. If it is inaccurate and irrelevant, move on.
Accept that you cannot control every interpretation of you.
Correct important factual errors. Take responsibility where it belongs. Do not overexplain. Then keep behaving consistently.
Most reputational repair comes from consistent future behaviour. One perfect statement cannot do that work alone.
Behave your way out. Do not talk your way out.
Small lies carry ongoing maintenance costs. Tell the truth tactfully and early where you can.
Do not borrow comfort from the future at compound interest.
- Protect money, accounts, legal position, information, reputation and physical safety.
- Document the facts.
- Then decide whether the relationship can be repaired.
Protection first. Judgement second. Revenge never as strategy.
Liking a city is the small question. Consider people, professional opportunity, cost, culture, safety, lifestyle, relationships, learning and future mobility.
Places change behaviour by changing what counts as normal.
Environments edit you slowly and without asking.
Someone can be brilliant at making money and terrible at living. Someone can be famous and privately miserable. Someone can be accomplished and destructive to everyone near them.
Never copy a strategy without examining the life it produces.
- Learn
- Practise
- Produce
- Get feedback
- Correct
- Repeat
Capability grows when you apply information in practice.
If you cannot use it, you do not own it yet.
It is usually uncertainty, possible failure, boredom, embarrassment, complexity, or commitment.
Shrink the first step until avoiding it takes more effort than doing it. Then begin.
Name the discomfort and the task gets smaller.
Some mistakes are expensive. Most are harmless. Spend perfection only where errors genuinely matter.
Precision is a resource. Allocate it intelligently.
Protect the physical system that makes every other ambition possible. Get proper care, avoid self-diagnosis, and reduce the load.
Health is the foundation that makes success possible.
Loneliness lowers standards. Build connection deliberately through friends, family, communities, hobbies, professional groups, volunteering and shared learning.
Temporary loneliness is sometimes the cost of leaving the wrong environment first.
Do not destroy something stable simply to feel alive. Add novelty deliberately before creating chaos by accident.
Add novelty deliberately while preserving what still works.
Separate what you genuinely desire from what you want others to see you possessing.
Use envy as information. Never as a decision-maker.
Use envy to identify a desire, then decide whether that desire deserves pursuit.
Compare trajectories over time. You rarely know another person's starting point, debt, support, private suffering, luck, sacrifices or hidden advantages.
Compare trajectories over time.
Enjoy it. But if praise sets your direction, criticism will also control you.
Receive validation without becoming dependent on it.
This is one of the most dangerous moments. Income can rise while health deteriorates, relationships weaken, curiosity disappears, freedom shrinks and responsibility becomes unbearable.
Measure the whole life across every important dimension.
Separate bad strategy, bad timing, bad execution, insufficient skill, insufficient resources, random bad luck, and a fundamentally bad idea. They have different fixes.
A mistake becomes expensive only when you refuse to learn from it.
After the third serious repetition, stop calling it bad luck. Ask what warning you ignored, what assumption keeps returning, what kind of person or environment keeps producing this, and what boundary should have existed earlier.
Repeated pain usually points to a problem in the system.
Opportunity has a hidden cost, and the cost is fragmentation. Prefer one direction that compounds over five unrelated ones that consume attention.
A good opportunity can still be the wrong opportunity.
Ask which teaches more, puts better people around you, increases ownership, preserves flexibility, and exposes you to valuable problems.
Choose according to the long-term options each path preserves.
Marriage. Major debt. Children. Selling a company. Personal guarantees. Major legal commitments. Permanent relocation. Ending an important relationship.
Slow down. Get independent perspectives. Consider the downside honestly. Do not let urgency created by another person replace your own judgement.
The harder a decision is to reverse, the higher the evidence threshold.
A pilot project, a short contract, a small investment of time, a temporary relocation, a prototype, a trial collaboration.
Months of speculation lose to one cheap experiment.
Reversible decisions deserve speed. Irreversible ones deserve patience.
Do not defend the old plan out of habit. Plans exist to serve reality, and reality owes your plan nothing.
Accept the facts and update the plan.
Say it plainly. I was wrong. Then find the cause and change the process that produced the conclusion.
Being wrong is temporary. Refusing to update makes it permanent.
Become slightly suspicious. Go and find someone intelligent who disagrees, especially before a major financial, professional or strategic commitment.
Treat unanimous agreement as a reason to check for missing dissent.
Do not assume you are visionary. You may simply be wrong. Search for evidence and let reality arbitrate.
Independence requires your own reasoning and a willingness to agree when the evidence supports agreement.
Prepare quietly. Maintain savings, health, relationships, skills, humility and alternatives.
Good periods create the resources that difficult periods spend.
Do not consume everything prosperity gives you.
- Stop unnecessary damage.
- Regain stability.
- Recover information.
- Rebuild options.
Do not demand that one decision repair everything at once.
Survival first. Positioning second. Expansion third.
04 Move through the operating sequence
These steps stop me from making a major decision before I understand the problem, protect the essentials, and test an option.
Sequence
Eight steps, in order
Unless delay creates immediate danger, pause until you can assess the situation clearly.
Record only what you observed. Leave out blame, predictions and guesses about motives.
Label each statement as fact, fear, assumption, pride or someone else's opinion.
Secure your health, money, legal position, reputation and important relationships before making a larger decision.
State the issue clearly to the person involved. Waiting can make the problem harder to resolve.
Choose the least costly action that will give you useful information.
Base the decision on observed results. Your mood at the time is weak evidence.
Commit more time, money or attention only after the smaller test succeeds.
Do not choose a direction while the basics remain at risk. Protect your health, money, legal position, reputation and key relationships first.
05 Protect the floor
When several problems arrive at once, I protect these five first.
Health
Without it, every other advantage becomes harder to use.
Integrity
Protect the trust that lets people rely on your word and work.
Financial runway
Savings give you time to reject bad terms and make a considered decision.
Your best relationships
Protect the people who provide honest help and accept it from you in return.
The ability to walk away
Never build a life where one employer, customer, person, debt, status symbol or institution controls your future.
Five trades that should remain temporary
A temporary trade may be necessary. I require strong evidence before making any of these trades permanent.
06 One principle for every obstacle
When something difficult happens, do not ask how do I make this discomfort disappear. Ask what action protects the future while dealing honestly with the present.
When uncertainty remains, protect the downside. Tell the truth early. Keep good options open. Test before committing. Leave when the structure is fundamentally wrong. Commit deeply when reality repeatedly proves that it is right.
On this page. This guide records the standards I set for myself. I keep it because the states it covers are exactly the states in which I reason worst, and a written answer beats an improvised one when I am angry or tired.
This manual also reflects my research on calibration. In both models and people, sound decisions require an honest account of uncertainty. Questions three and four apply that idea directly: what could go wrong, and how much evidence do I need before the choice becomes hard to reverse?
Nothing you type here is transmitted anywhere. The checklist and the dial are held in your browser's local storage and clearing your browser data removes them.
If you find the interactive format useful, the same treatment is applied to my notes on George Mack's High Agency.