TL;DR
I may never get the ordinary chance to have some of these conversations with my sons, so I decided to write them down.
The 100 things below cover thinking clearly, AI, relationships, work, money, health, technology, forgiveness and love.
This isn’t a demand for agreement or contact. Take what is useful. Leave the rest.
I assumed I would get to have some ordinary conversations with my sons when they became men.
Money. Love. Work. How to tell when someone is full of shit. How to know when you’re the one who is wrong. How to use a tool without letting it use you. The kind of things a father usually passes along badly and incompletely over years: in a car, over dinner, during a walk, in the middle of something else.
Estrangement took away the ordinary version of those conversations.
Last week I wrote about the question of what a parent still gets to pass forward when the relationship itself is gone or uncertain. Jonna Ojalammi’s study used the word generativity: the things we teach, build, hand down and leave behind.
I kept thinking about that word.
A week ago, my wife Wendy suggested something simple: if I may never get to have all of those conversations the ordinary way, I can still write them down.
So this is me doing some of it.
These aren’t commandments. They aren’t a test of whether my sons became the men I wanted them to become. They don’t owe me agreement, a reply or even the time it takes to read this.
A lot of this took me too long to learn. Some of it I’m still learning.
If you ever read this: take what is useful. Throw away what isn’t. Question me too.
Learn to think before someone else does it for you
1. Ask yourself what would change your mind.
If the honest answer is “nothing,” you may be defending an identity instead of examining an idea.
2. Separate what happened from what you think it means.
Those are two different sentences. Learn to write both.
3. Confidence isn’t evidence.
A person can sound completely certain and still be wrong. So can you. So can I.
4. One story isn’t a trend.
A powerful example can show that something happened. It can’t tell you how often it happens.
5. Repetition isn’t independent confirmation.
Ten people repeating the same claim may still trace back to one source.
6. When the stakes are high, get as close to the original source as you can.
Read the document. Watch the full recording. Look at the actual data.
7. Ask what evidence is missing.
A story can contain only true facts and still mislead you through what was left out.
8. Learn to explain the strongest version of the argument you disagree with.
If you can only defeat the dumb version, you probably haven’t understood the other side.
9. “I don’t know” is an intelligent answer.
Use it until you know more.
10. Change your mind without being embarrassed about it.
Updating when the evidence changes is what thinking is supposed to look like.
11. Expertise matters, but experts aren’t infallible.
Question people with credentials. Just don’t confuse questioning expertise with having the expertise yourself.
12. Incentives are clues, not proof of motive.
Knowing that someone benefits from an outcome tells you what to examine. It doesn’t tell you what was inside their head.
13. Correlation isn’t causation.
Two things moving together doesn’t prove that one caused the other.
14. Memory can be sincere and still be wrong.
When something really matters, records help. Memory is rebuilt when we recall it, not replayed like a video.
15. Don’t make an opinion so central to your identity that changing it feels like losing yourself.
If being wrong about one belief feels like becoming a different person, you’ll start defending the belief instead of examining it.
16. Treat AI as a tool, not an authority.
Fluent language can make an answer feel reliable. That doesn’t make it true.
17. If an AI answer matters, verify it.
The more consequential the decision, the less comfortable you should be with “the model said so.”
18. Ask AI for sources, then inspect them yourself.
Check whether the sources support the claims you’re relying on. Then look for a credible source the system didn’t show you.
19. Don’t let AI decide what you value or whom you love.
It can help you think. It doesn’t get a vote on the meaning of your life.
20. Don’t let an algorithm choose your entire information diet.
Many recommendation feeds are designed to hold attention. Choose some of what enters your head on purpose.
Choose people without giving them your steering wheel
21. No parent, partner, boss, pastor, politician, influencer, movement, algorithm or AI gets a permanent exemption from questions.
If someone’s authority depends on you never examining what they say, that authority deserves more examination, not less.
22. If belonging makes curiosity feel like betrayal, pay attention.
A healthy group can survive honest questions. If asking one threatens your place in the group, the belonging may be doing some of the thinking for you.
23. If a group requires you to cut off everyone outside it, pay attention again.
There are legitimate safety reasons to leave people. Isolation as a loyalty test is something different.
24. Loyalty doesn’t require you to surrender your judgment.
You can care about a person or group deeply and still decide they’re wrong about something.
25. Don’t let someone appoint your enemies for you.
Make your own decisions about people.
26. When it’s safe and possible, hear people directly.
Someone else’s description of a person is still a description.
27. Disagreement isn’t betrayal.
Healthy relationships can survive two people seeing something differently.
28. Never punish someone for giving you the honesty you asked for.
If people learn that telling you the truth costs them the relationship, eventually they’ll start giving you the answer that feels safest instead.
29. Pay attention to how someone responds to the word “no.”
You learn a lot about a person when they don’t get what they wanted.
30. A boundary is about what you will do.
It shouldn’t be a prettier word for controlling somebody else.
31. If you need space and it’s safe to say so, say so.
Taking space is different from using silence to punish someone.
32. Don’t confuse intensity with intimacy.
Fast, overwhelming and dramatic can feel powerful without being safe or durable.
33. Watch how someone handles conflict before you build a life with them.
Chemistry gets the attention. Repair keeps relationships alive.
34. Say what you need.
Don’t turn love into a test the other person doesn’t know they’re taking.
35. A good apology names what you did, recognizes what it cost and changes what happens next.
“I’m sorry you were hurt” isn’t the same as owning the thing you did. The apology becomes believable when the behavior changes.
36. Kindness isn’t weakness, and cruelty isn’t strength.
You can be direct, hold a boundary and refuse to be pushed around without humiliating somebody in the process.
37. Watch how people treat someone who has nothing to offer them.
Charm is easy when there’s something to gain. Character shows up more clearly when there isn’t.
38. Keep at least one person in your life who can tell you that you’re wrong without the relationship ending.
If everyone around you has learned to protect your feelings instead of challenging your thinking, you’re building an echo chamber around yourself.
39. Don’t gossip your way into belonging.
Eventually everyone in that circle understands what will happen to them when they leave the room.
40. Trust is built in small promises kept.
You don’t create it with one big speech or gesture. You create it by doing what you said you’d do, telling the truth when it’s inconvenient and showing up often enough that people stop wondering if you will.
Build skills, money and options
41. Learn how you learn.
That skill will survive every technology change.
42. Fundamentals usually outlast tools.
Know enough about the underlying thing that a new app doesn’t erase your competence.
43. Learn enough about anything you outsource to recognize bad output.
That now includes work you hand to AI.
44. Use AI to remove drudgery carefully.
Don’t automatically remove the repetitions that are teaching you the skill.
45. Sometimes do the important thing without AI.
It’s useful to know what you still understand when the assistant is gone.
46. Pay attention to what you repeat. Your life will eventually look like it.
Most habits feel too small to matter on any single day. Give them a few years and they can become your health, your skills, your relationships and the way you think.
47. Seek feedback from people who can explain why something isn’t working.
A verdict teaches less than a diagnosis.
48. Teach what you know.
Trying to explain something clearly is a brutal test of whether you understand it.
49. Finish versions, then improve them.
A first version teaches you more than a perfect idea that never leaves your head.
50. Leave useful notes.
Future you is a real person and won’t remember why present you made that weird decision.
51. Build things, not only a life of consuming things.
Code. Music. Furniture. A garden. A business. Dinner. Something that wasn’t there before you started.
52. Don’t build your identity out of things other people can take away.
Titles, applause, status, followers and access can all disappear. Build enough of your identity around your values, skills and character that you’re still you when one of them does.
53. A company can value you and still remove your role.
Keep building skills and relationships beyond this job, and savings you can draw on if it ends.
54. Negotiate.
Compensation, contracts, fees and terms are often less fixed than they first appear.
55. Read what you sign.
Especially when someone tells you it’s “standard.”
56. Spend less than you earn often enough that it becomes normal.
You don’t have to optimize every dollar, but regularly creating some space between what comes in and what goes out gives you options when life changes.
57. Build an emergency fund.
Savings buy more than repairs and surprise bills. They buy time and the ability to say no.
58. Treat high-interest debt like something to fix, not something to carry casually.
It can eat up the flexibility you’re trying to build everywhere else.
59. Start investing earlier than feels necessary, keep doing it and diversify.
Time and compounding matter. So do fees.
60. Learn what enough means before somebody else decides it for you.
There will always be a nicer house, newer car, bigger title or more expensive version of whatever you already have. Don’t go into debt trying to prove to strangers that you’ve arrived. If contentment always starts after the next upgrade, it never starts.
Protect your body, attention and digital life
61. Protect your sleep.
For most adults, seven hours is a minimum worth taking seriously. If sleep is consistently bad, don’t treat exhaustion as a personality trait.
62. Move your body and keep some strength.
You don’t need to become an athlete. You do need to keep using the machinery.
63. Protect your hearing.
You don’t get a fresh pair of ears later.
64. Learn to cook a handful of meals you actually like.
It saves money, gives you control over what you eat and is a useful way to care for other people.
65. Go to the doctor and dentist before something hurts enough to force you.
Ask your doctor and dentist what preventive care makes sense for you.
66. Don’t let alcohol, drugs or anything else become the only switch you know for changing how you feel.
You need more than one way to calm down, celebrate, sleep, escape or cope. If one substance becomes the answer to every emotional state, it starts owning more of your life than you may realize.
67. Ask for qualified help before the crisis makes the decision for you.
You don’t have to wait until something is completely falling apart before talking to a doctor, therapist, lawyer, financial adviser or other professional who actually knows the problem.
68. Your phone can take every minute you fail to protect.
There will always be one more message, video, notification or thing to scroll. Decide when you’re using the phone instead of letting the phone decide when it gets you.
69. Boredom isn’t an emergency.
Some thoughts need a quiet room before they show up.
70. Protect stretches of uninterrupted attention.
Give some hard things your full attention instead of training yourself to switch away every few seconds.
71. Keep part of your life private.
Privacy preserves future choices.
72. Protect your accounts like they matter.
Use a different password for each account, or a passkey that lets you sign in by unlocking your device. If you use a password, turn on multifactor authentication when it’s available: a second check, such as a code from an authenticator app. The inconvenience is smaller than recovering an account somebody else is using.
73. If losing a file would hurt, keep more than one copy.
“Important” and “only copy” should rarely appear in the same sentence.
74. In 2026, a familiar voice or convincing video isn’t proof of identity.
If money, access or reputation is involved, verify through another channel.
75. Urgency, secrecy and money are a bad combination.
When somebody needs all three from you, slow down.
76. Don’t send money or give someone access to an account just because a message tells you to.
Find the person, bank or company through a channel you already trust.
77. A clip isn’t the whole event. A screenshot isn’t the whole conversation.
Both can be real and still leave out what happened immediately before or after. Get more context before deciding what the fragment proves.
78. Don’t confuse being informed with being continuously stimulated.
Knowing what happened matters. Refreshing feeds all day can make you feel informed without helping you understand what happened.
79. Don’t build a life that only works when it’s about you.
Love people. Help people. Build things that are useful to somebody besides yourself. A lot of meaning shows up where your life touches someone else’s.
80. Learn to enjoy being alone without turning isolation into a place to hide.
Being comfortable by yourself is healthy. Using solitude to avoid every difficult relationship, conversation or part of life is something different.
Love people without losing yourself
81. Tell people you love them while they can still hear you say it.
Don’t assume people know what you feel just because you’ve carried it for a long time. Say it while the person is still there to receive it.
82. Ask older people about their lives before you lose the chance.
At some point, there are questions you can no longer ask.
83. People can love you and still fail you badly.
Both things can be true.
84. You can love someone and still limit what access they have to you.
Love doesn’t require unlimited proximity. Sometimes caring about someone and protecting yourself have to exist at the same time.
85. Forgiveness and reconciliation aren’t the same thing.
Forgiveness is something you can work on inside yourself. Rebuilding a relationship requires more than one person.
86. Reconciliation needs changed behavior, not only a conversation about changing.
Talking about what went wrong matters, but the relationship only really changes when the pattern that caused the damage changes too.
87. If you become a parent, keep adult conflict with adults.
Children shouldn’t have to carry messages, gather information or manage the emotions of grown people.
88. Don’t make a child prove loyalty by rejecting somebody they love.
Protecting a child from someone unsafe is different from asking them to take sides. Let them form their own bonds and their own judgments when it’s safe to do so.
89. Don’t let a third person decide a relationship you can safely examine for yourself.
If someone tells you who another person is, listen, but remember that you’re still hearing their version. When it’s safe, make room for your own experience too.
90. If a hard conversation matters and it’s safe to have it, don’t assume time will have it for you.
Time can soften some things, but it can also turn an unresolved problem into years of distance. Sometimes the conversation only happens if somebody actually starts it.
91. Make amends while people are alive.
Some conversations become impossible after a death.
92. You may never receive the closure you think you need.
At some point you may have to decide what kind of life you can live without it.
93. Don’t let one painful ending rewrite every good thing that happened before it.
A relationship can end badly without making every earlier memory fake. The ending is part of the story, not necessarily the whole story.
94. You don’t have to inherit somebody else’s resentment.
And you don’t have to hand yours to the next generation.
95. Missing someone doesn’t obligate you to return to an unhealthy relationship.
Love, grief and access are different things.
96. Build something that can outlive you.
A skill. A tradition. A body of work. A story somebody younger remembers.
97. Protect your curiosity.
Keep learning things that have no obvious career value.
98. Notice ordinary days.
The milestones are easy to remember. Most of your time will be the days between them.
99. You don’t owe me agreement.
If something I taught you doesn’t survive your own honest examination, change it.
100. Love people fiercely without surrendering your curiosity, your judgment or yourself to prove it.
The healthiest love I know still leaves room for questions, disagreement and an independent mind. If proving your love requires giving those things up, something important has gone wrong.
I don’t know if my sons will ever read any of this.
I don’t know which of these I would have said badly over dinner, which one would have turned into an argument, or which one I would have forgotten until ten years after they needed it.
I also know advice is easier to write than to live. I’ve violated some of my own rules here. That may be part of why they made the list.
I wrote before about trying to practice love without leverage. This belongs to the same discipline. The words can exist without becoming a demand.
Even if my sons never read these words, I wanted them to exist.
UPDATE (Sunday evening, October 4, 2026):
Of course I thought of a few more after hitting publish. Maybe that’s appropriate. I’m still learning too.
A few bonus ones for my sons, if they ever find their way here:
101. If the same problem keeps happening, study the sequence.
What happens right before it? What do you notice, tell yourself, feel and then do? Sometimes the easiest way to change an outcome is to change one small part of the chain that keeps producing it.
102. Before you decide a trait is a flaw, ask what that same trait is good at.
Worry can become preparation. Stubbornness can become persistence. Perfectionism can become a really good final quality check. Sometimes the ability isn’t the problem. It’s where you’re pointing it.
103. Practice the response you want before you need it.
Don’t only imagine the outcome you want. Rehearse what you’ll actually do when the difficult moment arrives: the first sentence, the next decision, the breath before you answer, the choice not to react the old way.
104. Automatic doesn’t always mean permanent.
Some reactions feel like “that’s just who I am” because you’ve repeated them for years. Before you make them part of your identity, consider the possibility that they’re patterns. Patterns can change.
And maybe one more:
105. Pay attention to what your attention is doing.
What you keep looking for becomes easier to notice. That’s useful when you’re looking for an answer and dangerous when you’re only looking for proof that you were already right. Sometimes the thing to question isn’t your conclusion yet. It’s what you’ve been training yourself to notice.
Okay… now I’ll stop at 105. Probably.
Author’s Note
This is a personal legacy document, not clinical, legal or financial advice. The research behind several items is listed below, but many of the 100 are values and judgments I have formed from my own life rather than scientific claims. Nothing here is intended to diagnose, characterize or assign motives to any member of my family. References to estrangement reflect my perspective and previously documented experience.
Resources
Zixi Li and Jingyuan Shi, “Message effects on psychological reactance: meta-analyses”, Human Communication Research, published online June 30, 2025. Meta-analysis of 28 articles covering 33 studies and 146 effect sizes.
Ciera E. Kirkpatrick, Sisi Hu, Yoorim Hong, Namyeon Lee, Sungkyoung Lee and Amanda Hinnant, “I Respect Whatever Decision You Make!”, Health Communication, published online May 1, 2025. In a clinical-trial recruitment experiment, language that respected people’s freedom to decide reduced reactance: resistance to feeling pressured.
Gabriel R. Lau, Wei Yan Low, Louis Tay, Ysabel A. Guevarra, Dragan Gašević and Andree Hartanto, “Understanding critical thinking in generative artificial intelligence use”, Computers in Human Behavior Reports, May 2026. Across six studies, the authors developed a scale covering verification of AI output, the desire to understand how AI works and reflection on the consequences of relying on it.
National Research Council, Identifying the Culprit: Assessing Eyewitness Identification, National Academies Press. Review of evidence on the limits and reconstructive nature of perception and memory.
World Health Organization, From loneliness to social connection: charting a path to healthier societies, June 30, 2025.
Federal Reserve Board, Economic Well-Being of U.S. Households in 2025, May 13, 2026.
U.S. Securities and Exchange Commission / Investor.gov, “Introduction to Investing”, including compound growth, diversification, high-interest debt and emergency savings.
Federal Trade Commission, “Scammers Use Fake Emergencies To Steal Your Money”, including current guidance on AI voice-cloning scams and independent verification.
Centers for Disease Control and Prevention, “About Sleep”, adult sleep recommendations; “Adding Physical Activity as an Adult”, current activity guidance; and “Preventing Noise-Induced Hearing Loss”, updated April 13, 2026.
National Institute on Alcohol Abuse and Alcoholism, “Alcohol and the Human Body”, updated March 2026.
American Academy of Pediatrics, “Helping Children and Families Deal With Divorce and Separation”, clinical guidance emphasizing keeping children out of parental conflict and avoiding loyalty binds.
Richard G. Cowden and colleagues, “Longitudinal associations of dispositional forgivingness with multidimensional well-being”, npj Mental Health Research, January 21, 2026. The reported associations were generally small and do not imply that forgiveness requires reconciliation.
Research note: several of these sources support broad principles rather than proving a particular maxim. Where an item is a value judgment, I have left it as a value judgment rather than dressing it up as science.