Lessons for the second half
Everything I learned from the movies was wrong.
There is no closure with most stories … they just stop at a certain, sometimes random seeming point. I will rarely have some big moment of realization with someone who has done me wrong, nor they with me.
The plot of Life never follows a neat narrative Arc. I’ve driven myself mad trying to force it to do so.
The more I let myself follow a path that feels right to me, the happier I’ve been in my life, even as that path has diverged more and more from what I was taught.
My criteria for helping someone with a problem is not identifying that I could help them with it … it’s them explicitly asking for help.
And even in the rare circumstance they do ask for help, I will only follow up with them if they take the action I’ve suggested. I always frame my help in the same way – “Here is what I suggest based on my experience, give this a shot, and come back to me and tell me what you learned.” I leave the burden on them to return to me, because I have found, when I follow up with them, that they’ve rarely done it…and also they often feel annoyed at me for following up! So, until someone has demonstrated they will do the thing I’ve advised them to do, I don’t believe their ask for help is genuine. It’s only when they actually take action on the help that I offer that I know they mean it.
In almost every case, the reason someone is in trouble is the same reason they will resist the necessary help getting out of trouble. If someone has trouble with their employees because they’ve avoided setting boundaries, when I suggest they set boundaries, they will not do it … because that’s how they got here in the first place. Most people lack the introspective capacity to identify how they are involved in the trouble they have and most people lack the fortitude to make changes to their behavior to resolve the problems they face. This feels really judgey. Also, at the age of 40, I’ve seen it so often I know it’s basically true.
Something popular culture conveys that is exactly and totally wrong is that one big moment, one big gesture, one big thing is what matters. It doesn’t — one big moment is almost never anything. What matters is persistent, small things over time.
There are almost no aha moments in life. There are almost no game-changers in a single moment. When a business fails, it is often attributed to the proximate cause — the final nail in the coffin, as the saying goes — and that’s never actually the case. It’s usually death by a thousand cuts. It’s the failure to do a million little things over and over again that eventually leads to the day the bank account plummets to zero.
I’ve learned not to underestimate people’s willingness to go bankrupt to avoid having difficult conversations or holding people accountable. It’s akin to fearing public speaking more than death … many people would prefer their business fail over having to do the scary parts of managing staff and clients, setting boundaries, and demanding performance for the money they spend.
People worry way too much about their intellectual property or their secret sauce … knowledge is never the problem. The problem is always wisdom. I can’t tell you how many times I’ve seen someone say “we got this set of policies and procedures from our well-run competitor,” or “we got this recipe from someone else.” They’re very pleased and they think that’s going to matter but it never does because it’s not theirs. Knowledge is having the information, but it’s basically useless without wisdom. I can own a library but that doesn’t mean I’ll learn its lessons. Wisdom is the hard wonthing. Wisdom is the ability to take knowledge and incorporate it into thoughts and actions and behaviors.
A high-functioning team of mediocre players will always kick the pants off of a low-functioning team of rockstars. But we undervalue the power of a good team because it’s very difficult to measure on a sports chart in a KPI or a metric. People think they can just take one person out and then put another person in who’s “better,” and that will improve the overall performance of the team, but it doesn’t. It makes it worse until they are incorporated into the team. We over-focus on the results of individuals and under-focus on how the group contributes to those results.
I’ve never been able to find a way to teach empathy to someone who doesn’t have it. It’s very sad because I think empathy, along with kindness and boundaries, is at the core of a happy life.
To the extent that I have discovered, at least for myself, what it takes for a life to be happy, I have found it to be about three things: kindness, empathy, and boundaries. They are three legs of a stool and without any of the legs, life falls out of balance and into unhappiness.
Without kindness, even with empathy and boundaries, a person pushes everyone else away and they are alone, and they are lonely.
Without empathy, with only kindness and boundaries, one finds that they cannot connect with others in the world and thus they are again lonely even though they are kind.
With kindness and empathy, but without boundaries, people give too much of themselves until they are hollow shells or husks of the humans that they might once have been.
With kindness, empathy, and boundaries, people are able to understand, be drawn to, and draw others to themselves, while also maintaining and holding enough for themselves that they can enjoy their lives.
All of them exist on a spectrum. There is too much kindness and not enough kindness. There’s too much empathy and not enough empathy, and there are too many boundaries and not enough boundaries. The pivot points are invisible and, often, one does not know that one has fallen to the other side until one wakes up with their teeter-totter in the muck and has to steer it back to the other side.
I have found that everyone, at various points in time, is more afraid of change than they are of maintaining a horrible situation. They would rather stay in a situation that they hate, that is killing them, that is tearing them apart, than face the fear of changing the situation. This is simply an observable fact. It’s not a judgment.
I don’t exactly know what the difference is between people who go through hard things and come out of them more resilient and kind and wonderful than people who go through hard things and come out of them bitter and resentful. Going through hard things is a bit like being bitten by a spider in a science lab. It’s going to give you some special powers but it’s hard to know which ones. Why can the same tragedy create monsters and saints?
I know people who make minimum wage working part-time and I also know billionaires. Something they have in common is always thinking they need more money and how much they have now is not enough. One of the saddest things I see regularly in the universe is a business owner in their ’50s or ’60s, approaching the late stages of life, with a business that, if they sold it, would give them enough money to do anything they want whenever they want for as long as they want, but still they choose to work 60-hour weeks and spend all their days fretting. See the previous note about how people would rather stay in pain than face the fear of change.
One of the saddest things I’ve ever seen is a business leader who realizes, only after they’ve sold their business, that nobody ever liked them. They find the only reason they got so much attention is because they controlled money that other people wanted.
I once had a customer that I loathed, but they were one of my largest accounts. He was sexist and he was arrogant and he definitely had no kindness or empathy, but he had a lot of money, which he gave to my company. After he retired he reached out to me twice — once to get together for lunch and once to invite me to a birthday party. I did not respond to either invitation. I never wanted to speak to that individual again. I wonder how they internalized the social rejection they experienced after they no longer had the thing people wanted.
I assume they just raged without understanding. I think they lacked the introspection they would’ve needed to figure it out.
I’ve come to realize that many of my behaviors and beliefs were instilled through past experiences, triggering emotional responses even when I’m doing what’s best for myself. For instance, while I understand intellectually that setting boundaries is crucial, I’ve been in relationships where enforcing boundaries led to punishment from partners, making me now struggle with setting them. It often takes me conscious effort to remember that if someone reacts angrily to my boundaries, the problem lies with them, not me. Sometimes I feel guilty and anxious about potential reactions, and that makes it even harder to assert myself. However, I’m working on recognizing that these feelings stem from past conditioning rather than reflecting the current reality or what’s truly best for me.
People like to give advice. I’ve learned not to take advice from people’s lives that I do not want. Their advice is essentially the instruction manual for how to become them; if I don’t want to become them, why would I take their advice?
One of the lessons I’ve learned that I hate most of all is that there are, in fact, people in this world who are actually bad. Not misunderstood, not traumatized, not confused, but people who make it their life’s mission to receive joy from causing harm to others. These people cannot be fixed. They cannot be reasoned with. They cannot be fought with and beaten. They must simply be avoided and excluded from one’s life.
I use the words good and bad sparingly because I don’t think they have a clear meaning. But in this case, I’m comfortable with it because I do think that someone who causes harm to others for their own personal enjoyment is in fact bad. And in day-to-day life, someone who manipulates others, to one person’s detriment and for their own personal gain, is also bad.
I’ve learned that for absolutely every rule, life, lesson, and belief there is a specific scenario that counters it and renders it incorrect. There is also a person, I’ll call him Rod, who will point it out when someone speaks. “Well, sure, but what about the Third Invasion of the Bug People in Alpha Prime in the year 92 AD? That renders the only 1,000 examples invalid, right?”
I’ve found that these people exist in every community. And, they, the ones who respond to every life lesson and broadly applicable situation by pointing out the one situation in which it does not apply, are not the sorts of people who are capable of learning. So I have learned to ignore them.
I learned that if people don’t ask a question, they don’t want an answer. I’ve learned that when people say things that are wrong or stupid or false without following up by asking “what do you think” or “do you think I’m right,” they are not interested in your opinion. If I respond by saying that is wrong or stupid or false, they will just double down on their original notion, and I will be frustrated.
I’ve learned that stories matter a great deal more than facts and that if I want people to understand my facts, I need to start by finding or making up a story that incorporates those facts into the kind of neat narrative that I earlier said doesn’t actually exist. Tidy stories are not how reality works, but they sound like how people believe reality works and that’s really all that matters.
I’ve learned that friendships and social relationships are sometimes like eating vegetables, a thing that one does because it is healthy, not necessarily because one wants to in that particular moment.
As someone who is introverted and often prefers isolation, I have the certain knowledge that what makes for a happy life is meaningful social connections — and I’m annoyed about that. I would like for meaningful life to be made of cats and spreadsheets. It’s not though.
I’ve learned that the most important question in determining if someone is going to lead a happy, long, and healthy life is not how often they exercise or what they eat or how much stress they have. Instead, it’s how many people they could call right now in this moment and say, “My car died. Will you come pick me up?” And the other person will either say yes or they will say “Well I don’t live where you live but let me send you a taxi.” The people who have at least five to 10 people they could call live long, happy lives. For each number lower than five, the less happy the person.
I’ve learned that love is not conditional, nor is it earned, nor is it spent. Love is something that exists between people who have it at all times and in all ways for all reasons. But, also, love is never enough. The existence of love does not make everything okay, nor does it mean the relationship will work. Love is simply a single factor.
I’ve learned about prosocial maladaptations, which are things we do for which we get societal praise, but are from unhealthy sources and for healthy reasons. To some extent, this can describe the accumulation of wealth, which is praised and so people don’t stop to see that it is often hurting or killing them. What could be sadder than a 70-year-old billionaire with a house on the beach, who spends more time staring at his computer monitor and watching the stock market than looking out the window and seeing the waves.
I’ve learned to respect the balancing act of how much responsibility I take for other people’s feelings. There is too much, and not enough. When someone tries to pretend at being a Stoic – “Your feelings are your own, my actions have no impact on them!” That is wrong. It takes not enough responsibility. However, I’ve seen people with too much empathy who will take full responsibility for all of someone else’s feelings. This is also probably wrong. It is unlikely (absent bad people, as discussed above) that they meant to cause that outcome. Why people feel the things they feel when they feel them is very complicated, and is almost never one person’s “fault” exclusively. Beware of people who play emotional blame games or demand apologies. They don’t understand this lesson.
I’ve learned that happiness is not changing to fit other people, but rather finding other people that I already fit.
I’ve learned that change is a long, slow process, and that if I need someone to change in some significant way in order to be someone that I want to give my time or effort or money to, I need to move on.
I’ve learned that the more excited someone is about something, the less they understand it. This is particularly true when people get excited about investment opportunities and new businesses and new relationships. Actual experts always talk with a thousand caveats and a bunch of “on the one hand, on the other hand” speech. But in general people don’t want to listen to them because they would rather be excited. I’ve learned to be wary of people who are excited about things, or at least to use that excitement to say, “Well, what are all the things we’re not thinking about …?”
I’ve learned that the world was designed for people who look like me and talk like me, and that my experience interacting with people is frequently very different from others, even with the same individuals.
I met a friend once — someone whom I really liked and enjoyed spending time with — and then I happened to make a different friend who had previously dated him. And she told me about how he treated women, which was so different from how he treated me that I could scarcely comprehend it. I’ve experienced this enough times now to know that it is, sadly, kind of normal.
I’ve learned that a question does not require a response. An email can be deleted unread. I don’t need to respond to everything … sometimes I just click delete and move on with my life.
I’ve learned to be annoyed that carbs are both bad for me and also taste really good.
I’ve learned that many people will vote against their best interest. Many people will make choices that are explicitly, actively, and clearly bad for them, and there is nothing I can do about it except try to protect myself from the influence of those people.
I’ve learned that most people prefer a comfortable lie to an uncomfortable truth.
I’ve learned to put energy into things in proportion to my ability to have that energy influence the thing.
I used to care a lot about politics and put a lot of energy into caring about it … but at a certain point, I realized that I have essentially no influence on who is in charge or what happens. I stopped putting so much energy into and stopped having so many emotions about it, and it continued to happen in exactly the same way as it had been … but it didn’t hurt me as much anymore.
I’ve learned that a cat sitting quietly on your lap and purring is possibly the greatest experience in life.
I’ve learned that just because a relationship ends does not mean it was a failure. Some relationships have a course to run, a lesson to teach, a moment in which they are correct. And then they do not anymore and that’s okay.
I’ve learned that emotions only exist in opposition to each other. I used to think the point of life was to be happy all the time, but it turns out that’s literally impossible because there is only happiness in relation to unhappiness. There is only joy in relation to sadness. Anything felt for too long becomes ignored. When was the last time you thought about how your left toe does not hurt? And yet, if tomorrow it hurts and then a week later it stops hurting, I guarantee that you will be aware of it for at least a time because you will know it in comparison.
I’ve learned to be grateful any day that I wake up and my body does not hurt and I’m easily able to breathe and walk around unassisted. The day will come when those things are no longer true, and I would regret enormously not having enjoyed them when they were present.
I learned that everybody wants to talk about it but nobody wants to start the conversation. I’ve learned that if I start the conversation, everybody will talk about it.
I’ve learned that laughter is another form of applause and that when people are applauding you would not interrupt, so neither should you when they are laughing
I’ve learned that you cannot make someone believe something about themselves that they do not already believe. But I’ve also learned that people give compliments for themselves as well as for you and that if you reject a compliment, you reject them.
Marie Kondo taught me that the point of a gift is to be given and not to be kept.
My house got a lot less cluttered once I gave myself permission to throw away gifts I did not want. I don’t know why, but I just had this belief that anything ever given to me as a gift should be kept forever for some reason. But nobody else has the right to take up real estate in my house without my permission.
I’ve learned that plants are necessary for emotional nourishment. I don’t know how to keep a plant alive for the life of me, but I can afford to pay someone to come to my house and keep them alive for me. Even if you can’t afford that, find a way to get some plants in your life — it makes everything better.
I’ve learned that when it comes to changing people’s negative behaviors, there is a bottom 25% who will never change and a top 25% who will always do the right thing. But you can alter environments in a way that makes the middle 50% do something different.
My favorite example of this: Imagine a bus stop at which there is no garbage can. There will probably be lots of garbage on the ground because even though 25% of people will take their garbage with them no matter what, another 25% will always throw their garbage on the ground whether or not a garbage can is available. But another 50% would put their garbage in the garbage can if it were there but might throw it on the ground if it’s not.
Having a garbage can yet still finding garbage on the ground does not mean the can has failed. It simply means you have not changed the behavior of the bottom 25% whose behavior is not changeable, but you have changed the behavior of the middle 50% and that’s worth a lot.
I’ve learned that willpower is an extremely weak force and that setting up an environment for success matters a thousand times more. Blaming people for having weak willpower or a lack of willpower as a reason they are in difficult circumstances is always wrong. But it’s a much more convenient excuse because it makes it their fault and that means we don’t have to think about what actually caused it. Again, we prefer simple lies to complex truths.
I’ve learned that the phrase “avoid it like the plague” is false because we had COVID-19, which was essentially a plague, and many people not only did not avoid it, but in fact actively sought it out.
I’ve learned about the importance of making room for the $10,000 hours. Not all the hours are equivalently valuable. Many of the hours are not valuable at all and it’s important that in our lives we make space for the hours that are worth $10,000 or $100,000 or a million dollars.
I’ve learned that productivity has only a weak relationship with time. And that people who measure time as a proxy for productivity are wrong.
I’ve learned that the point of therapy is not to fix what’s wrong with someone’s brain. What therapy does is help us understand why our brains do the things we do so that when it’s happening we can say “oh look it’s that thing.” But it never actually changes those thoughts. It just makes us aware of what they are and what we can do about them when they come up.
I’ve learned there’s no such thing as a good or bad book. There is only the right or wrong book for a moment in time. I’ve learned not to recommend books universally or randomly but rather to identify a book as fitting at a particular moment. I have read books that fell completely flat, but suddenly understood them when I read them again years later.
I’ve learned that the vast majority of business books are dumb and useless. Most are a brief blog post, made long enough to fit on a bookshelf. When people ask for business books to read, I always suggest fiction books with realistic character motivations and complex plots and endings. This is the most useful thing to learn – how people think and interact and why they do what they do. That is business. More often than not, business leaders lack emotional intelligence, not “how to run a productive line efficiently” intelligence.
I’ve learned that people are extremely afraid to be alone with their own thoughts and have a quiet mind. No matter how small the interval, even just a simple elevator ride, some people will immediately pull out their phone rather than sitting quietly with their thoughts for 15 seconds. I’ve learned that the time that I spend being quiet and alone with my thoughts is sometimes terrifying, but also often very beneficial.
I once learned a lesson that turned out to be totally wrong and I’ve had to unteach myself. That lesson is that if you believe in yourself and you believe in your idea, you should just keep going because eventually you will persevere and succeed.
It’s a form of success bias.
We hear stories about people who are successful, but we don’t hear about all the people who toil their entire lives only to end up bankrupt and destitute, never amounting to anything, because they don’t have fabulous stories written about them. But there are tons of them. The fact that something did work in a few cases does not mean it is the right way to do something … that’s just where we’ve put all of our focus.
Somewhere along the way politicians made us believe that it was a bad idea to change our minds, that it was something to be scorned — and it turns out that’s totally wrong. The ability to learn new information and change an opinion is absolutely critical to living a happy life. I’ve watched so many businesses and business owners plummet to failure because they cling to an idea and refuse to ever let it go.
I’ve learned that it’s the not doing that kills people. It’s never the things they do — it’s always the things they don’t do, the actions they don’t take. I haven’t seen many businesses fail because they did too much … spent too much … put themselves too far out on a limb and then collapsed on their faces. I’ve seen some, but not a lot. Mostly I’ve seen businesses fail because they refuse to do things. They refuse to fire people. They refuse to close things. They refuse to learn lessons. They refuse to cut back. They refuse to pour water on the fire while it’s still small and instead they wait until it’s a bonfire and then it consumes them. It’s the not doing that ends people, not the doing.
I’ve learned that it’s more important to say “no” than to say “later.” “Later” stays on my mind and eats up bandwidth, but “no” lets it go. I’ve also learned that “delay” is another way of saying “never” and it would be better to just say “never.”
I’ve learned that if it makes me happy and it doesn’t harm anyone, then people who make fun of me for it are people I don’t want in my life. When I fly I like to sit in seat 2C. It feels warm and comforting and homey. To be in that seat makes me happy and that is the entire and only reason I need. Anyone who judges the things that make you happy or thinks you ought to have a better reason can go suck an ice cube.
I’ve learned that when people ask “why?” they usually mean – “I want to argue you out of your position.” When you meet people who ask why because they really want to know – hold onto them, They are rare and precious.
I’ve learned that people are very comfortable judging others and very uncomfortable being judged themselves, and I’ve also learned that the more comfortable someone is judging others, the less comfortable they are being judged.
I’ve learned that a 20-second hug from someone you love is one of the best feelings in this universe. Not as good as a cat in your lap, but still, really good. Also more predictable. Why is my cat napping on the bathroom rug 5 feet away from me right now? My lap is lovely…
I’ve learned that there is not enough, just enough, and too much of everything. From chocolate to sex to money to sunshine … anything I can imagine has the possibility of there not being enough of it, being as much as I want, and being too much. There is nothing for which more is always better.
I’ve learned that the most important person to be kind to is myself.
I’ve learned that it’s far more important to know how to fix a mistake and apologize for an error than it is to never make one. If I have the opportunity to work on getting better at avoiding mistakes or work on getting better at repairing damage, I would choose the latter.
I’ve learned that the most important quality and characteristic in people who get what they want is flexibility. It’s the ability to decide that the outcome is what matters, not the journey or the process, and to be willing to try other paths and other methods of getting where they want to go.
This doesn’t mean don’t plan, it doesn’t mean go to the airport without a ticket. But it does mean that the best vacation is one where you have a rough itinerary and a basic idea of what you want to do, and not one in which you have scheduled every minute of every day without leaving room for the $10,000 hours or happenstance.
If you feel the need to prove yourself to someone, there is something wrong with the situation.
Some people will not like you. That’s okay.
My thoughts happen like clouds in my head, my self exists in my belly. When I don’t like the thoughts in my head, I can burrow into my belly and wait for them to pass. The existence of a thought does not require the acknowledgment of the thought. Or the agreement or belief with the thought. It can just be there.
Somebody can be wrong for a really long time and look like a genius. This is extremely true in the stock market. There are so many trends that were true and accurate for 10 or 20 years and have never been true or accurate before and are never true or accurate again after. But can you imagine being in year five of telling someone that that plan is stupid? They have a 5-year track record of success!
The news media likes to label things as “game changers.” A new car, a new technology, a new planet. It’s so rare that anything called a “game changer” actually changes the game. Instead, the real “game changers” happen slowly, subtly, under the water line, and then all at once, they are everywhere. Most game changers never get the label, and most of the things that get the label flame out without anybody noticing.
How we react matters so much more than how we plan.
U.S. laws were written by wealthy white landowners. The tax system is incredibly unfair and totally geared toward landowners. Own property, not businesses. A million dollars in rental income is taxed at a much much lower rate than a million dollars in business profits. Not saying it’s good, just saying it is.
It’s also important to know that how you work the system matters most. When someone is selling the business, the question is not “What will the purchase price be?” The question is how much will be left after the tax strategy. You can sell a business for $100 million and end up with $50 million in your pocket or $80 million depending on how you handle it. Sometimes the tax strategy becomes the deal breaker rather than the purchase price.
Do not buy your primary residence as an investment. Home is a special, magical thing. Don’t f*** it up by thinking it’s about money. Your second property though …
The market can stay irrational longer than you can stay solvent. Yes, it is a bubble; yes, it will pop; no, you can’t time it well enough to know when it will pop so that you can bet against it and make money on it. You will run out of money first.
Being right about the concept and right about the timing are completely different. The first one is completely useless without the second one.
Before saying something, consider if it is kind, necessary, and the right time. If it’s not, then you’re saying it for you and not for them and shut up.
Lying always comes back around to bite you in the ass. The pain that I plan to avoid by lying today is always 10 times worse when it’s discovered in a month or a year. This includes lying to myself.
Don’t let people tell you that it’s not valuable because it can’t be measured. Many of the best experiences and things in life do not work according to a measurable metric. They just feel good.
Don’t be surprised by someone’s ignorance when their paycheck depends on that ignorance.
Everyone in every situation has an incentive … know what that incentive is or be blindsided by it.
There is not a sucker in every transaction. If you believe that there is, then I do not want to do business with you. There are lots and lots of win-win situations.
It’s not true that a successful negotiation is one in which both parties are equally unhappy.
When you go into a negotiation, know what you actually want. Work on getting that thing and that thing alone. It’s not about who’s right or who’s wrong. It’s about what you want and what they want and finding out if there is a way to get those things. I’ve seen so many people losing negotiation because they are obsessing about being right instead of getting what they want.
John and Julie Gottman are right about everything. I’m not going to spend time here going over all of their theories about successful relationships. Only that I have tested all of them and they are correct on every count.
Home is a concept, not a place.
Feel pity for anybody over the age of 20 who still thinks the most important thing about them is what they own and not who they are.
Ignore words, and watch behaviors; they tell you what you want to know.
There will be many situations when someone’s words will tell you what you want to hear, but their actions are not aligned. They say they love you, but they never make time for you. They say they want to learn from you, but they never take your advice. In these moments, it is so tempting to accept their words and ignore their actions. And yet, in these moments it becomes the most important thing to see their actions as their true intention instead of their words.
What matters is persistent, small things over time. There are almost no aha moments in life. There are almost no game-changers in a single moment.