Issue 32 · October 11, 2026
What I want my kids to know about making mistakes.
Written without AI, aside from spelling, grammar, organization, and formatting.
You will make lots of them. Everyone does, even - and perhaps especially - intelligent and motivated people taking on big challenges. Aiming to minimize mistakes is good, but mistakes can never be fully eliminated. The negative consequences can be, and often should be, massive, irreparable, and permanent.
Often, these mistakes will be maximally embarrassing, painful, and inexplicable - the Samson & Delilah type of mistake. The unforced error you commit despite many warnings. The overwhelming evidence you ignore. You should have known better. You did know better. Any child would know better, but you did it anyway.
Worse, these Samson Style mistakes will sometimes have major consequences for friends and family members you care about most. Massive, irreparable, and permanent.
In short, the fault will be yours, the fallout will be massive, and you will have no defense.
While I have a growing collection of Samson Style mistakes, my biggest so far include relationship and investing blunders. If you would like to know the details, we can discuss any time in person.
The question is, how does one have a purposeful and meaningful life in the setting of past - and almost certainly future - Samson Style mistakes?
I don’t know. Definitive answers are lacking as far as I can tell. I can, however, share what is working for me.
Recognize that you are not alone. You and Samson aren’t the only ones to make Samson Style mistakes. Other notables include:
Julius Caesar - one-upped Samson with the sheer density of explicit warnings he ignores leading up to his assassination.
Napoleon Bonaparte, the military genius, driven by the illusion of his own invincibility, ignored all common sense and lost 500,000 out of his 600,000 men in the Russian campaign of 1812.
Steve Jobs: When diagnosed with a rare, highly treatable form of pancreatic cancer, Jobs refused the immediate surgery recommended by the world's best doctors. Instead, he tried to cure it using alternative methods like special fruit diets, juices, and acupuncture.
LeBron James, one of the greatest, most media-savvy basketball players of all time, known for his high sports IQ, immense charity work, and generally spotless public image, hosted “The Decision” to announce his departure from his hometown in a live, hour long, national television special in front of millions of heartbroken fans - and thus became an instant global sports villain and spent years dealing with intense public backlash before he could rebuild his image.
Elon Musk, the most successful business man of all time, massively overpaid for twitter/X, and although he subsequently bailed out X by rolling it into Space X along with X AI, the overpayment remains. He could have & should have paid substantially less for X.
Samson Style mistakes create very sticky/durable knowledge. Given a choice, learning from books and other peoples mistakes is immeasurably preferable, but once the mistake is made, it’s unlikely to occur - at least in the same category/domain - again.
You can always do your best. In any situation, no matter how bad, how you got there, how much or the fault is yours, and whether or not you have any plausible expiation/defense for your actions, just “doing your best” can provide purpose and meaning despite overwhelmingly negative circumstances. In “Man’s Search for Meaning”, based on his inconceivably horrific experiences in the holocaust, Viktor Frankl explains how “he who has a why to live can bear almost any how,” Stated another way, “everything can be taken from a man but one thing: the last of the human freedoms - to choose one's attitude in any given set of circumstances.” And Carol S. Dweck’s “Mindset” is a wonderful complement on fixed vs growth mindset.
None of this will erase the consequences, accountability, and responsibility, nor should it. One unfortunate side effects of Samson Style mistakes is that “alignment of interests” can become somewhat diffuse, so “doing the right thing” becomes highly contextual, and you may not be able to “do the right thing” in one context without potentially causing harm in other contexts. Regardless, you can and should keep doing your best even when you can’t see any measurable improvement.
Living with meaning and purpose (despite Samson Style mistakes) is possible and closer than you might think when you accept the reality of permanent consequences and continue doing your best anyway.