Why You Shouldn’t “Wing It”

The Bridge Builder’s Dilemma Imagine someone offers you a million dollars to build a bridge across the Hudson River. They provide the tools, the equipment, and the manpower. There is only one condition: you are the sole engineer on the job. Would you take it?

If you were “Larry from Ohio,” you might feel a surge of confidence. But standing on the banks of that massive river, reality would set in. You wouldn’t just “stick a few beams in” or “fill the place with dirt” to see what happens. You would realize that it took mankind thousands of years to master the physics of bridge building. You’d tell the benefactor: “Give me a year. I’ll go to MIT, work hard, and come back when I actually know what I’m doing.”

Yet, when it comes to the most complex architectures of our lives—marriage, parenting, and sustainable happiness—we take the opposite approach. We decide to “play it by ear.” We assume we can figure it out as we go, and if the bridge collapses, we simply lick our wounds and try again. This is the ultimate double standard: we demand rigorous engineering for steel and stone, but we attempt to “wing it” with our most precious assets. This is why we need Shimush Chachomim —the ancient Jewish wisdom of “serving the wise.”

Takeaway 1: Acknowledge Your Hidden Prejudice Against Learning

The first hurdle to living wisely is recognizing a fundamental flaw in human nature: we have a deep-seated prejudice against being taught. Most of us prefer to be the source of instruction, not the recipient. We want to feel self-sufficient and important.

We are often comfortable with the “path of discovery” only as long as we don’t have to acknowledge a teacher is leading us. We tell ourselves, “I’ll discover wisdom on my own,” because the ego hates admitting it needs someone else’s data. This resistance is the primary barrier to reaching our potential.

“Everyone wants to think, ‘I’ll learn it myself.’ We say, ‘Come on, we’ll teach you about living,’ and the reaction is, ‘I’ll learn it by myself... I’ll discover wisdom. I know I’m smart.’”

Takeaway 2: Stop Using Trial and Error for Your Most Precious Assets

Life is significantly more complicated than surgery or engineering. You would never trust a doctor who wanted to “rediscover the circulation of the bloodstream” through trial and error on your operating table.

Yet, we treat our lives as a series of experiments. People kid themselves into thinking that general experiences equate to specific wisdom. It is like a man who wants to be an engineer but enrolls in the Juilliard School of Music, or someone who thinks they are learning bridge building because they “visit all the major bridges in the summer” to look at them. Traveling through Europe and “seeing people walking down the street” doesn’t teach you the mechanics of a successful marriage any more than looking at a bridge teaches you how to support ten thousand tons of steel.

Stop experimenting with your life. You cannot rediscover the laws of the soul in a single lifetime.

Takeaway 3: The Five-Year Time Machine Strategy

To realize the necessity of a mentor, perform a mental exercise: Look at yourself five years ago. If you could meet that younger version of yourself today, would you have anything to teach them? You likely have a list of pitfalls to avoid, strategies for better time management, and insights on what truly matters.

Now, ask yourself: Would that younger version of you have even listened?

If you recognize that your younger self would have been a fool to ignore the version of you that exists today, then apply that logic to your current situation. There are people 10 or 20 years older than you who have already navigated the waters you are currently in. This includes your parents, who often possess a repository of wisdom we overlook in our youth. As Mark Twain famously noted, it is remarkable how much parents seem to “grow in wisdom” as we get older and realize our own ignorance.

Takeaway 4: Learn from Other People’s Mistakes (The Slogan of the Wise)

There is a profound efficiency in mentorship. You do not have enough time to make every mistake yourself and still build a great life. If you wouldn’t ignore your own five-year-older self, why waste time making mistakes that others have already documented?

“A fool learns from his own mistakes; a wise man learns from other people’s mistakes.”

Seeking out those who are “good at living” allows you to bypass the pain of unnecessary errors.

Takeaway 5: “Shop” for a Teacher, Not a Comfort Zone

Finding a mentor requires the same pragmatism you would use when choosing a flying school. You wouldn’t just pick a name; you’d look for government regulations, a solid reputation, and pilots who “haven’t crashed lately.”

In the realm of wisdom, don’t look for a school of “techniques” like Yoga or Sufism. Look for a Yeshiva —a dedicated “school of wisdom.” A true school of wisdom doesn’t just give you exercises; it gives you concrete definitions for good, love, happiness, and meaning.

However, be warned: do not shop for a teacher who only tells you what you want to hear. The temptation is to find a mentor who is “comfortable” and doesn’t challenge your prejudices. To grow, you must find a teacher you trust and stick with them. Switching teachers every time you feel challenged is just a way to remain stagnant.

Takeaway 6: The Art of Serving the Wise

The concept of Shimush Chachomim implies more than just sitting in a lecture. It means “serving” the wise man. This isn’t about servitude; it’s about honor as a tool for extraction.

If the President of the United States visited your home, you would jump up to get him fruit and be eager to help him, regardless of your politics, because you respect the importance of the office. We must transfer that “Presidential” level of honor to the wise. When you honor a teacher, you become alert, anxious, and eager to listen. You “pump” them for information like you would an auto mechanic when you want to understand every part of the car, from the carburetor to the spark plugs.

Takeaway 7: The King Solomon Effect and the Discipline of Disagreement

In Jewish tradition, Shlomo (King Solomon) was the wisest man to ever live. Yet, the rabbis note that as long as his teacher, Shimi Ben Gera, was alive, Solomon made no mistakes. It was only after his teacher passed away that Solomon succumbed to errors—taking too much gold and too many wives—rationalizing that “it will be okay” because of his own great wisdom.

The power of a teacher lies in the discipline of disagreement . With a friend, you can say, “You go your way, I’ll go mine.” With a teacher, you lose the luxury of dismissal. You have two choices:

• Straighten them out: Use rigorous logic to prove they are wrong.
• Get yourself straightened out: Admit your subjectivity was clouding your judgment.

This lack of “dismissibility” is the only thing that forces us to move past our blind spots.

Takeaway 8: Ignorance is the Ultimate “Insanity”

We often view ignorance as a passive lack of data, but the source defines it as a “virulent form of insanity.” It is a disconnect from reality that leads to total destruction. People don’t commit suicide or destroy their children’s lives because of leukemia or smallpox; they do it because of the plague of ignorance. Finding a teacher is not an elective; it is an act of survival.

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Your Wisdom Shopping List

There are 48 tools (the “48 Ways”) required to fully use your life. Finding a teacher is the 10th way, and it is the key to unlocking the rest. It is estimated that most humans use only 2% of their potential —leaving 98% untapped. To begin your journey toward that 98%, complete these two assignments:

• The Counsel Test: Ask three people you respect for advice on how one should pursue wisdom. Do not just take notes— argue with them. Test their logic. If you have decided to relate to them as a teacher, you have a responsibility to pay attention, but also to “straighten them out” if you disagree.
• The Life Question List: Create a list of 10 “life questions” that genuinely bother you. Dig deep. Do not settle for mediocrity. Ask: How do I make a marriage truly successful?
• How do I break out of laziness?
• How do I use my full, infinite potential?
• How do I get more joy out of living?

Take this list and go “shopping.” Find someone who has the answers and don’t let go. Are you ready to stop playing it by ear?