How To Actually Build Discipline - Gen. Stanley McChrystal
Here are the top 10 key takeaways from General Stanley McChrystal's conversation with Chris Williamson that reveal powerful insights about discipline, leadership, and character development.
1. Discipline as the most significant predictor of success
General McChrystal believes discipline is the strongest predictor of success. He defines self-discipline as the ability to make yourself do things you've decided you should do. This quality distinguishes exceptional leaders from average ones and manifests in every aspect of life.
Discipline is such a powerful indicator because it's not universally cultivated in society. It's largely learned through experience rather than being innate. McChrystal notes that special forces units like Navy SEALs and Army Rangers aren't necessarily composed of superhuman individuals. Their selection processes primarily identify those with extraordinary discipline - people who simply refuse to quit despite difficult circumstances.
2. The importance of standards in organizational rebuilding
Following Vietnam, the U.S. Army was in disarray with deteriorating discipline, integrity, and professional standards. In 1973, General Abrams formed two Ranger battalions with exceptionally high standards for everything from haircuts to physical fitness. These units became a gravitational force that pulled the rest of the Army toward higher standards.
The Rangers' influence spread organically as officers who served in these battalions moved to other positions throughout the Army. McChrystal notes that years later, a disproportionate number of division commanders (around 80%) had Ranger backgrounds. This demonstrates how setting high standards in even a small part of an organization can transform the culture of the entire institution over time.
3. Learning from failure depends on the final outcome
McChrystal recounts nearly being expelled from West Point due to discipline issues. While he didn't learn much during his struggles, the lessons became clear in retrospect. He admits that had he actually been expelled, the experience would not be the "funny story" it is today but rather a painful missed opportunity he might not even mention.
The conversation highlights how our ability to extract valuable lessons from failures is often contingent on eventual redemption. Chris Williamson references the "peak-end rule" from psychology, which suggests that the most emotionally intense and final moments of an experience are most salient in memory. This explains why it's difficult to gain perspective during uncomfortable situations and why a string of failures can feel especially crushing.
4. The power of belief from respected mentors
A tactical officer dramatically changed McChrystal's trajectory at West Point by telling him, "I think you're going to be a great army officer." This vote of confidence from someone he respected made McChrystal believe in himself. The officer pointed out that McChrystal's struggles were specific to the West Point environment and wouldn't necessarily hinder his future military career.
This mentorship moment illustrates how powerful it can be when someone you respect expresses genuine faith in your abilities. Whether the officer truly believed what he said or not, his words had a profound effect on McChrystal's self-perception. It gave him the motivation to persist through challenges by focusing on his end goal of becoming a soldier.
5. The journey matters more than the destination
When McChrystal left military service after 34 years, he co-founded a company primarily to recreate the team environment he valued. He wasn't concerned about the specific business or making money - he wanted "a place to go, a jersey to wear, comrades." This reveals his understanding that the path and relationships formed along the way are more meaningful than achievements themselves.
The discussion highlights that fixating solely on goals often leads to disappointment even when those goals are achieved. Many successful people experience an existential crisis after reaching major milestones. McChrystal suggests embracing the journey itself as the true reward, recognizing that life happens between the starting point and destination.
6. Character as the essence of who we are
General McChrystal defines character as the combination of our tested convictions and the discipline to live up to them. He views life as a journey toward developing character - discovering what we truly believe and cultivating the discipline to live accordingly. This perspective echoes Stoic philosophy, particularly Marcus Aurelius' approach to doing things to a certain standard simply because it's right.
Character isn't innate but developed through experience and learning. While certain traits like stubbornness might have genetic components, McChrystal believes most character elements are acquired. He maintains personal habits and routines that others might find amusing or excessive because they've served him well. This demonstrates how character development involves establishing standards for oneself and maintaining them regardless of external reactions.
7. The value of camaraderie in pursuing difficult goals
The discussion highlights how the modern glorification of "lone wolf" achievement underestimates the importance of team relationships. McChrystal notes that Rangers endure considerable hardship willingly because they're part of something special with equally committed peers. The greatest punishment is being released from the unit for failing to meet standards.
This shared purpose extends beyond the soldiers to their families. Spouses take pride in their partners' elite status despite the sacrifices involved. Williamson reflects on his own evolution from solo training to preferring group workouts, suggesting that while individual drive can fuel initial progress, long-term sustainability often requires community. McChrystal confirms this by sharing that his primary motivation for starting a company after retirement was creating a team environment.
8. The necessity of humility in leadership
True humility involves realistic self-assessment - recognizing your advantages, limitations, and the contributions of others. McChrystal distinguishes between performative humility (acting humble while remaining arrogant) and genuine humility that acknowledges you're not as special as you might like to believe.
In organizational contexts, humility manifests as respect for others and the institution itself. It means recognizing that leadership positions are roles to be played rather than pedestals that elevate you above others. This approach makes leaders more approachable and effective. The conversation suggests that balancing humility with a sense of humor creates resilience against challenges and insults while offsetting the intensity of ambition and drive.
9. The benefits of determined commitment versus partial effort
McChrystal cautions against half-hearted efforts, noting that people who approach challenges at 70% effort will always wonder what might have been. He values the "purity and satisfaction that comes with obsession" - the willingness to work intensely for what you want and to discover your full potential.
This perspective counters contemporary attitudes that sometimes frame hard work and dedication as foolish or imbalanced. McChrystal believes that testing yourself through full commitment provides self-knowledge that can't be gained otherwise. While acknowledging the importance of balance, he suggests that certain pursuits warrant the intensity of obsession to achieve excellence.
10. The redemptive power of stubbornness
Williamson reflects that what appears to be discipline in his career might actually be stubbornness "masquerading as discipline." McChrystal agrees, suggesting that stubbornness and pride can function similarly to discipline when properly channeled. This reframes a trait often seen as negative into a potential strength.
The conversation implies that persistent character traits can be directed toward constructive purposes. While stubbornness might create challenges in personal relationships, it can provide the determination needed to persist through difficulties. This perspective offers encouragement for people who identify with stubbornness - rather than trying to eliminate this trait, they might focus on harnessing it toward meaningful goals.