Lesson 6: The Long Game: Humility, Time Horizons & Keeping on Running

Introduction: You’ve Achieved Success. Now What?

Congratulations! You’ve been working hard, making smart decisions, and things are going well. Your bank balance is growing, your career is progressing, and people are starting to take notice of your success. You should feel proud – you’ve earned it. But here’s a question that might make you uncomfortable: what’s your biggest threat now? Is it market volatility? Economic uncertainty? Competition? Actually, it might be something much closer to home: complacency.

Today, we’re exploring one of the most insidious dangers of success – the tendency to stop doing the things that made you successful in the first place. We’ll also dive into the importance of humility, understanding your evolving time horizons, and defining what a ‘rich life’ truly means to you beyond just financial metrics.

Core Concept: Success Has Its Own Gravity

There’s a profound truth that many successful people discover too late: competitive advantages tend to be short-lived, often because their success plants the seeds of their own decline [1]. Success creates its own gravitational pull, drawing you away from the very behaviours and mindsets that created that success in the first place.

The Complacency Trap: When you’re struggling, you’re naturally motivated. You work harder, think more creatively, and push yourself out of your comfort zone. But once you achieve a certain level of success, several things happen:

1. You get comfortable: The urgency that drove you diminishes. Why change what’s working?
2. You become risk-averse: You have more to lose now, so you start playing defence rather than offence.
3. You lose touch with your original advantages: The scrappy, innovative thinking that got you here gets replaced by more formal, bureaucratic approaches.
4. Your expectations rise: What once felt like amazing success becomes your new baseline.

The Jerry Seinfeld Example: Seinfeld quit his massively successful TV show while it was still at its peak because he recognised that what made the show successful was starting to disappear [1]. When he was less famous, he could sit in coffee shops and observe how people behaved, turning these observations into comedy gold. But as he became more famous, he could no longer do this – people recognised him everywhere. He realised that his source of material was drying up, so he made the difficult decision to end the show before it declined.

The Startup Founder Dilemma: Many entrepreneurs face a similar challenge. The skills that make someone excellent at building a scrappy startup – product development, rapid iteration, hands-on problem-solving – are very different from the skills needed to manage a large, established company – HR management, financial planning, strategic oversight [1]. What made them successful initially can actually become a liability as the company grows.

The Evolution of Motivation

Here’s something that successful people often struggle to acknowledge: your motivations will change over time, and that’s perfectly normal. The hunger that drove you when you were starting out – perhaps fear of failure, desire to prove yourself, or financial necessity – may no longer be as powerful once you’ve achieved a certain level of success.

This isn’t a character flaw; it’s human nature. The challenge is recognising when this shift happens and consciously choosing how to respond. You have several options:

1. Find new challenges: Like Elon Musk buying Twitter when he was already the world’s richest person, taking on something that’s genuinely difficult and uncertain.
2. Redefine success: Shift from accumulating wealth to creating impact, from building your own empire to mentoring others.
3. Accept the change: Acknowledge that you’re no longer as hungry as you once were and adjust your goals accordingly.

Key Takeaway: Stay Humble, Keep Learning, and Never Stop Adapting

The antidote to complacency is humility. True humility isn’t false modesty or downplaying your achievements. It’s acknowledging that you’re fallible, that circumstances change, and that past success doesn’t guarantee future success. It’s surrounding yourself with people who will challenge your thinking and tell you when you’re wrong.

Warren Buffett and Charlie Munger exemplify this perfectly [1]. Despite being incredibly successful investors, they constantly challenge each other’s ideas. Munger’s role often involves telling Buffett when he’s being an idiot, and Buffett trusts him enough to listen. This dynamic has been crucial to their long-term success.

Understanding Your Time Horizons

As your life evolves, so do your time horizons and priorities. What makes sense at one stage of life may not make sense at another. Morgan Housel shares his own example: in his twenties and early thirties, he and his wife lived in seven different cities, valuing mobility and flexibility above all else [1]. But once they had children, stability became more important than mobility. They bought a house not as an investment, but because they wanted a secure home base for their family.

This is a crucial point: financial decisions should align with your life stage and values, not just with what makes the most mathematical sense. Sometimes the ‘right’ financial decision is the one that serves your emotional and social needs, even if it’s not optimal on a spreadsheet.

Interactive Element: The Complacency Check

Let’s do an honest assessment. Think about an area of your life where you’ve achieved some success – your career, finances, relationships, health, or personal development. Now ask yourself:

• Am I still doing the things that got me here?
• Have I become more risk-averse than I should be?
• Am I coasting on past achievements rather than pushing for new growth?
• What would someone who’s hungry for my position do differently?

(In a group setting, this could be a discussion about recognising the signs of complacency and strategies for maintaining motivation and growth.)

Activity: Defining Your Rich Life

This is perhaps the most important exercise in the entire course. Take some time to define what a ‘rich life’ means to you, beyond just financial metrics. Consider:

Relationships: What kind of relationships do you want? How much time do you want to spend with family and friends?

Work: Do you want to work until you’re 65? Retire early? Build a business? Make an impact in a particular field?

Lifestyle: Where do you want to live? How do you want to spend your time? What experiences matter most to you?

Values: What principles are non-negotiable for you? What legacy do you want to leave?

Financial: Yes, money matters, but how much is enough? What does financial security look like for your specific situation and goals?

Write this down. Be specific. This becomes your North Star, helping you make decisions that align with your true priorities rather than society’s expectations.

Conclusion:

Today, we’ve tackled one of the most challenging aspects of long-term success: maintaining the drive and humility that got you there while adapting to changing circumstances and motivations. By staying conscious of the complacency trap, regularly reassessing your goals, and defining your own version of a rich life, you’re setting yourself up for sustained success and fulfilment. In our final lesson, we’ll bring everything together to create your personal blueprint for integrating wealth, happiness, and growth into a coherent life strategy.

References:

[1] Podcast Transcript: The Savings Expert: “Do Not Buy A House!” Do THIS Instead! - Morgan Housel - YouTube, https://www.youtube.com/watch?v=vOvLFT4v4LQ