Quit

1. Quitting is a crucial decision-making tool, not a sign of failure

Quitting is the tool that allows you to react to the way the world has changed, your state of knowledge has changed, or how you have changed.

Quitting enables adaptation. In an uncertain world, the ability to quit allows us to respond to new information and changing circumstances. It's not a sign of weakness, but a vital skill for making good decisions. Quitting frees up resources – time, energy, and money – that can be reinvested in more promising opportunities.

Examples of smart quitting:

• Stewart Butterfield quitting Glitch to focus on Slack
• Philips divesting its lighting business to focus on healthcare technology
• Alex Honnold abandoning his first attempt to free solo El Capitan

Contrary to popular belief, winners often quit many times on their path to success. The key is knowing when to persevere and when to walk away.

2. The sunk cost fallacy impedes rational quitting decisions

We tend to think only about one side of the human response to adversity: the ones who go for it.

Past investments cloud judgment. The sunk cost fallacy causes us to consider resources we've already spent when making decisions about whether to continue. This leads to irrational escalation of commitment, where we throw good money (or time) after bad.

Examples of sunk cost fallacy:

• Continuing to watch a bad movie because you've already invested time
• Persisting with a failing business venture to recoup initial investment
• Staying in a unfulfilling relationship because of time already spent together

To make better decisions, focus on future costs and benefits, not past investments. Ask yourself: "If I were approaching this decision fresh, would I choose to start this project/relationship/venture now?"

3. Goals can hinder smart quitting by creating inflexibility

Inflexible goals aren't a good fit for a flexible world.

Goals create tunnel vision. While setting specific goals can be motivating, they can also lead to myopia and escalation of commitment. The pass-fail nature of goals makes it difficult to recognize when it's time to quit, even when circumstances have changed dramatically.

Problems with rigid goals:

• Ignoring new information that suggests a change in direction
• Persisting with outdated strategies to reach arbitrary targets
• Neglecting potentially better opportunities outside the goal's scope

Instead of fixed goals, consider setting flexible objectives with built-in "unless" conditions. This allows for adaptation while still providing direction. Regularly reassess goals in light of new information and changing circumstances.

4. Our identity often prevents us from walking away when we should

When it comes to quitting, the most painful thing to quit is who you are.

Identity shapes decisions. Our self-concept and how others perceive us can make it extremely difficult to walk away from pursuits that have become part of our identity. This is why professional athletes struggle to retire, and why companies persist with failing core businesses.

Examples of identity-driven persistence:

• Sears holding onto its retail business despite better opportunities in financial services
• Sasha Cohen continuing figure skating despite unhappiness
• Academics persisting with unproductive research to maintain their professional identity

To overcome identity-driven escalation:

• Cultivate a more flexible self-concept
• Seek perspectives from those outside your field or social circle
• Frame quitting as growth and adaptation rather than failure

5. Exploration is essential for discovering better opportunities

Never stop exploring.

Continuous exploration prevents stagnation. Like ants that continue to scout for food sources even when they've found a good one, humans benefit from ongoing exploration. This creates a diversified portfolio of skills, interests, and opportunities that can protect against uncertainty and reveal better paths.

Benefits of exploration:

• Discovering unexpected opportunities (e.g., Stewart Butterfield finding Slack)
• Developing transferable skills
• Building a network across diverse fields
• Increasing adaptability in changing circumstances

Strategies for exploration:

• Allocate time for learning new skills unrelated to your current work
• Attend conferences or events outside your field
• Take on side projects or volunteer work in different domains
• Regularly connect with people from diverse backgrounds

6. Quitting coaches help overcome cognitive biases in decision-making

Find someone who loves you but doesn't care about hurt feelings in the moment.

External perspective improves decisions. Our cognitive biases make it difficult to rationally assess when to quit. A quitting coach – someone who cares about our long-term well-being but isn't emotionally invested in our current pursuits – can provide valuable outside perspective.

Characteristics of a good quitting coach:

• Cares about your long-term success
• Willing to have difficult conversations
• Understands your field but isn't too closely tied to it
• Helps set clear benchmarks for success and failure

Examples of effective quitting coaches:

• Ron Conway for startup founders
• Richard Thaler for Daniel Kahneman
• Trusted mentors or advisors in any field

7. Reframe waste and failure to make quitting easier

Waste is a forward-looking problem, not a backward-looking one.

Redefine waste and failure. Our fear of wasting resources already invested and being seen as a failure often prevents smart quitting. By reframing these concepts, we can make better decisions:

Reframing waste:

• True waste is continuing to invest in something no longer worthwhile
• Resources already spent are gone, regardless of future decisions
• Quitting frees up resources for better opportunities

Reframing failure:

• Failure is persisting with a poor strategy, not walking away from one
• Quitting at the right time is a success, not a failure
• Learning and growth often come from abandoned pursuits

Questions to ask:

• "What's the opportunity cost of continuing?"
• "What could I accomplish if I redirected these resources?"
• "What have I learned that I can apply elsewhere?"

8. Setting flexible goals with "unless" conditions improves decision-making

Every goal needs at least one unless.

Build flexibility into goals. Instead of rigid, all-or-nothing objectives, set goals with built-in flexibility. This allows for adaptation to changing circumstances while still providing direction.

Components of flexible goals:

• Clear objective
• Timeframe or milestones
• "Unless" conditions that trigger reassessment
• Regular check-ins to evaluate progress and relevance

Example: "I'll pursue this business idea for 6 months, unless:

• We don't hit our customer acquisition targets
• A better opportunity presents itself
• The market conditions change dramatically"

By incorporating "unless" conditions, you create natural points to reassess and potentially quit without feeling like a failure.

9. Diversifying skills and interests protects against uncertainty

Backup plans are good to have especially because some backup plans can turn out to be better than what we're already pursuing.

Diversification reduces risk. Just as investors diversify their portfolios to mitigate risk, individuals can benefit from diversifying their skills, interests, and opportunities. This creates resilience in the face of uncertainty and increases the chances of discovering unexpectedly rewarding paths.

Benefits of diversification:

• Provides options when forced to quit (e.g., injury, job loss)
• Increases adaptability to changing circumstances
• Reveals unexpected synergies between different domains
• Reduces the emotional impact of quitting any single pursuit

Strategies for diversification:

• Develop skills adjacent to your primary field
• Cultivate hobbies and interests unrelated to your work
• Build a network across diverse industries
• Regularly expose yourself to new ideas and perspectives

Remember: What starts as a "backup plan" may become your primary path to success and fulfillment.

Last updated: January 23, 2025