What I Learned From My 5 Worst Decisions
Every mistake had a pattern. Here are the patterns.
I don't regret my bad decisions. I regret that it took five of them before I saw the patterns.
Looking back at the five worst decisions of my life — across career, investing, relationships, and personal projects — I found that each one was caused by one of five predictable, avoidable patterns.
If I'd had a framework, I would have caught them. I didn't. So here are the lessons, in case they save you a few years.
Bad Decision #1: Taking a Job for the Title
The offer was impressive on paper. Senior title. Big company name. 30% salary increase. I accepted within 48 hours.
Six months in, I was miserable. The work was bureaucratic. My manager was absent. The team was demoralized. The impressive title meant nothing inside a toxic culture.
The pattern: Optimizing for the visible metric, ignoring the invisible ones.
Title and salary are easy to measure. Culture, learning opportunity, manager quality, and team energy are hard to measure. So we default to what's easy. Every time.
The fix: For any job decision, spend as much time evaluating the intangibles as the tangibles. Talk to people who left the company, not just the recruiter. Ask "why did the last person in this role leave?"
Bad Decision #2: Investing Based on a Story
A friend told me about a company that was "going to change everything." The story was compelling. The technology sounded revolutionary. I invested a meaningful amount without ever looking at the financials.
The stock dropped 70% over 18 months. The story was true — the technology was genuinely innovative. But innovation without a viable business model is just expensive research.
The pattern: Falling in love with the narrative and skipping the numbers.
Stories activate our emotions. Numbers activate our analysis. When you lead with story, your analytical brain never gets a chance to object.
The fix: Numbers first, story second. Before you let anyone pitch you a vision, look at revenue, margins, cash flow, and competitive position. If the numbers don't work, no story can save it.
Bad Decision #3: Staying Too Long Out of Loyalty
I stayed in a business partnership for two years longer than I should have. The partnership wasn't working — our visions had diverged, our working styles clashed, and the results showed it. But I felt loyal. We'd started together. Walking away felt like betrayal.
Those two years cost me more than any other decision on this list.
The pattern: Confusing loyalty with sunk cost fallacy.
Loyalty is admirable. But loyalty to a situation that isn't working — at the cost of your own growth and wellbeing — isn't loyalty. It's avoidance.
The fix: Schedule regular "if I were starting fresh" reviews. Every quarter, ask: "If I were choosing partners/projects/commitments from scratch today, would I choose this one?" If the answer is no more than twice in a row, start planning an exit.
Bad Decision #4: Making a Big Decision While Emotional
After a terrible week at work, I impulsively committed to a side project that "would replace my income in 6 months." I didn't research the market. I didn't talk to potential customers. I just wanted an escape from my current frustration.
The project consumed six months of nights and weekends, produced no income, and the real problem (my frustration at work) could have been solved with a direct conversation with my manager.
The pattern: Using a new decision to avoid confronting the real problem.
Emotional decisions feel productive. "I'm taking action!" But they're usually running from something rather than running toward something. The direction matters.
The fix: The 48-hour rule for any decision made during a strong emotional state. Excited, angry, anxious, frustrated — any heightened emotion. Write down the decision. Wait 48 hours. If it still makes sense when you're calm, proceed. Most won't.
Bad Decision #5: Ignoring My Own Pattern
This is the meta-mistake. After decisions #1 through #4, I had all the data I needed. The patterns were clear. But I didn't review my decisions systematically, so I kept making variations of the same mistakes.
The pattern: Not having a system for learning from past decisions.
Experience is only valuable if you extract lessons from it. Otherwise, you don't have 10 years of experience — you have 1 year of experience repeated 10 times.
The fix: Start a decision journal. Write down major decisions, your reasoning, and expected outcomes. Review quarterly. The patterns will emerge faster than you expect.
The Common Thread
All five bad decisions shared one characteristic: I relied on instinct when I should have used a framework.
Instinct works for decisions within your expertise and experience. For everything else — new situations, high stakes, emotional states — you need a system.
Since building my own decision system, I've been studying how great decision-makers avoid these exact traps. KeepRule collects decision scenarios from Buffett, Munger, and others, organized by the type of decision you're facing. It's become part of my framework for catching patterns before they become expensive mistakes.
Your Turn
Look at your last three bad decisions. What patterns do you see? I'd bet they're variations of:
- Optimizing for the wrong metric
- Leading with story instead of data
- Staying out of loyalty/sunk cost
- Deciding while emotional
- Not learning from previous mistakes
Name the pattern. Build a rule against it. That's the entire game.
Learn from the best decision-makers instead of just your own mistakes. Explore scenarios at KeepRule.
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