MicroConf On Air MicroConf Tactics: NEVER Make These 6 Mistakes (Lessons from 20 Years in Business)
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Nov 5, 2025 Rob Walling dives into six costly founder regrets that almost derailed his business. He discusses the pitfalls of overconfidence after early wins and how the arrival fallacy can lead to dissatisfaction. Walling shares insights on addressing anxiety, celebrating successes, and the importance of internalizing achievements. He emphasizes the limitations of a solopreneur mindset and the necessity of hiring the right people. Finally, he advises filtering feedback carefully, focusing on trusted sources over random online noise.
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Early Wins Fueled Risky Overconfidence
- Rob Walling overestimated his abilities after early wins and launched new products assuming they'd succeed.
- That overconfidence led to financial strain, burnout, and relationship stress around 2014–2015.
The Arrival Fallacy Is A Moving Target
- The arrival fallacy is believing happiness lies just past the next milestone.
- Entrepreneurship has no final finish line, so milestones bring only short-lived happiness.
Use Wins To Build Real Confidence
- Let your wins build genuine confidence instead of dismissing them as luck.
- Use that confidence to take progressively larger, manageable bets to grow your career.