The Top 10 Biggest Regrets of Entrepreneurs
One of the greatest regrets of entrepreneurs isn’t failing—it’s not failing enough. They played it safe, took too few risks, and waited too long to act. Every massive success is built on a foundation of failures, missteps, and lessons learned.
Entrepreneurship is a journey of risk, resilience, and relentless pursuit. But ask any seasoned entrepreneur, and they’ll tell you—regret often comes from what they didn’t do, not from what they did.
While success stories dominate headlines, what often gets overlooked are the lessons learned from missed opportunities, fear-based decisions, and roads not taken. If you’re on the path of building something great, take note—here are the 10 biggest regrets entrepreneurs wish they could go back and change.
1. Not Taking More Swings at the Bat
One of the greatest regrets of entrepreneurs isn’t failing—it’s not failing enough. They played it safe, took too few risks, and waited too long to act. Every massive success is built on a foundation of failures, missteps, and lessons learned. The more swings you take, the better your chances of hitting a home run. The entrepreneurs who regret the most are the ones who let fear keep them from taking enough shots.
“You miss 100% of the shots you don’t take.” – Wayne Gretzky
2. Waiting Too Long to Start
Many entrepreneurs spend years “getting ready.” They overanalyze, overplan, and wait for the “perfect” moment. Spoiler alert: it never comes. The biggest breakthroughs come from taking messy, imperfect action. Those who waited too long often regret not starting earlier.
3. Ignoring Their Gut Instincts
Successful entrepreneurs develop strong instincts, but too many regret ignoring their inner voice. Whether it was hiring the wrong person, sticking with a failing strategy, or passing on an opportunity that felt right—listening to logic alone often leads to regret. Your gut is often smarter than you think.
4. Staying in a Bad Business Too Long
Entrepreneurs fall in love with their ideas. But sometimes, an idea isn’t working, and the best move is to pivot or walk away. Many regret the years spent clinging to a failing business instead of adapting sooner. The most successful founders know when to cut their losses and shift direction.
"One of my greatest strengths is the ability to quickly recognize when something isn’t working and make the call to shut it down." – Jeff Hammer
5. Not Investing in the Right People
A business is only as strong as its team. Too many entrepreneurs try to do everything themselves or settle for mediocre hires. Regret sets in when they realize they should have hired smarter, faster, and built a team of A-players.
"If you want to go fast, go alone. If you want to go far, go together." – African Proverb
6. Focusing on Revenue Instead of Profit
Chasing big revenue numbers is exciting—but what good is it if there’s no profit? Many entrepreneurs regret growing fast but without financial discipline. A business that makes $5 million in revenue with no profit is worse off than one making $1 million with a strong bottom line.
7. Not Building a Personal Brand Sooner
Entrepreneurs who focus only on their business and not their personal brand often realize too late that their name, reputation, and network are their most valuable assets. Those who built strong personal brands found it easier to pivot, attract opportunities, and future-proof their careers.
8. Letting Fear Hold Them Back
Fear of failure. Fear of rejection. Fear of looking stupid. Fear is the single biggest killer of dreams. Entrepreneurs who played small, hesitated, or avoided risk often look back with regret, realizing that fear was the only thing standing between them and greatness.
9. Failing to Prioritize Health and Relationships
Too many entrepreneurs grind 24/7, sacrificing their health, family, and friendships. But later in life, they realize that success means nothing if you’re burned out, alone, or unhealthy. Regret sets in when they see that balance wasn’t just possible—it was necessary.
10. Not Thinking Bigger, Sooner
Entrepreneurs who played small, focused only on short-term wins, or failed to dream big enough often regret not scaling sooner, thinking globally, or going after bigger goals. The lesson? You can only achieve what you believe is possible.
Final Thoughts: No Regrets, Just Lessons
If you’re in the game of entrepreneurship, learn from those who’ve been there. Regret isn’t about making mistakes—it’s about not taking enough chances, not listening to your instincts, and not pushing yourself hard enough.
The best way to avoid regret? Take more swings at the bat. Make bold moves, take smart risks, and remember—every failure is just a lesson leading to your next big win.
🚀 Which of these regrets hit home for you? What’s one bold move you can make today to ensure you have fewer regrets tomorrow?
Author Bio
Jeff Hammer is a Mindset Architect and success strategist dedicated to helping individuals break through limiting beliefs, shift their mindset, and unlock their full potential. With decades of entrepreneurial experience, Jeff has built and sold successful businesses, proving firsthand the power of mindset in achieving extraordinary results.
As the founder of DominatingEdge.com, Jeff provides transformational insights, guiding people to reprogram their thinking, overcome self-doubt, and take bold action toward their dreams. His approach blends practical wisdom with high-performance strategies, empowering individuals to create lasting success in business, wealth, and personal growth.
Jeff’s mission is simple: help others master their mindset so they can master their lives.
