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Isaac and Jesse with Launching Pros with title Taught to Fail

Learned Failure: Why Small Wins Build Big Success in Business and Life

September 17, 20253 min read
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Why do some people thrive while others give up? We often assume it’s intelligence, money, or being in the right place at the right time. While luck and timing matter, research shows that mindset plays a much bigger role than most realize.

One experiment on “learned helplessness” reveals a powerful truth about why momentum and small wins are critical for entrepreneurs, business owners, and even parents.


The Psychology of Learned Failure

In the experiment, two groups were given word puzzles:

  • Group A started with two impossible puzzles followed by a solvable one.

  • Group B started with two easy puzzles followed by the same solvable one.

The results?

  • Group B, set up for small wins, mostly solved the harder puzzle.

  • Group A, set up for failure, felt rushed, discouraged, and most gave up even though the last puzzle was solvable.

This effect is called learned helplessness — when repeated failure convinces us we can’t succeed, even when the opportunity is right in front of us.


What Entrepreneurs Can Learn

Entrepreneurs face the same challenge daily. If you start with a string of failures, it’s easy to believe you’re “not cut out for business.” But if you design your journey around quick wins, momentum builds and confidence grows.

  • Social media magnifies the problem. We compare ourselves to people claiming massive monthly income. Often those numbers are exaggerated, but the impact is the same: we feel like failures.

  • Define success on your terms. Maybe you don’t want to build a $100M empire. Maybe success for you is steady income, time with family, and flexibility. That’s just as valid.


Momentum: The Key to Progress

Momentum works in business the way it does in sports. Coaches build rookies’ confidence with short passes or easy plays to get the ball moving. Once momentum builds, the entire team performs better.

In business:

  • First clients often come at low prices. You undercharge, overwork, and doubt yourself.

  • But each win matters. Landing that first deal proves you can do it. The next one feels easier. Confidence compounds.

  • Over time, small wins snowball into sustainable growth.

The same applies to parenting. Constant criticism can convince kids they “can’t do anything right.” Balanced praise and constructive feedback help them build momentum and confidence, just like in business.


Practical Takeaways

  1. Start with achievable goals. Break big tasks into smaller ones so you can check off progress daily.

  2. Track your wins. Even calling five potential clients without closing a deal is still forward motion.

  3. Avoid unhealthy comparisons. Your success doesn’t need to look like someone else’s.

  4. Plan in sub-steps. Often, procrastination is simply poor planning. Breaking tasks down makes them less overwhelming.

  5. Celebrate momentum. Recognize when confidence builds, because it fuels long-term success.


Final Thoughts

Failure is inevitable, but learned failure doesn’t have to be. Entrepreneurs who build momentum through small wins are far more likely to push through challenges, grow their businesses, and find fulfillment on their own terms.

Instead of comparing yourself to someone else’s highlight reel, ask:

  • What does success look like for me?

  • What small step can I take today to get closer to it?

When you stack enough small wins, big success follows.

Isaac Johnson

Isaac started his career in digital marketing over 20 years ago. He has had the privilege to work on some great teams and work in depth in SEO, advertising, web design, user-experience design, video product and more. His true passion is helping small businesses and entrepreneurs grow their business so they. can live their dream and support themselves and their families.

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