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Overthinking and Fear: How Our Brain Tricks Us Into Staying Stuck Financially


Have you ever had a great financial opportunity in front of you—one that made sense, had low risk, and promised high potential—but still, you hesitated? Maybe you overthought it, analyzed it to death, or even talked yourself out of it entirely. You’re not alone. This is your brain’s natural defense mechanism at work, trying to protect you but, in the process, keeping you stuck.


Our brains are wired to prioritize safety and avoid risk, even when the risk is small, and the potential reward is great. When paired with the emotional baggage of past financial failures, this instinct can become a barrier to growth, keeping us in our comfort zones and preventing us from reaching our financial goals.

Let’s explore how this works, why it happens, and, most importantly, how to overcome it.


The Brain’s Trick: Overthinking as Protection

Your brain’s number one job is to keep you safe. It evolved to recognize threats and react quickly to ensure survival. While this served our ancestors well when facing predators, it’s less helpful when deciding whether to invest in a new opportunity, start a side hustle, or try a different financial strategy.


Here’s how the brain works against you financially:

  1. Fear of the Unknown: Your brain sees anything unfamiliar as a potential threat. Instead of focusing on the possible rewards, it fixates on everything that could go wrong.

  2. Overthinking and Analysis Paralysis: To avoid making a “wrong” decision, your brain leads you to overanalyze. You go through endless scenarios, second-guess yourself, and ultimately decide it’s safer not to act.

  3. Reinforcing the Comfort Zone: Your brain loves the comfort zone—it’s predictable, safe, and familiar. Venturing out of it feels uncomfortable, so your brain convinces you to stay put, even if that means staying stuck.


The Weight of Past Financial Failures

If you’ve had a financial setback in the past—whether it was a bad investment, job loss, or a failed business—it adds another layer to this mental game. Your brain remembers the pain, embarrassment, or loss and works overtime to ensure you don’t feel that way again.

  1. Fear of Repeating Mistakes: You may believe that trying again will lead to the same failure, even if the circumstances are different.

  2. Loss Aversion: Studies show that humans feel the pain of loss twice as strongly as the pleasure of gain. This means even a small risk of loss can feel unbearable, while the potential for a significant gain feels less motivating.

  3. Self-Doubt: Past failures can chip away at your confidence, making you question your ability to make sound financial decisions.


The Cost of Staying Stuck

While your brain thinks it’s protecting you, staying in the comfort zone has its own risks:

  • Missed Opportunities: How many times have you looked back and thought, “I should have taken that chance”? Those missed opportunities add up and can cost you time, money, and growth.

  • Stagnation: Without taking calculated risks, you’re unlikely to move forward financially. Sticking to “safe” options often means staying in the same place—or falling behind.

  • Regret: Over time, the regret of not trying can outweigh the fear of failure. Wondering “what if” can be more painful than taking a chance and learning from it.


How to Overcome the Brain’s Tricks

  1. Recognize the Fear for What It Is

    • Understand that fear is your brain’s way of trying to protect you. Acknowledge it, but don’t let it control your decisions. Ask yourself, “Is this fear rational, or is it just my brain playing tricks on me?”

  2. Reframe Failure as Learning

    • Instead of seeing past financial failures as defeats, view them as lessons. What did you learn from the experience? How can you apply that knowledge to make better decisions moving forward?

  3. Take Small Steps

    • If the idea of a big leap feels overwhelming, break it into smaller, manageable steps. Start small with a low-risk financial decision to build confidence and ease your brain’s fear of loss.

  4. Focus on Potential Gains

    • Shift your mindset from “What if I lose?” to “What could I gain?” Write down the potential benefits and remind yourself why the opportunity excites you.

  5. Educate Yourself

    • Fear often stems from uncertainty. The more you understand an opportunity, the less intimidating it becomes. Take the time to research, ask questions, and gather information to make an informed decision.

  6. Seek Support

    • Talk to mentors, or trusted friends who have experience in the area you’re considering. Their insights and encouragement can help you move past fear and make confident choices.

  7. Practice Gratitude for What You Have

    • Gratitude shifts your focus from fear and lack to abundance and possibility. By appreciating your current financial situation, you can make decisions from a place of confidence rather than desperation.


Your brain’s instinct to protect you is powerful, but it doesn’t have to control your financial future. Recognize when fear and overthinking are holding you back and take proactive steps to push through. Yes, trying something new can be scary, but staying stuck in the same place is far scarier in the long run.

Remember, every great financial success starts with a willingness to step outside your comfort zone. Trust yourself, take small, calculated risks, and watch how your courage creates opportunities and growth. Your brain may be wired to keep you safe, but your heart knows you’re meant to thrive. Choose to follow it—and take that first step today.





















Darrell (MSCIA, Author, Retired Marine Corps Vet, Speaker, Coach)

Right Side of Money LLC










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