Want To Take Risks But Don't Know How? Learn How To Start

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Have you always been someone who plays it safe and feels unsure about how to break out of that zone? You’re not alone, and I’m here to help. But first, let me share a personal story that may resonate with you.

Growing up, I was an introverted person who was scared to speak in class, hesitant to go places alone, and afraid to make certain decisions. I often accepted whatever life threw at me, which left me feeling stuck. I felt like I hadn’t achieved enough and wasn’t putting myself out there or doing my best. At times, I gave up easily, exhausted by my fears. So, I made up my mind to push myself beyond my limits, no matter how hard it might be, even if it meant starting small.

I decided to begin by doing something different with my hairstyle. I had always played it safe, sticking to familiar hairstyles that I knew looked good, or allowing my sister to try new styles at salons before I did. But this time, with my new mindset, I chose not to settle for safety—I went for what I wanted. I decided to try a hairstyle I had always been afraid to attempt, done by someone who wasn’t my regular hairstylist. And you know how intimidating it can be to go to someone unfamiliar, right?

During the process, I was anxious; I didn’t want to spend money on something I didn’t like. But in the end, did I like it? Yes, I did, and I had no regrets.

You might be thinking, “What if it didn’t turn out well, and I regretted it?” Here’s the thing: besides the sense of satisfaction I felt when it was done, there’s always another opportunity to try until I find what I truly like. The biggest obstacle to risk-taking is fear, and that fear often stems from uncertainty about the outcome of venturing beyond your comfort zone.

Understanding Different Categories of Risk

When someone tells you to take a risk, the first thing that might come to mind is money, right? Well, there’s much more to it than that. Risks can be categorized based on context: 

  • Personal: Everyone experiences personal risks at some point, as they relate to our everyday lives. They affect our social, health, career, and emotional well-being. The story I shared earlier falls into this category. For instance, there may be moments when you need to open up about past traumas or insecurities, quit a well-paying job to pursue your passion or use your voice in challenging situations. It’s essential to choose growth over fear because fear is merely a distraction.

  • Financial: This is the most commonly recognized type, involving financial decisions that can either lead to losses or profits. This might include investing in a business or lending money to a friend. Many people look for quick ways to make money through get-rich-quick schemes based on luck rather than skill, and they often end up losing their investments. Losing money isn’t limited to these schemes; investing in a business or the stock market carries risks as well. This is why weighing the pros and cons before making financial decisions is crucial.

  • Business: If you are a leader or employee in an organization, an entrepreneur, or involved in any profit-generating venture, business risks will apply to you. These risks might include uncertainties or potential losses that could impact your ability to achieve goals, maintain profitability, or ensure long-term growth. Recognizing potential issues early on can help you protect your business and remain competitive in the market.


Taking risks is essential for personal growth. You may have heard stories about great men and women throughout history who accomplished remarkable things. For example:
  • Neil Armstrong was the first person to walk on the moon.
  • Bill Gates was a programmer who founded Microsoft.
  • Thomas Edison attempted to create the electric light bulb 999 times before he succeeded on the 1000th attempt.
These examples show that pushing your limits may not be easy, but it’s certainly worth it. Here’s why:
  •  Taking risks can place you in situations that distinguish you from others. While many settle for the average, you have the opportunity to push yourself beyond the norm and achieve something remarkable.
  • It is an inevitable part of life, encountered in nearly every journey. Approaching with caution can enable you to do extraordinary things.




This process involves taking strategic actions by carefully weighing the pros and cons to minimize potential downsides while achieving something significant. Here’s how to carry this out:

  •  Define Your Goal: Understand why taking these chances is necessary and familiarize yourself with the specific challenge you are considering.

  • Research: Gather all the information you  , including expert research and data.
  • Assess Probability: Weigh the pros and cons to determine if the potential gain is worth the challenge.
  • Start Small: Experiment with a smaller test before scaling up your efforts.
  • Consider the Worst-case Scenario: Assess the situation to understand the worst possible outcome and determine if you can handle it.
  • Manage Your Emotions: Fear can hinder your success; but when you prepare and see it as a signal and not a stop sign, you can fulfill your goals.
  •  Take Action: Once you’ve made your decisions, put your plans into action and be productive.
  • Monitor Progress: Check your progress, make adjustments as necessary, and learn from the outcomes.

Most importantly, remember, any risk you want to take should not be based on chance. Instead, they should rely on skills and effort. By doing so, you can create lasting value and avoid spiraling into harm without gaining anything meaningful.

4 Benefits of Taking Risks in Life

  • Accelerated Personal Growth and Development: Stepping out of your comfort zone pushes you to develop new skills and take on new challenges. This process helps build your confidence, self-esteem, and resilience, while also allowing you to learn from your mistakes.

  • Increased Opportunities: Taking risks exposes you to new experiences and people you might not have encountered otherwise. 

  • Sense of Satisfaction: Confronting the fears that hold you back brings a sense of pride and accomplishment. You prove to yourself that you are capable of tackling tough challenges. Even if the outcome is not what you hoped for, you gain confidence simply from the act of trying.

  • Improved Decision-Making: Engaging in risk-taking fosters the habit of thinking ahead, analyzing situations, and considering potential consequences. This leads to more informed decision-making.

Best Books on Risk-Taking to Guide Your Decisions

The mind is a powerful tool that controls our actions based on what we feed it—be it what we see, hear, read, or otherwise absorb. This influence can either benefit or hinder us, shaping our risk-taking behaviors based on what we know.

In this context, your mindset affects how you approach risk, guiding you toward either positive (calculated) or negative (impulsive) decisions. 

I've gathered useful resources on risk-taking in finance, personal development, and business that can help you take calculated steps, even subconsciously, to guide your decisions and influence your actions. 

  1. Financial Risk 
  Photo credit: Pinterest 


This book highlights the impact of emotions on financial decisions. In "The Psychology of Money," Morgan Housel explores how our emotions, upbringing, and life experiences shape our perceptions of money and influence our willingness to take financial risks. The book offers practical wisdom applicable to every stage of life.

It is recommended for:
  • Investors who wish to understand the emotional aspects of decision-making.
  • People who struggle with saving or spending habits.
  • Entrepreneurs and creatives who want to earn money on their terms.
  • Individuals assessing their risk.
The Psychology of Money isn’t just about finance — it’s about how you think. A must-read for anyone ready to build smarter habits and lasting wealth.

  2. Personal Risk

  Photo credit: Pinterest
 

This book is an excellent self-help book that encourages taking risks despite fear. It emphasizes that fear is a natural part of life but should not control us.

The excerpt, “The fear will never go away as long as I continue to grow,” serves as a reminder that fear is an ongoing companion as we evolve. As we push ourselves out of our comfort zones, we will inevitably encounter fear. Instead of avoiding it, we should recognize it as a sign of growth and progress.

This book is an encouraging read for:
  •  Anyone feeling stuck or held back by fear, whether it’s fear of failure, change, or the unknown.
  • Those seeking ways to break through personal barriers and take meaningful action.
  • Individuals who question their abilities and struggle with confidence.
  •  People embarking on new chapters in their lives.
The book provides practical tools and mindset shifts to help overcome these challenges.

   3.Business Risk

      Photo credit: Pinterest
   

Jim Collins examines why some companies successfully transition from being good to great and manage to maintain that greatness, while others fail. This book is filled with research-backed insights and strategies that can guide businesses in moving from mediocrity to excellence. The main takeaway is that achieving greatness isn't about radical changes or flashy tactics; it's about consistent effort, disciplined leadership, and a focused commitment to the right priorities.

The excerpt “Good is the enemy of great” illustrates how few people strive for great lives, while many settle for good lives simply because it is easier.

This book is ideal for:
  • Individuals who refuse to accept mediocrity.
  • Anyone aiming to elevate their career.
  • Aspiring entrepreneurs who are starting out and seeking to grow.
  • Business leaders and CEOs responsible for guiding companies or organizations.
Taking risks doesn’t have to mean making wild or reckless decisions. It’s about stepping out of your comfort zone with intention, learning as you go, and being okay with not having everything figured out. Whether you’re starting small or going all in, the key is to start — and stay curious.

The books recommended above are great companions on this journey, so take the first step even if it's a small one. 




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