Unleashing Your Entrepreneurial Spirit by Conquering the Fear of Judgment
- The Freedom Resource Hub
- 7 days ago
- 8 min read
Updated: 4 days ago
When I reflect on how many people marry, befriend, or even start businesses with others, thinking they truly know them, I realize how often we miss the mark. This is especially true for those of us in our forties, fifties, and sixties.
Growing up in the Western world, many of us were raised with conservative values, respect, and a strong sense of morality.
These values shaped how we viewed relationships and success. Yet, despite this foundation, I’ve seen countless stories where people, including myself, didn’t really know the person they committed to or the path they chose. This disconnect can also affect our entrepreneurial journey, especially when we care too much about what others think.
The Weight of External Opinions on Your Drive
Many entrepreneurs, especially those chasing financial freedom, face a hidden challenge: the fear of judgment. This fear often comes from the values instilled in us during our upbringing. In the past, being conservative and caring about others’ opinions was seen as a sign of respect and wisdom. But in today’s fast-changing world, this mindset can hold us back.
When you constantly worry about how others perceive your choices, you might:
Avoid taking risks that could lead to growth
Stick to safe, conventional paths instead of innovative ones
Delay or abandon your entrepreneurial dreams to fit in
This misplaced emphasis on external approval can dampen your entrepreneurial fire. It creates a barrier between your true potential and the reality you want to build.
My parents grew up in Jamaica, where traditions and religious values were deeply respected. Marriage was approached with caution, and relationships were often hands-off until certain milestones. These values were passed down to me, and I carried them into my adult life in the United States. I noticed that many adults, even those not raised in religious homes, shared similar conservative views.
Yet, despite these shared values, divorce rates remain high, even in religious communities. This suggests that knowing someone superficially or adhering to societal expectations doesn’t guarantee success in relationships or ventures. The same applies to entrepreneurship. If you start a business just to meet others’ expectations or to avoid judgment, you might not truly know your own goals or capabilities.
Rethinking Your Thinking
It’s time to pause and really reconsider how we view life and ourselves. So often, we unconsciously perceive entrepreneurship and business ownership more negatively than positively, without even realizing it.
Think about it: we meet people everywhere—at school, work, a party, on a bus, or even through an app. And what do we notice first? Usually, it’s the image, the polished version of someone they present to the world.
We rarely see the real, unfiltered person: messy hair, no makeup, unbrushed teeth, or even morning breath. Yet somehow, that curated image draws us in. It excites our curiosity, sparks interest, and shapes our first impressions.
The question is, how much of the true person do we actually perceive? And more importantly, how often do we let these surface impressions limit how we view potential, opportunity, and even ourselves?
Rethinking our thinking isn’t just about noticing others differently; it’s about breaking free from old conditioning, seeing potential where others don’t, and embracing the possibilities in business, life, and personal growth.
How Conditioning Shapes Our Choices More Than We Realize
Growing up in a culture where others' opinions hold significant importance deeply influences us, often more than we acknowledge, especially on a subconscious level. The paths we take in life, such as our field of study, career choices, and even whom we marry, are frequently shaped by the subtle pressure of public opinion. Before we label it as “choice,” we have already been conditioned. I believe we are more conditioned and conformist than we realize.
This conditioning extends beyond relationships and education, significantly affecting how we earn a living. Nowadays, the concept of a side hustle is celebrated and encouraged. However, for many years, earning money outside of a traditional job was seen as undesirable or even embarrassing, often considered suitable only for those without a college degree or a “proper” education. This mindset confined many people to limitations that were never truly theirs.
Fortunately, the narrative is shifting. More individuals are recognizing that creating additional income streams is not a sign of failure but a mark of awareness, adaptability, and courage.
Financial Security: A side hustle provides an additional income stream, creating a financial cushion in the event of job loss, rising expenses, or unexpected life changes. It offers peace of mind and greater control over your financial future.
Skill Development: Side hustles allow you to learn new skills or strengthen existing ones. These skills often transfer into improved confidence, expanded opportunities, and even career advancement in ways traditional employment may not offer.
Pursuing Passions: A side hustle gives you the freedom to explore interests outside your primary job. What begins as a passion or hobby can evolve into a profitable venture that brings both fulfillment and financial reward.
When we begin to challenge old conditioning and question why we believe what we believe, we open the door to possibilities that were always available, just waiting for us to see them differently.
Stack and Grow
Remember 10, 15, 20 years ago when starting a side hustle felt impossible without mountains of capital? Back then, opportunity often came with flashy promises and catchy phrases like “Fire your boss!”, “30-day financial freedom!”, “Push through all the NOs to get your YES!”
I’ll admit it, those words were music to my ears. They got me excited, motivated, and yes… sometimes led me into opportunities that didn’t pan out. Many of us know that feeling meeting someone all dressed up, looking perfect and confident, only to realize the reality isn’t quite as glamorous.
Here’s the good news: today, the game has completely changed. Technology has leveled the playing field. You can:
Write a book in minutes
Build a website in seconds
Create an app without knowing a single line of code
Draft a business plan effortlessly… and all of this with AI tools at your fingertips.
No massive loans. No quitting your job. No exposing your ideas to skeptical friends or family. You can start small, smart, and strong.
So why aren’t more people doing it?
Fear of failure
Believing it’s too hard
Thinking a job is the only sensible option
Feeling overwhelmed by too many tools
Here’s the mindset shift: seeing what’s already been created is motivation, not limitation. Why reinvent the wheel when you can build on it? Someone else did the testing, the research, and the groundwork; now you can take 90% of it, make it your own, and start growing.
Stack your tools. Stack your skills. Stack your ideas. Then grow. The resources are here, the knowledge is here, and the opportunity is yours if you’re ready to take it.
Your Circle, Your Currency
Success isn’t just about what you know; it’s about who you surround yourself with. The owner of One Marketplace understood this perfectly. After noticing a pattern in his previous company where people joined as fast as they left, he realized the old model was no longer working. Short-term excitement wasn’t translating into long-term success.
By creating One Marketplace, he broke the cycle. Today, the platform enjoys retention rates that are highly encouraging, and members are thriving as “Smart Shoppers,” sharing the platform and helping others start their own businesses. The takeaway? Your circle can make or break your success, but only if you know how to leverage it.
We have the power to make our circles as small or as large as we choose, but it’s not enough to just have a network; it’s about maximizing it.
Financial Freedom: A strong circle can help you create passive income, giving you the freedom to earn without being tied to a desk or a fixed schedule. Financial independence becomes a real possibility when you tap into your network strategically.
Flexibility and Convenience: Passive income on the go lets you work from anywhere, giving you the convenience and freedom to manage your time effectively. Your side hustle can fit your life, not the other way around.
Networking and Collaboration: Engage actively with your current network. Attend events, join online communities, and leverage social media platforms. Share your side hustle, seek referrals, and collaborate with like-minded individuals to expand your reach.
Value Exchange: Offer value to your network in return—mentorship, skill swaps, shared resources, or guidance. Mutually beneficial relationships make your circle stronger and your side hustle more successful.
When you treat your circle as currency, every connection becomes an opportunity to grow, collaborate, and succeed. The bigger and smarter your circle, the further your side hustle can go.
Mobile Money Moves
Starting a side hustle today is more accessible than ever and doesn't have to involve much risk. Give something a try, see how it feels, and if it's not for you, move on. There's no need for a large investment or fear of a big loss.
Alternatively, you might find a passion for it and achieve genuine success. That additional income is empowering, providing you with freedom and the opportunity to leave a legacy. With the help of modern tools, coaching, and mentorship, you can achieve results without dedicating endless hours.
Rest assured, we're not suggesting strenuous, labor-intensive work like house cleaning, dog walking, or lawn care. These are intelligent, modern, mobile-friendly ways to earn money from anywhere, on your own schedule.
Financial Freedom & Flexibility: Passive income enables you to meet living expenses without being confined to a traditional 9-to-5 job. With a consistent income flow, you have the freedom to follow your passions, travel, and enjoy quality time with family, all while your business continues to generate earnings in the background.
Personal Growth & Empowerment: Managing an online business enhances confidence, skills, and problem-solving capabilities. Whether it's digital marketing or automation strategies, each phase of the journey contributes to your personal and professional development. The satisfaction of creating a self-sustaining business that operates on your behalf is unparalleled.
You don’t have to wait for passion to strike. It’s perfectly fine to start from an economic standpoint, focus on earning first, then let passion grow along the way. Small wins matter; they build momentum, confidence, and often lead to big breakthroughs. Celebrate every little success. Be grateful. Cultivate the habit of progress, and watch your mobile money
moves turn into freedom, empowerment, and opportunity.
Join a community of Freedom Chasers, where you can unleash your entrepreneurial spirit, discover your strengths, enhance your strategy, and maintain accountability.
Take action today. Reflect on your mindset, evaluate your circle, and seek new opportunities. Your journey towards financial freedom and personal success starts now.
Act today. Discover new opportunities, utilize your skills, and begin crafting the future you deserve. Don’t hesitate—your freedom, growth, and success are just one bold step away.
Moments For Partnership
Right now, through our Moment for Partnership, we’re working toward a simple but powerful goal — raising $500 each month to support Gospel Foundation International Healing Ministries.
GFIHM is a Bible-based, Spirit-led ministry reaching families through prayer, healing, teaching, and global digital outreach. Your support helps keep this work going and growing.
Whether it’s $10, $25, or more, every tax-deductible donation makes a difference.
If you feel led to give, visit gfihministries.org/give.
That link is in the show notes.
Together, we can meet the goal — and make real impact.
Through our Moment for Partnership, we’re working toward a monthly goal of $500 to support Women & Men of Excellence Outreach Ministries.
WAMOE is dedicated to strengthening individuals, families, and communities through faith, leadership development, and outreach rooted in excellence and purpose.
Your support helps expand their programs, empower leaders, and create lasting community impact. Whether you give $10, $25, or more, every tax-deductible donation moves the mission forward.
If this aligns with you, visit wamoe.org/give to donate.
Let’s build excellence — together.
Watch Full Episode below:
Blog by Keith Marrett
Edited by AR Desire Creations
Comments