Overcoming Fear: The Key to Success in the Entrepreneur's Journey
Keith Orlean
Transforming Sales Teams into Consistent Closers | Driving Growth Through Innovative HR & Business Solutions | Sales, Marketing & Brand Strategist
As an entrepreneur, fear is something I’ve grown intimately familiar with over the years. Whether you're launching a startup or scaling an existing business, fear often looms over every major decision. It’s a shadow that can either paralyze you or propel you forward, depending on how you manage it. Learning to embrace the fear and push through is a critical skill for any entrepreneur.
I've always been fascinated by the difference between reasonable and unreasonable fears in entrepreneurship. A reasonable fear might be the challenge of managing cash flow, while an unreasonable one could be the fear that no one will ever walk into your store—despite all your efforts to prepare and promote. The distinction lies in understanding which fears are signals to act on and which are simply distractions.
Take my own experience. I remember opening a new store, feeling proud and excited. I had carefully filled it with inventory, ensured the signage was right, and advertised effectively. Yet, for three days straight, nobody walked through the door. I started to think, "Have I made a big mistake? Did I misjudge the demand?" When a customer finally bought a simple eyeglass chain on the fourth day, it felt like a lifeline. Those first few days, however, could have easily thrown me into a panic, and that’s the nature of fear—it amplifies doubt and makes you question your decisions, even when you’ve done everything by the book.
The key to success is in how you respond when fear threatens to take over. This is where coaching, mentorship, and having a network come into play. If you're stuck, having someone who’s been there before can calm your nerves and help you separate temporary challenges from systemic problems. I’ve learned that it’s not about eliminating fear but rather managing it so that it doesn’t dictate your actions.
The Role of Mentorship in Overcoming Fear
One of the most valuable assets in business is having a mentor or advisor who can guide you through the rough patches. When I think about my early days, I didn’t always have a seasoned mentor to turn to, and the absence of that guidance made the path more challenging. It wasn’t until later that I realized the profound difference it could make.
A mentor can help you see that a slow start doesn’t mean failure, and they can help put things in perspective. I remember times when I reached out to more experienced business owners, who reassured me that quiet periods are a normal part of business, especially in the early days. Their insights helped me avoid overreacting and making rash decisions.
Sometimes, entrepreneurs get caught up in what I call "panic mode"—when business isn’t coming in as expected, the instinct is to start throwing money at the problem without understanding the root cause. A mentor can help ground you, encouraging a more measured approach. They can remind you that building a business is a marathon, not a sprint, and that consistent, incremental improvements often yield more sustainable results than quick fixes.
Embracing the Cycles of a Business Entrepreneur
In many ways, entrepreneurship mirrors the cycles of life. There will be times when everything seems to be going your way, and other times when it feels like you can’t catch a break. I often compare it to sports, where even the best athletes go through slumps. Just because you’re in a downturn doesn’t mean you’ve lost your skills or that success is out of reach. It’s during these low points that the true character of an entrepreneur is revealed.
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One experience that taught me about the natural ebb and flow of business was a time when I opened a new store in a brand-new shopping center. The anchor tenant was open, but many of the other stores were still vacant. I quickly learned that while the location seemed promising, it lacked the foot traffic I had anticipated because the shopping center wasn’t fully developed yet. I had to make a choice: do I double down and invest more in advertising, or do I ride out the slow period until the other businesses opened? I chose the latter, and over time, as the shopping center filled up, business picked up as well.
Risk, Reward, and the Unknown
It’s important to understand that doing nothing out of fear can be more dangerous than taking the plunge. One of the biggest risks I’ve taken was investing significant capital into my business. The fear of losing that money was real, but I always asked myself, "What’s the worst that could happen?" If the answer was something I could live with, then it was a risk worth taking. For me, the worst-case scenario often boiled down to having to start over—a daunting but not insurmountable possibility.
Many people hesitate to start a business because they’re afraid of losing money or not meeting their own expectations. The reality is that not all fears are rational, and some of the most rewarding experiences come from pushing through those fears. Over the years, I’ve come to realize that the biggest growth happens not when everything is going well, but when things go wrong, and you’re forced to adapt.
Why Some Thrive and Others Don’t
I've seen people leave stable jobs to become entrepreneurs because they felt unfulfilled working for someone else. They wanted the freedom to control their destiny. Surprisingly, some of these individuals weren’t the best employees—they struggled with structure and preferred to give directions rather than take them. Yet, when they stepped into the role of business owner, they thrived because they could finally operate on their terms. Their businesses became an extension of themselves, and they were able to create work environments that reflected their values.
For others, entrepreneurship may not be the right path, and that’s okay. It’s not for everyone, and that’s part of what makes it so special. It requires a certain resilience and willingness to accept that there are no guarantees. Some people need the security of a steady paycheck, and there’s no shame in that. The important thing is knowing what you’re suited for and being honest with yourself about your capacity to handle uncertainty.
Learning from Failure
Failure has been one of my greatest teachers. In fact, I’ve learned more from my mistakes than from my successes. When I look back, I see that each failure brought me closer to understanding what it takes to build a successful business. The experience is something that no amount of money can buy. It’s about more than just financial gain; it’s about personal growth, resilience, and finding fulfillment in the journey itself.
When fear is managed properly, it can be a powerful motivator rather than a debilitating force. As I continue on my entrepreneurial path, I’m more comfortable with uncertainty than I’ve ever been. It’s not about eliminating fear but rather learning to dance with it.