Why do many high-performing employees struggle to find similar success as entrepreneurs? The transition from employee to entrepreneur often reveals hidden challenges that weren’t apparent in a structured work environment. This article explores five key reasons why the leap from employee to entrepreneur is harder than it seems

Using current jobs as a crutch

Professionals use their careers as a safety net if things don't work out. This also explains why many peoples‘ side hustle never get off the ground because the ease of bending to fit salaries is simpler than the hustle of starting something new. According to a 2022 Global Entrepreneurship Monitor (GEM) report, 47.3% of adults globally cited fear of failure as a major barrier to starting a business.

Overthinking (challenges in shifting mindset)

In a Youtube video by Finance channel how money works titled Why Dumb People Earn More Than Smart People , research consistently shows that successful entrepreneurs are not necessarily smarter than the average person, they rather have the tenacity and are open to exhausting all their options.

Lack of Self Discipline & Structure

In any given company there’s structure and hierarchy.

Junior staff reports to the supervisor

Supervisor reports to the manager

Manager reports to the director

Director reports to the CEO

CEO reports to the board

Structured environments with clear goals, job descriptions and oversight makes it smoother for employees to thrive which is a sharp contrast to the chaotic and dynamic nature of entrepreneurship
A 2023 survey by McKinsey revealed that 59% of employees in traditional roles prefer structured work environments with clear expectations. This reliance on structure contrasts sharply with the dynamic, ambiguous nature of entrepreneurship, where self-direction is key

Limited understanding of business operation

Going into business requires having a firm grasp of overall business process which can be challenging. Accounting, Marketing, production, Supply Chain Management etc all lies in an entrepreneurs hands.
A report by CB Insights (2021) found that 38% of startups fail because of cash flow mismanagement, a common pitfall for entrepreneurs without financial expertise. Employees specialized in single roles often lack the cross-functional knowledge necessary to manage all aspects of a business effectively.

Lack of risk tolerance

Employees often operate in environments with predictable income and minimal personal financial risk. Entrepreneurship, however, requires accepting uncertainty, financial instability, and the possibility of failure. This shift can be overwhelming for those accustomed to structured safety nets.
The GEM 2022 report also highlighted that only 10% of new entrepreneurs felt fully prepared to handle the challenges of starting a business, reflecting the high prevalence of fear and hesitation in taking bold risks.