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The 5 Biggest Challenges Entrepreneurs Face, and How to Solve Them

Being an entrepreneur can be stressful. But, there are ways to make your life easier. Here are some common challenges, and three ways to face them head on.

TC North //February 14, 2024//

The 5 Biggest Challenges Entrepreneurs Face, and How to Solve Them

Being an entrepreneur can be stressful. But, there are ways to make your life easier. Here are some common challenges, and three ways to face them head on.

TC North //February 14, 2024//

Entrepreneurs start a business for various reasons: to attain more freedom, to have more control of their life or income, to build something great, or to make a difference — or for all these reasons. As entrepreneurs build their leadership team, the new leaders typically want the same things.

But what frustrations do entrepreneurs encounter while pursuing their dream that may turn it into a nightmare? During my three decades of working with them, I’ve noticed that most experience the following five frustrations.

READ: Mastering Work-Life Balance — Practical Steps for Entrepreneurs to Thrive

1. Lack of control

Typical entrepreneurs want to feel in control of their life and business, but most find that their business controls them and their life. I’ve heard comments like, “I’m overwhelmed,” “I’m exhausted” or “I have no personal life” from more entrepreneurs than I can count. They want to control their time, yet the needs and demands of customers, potential customers and employees often dictate how their time is allocated.

2. Nothing’s working

When leaders keep trying to improve their organization but nothing helps, this can cause desperation, anxiety and depression. I recently coached an entrepreneur I last worked with 11 years ago. He had a great run, and his business made the Inc. 5000 fastest-growing private companies in the U.S. several years running. He recently came in because his top line and net revenue had significantly decreased the past three years. He had hired several consultants and implemented everything they suggested, but nothing significantly moved the needle, leaving him slightly depressed.

3. Revenue, profit, and cash flow challenges

The entrepreneurial dream almost always has a financial win, usually a big one. However, especially in the early years, there’s often a month-to-month struggle to bring in revenue, be profitable, pay the bills and make payroll. Almost every entrepreneur has, at some point, lost sleep because they feared they couldn’t make payroll.

When there’s a cash flow issue, the entrepreneur typically either doesn’t take a salary or takes a small salary until the cash flow can support it. In contrast to the animal world where the alpha of the pack eats first, in the entrepreneurial world, the original entrepreneur — and often the other leaders — eat the leftovers (if there are any) when times are tough. 

READ: Managing Stress as an Entrepreneur — How Stress Can Impact Your Work, and How to Regain Control

4. People problems

This is one of the most prominent and persistent of all frustrations. In a survey by EOS Worldwide, the company that teaches the Entrepreneur Operating System® (EOS®), 82 percent of the leaders who came to them for help cited employee problems as their biggest concern.

In fact, a CEO once said to me that his company “would be a great business except for the employees and customers.” He wasn’t exactly a people person, but he drove home the point. Just this week a CEO asked my advice on how to deal with a member of the leadership team that hadn’t been meeting expectations. During every EOS quarterly planning session with leadership teams, we address the question, “Are there any right people, right seat issues”? Then we go through an issue-solving process to determine the best way to address those issues.

5. Hitting the ceiling

When a business hits a growth ceiling, it either: (1) breaks through and has a growth spurt, (2) stays the same or (3) crashes and either shrinks or goes out of business.

Every company hits ceilings. That’s completely normal. How the company has prepared for those ceilings and how the company reacts when those ceilings eventually stunt consistent growth determines which of the three outcomes is the result.

About a decade ago, one of my small professional service business entrepreneurs was stuck at $700k in annual revenue. He was doing all the service delivery and was ready to close the business. He worked through a major mental block became a member of the Inc. 5000 for several years in a row. His company was recently acquired for $39 million.

READ: Essential Tips for Starting a Business — How to Ensure Longevity and Sustained Growth

The 3 requirements to solve the 5 frustrations

These five frustrations are mostly resolvable (never 100 percent — where’s the fun in that?). The solutions have various parts, some specific to the individual company, but there are three requirements that a company or team always needs to maximize growth and minimize frustration:

  1. A high-performing leadership team that has a great leadership and management system that scales for growth.
  2. A company culture where people thrive.
  3. An environment where almost everyone is in a role where they are in their brilliance.

Before you hit your next ceiling, or if you already have, consider addressing these three requirements to maximize growth and minimize frustration.


TC North, PhD is a Certified EOS Implementer® and international speaker. He is co-author of the best-selling book, “Fearless Leaders,” and Techstars All-Star Mentor/Coach. He has coached 100s of entrepreneurs to become high-performers and in recent years he has helped two entrepreneurs go from years of frustration and flat revenues to become members of the Inc. 5000 fastest-growing private companies in the US.