top of page
  • Writer's pictureDr. Cristina DiPietropolo

9 Biggest Challenges Every Entrepreneur Should Learn to Overcome – Part 2

Entrepreneurship can bring out a wide array of emotions in your life. It can sometimes be exhilarating, challenging, and exhausting, but that's not necessarily a bad thing as long as you know how to navigate through those emotions effectively.

In our last blog post, we shared our insights on some of the challenging aspects entrepreneurs face running a business, including Fundraising and Cash Flow, Delegating Tasks, and Time Management. In the final installment of this two-part series, we will focus our discussion on the following: Dealing with uncertainty, Make it happen, Decision-making and isolation, Speed or perfection, Dealing with competition.

5. Dealing with uncertainty

Entrepreneurship is unique, and no two entrepreneurs have the same journey. That leaves a lot of room for uncertainty. The fear of the unknown can often trigger you to make bad decisions, and the pressure of trying to make the right choices can take a significant toll on your psyche.

So, how can you deal with the day-to-day unknowns? What should you do to drive your company through the darkness of uncertainty? The first thing that we suggest you do is to stop worrying. Easier said than done, but the reality is that emotional intelligence, particularly self-awareness, is vital in helping you as an entrepreneur.

The list of 'might haves' and 'would haves' can be endless. You cannot lead an organization in the constant fear of what might happen in the future. As a successful entrepreneur, you have to embrace uncertainty as a challenge, not a threat, and stay on your journey.

6. Make it happen

Another massive challenge entrepreneurs face is executing ideas that look extremely profitable on paper. In other words, they lack the ability to develop a blueprint of how to put a specific idea into action.

To nail execution, you should learn how to develop a blueprint around an idea and create a process to maximize the probability of success. So, what does the process of 'making it happen' look like?

Entrepreneurs have to begin by focusing on strategy execution. You need to define a system or methodology that enables you to execute the idea, including writing a solid and measurable plan that effectively manages and prioritizes tasks. Every person involved in the plan should be aligned and trained, if necessary, to bring the strategy to fruition. Lastly, you should measure the idea's success and further innovate or optimize the strategy to generate better results. In other words, entrepreneurs should learn, adapt, and innovate.

7. Decision making and isolation

The entrepreneur is solely responsible for making decisions that impact the growth of an enterprise and the employees working for it. At the same time, entrepreneurs are responsible when the business doesn't perform as expected. In other words, as an entrepreneur, you are always in the line of fire. Such massive pressure can psychologically impact a person and cause a disconnect within the company.

How can entrepreneurs mitigate the impact of this ever-increasing responsibility? First, you have to figure out how to embrace the pressure because it comes with lucrative rewards. Endure and deal with the stress head-on. Second, don't push yourself to make every decision for the company. Find people you can trust and confide in. Create a small team of people that share your same goals and vision. Use the team to brainstorm ideas and solutions to a problem. You don't have to bear the weight of the world on your shoulders. Be humble and reach out to people. You'll be amazed at how willing people are to come alongside you.

8. Speed or perfection?

As an entrepreneur, the never-ending pursuit of perfection can slow your progress. But, paying attention to the details is important too. So, how should entrepreneurs maneuver to strike a balance between progress and perfection?[1]

'Analysis paralysis' is real and can make you spend hours analyzing a situation without reaching a definite conclusion. Since entrepreneurs have to make countless decisions in a day, it makes sense to figure out ways to distinguish between small and significant problems.

Figure out the importance of the decision you are making. If it's a minor decision, don't waste much time on it. The impact of your decision isn't going to be massive. Make a decision and move forward. However, when dealing with major problems, make sure you have all the information required to make a solid decision. Postpone the decision-making if you still need more information and avoid making decisions under stress or extreme pressure. No one ever makes a good decision under these types of circumstances.

9. Dealing with competition

Lastly, know that other companies in your niche will not lose an opportunity to knock you out of business. Competition can be fierce, and that's how it will always be. Entrepreneurs need to learn how to cope with increasing competition. From conducting extensive competitor analysis to becoming an early adopter of major industry trends, prepare yourself to leverage every opportunity to beat the competition.

Develop a solid marketing game plan to double down on your strengths and focus on what you do best. Build a community around your brand and stay connected with your audience by developing a social media strategy that creates long-lasting relationships with your customers. Take the time to profile your customers and your market.[2]

While benchmarking is crucial in any business, you need to stay true to your core competencies, and benchmarking is a great way to do that. It's not only about what the competition is doing. It's also learning what you don't want to do as an entrepreneur.

I never worry about what my competitors are doing. Instead, I focus on my clients and leverage my talents and resources to help them execute their strategies. Truth be told, the only person I compete with is myself!! I'm always trying to see how much further I can go and take things to the next level to acquire more knowledge to share with others.

Keep reading!

There you have it. In this two-part blog series, we have shared some of the most challenging aspects of running a business that every entrepreneur should endure. Haven't had a chance to read Part 1? No problem, click here, and don't forget to check out our other informative posts on the blog!

People also read

Dr. Cristina Rosario DiPietropolo is the Founder and Chief Executive Officer at Leader Essentials Group, with extensive experience across multiple industries and highly skilled in the areas of strategic planning, organizational behavior, human resource management, change management, leadership, and digital marketing. Over ten years of teaching experience as a university professor of management, with a special focus on leadership in entrepreneurship, organizational behavior, and international management.


[1] Cremades, A. (2019). The 10 biggest challenges every entrepreneur faces (and how to Conquer Them). Forbes. 06/14/21. [2]Polson, B. (2019, May 31). Council post: Three steps for startups to get ahead of competition. Forbes.

17 views0 comments


bottom of page