Overcoming the Dark Side of Entrepreneurship

 · 7 min · Nasir

Being an entrepreneur has its awesome benefits. Lets take a look at some entrepreneurial challenges and some tips to manage them.


Being an entrepreneur is, generally, doing what you love and getting paid for it; having the freedom to run your own business, getting empowered by watching it grow and bringing your creativity to life. We have heard many successful entrepreneurship stories, and we know for a fact that it is a mountain to climb; around 90% of start-ups fail.


These are some tips that I’ve compiled and hoped that they may help you in overcoming the dark side of entrepreneurship. For this article, lets examine suitable actions that can be taken based on the 5 stages of The Emotional Cycle of Change by Don Kelley and Daryl Conner.

Which stage do you think you are in? Do share in the comment section here.

Uninformed Optimism

When we hear of the inspiring success stories, there is an air of optimism that devours us and is the most exciting stage. You are motivated, wanting to push yourself further and change for the better.

Failing to plan is planning to fail. This stage is where planning is crucial. The mistake that most people make is to not be prepared for what comes next in their journey of entrepreneurship. For a business to run and grow, fundamentally, you need these three things:

NeedsQuestions to Ask
KnowledgeHow do I progress? What is the knowledge base required? Do I need to take any educational course? Is it paid or free? How long do I need to master the knowledge?
MoneyHow is my cash flow? Do I have any stable income, liabilities, sponsorship, loan, dependencies? Do I recruit partners? What are the costs breakdown?
TimeIs this your side hustle or a full-time venture? Do you have another job/business? Do you have time for your family? How will you balance them? How much of your time are you willing to invest?

Even with such careful planning, the venture still has a risk of failing. Some common reasons are

  • not having enough finances,
  • marketing flaws,
  • a partnership that did not work out, and
  • lack of resources to cope with the struggle.

Informed Pessimism

Business Venture
A business venture can be exciting but also scary

So you started your business. It is running, and you are faced with your first problem, the second problem, the third problem. And then you started to think whether or not you are doing the right thing.

All that positive energy from the initial stage turns negative when you start to learn more about the burdens of your demanding path. You shrug it off, pretend that everything is normal. And then it gets worse. At this stage, here are some of the things that you can do:

Design a Business Plan.

Normally, a business plan is created to apply for financing. You can do that. Or you can also get it done as a measure of self-assurance and to know how to move forward in your venture. Review and revise it periodically to get it relevant to whatever stage you are. A business plan depicts the detail specifications of the products/services you do, your competition, management, marketing, and, finances of the company.

Start Small.

As a start-up, your resources may not be huge. Therefore, serve those based on it. You’d want to grow at scale with the demand for your products or services. Trying to serve more than what you can handle may cause burnout which is a detrimental state to you and your business. Have a target audience and keep your production line simple and basic. As you and your business get more confident, only then, you can grow and diversify to maintain your quality and loyal customers.

Find your Passion

Entrepreneurship is being able to do something that you love at no cost. This sentiment is because most of the start-ups will not gain any substantial profit from hefty initial costs of company creation, production and marketing to grow your business. The profit that you gained may only cover the bare necessities or might even be at a loss. So you need to have the passion and perserve by having to work for free during early stages.

Valley of Despair

Failing and giving up is not the same

This duration is the point where many entrepreneurs fail and give up. After all that disappointment and frustration, all the naysayers egging you, saying that you can’t make it.

This is the turning point where a few passes and most fall back to the first stage and find a different uninformed optimism. There is a difference between failing and giving up.

  • Failing is making mistakes; you learn from it, and it builds your character, knowledge and experience.
  • Giving up is throwing all of it away and going to a different direction.

Sometimes, it is better to give up and start fresh. But most of the time, you would want to escape that deadly cycle and persevere to get past this stage. The stage that will test how passionate you are about the things that you do.

Informed Optimism

When you pass the lowest stage, you start to feel that you can surpass anything. You’re confident, and you are able to see how your business benefits yourself and those around you. As you learn more about the industry you’re in, you will know how to overcome difficult situations, have a Frequently Asked Questions (FAQs) list, and, the market trend of demand and supply. It also means that you are doing the right things, so you should keep doing it and do it better. Always increase your knowledge-base, as have these successful leaders:


Success feels great
Success feels great! That's what we all hope to achieve.

The success or fulfilment stage is when you find your once difficult situation becoming a breeze as you set your standard operating procedure to mitigate it.

Success can be a very subjective stage. How would you define your success? In a broad term, it is defined as reaching your goals set at the beginning.

However, if you place a numerical value as your goal, it can have limitations. For example, if your goal is to reach a million dollars and you did. Where do you go from there? The obvious answer is, well, two million dollars.

For me, I believe the challenge is to be better than who you were yesterday._ Always compete with yourself to keep up with the ever-changing market and technology. Don’t exhaust yourself trying to be best as this might cause new entrepreneurs to give up more easily.


Some of the catastrophes that withhold entrepreneurs from success are unavoidable. But most of the time we can change our outlook on it. Our attitude is the main factor of our success. Rather than wasting time complaining, use it to find solutions instead. You might ask, where do you find the solutions to your problem?

Being resourceful is also another skill to learn. You don’t need an expensive college degree to get information. You only need to know where to look. It can be on the World Wide Web.

Some of the time, however, you would need to seek it from experience; either your own or someone else’s. Entrepreneurship, at its core, is to solve a problem.

So, to start your entrepreneurship journey:

  • find a problem,
  • master the skills to solve it,
  • have the passion to solve that problem for free,
  • build a business model around it, and,
  • endure the challenges at any cost.

Thank you for reading till the end. I hope that you will get through your entrepreneurship journey and reach your goals!

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