Since joining the world of entrepreneurship in September 2014, I have learned a lot about startups, team building and lean business models. But I learned even more about myself in the process. At the risk of sounding like a self-help cliché, I really think that entrepreneurship is one of the most rewarding, yet exhausting, journeys that a person can take into themselves. While many might blame the lack of investors, limited budgets or an unprepared team for the failure of a business, I’ve found that most successes and failures stem from an entrepreneurs’ unwillingness or inability to understand themselves.

Business is all about personalities. So, while you may have an MBA from UPENN or Stanford, if you don’t understand your strengths and weaknesses and how “to hack” your
personality, that degree isn’t going to do much for you. In the startup world, understanding what you’re all about is even more important for two reasons. Firstly, a 7LJXUWVX9Sstartup’s “persona” is heavily dependent on the personality of its founder. So, whatever strengths or weaknesses you have as an individual will inevitably be reflected in your startup in some way shape or form. Seeing as most startups have small teams with tight budgets, they don’t have the luxury of outsourcing your “weaknesses” to another department. Consequently, it is imperative for startup leaders to know themselves if they want to be successful.

Another important thing to realize is that the startup world is completely different from the corporate world. So, don’t think that an ivy league education or a long career in fortune 500 companies will completely prepare you for grassroot entrepreneurship- especially in the Arab world. Whether you “fail” or succeed in entrepreneurship, there is so much that you can learn about who you are, what matters and purpose. If you are open to change, that is. If you are considering joining the startup world, in the MENA region or beyond, here are 5 questions you need to ask yourself before you take the leap:

1) Why am I doing this?

This is one of the most important questions to ask yourself, because your reasoning will inform all the decisions and actions that you take in your entrepreneurial journey. Having the right intention is crucial when you are trying to do something and succeed. Wanting to become an entrepreneur because you want to be rich, famous or Steve Jobs is not good enough. This kind of thinking will not carry you through the tough times, and there will be many of them, which is why you want to choose a reason, or reasons, that will provide you some kind of sustainable momentum. Passion will ebb and flow, but if your intention is good, i.e. to improve people’s lives, make the world a cleaner, more sustainable place etc, you will always find a way to propel yourself forward. Thought is the basis of any action, so make sure that your thoughts are clear and purposeful, so your actions are the same. Be real and you will find real purpose.

2) Do I have a positive relationship with myself?

For some people, this might seem like a strange question, but believe me when I say that your personal and entrepreneurial success rely heavily upon the kind of relationship that you have cultivated with yourself throughout your life. If you are the kind of person who is overly self-critical or self-loathing, you’re probably also the kind of person who looks for external approval. In an ecosystem that is defined by risk-taking, quirky personalities and a colorful array of positive and negative feedback, an entrepreneur with low self-esteem will not do well. Entrepreneurship is all about breaking social, economic and cultural norms, so by its very nature entrepreneurship is an act of rebellion that goes unappreciated by most. Being able to be comfortable with who you are, making mistakes, admitting you are wrong and, last but not least, being able to recalibrate accordingly are all  traits that make a great entrepreneur. Be comfortable in your skin and you will find the confidence to navigate any situation.

3) Am I a reflective person?

The ability to review what you have done in the past and identify new ways to improve yourself and your business is essential when it comes to running a successful startup. Nobody grows by staying the same and the only way you can stay the same is to persist in a never-ending state of denial. Just remember, you can’t be good at everything, but entrepreneurship is not about being the best solo act in town. That’s why you have a team! Not only can finding the right team mates optimize your strengths, they can also reduce your weaknesses as a business. So, make sure to take some time to understand your quirks, ticks and triggers, because the more you understand them the easier it will be for you and your team to deal with them and thrive. By regularly reflecting on your life and business you will be able to understand what each needs, which will ultimately help you make the decisions that need to be made to make your startup a success at each stage. Be willing to understand yourself and you will make wiser choices.

4) How do I like to work?

Do you work well under pressure? Do you like to work at night? Can you work at home? These are all questions that you should have the answers to before you take the entrepreneurial leap, as they will help you streamline your schedule and improve your efficacy. One of the reasons that most entrepreneurs leave the “conventional workforce” is because they don’t like the rigidity of the 9-5 life, so why would you try to reproduce it in your own startup? Sometimes the uncertainty of the entrepreneurial lifestyle makes us slip into old routines and “comfortable” habits. But the problem is that those habits were never comfortable because you liked them, they were comfortable because you got used to them. That being so, entrepreneurship is all about “hacking” your lifestyle, so don’t slip into old habits, especially if they promote inefficient and unproductive workstyles. With that in mind, take some time to identify when and how you do your best work and make sure you do it that way. Be true to your internal rhythms, so you can find that “optimal groove.”


5) Do I know how to say no? 

Setting boundaries for yourself can be difficult, especially if you live in an Asian, African or Arab context. In these cultures, saving face is a big deal. So, if you’re new to the Arab and entrepreneurial world, you will probably find yourself asking: was that insh’Allah a yes or a no? Is that person avoiding my calls, so they don’t have to say no and disappoint me? These are just two examples of how someone might try to politely say no in the Arab world. In fact, if you grew up in the East, you might find yourself using some of these strategies, especially with family members. While the “cultures of no” may differ around the world, one thing remains true: saying yes may feel easier than saying no in the moment, but every yes has a “cost.” Regardless of your culture, you should try to train yourself to say no when it counts, because saying yes all the time will affect you and your startup adversely at some point. Be willing to say no, so your family, friends and team mates will appreciate it when you say yes.

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4 thoughts on “5 Questions Every Entrepreneur Needs to Ask Themselves Before Starting a Business

  1. why does starting your own business have to be such a “personal” journey. Surely, Donald Trump didn’t think about his personal habits or traits before he got into business.

    Liked by 1 person

    1. Thank you for your comment Omzeen. To answer your question, everything you do in Life is personal, no matter what people might say. There is no such thing as true detachment. Mr. Trump has the luxury of having lots of money to cover up the mistakes that come as a result of his personal shortcomings. A bootstrapping entrepreneur does not. Therefore, they must rely completely on their own personality, wit and resources to survive and then, hopefully, thrive. I hope that answers your question.


  2. So the best way to cover up personal flaws or serious character deficiencies is by having a lot of money? Interesting…..


    1. No, not necessarily Omzeen, but having connections and the right “funding” goes a long way. In the Conceptual age, the workforce has transformed into a completely different “animal.” More millenials are looking for a higher quality of life versus a higher standard of living. So, young people aren’t willing to become entrepreneurs or create teams for just any old reason. They want to provide nurturing and positive work environments, where people can thrive. This has made business “more personal.” It’s not just about the corner office anymore, it’s not about hierarchies as much, it’s about creating cultures that foster personal growth and healthy work-life balance.


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