Entrepreneurship: 8 Questions to Ask Yourself Before You Jump

Hello world. Sooooo, for my very first blog post, I figured this was a great topic to start with. It’s kinda like…what you need to know before the beginning.


How do you know if you got what it takes to be an entrepreneur? I read somewhere that it’s when you love and live for the tides, thrill and torture of your life being pretty damn amazing and pretty f–ked up at the same time. Not knowing whether you will sink or swim in the ocean when you can’t see the shore but you still jump in anyways, pressing forward. Kinda psychotic, I know. But guess what? I agree 1000%, because that’s exactly what it takes. It takes real risk, but you get to write the end of that story. That’s my definition of badassery!


When you think about it, the pursuit of an entrepreneurial venture is a lot like becoming a parent. If you have a kid or kids, then this will hit home with you. Besides preparing emotionally and financially, you have to be committed to your startup until it is mature enough to run on its own, much like your kid learning to walk or potty training. And even after reaching that point, a business will always need you in some capacity (just like a child), no matter how old it gets. Haha, the irony of it all, right? 🙂

Before taking the plunge into the murky waters (literally!) of entrepreneurship, there are certain considerations that you must address first. These concerns revolve around three critical aspects:

  1. Your reasons for wanting to start a business (seriously, it should be deeper than just wanting to make a shit load of money and laying on the beach in some remote island off the coast of Santorini, even though that will come eventually.)
  2. Coming to terms with what it means to be an entrepreneur (It’s not for the weak minded or faint of heart, you’ve got to put on your big girl panties and be ready to grow some badass balls)
  3. What you must do to get to where you want to be.

With that in mind, here are 8 more questions to ask yourself before you decide to pursue entrepreneurship.

Q1: Yachts and private planes are nice. What’s your motivation?

Every entrepreneur has a reason for starting a business. Motivation matters a lot when it comes to entrepreneurship because if you’re venturing into business for the wrong reasons (like trying to get rich overnight), chances are you’ll be on the gigantic highway to financial destruction. Sounds pretty dramatic, I know, but it’s the truth.

If you dream about starting a business because you think it’s prestigious to be a “boss,” or “boss chic” want to work fewer hours, or simply hoping to attain fame, then unfortunately, you’ll need to change your mindset. I hate to be the one that crushes all your hopes and dreams, but you’ll need to wake the hell up because such incentives are poor motivations to start a business since they’re largely false notions of what entrepreneurship is all about.

That being said, starting your own business can still be highly fulfilling and some good reasons for becoming an entrepreneur include:

  • Being able to follow your own passion and eventually earn money from doing what you love
  • The ability to create new products and solutions to add value to other people’s lives
  • Doing something that makes a positive difference

These are more solid reasons for venturing into entrepreneurship because they’re realistic expectations.


Q2: Are you comfortable with uncertainty and taking risks?

Results are never guaranteed as an entrepreneur and you need to be willing to sacrifice your income with no certainty that your business might pay off at all. And even if your business plan is well thought out, there’s always a certain element of risk involved. Simply put, entrepreneurship is not for the faint of hearts. You will need some serious girl balls (and if you are a dude..well some major ones). So, whether it’s quitting your day job or signing a lease for new space, risk taking should become second nature once you’ve decide to venture into the world of business. High risk, high rewards. This is a mantra that I recite quite often almost on a daily basis.

With that said, however, it’s not wise to take gambles blindly. I always say, if and when possible, take calculated risks. Any successful entrepreneur will tell you that risk is part business but it should not be underestimated. When you encounter potential risks, you should handle them strategically. Smart business owners perform a cost-benefit analysis in order to make well-informed decision on whether or not to pursue an action.

Ask yourself if you’re the type of person who can make decisions calmly even in times of panic. If so, then you may be the type of person who’s cut out for success. However, if you’re not a person who can take decisive and well-though out actions, then it’s best to gain some small scale experience first before going full-in with a business.


Q3: How bad do you want it?

The truth is… not everyone is cut out to become an entrepreneur, well a successful one to be more precise. People can have a strong desire to start a business and even come up with great ideas. I always say ideas are a dime a dozen. However, being a successful entrepreneur requires more than that. It takes determination, creativity, persistence, patience, flexibility, and the ability to keep learning new things. To develop these traits, you’ll need to demonstrate an unwavering commitment to building a successful business despite endless setbacks, failures, dead ends, and forced changes of direction. You’ve got to have the cojones to pick yourself back up and brush your shoulders off.


Q4: Are you willing to take on numerous responsibilities?

Unlike employees who only need to focus on specific skills within a larger organization, entrepreneurs must be ready to assume a variety of roles when running a business. Ahhh, the many hats I’ve worn. When I launched You! Lingerie, it was just me and my little sister. She and I prepped, fulfilled and shipped every order. In addition to that, I was Customer Service, Sales & Marketing, Operations, Accountant, CEO, Designer, Blogger, hell, even the janitor. Whatever the business needed, I happily became. This is often the case with the majority of solo startups, which require the business owner to juggle from being the marketer and bookkeeper, to being the staff supervisor, consultant, data entry clerk and hiring manager. If you cannot handle numerous responsibilities, then entrepreneurship might not be for you.


Q5: Is your business idea new or are there similar ventures already?

With all the startups being launched these days, how can you make your business stand out from the rest? Everyone will tell you all you need to do is come up with a new and viable business idea to set yourself apart as an entrepreneur. But in reality, that is much harder than it sounds. Much!

The reality is not everyone is capable of bringing something new and unique to the market and even then, consumers may not even be looking for new inventions. Just how many Apple Inc. are there in the world? And just how many people even have the budget to market a product like Apple does in order to sell consumers technologies that aren’t all that new and also command premium prices?

But then again, even if many established businesses have already executed your idea, it isn’t always a bad thing for you. This is because you’ll know for sure that there’s a huge demand for products in a particular market, and it’s possible to have a piece of the pie by taking a slightly different approach. In order to achieve this goal, however, it’s important to carefully evaluate the competition and your unique selling points before starting your business.


Q6: Do you have the financial means to get started?

Whether you’re starting from nothing or buying a franchise, every business needs startup capital (insert the voice of Jerry McGuire here…Show Me The Money). If you’re serious about being an entrepreneur, how will you fund your business venture? Will you dip into your personal savings, form a partnership with an investor, or get a loan from the bank? While all of these are possible options, they have their own pros and cons. Therefore, it’s important to do your homework before choosing a method to fund your business.


Q7: Will the business be profitable enough to sustain your growth?

Research indicates that 8 out of every 10 new businesses in the US fail within the first 18 months. Those are some scary stats. WHOA! And the #1 mistake that kills most startups is not forecasting cash flow. Cash is king. Repeat after me…CASH IS KING. If your business doesn’t turn a profit or have cash flow, you’ll ultimately be forced to close it.

A simple way to avoid crippling periods of cash shortages is to write a business plan. By writing a comprehensive business plan, entrepreneurs can anticipate potential risks and formulate contingency plans to avert them.


Q8: How will you get the hell out? Got an exit plan?

Although this may be hard truth to swallow (GULP!), there’s a chance that your business might not succeed. Should that happen, it’s prudent to have a fallback plan. For instance, you could set aside some funds in case your business venture does not work out. Having a safety net will make it much easier to recover from the disappointment of suffering a loss after pouring your heart and soul into a failed business. But of course, this is not going to be your story. That’s why you are here… reading this.


In the end, being an entrepreneur can be very lucrative and a boat load of fun, but it’s not easy and comes with many responsibilities. I’ve had my fair share of ups and downs, not knowing if we’ll make it, I have won, lost, tried again, cried, laughed, stayed up late worrying about stuff, made lots of money, lost lots of money, learned, created, and so many more, the list goes on and on, trust me. And I will still choose this life over and over. But if you’re serious about starting your own business, or you just started to dabble in the world of entrepreneurship, you’ll need to consider these questions above so as to determine whether entrepreneurship is really for you. No bullshit. No excuses. When you decide to make that leap and take the road less traveled, you challenge the universe and we all know that the universe loves challenges. You’ve got this. So embrace your badassery and let’s kick some ass!

Next Post

You Might Also Like


  • Reply Tricia August 19, 2015 at 1:52 pm

    Congrats Uyo! This first blog is very relevant and necessary. Thanks for your candor. The biggest hurdle is the first…to start, believe in self and continuously choose to take another step! I look forward to more postings.

  • Reply Peace August 19, 2015 at 2:16 pm

    This blogpost is amazing Uyo. Thanks for sharing. I’ve certainly taken home some valuable points.

  • Leave a Reply