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  • Writer's pictureViv and Ginny

Should I start a business (or thing)? The top questions to answer before starting any venture

So you want to start something, anything – a nonprofit, business, group, a project – since it seems like everyone is doing it these days. You’ve seen eye-catching humble brags (ahem…announcements) on LinkedIn, received emails marking a colleague’s transition from coworker to cofounder, or listened to “invest in yourself” pep talks from your friends. In the wake of 2020’s racial reckoning, you probably also noticed an exponential increase in awareness and programs to improve equity for women and minority-led businesses. Diverse businesses seem to have more opportunity – resources, capital, and visibility – than ever before.

You might be tempted to take advantage of the current climate and start a venture of your own. You are intelligent, driven, and great at what you do, so why not? As we have learned from our clients and even when launching our business Vivian & Virginia Ventures, a better question is actually: Why yes?

Intelligence and work ethic are necessary for success in any endeavor but starting and sustaining a venture requires much more.

Before doing extensive market research or developing solutions to unvetted problems, first take a step back and go within. Asking and answering a few tough questions now lays the groundwork for every tough, rewarding, and fun moment to come.

Here are the critical questions every prospective founder should ask themselves.


What is your why?

Before investing time and energy, it is critical to ask and answer honestly: Why? Why do you want to start a new venture? Each person’s “why” will be different – whether it is to make more money, create a solution to an existing problem, discover new challenges, leave a toxic work environment, pivot to a different industry, or serve the community – but by knowing your why you create an important rubric for success. Understanding your “why” will keep you energized and encouraged when the days are long and outcomes uncertain. Money and wealth generation are common “whys” (and that’s ok!), but ask yourself this: if your current company offered you the exact money you dream of making, would you be satisfied? Would you stay in your job for the comfort of having the resources you desire or would your dream of doing / founding / owning something else persist?

If your answer to that last question is yes, read on.

What do you value?

Our values are more than just aspirations. They are the tangible thoughts and actions influencing our experience of life. Core values shape life’s purpose. They are reflected in every action you take, including launching a new venture. Knowing your core values – such as creativity, integrity, and flexibility – helps you create the best strategy based on your unique strengths, passions, and opportunities for growth. If you choose to be a purpose-driven entrepreneur, a strong conviction to your values is essential. Entrepreneurs who have decided to align their actions with their purpose develop purpose-driven companies.

Purpose informs the mission and vision, influences the employee and customer experience, and acts as a rubric for management. An altruistic, “save-the-world” purpose is not appropriate for every venture.

But every successful venture is led with a strong sense of purpose. That’s why, according to a recent study, “Purpose-driven companies witness higher market share gains and grow three times faster on average than their competitors, all while achieving higher workforce and customer satisfaction.”

How do you work and lead?

Knowing who you are, truly, and how you engage with the world is critical for establishing an environment where you, and the people that work with you, can excel. We are all endowed with incredible gifts; but we are all also incredibly human. That’s why it’s important to be radically honest about your strengths and areas for growth. How do you handle rejection, criticism, disappointment? These are common experiences when seeking buy-in. Doing the work that is unique to your purpose is typically more rewarding, but also much higher stakes, than working towards someone else’s vision. As a founder, you will lead in every sense of the word. You will be accountable to your clients, community, stakeholders, and employees. In the beginning, praise may not be as effusive as criticism. Understand: Are you driven to excel based on intrinsic awards or extrinsic recognition? Do you like to work in teams or as an individual contributor? Are you comfortable leading others? Receiving and providing feedback?

How do you approach uncertainty?

One of the fundamental lessons in business is the relationship between risk and reward. As the saying goes, the higher the risk, the greater the reward. Launching a venture is extremely rewarding, but success isn’t guaranteed. Does the unknown motivate or scare you? Fear is a primal and useful emotion, but if it controls you, you’re unlikely to achieve your desired results. The world’s greatest leaders continually operate in the space outside of their comfort zone. They see fear not as a limiting belief but as an early indicator they are on the precipice of transformation. Uncertainty, like change, is constant. If fear of the unknown immobilizes you, it may be a good idea to address its root causes and take incremental steps towards your vision before a big leap.

Are you ready?

Work is not who we are, but what we do.

We don’t have to be a “CEO” or organizational leader to be valuable. Every person is intrinsically worthy, and valuable, just as they are. While no one is ever truly ready, if you have a vision and a resounding purpose that just won’t be silenced, the time may be right for you to make it a reality. You can intentionally choose to at any time. Just remember that what is right for you is the right answer. Whenever and whatever you choose, take stock of your well-being: spiritual, emotional, mental, and physical. The work we do can irreparably alter this well-being. It is worthwhile to ask: Am I ready for this challenge? What do I need to feel better prepared? How will I create a support system? What am I personally committing to? We have just this one life. When we are living the life we truly want, the whole world is better for it.


We encourage you to ask and answer these questions continuously. Write them down. Tell them to your trusted circle. The process alone is grounding and will make clear your path forward.

Need help catalyzing your venture? Reach out to us at

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