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6 Questions Aspiring Entrepreneurs Need to Ask Themselves

Susan McLaughlin

Chair, C200

Contemplating leaving the corporate life to set off on your own? Such a move can be vastly rewarding, but the journey isn’t for everyone. There are stark differences in the skill set that makes a successful entrepreneur versus a corporate executive. Much of it comes down to how you are able to manage issues around ambiguity, motivation, structure, discipline, resources and hustle.

I have a large petri dish from which to provide examples, including my own experience with moving from the C-Suite in Fortune 100 companies to a much more entrepreneurial. In addition, as the Chair of C200, a membership organization composed of the world’s most successful women entrepreneurs and C-Suite executives, I have seen huge successes and epic failures by some of the smartest, most talented women who have gone through this tricky transition. Here are six big questions to consider when contemplating making the change:

1. Can you handle uncertainty? 

As an entrepreneur, you’re the one making the quick decisions, likely without deep data analysis or the support of a committee.

2. What is your motivation?

If it is anything but passion for the product or service you will be offering, think again. Recently, I watched an entrepreneur nearly tank his business because he was consumed by visions of the money he would make on its eventual sale, not the actual selling of his very beneficial product.

3. How well do you operate without structure?  

Corporations have structure, rules and processes that provide momentum. As an entrepreneur, it is up to you and your team to create that momentum each and every day.

4. How disciplined are you? 

While I consider everything I do to be business development — articles, speaking engagements and events — the fact is that it can be difficult to stay focused when faced with the mundane daily tasks of running a business.

5. Can you handle risking your own capital?

Can you see yourself navigating a situation where you clearly know what needs to be done but don’t have the funds to do it?As an entrepreneur, it’s critical to be able to expertly time things, such as the addition of staff, with anticipated revenue growth.

6. Will you be comfortable with the hustle?

Entrepreneurs don’t have the benefit of an established brand to get them in the door.One of my colleagues who loves selling now describes her prior work in a major firm as merely “order taking.”Others, without the benefit of an established brand, have told me they found the work of selling and business development to be simply “too hard.”

While it is difficult, becoming an entrepreneur is also one of the most rewarding and exciting adventures there is.  Many women who make this transition tell me how fulfilling it is, after being “heads down” in their corporate career, to be introduced to a thriving ecosystem of entrepreneurial businesses. Get honest with yourself as you answer these questions, and if you are still feeling passionate about the opportunity to learn, grow, fail and fly, go for it.

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