Do I Dare? Becoming an Entrepreneur

A simple set of questions can clarify your purpose.

Ashely Batz Photography

Are you an aspiring founder or investor? Are you already building your own thing, or simply exploring an idea? Wherever you are on your path to calling yourself an “entrepreneur” our new group, Entrepreneurs at The Assembly, is for you. To kick things off, Harvard Business School Professor Sandra Sucher lead our first learning session. The goal? To help entrepreneurs clarify their purpose and create a plan of action. No more ruminating. It’s time to do something. 

Create your own opportunities and let the opportunities change you.

Professor Sucher opened with this quote: “Create your own opportunities and let the opportunities change you.” It comes from Hiromasa Ezoe, the founder of the massive Japanese company Recruit Holdings Co. Ltd. Conditions will shift on your path toward creating a business, Professor Sucher explained, but you have to be on the path for anything to happen. If you prioritize forward motion and have a bias toward action, you can achieve something great.

Professor Sucher believes Recruit Holdings makes a great case study. After suffering a massive scandal that took down the Japanese prime minister in the 1980, Recruit Holdings now has annual sales over $17 billion and has acquired both Indeed and Glassdoor.  If you want to start your own business, the company’s unique approach to growth offers insights. Recruit Holdings encourages current employees to start their own businesses within the group and wants its workers to feel like a team of entrepreneurs. In order to facilitate that, managers ask employees a set of questions every six months. Here’s the list:

Questions to Ask Yourself About Your Goals


  • What do you want to be doing in six months?
  • What do you want to be doing in three years?


  • What strengths will help you get to your goal?
  • What skill gaps or attitudes may keep you from getting to your goal?


  • Think of 1-2 “experiments” you can run to get closer to your goal.
  • Think of 1-2 “experiments” you can run to close your “Will/Can” gap.

These questions proved incredibly accessible and helpful for The Assembly entrepreneurs. During our class, we jotted down our answers and then bounced them off each other. We talked about how the voice of imposter syndrome might actually provide useful information about growth opportunities. We noted that thinking of actions as “experiments” gives us permission to take risks. The beauty of the questions: each entrepreneur could walk away with tangible next steps to get closer to her business goals, even if we all had radically different situations and needs.

Like any good teacher, Professor Sucher gave us some reading. If you’re thinking about taking the leap into entrepreneurship, check these out:

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