Every Entrepreneur Comes To This Fork In The Road—Here’s How To Decide Your Path

Many new business owners become overwhelmed by their obsession with profit, survival, and competition. It is impossible to have much else in the first year of hard work. Entrepreneurs are now aiming for a specific goal as they experience success: to either run a smaller business or make a lot of money in a larger company.

Noam Waterman, Harvard Business School’s author, refers to this as “the founder’s dilemma.” An entrepreneur can be wealthy and take on outside experts and investors to help expand their company beyond their capabilities. Or, they can be king, controlling the business but ultimately limiting its growth. The Bezos, Musks, Gates of the world, and rich do not often go hand. Wasserman discovered that four-fifths of five entrepreneurs must resign their CEOs shortly before going public.

Entrepreneurs need to be honest about their “why,” focus on their strengths and trust their team to overcome the founder’s dilemma. Here’s how.

Ask yourself: What does success mean?

In a startup, mode founders need to be vigilant about every aspect of their business to ensure it survives and thrives. They may have lost sight what success means.

A 1-3-5 exercise it’s essential to reflect on what you value most, now and in the future. While it may sound simple, an entrepreneur can have trouble thinking beyond the daily needs of a budding company. Founders often feel a deep commitment to their business that prevents them from asking questions. I want to continue to be involved in the industry in the future.

You can ask yourself these questions: “What is my life like in the next 1-3-5 years?” Are you going to work every single day? If so, what are your goals for the future?” “What kind of activities will be doing when I’m not there?” Although there’s no correct answer — every business is unique, and every entrepreneur’s definitions of success are different–but it’s essential to face the truth with yourself.

Only then can you define what sparks joy in your life.

IN THEIR BOOK ROCKET FUEL, Mark C. Winters, Gino Wickman, and Mark C. Winters note that visionary entrepreneurs will be less likely to reach their goals without the help of an integrator. Their point is that nearly no one can grow or scale a company successfully on their own. You shouldn’t try. 

Marie Kondo began a revolution by asking us to discover what “sparks happiness,” and entrepreneurs should do the same. A list should have two columns. It would be good if you wrote down everything you are passionate about in the first column. You can also write everything in the second column under “I hate …”. Perhaps you are looking to build a unique culture, create impactful jobs, and watch people grow. While you delegate the day-to-day operations, you might be more focused on creating a great culture. You can let go of things you don’t like or aren’t great at, so your business can flourish under expert supervision.

Tell your team about your dreams. Next, let your section run with it

Shake Shack founder and restaurateur Dan Meyer admitted that he could not read balance sheets, manage flow or run a restaurant. However, he knew that his goal was for people to be completely blown away at each one of his 29 restaurants.

He created a global team around “enlightened hosting,” which starts with happy employees and ends with satisfied customers. Their success in an industry plagued by high failure rates has allowed them to articulate and share a clear purpose that has made Shake Shack a multi-billion dollar brand.

A powerful strategy to overcome the founder’s dilemma is to identify your priorities and reinforce them through culture and communication. A team that understands its purpose and can make decisions in an apparent strategy framework will grow the company, whether the founder is present.

Every successful entrepreneur has to decide at some point. If you are honest about your purpose, the founder’s dilemma could be seen as a “founder’s enormous, exciting opportunity.” It is possible to let go and grow.

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Samatha Vale
Samatha a senior writer for HC's entertainment team. She is an entreprenuer, mother and an excellent writer. She's also an avid reader, music enthusiast and all around inquisitive person - which is just a nice way of saying she's nosy.

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