Entrepreneurs

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

Most new business owners are overwhelmed by their focus on profit, competition and survival—the first years of grinding it out don’t leave room for much else. But as they begin to taste success, entrepreneurs are also driving toward an inevitable fork in the road: to lead a small business or get rich in a bigger one.

Harvard Business School professor and author Noam Wasserman calls this “the founder’s dilemma.” Entrepreneurs can be rich, accepting investors and outside expertise to expand the company beyond the founder’s capabilities, or they can be king, staying in control of the business but ultimately hitting a ceiling on growth. Being rich and king rarely go hand in hand—the Bezoses, Musks and Gates of the world are outliers. In fact, Wasserman found that four out of five entrepreneurs are forced to step down as CEOs well before going public.

To overcome the founder’s dilemma and turn it into an opportunity, entrepreneurs have to be transparent about their “why,” focus on what they’re good at and trust in their team. Here’s how. 

Be honest: what does success really mean to you?

In startup mode, founders have to watch over every aspect of the business to survive and thrive. When it’s finally time to decide to expand or maintain the status quo, they may have lost sight of what success meant in the first place.

A 1-3-5 exercise highlights what’s truly meaningful to you one, three and five years down the line. It sounds simple, but thinking beyond the day-to-day needs of a budding business can be difficult for an entrepreneur hyper focused on the bottom line. Founders often feel a sense of commitment that precludes asking if they even want to be in the business in the future.

Consider things like, “What does my life look like in 1-3-5 years?” “Am I going into work every day, and if so, what am I doing there?” “What kinds of things will I be doing if I’m not at work?” There’s no right answer—every business is different and so is every entrepreneur’s definition of success—but being honest with yourself is the first step to overcoming the founder’s dilemma.

Define what sparks joy for you—and only do that

In their book Rocket Fuel, Gino Wickman and Mark C. Winters note that visionary entrepreneurs are less likely to realize the company’s goals without an integrator to help them get there. Their point is that almost no one can do what it takes to successfully grow and scale a business alone. And why should you try? If you’re the smartest person in the room, you’re in the wrong room.

Marie Kondo started a revolution by asking us to find what “sparks joy”—and entrepreneurs should do the same. Create a list with two columns. In the first column, under “I love…” jot down all the things you’re truly passionate about. In the second column, under “I dislike…” put down everything else. Maybe you want to focus on building an exceptional culture, creating impactful jobs and watching people grow while you delegate the nitty-gritty operations. Let go of the things you dislike or aren’t good at so those areas of your business can start to thrive under an expert.

Give your dream to your team. Then let them run with it

Shake Shack owner and restaurateur Dan Meyer admits he didn’t know how to read a balance sheet, manage flow, or run a kitchen. But he did know he wanted people to be blown away by their experience at every one of his 29 restaurants.

He aligned his global team around “enlightened hospitality,” which starts with happy employees and ends with happy customers. By articulating and sharing a clear purpose, they have succeeded in an industry with an incredibly high failure rate, turning Shake Shack into a billion-dollar brand.

Identifying your priorities and reinforcing them through culture and communications is a powerful way to overcome the founder’s dilemma. A team that understands their purpose and has the freedom to make decisions within a clear strategic framework will help grow the business—whether the founder’s around or not.


Every successful entrepreneur eventually has to choose between maintaining the status quo or finding ways to expand. But the founder’s dilemma can really be seen as the “founder’s huge, exciting opportunity” if you’re honest about your purpose and remember that letting go will help you grow.

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