The 5 Entrepreneurial Roadblocks You Never See Coming

Photo by Scott Jackson on Unsplash

Roadblocks are common in the startup world. Some seasoned entrepreneurs thrive on them, seeing them as exciting challenges that encourage them to innovate. Most new entrepreneurs are intimidated by them, seeing them as dangerous threats to their burgeoning businesses. No matter how you approach them, roadblocks have the power to destroy your business if you ignore them, and they have the potential to help your business evolve if you catch them and address them appropriately.

Some roadblocks are universal, and can be prepared for easily. For example, most entrepreneurs realize the importance of cash flow and monitor it closely to avoid coming up short of capital. But other roadblocks creep up more stealthily, take you by surprise, and are therefore far more difficult to deal with. Take these five for instance:

1. The Critical Partner Leaving. Many businesses have at least one critical partner. It could be the co-founder who shared your initial idea. It could be the mentor who’s guided you through most of the early stages of your startup. It could even be a critically talented team member who agreed to work well below market cost. Because you’ve hand-selected these partners and you work with them closely on a daily basis, you assume they’ll stick with you for the long haul. But the sad fact is, it’s almost certain that at least one of your starting team will leave within a few years. Few entrepreneurs have a backup plan for this massive shift because they’ve invested so heavily in the individuals involved, but it’s important to think about your options in advance so you aren’t blindsided by a rogue departure.

2. The Maverick Competitor Emerging. When you first start your business, you might be in a blue ocean with few competitors and a wide open market, or you might offer a niche solution similar to a handful of businesses already in operation (but with a unique twist or a competitive advantage). Either way, you enter the market with a carefully calculated competitive balance. What happens when a new competitor emerges out of nowhere and threatens your business by offering a better service (or the same service at better costs)? Few entrepreneurs prepare for this eventuality, but if your business is doing well, it’s inevitable. Try to get in your potential competitors’ heads — if you were a third party, what weaknesses do you see in your business? Try to improve on those yourself before an outside competitor takes advantage of that opening.

3. The Customer Adoption Plateau. When you first launch a business, you’re nervous about whether or not people will buy your products and services. When you grow a business, you’re nervous about whether your growth will be stable enough to support your new additions. These are foreseeable problems that entrepreneurs readily imagine. The roadblock that blindsides them is usually a customer adoption plateau — a point at which growth seems to come to a halt, or a point at which customers begin falling off the platform. This moment is nearly impossible to predict, but it needs to be considered, and you need to have a “plan B” or “plan C” as a lateral move to break through this plateau.

4. The Technology Turn. For modern entrepreneurs, technology is our friend. It connects us with more people, simplifies our lives, and grants us more resources to do our jobs and build our businesses effectively. Unfortunately, technology can also be our worst enemy. Technology develops quickly and often without warning, and can sometimes revolutionize an entire industry overnight. Think of how Uber suddenly threatened the once-untouchable taxicab industry, or how Amazon replaced countless physical book retailers. All it takes is one critical technological development to render your product or service obsolete — so always find new ways to improve.

5. The Crowded Door Problem. This is a roadblock you never see coming because you never think of it as a roadblock. You have too many ideas! You have so many thoughts about where the business can grow or develop, that you have the philosophical equivalent of nine people trying to get through the same door at the same time. Sometimes manifesting as shiny object syndrome and sometimes manifesting as trying to do everything at once, a disorganized mind is a hidden roadblock that can keep you from making meaningful progress.

These five roadblocks won’t necessarily spell doom for your company, but you will encounter trouble trying to predict and prepare for them. By their very nature, they tend to pop up quickly and without warning, and your reaction to their emergence could dictate your success in circumnavigating them. Prepare for the roadblocks you can, consider the roadblocks you can’t, and always be on the lookout for rogue surprises to challenge you along the way.

For more content like this, be sure to check out my podcast, The Entrepreneur Cast!

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