9 Unexpected Challenges to Prepare for in Your First 2 Years of Business

Running a business, like waging a war, goes exactly as planned right until the moment you start.

I mean that literally. When I started my first business in my early twenties, for example, I hedged my bets by informing my boss at the time that I’d work part-time for him but do my own thing on my days off and the weekend. That way, I’d enjoy at least one guaranteed source of income as a buffer as I experimented with small business ownership.

My position was complicated by the fact that my side-hustle – manufacturing and repairing commercial signs – was also what I did in my day job. If it turned out to be successful, in other words, I’d be competing with my boss.

To my relief, he agreed. In retrospect, I realize it was because he didn’t take me seriously. About a week later, when a fellow employee informed him that he’d spotted me working on a sign for a new customer out of my own truck, he flipped his lid.

He gave me an ultimatum: I could either abandon my silly dream of competing with him and work my way up through the ranks as his employee, or else. I chose the latter and he fired me without further ado.

This, I think, is an ideal example of the vagaries of entrepreneurial life. The minute you launch out on your own, it’s all or nothing. You can’t hedge your bets or strike cozy deals which allow you to have your cake and eat it too. The advantage of such stark realities is that they force you to grow up in a hurry.

To paraphrase Samuel Johnson, when you know you might starve if you don’t perform, it concentrates your mind wonderfully.

The main thing to remember is that small business owners will face numerous unexpected challenges in their first two years of operation, testing their resilience, adaptability, and determination. The challenges will continue, of course, but by then reacting appropriately will have become second nature.

1. Cash flow

One of the most significant challenges is managing cash flow effectively. Many new business owners underestimate the importance of maintaining a healthy cash flow, often struggling to balance expenses while trying to grow.

This can lead to difficulties in meeting payroll, paying vendors, or investing in necessary equipment and resources. To overcome this, entrepreneurs must develop robust financial management skills and possibly seek additional funding sources or adjust their business model.

2. Time, time, time

Another unexpected challenge is the time commitment required to run a small business. New owners often find themselves wearing multiple hats, from CEO to janitor. This can lead to serious burnout. Effective time management and learning to delegate tasks become crucial skills for survival and growth.

3. The ever-changing market

Market transformations and technological innovations pose another significant challenge. The business landscape is constantly evolving, and small businesses must adapt quickly to remain competitive.

For example, the rapid adoption of AI technologies since 2023 has forced many companies to reevaluate their processes and strategies. Staying informed about industry trends and being willing to pivot when necessary are essential for long-term success.

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4. Hiring

Hiring and retaining quality employees can also be an unexpected hurdle for small business owners. Finding individuals who share the company’s vision and work ethic can be challenging, especially when competing with larger corporations that offer more attractive benefits packages. Developing a strong company culture and offering unique perks can help attract and retain top talent.

5. Keeping up with regulations

Many entrepreneurs are surprised by the complexity of legal and regulatory compliance. Navigating tax laws, employment regulations, and industry-specific requirements can be overwhelming and time-consuming. Seeking professional advice and staying informed about relevant laws is crucial to avoid costly mistakes.

6. Attracting customers

Marketing and customer acquisition present another set of challenges. New business owners often struggle to develop effective marketing strategies and build a loyal customer base. This requires a deep understanding of the target audience and the ability to craft compelling messages that resonate with potential customers.

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7. Economic uncertainty

Unexpected external factors, such as economic downturns or global events like the recent pandemic, can also significantly impact small businesses. These events can disrupt supply chains, alter consumer behavior, and create financial instability. Developing contingency plans and maintaining financial reserves can help businesses weather such storms.

8. Training leaders

Reducing dependencies on the founding team is another challenge that many small business owners face. As the business grows, it becomes crucial to build a strong leadership team and delegate responsibilities effectively. This transition can be difficult for founders who are accustomed to being involved in every aspect of the business.

9. The temptation to compromise

Lastly, maintaining work quality while pursuing growth can be a delicate balance for small businesses. The pressure to expand and increase revenue can sometimes lead to compromises in product or service quality. Striking the right balance between growth and maintaining high standards is essential for long-term success and customer satisfaction.

By anticipating these hurdles and developing strategies to overcome them, small business owners can increase their chances of success and build a strong foundation for future growth. Looking back, accepting my boss’s challenge and pursuing my goals in spite of the uncertainty involved was the best decision I ever made.

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