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4 questions you’ll never know the answer to as an entrepreneur

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4 questions you’ll never know the answer to as an entrepreneur

Updated: April 25th, 2022

4 questions you’ll never know the answer to as an entrepreneur

One of the hallmarks of entrepreneurship — alongside innovation and a dependency on caffeine — is uncertainty. When you’re starting a business or creating a product, there are an incalculable number of risks involved, not to mention unforeseen obstacles and unexpected stress.

Of course, if you’re an entrepreneur, you also know the importance of gathering as much information as possible before you make judgment calls in your work. That includes noting trends and behaviors, processing news, analyzing data, and asking for help from trusted colleagues and mentors. Even with tedious research and smart measuring practices like these, however, there are still plenty of unknowns involved in business.  

Here are four questions you will never fully know the answer to as an entrepreneur.

1. How will my business develop?

You can make educated guesses about the trajectory of your business, but at the end of the day, you can’t anticipate exactly how your business will progress. You may end up scaling back on a portion of the company you thought you could expand, or scrap your original product to produce something in higher demand. You might add client services you never imagined offering, or have reason to double your employees down the road.

Despite how much time you spend conducting market research, analyzing website traffic, or searching for patterns in your sales orders, you’ll still never know the myriad ways your business will change with time. Stay flexible and prepare to adjust and adapt.

2. How will current events shift the market?

Go ahead and plan for the worst case scenario in your business, but just know: you can never be fully prepared for the specific political, economic, or cultural events that will indirectly or directly affect your company. Elections, trade sanctions, natural disasters, new laws, and mergers and acquisitions all play a role in dictating the economical climate. Even seemingly minor local changes, like the creation of a new shopping center or after-school program, can shift the landscape of your industry and either facilitate business or hamper it.

You can’t control these events, but you can control your response to them. Your flexibility, resilience, and willingness to adapt in the face of change is what will keep your business thriving.

3. When is it the right time to expand or sell my company?

You can pore over market data, talk to investors, and chat with a financial analyst to assess whether you’re in the right position to expand, sell, downsize, or otherwise dramatically change the size of your company or your role within it, but let’s face it: nothing is guaranteed. You could sell a major share of your company only to discover it would have been worth more if you waited two years. On the other hand, you could end up waiting years for the perfect investor to take interest in your business only to lose money in the process. That’s the nature of being an entrepreneur — no matter how secure you feel about your decision at the time, you’re still taking a risk.

That’s why the best strategy when faced with a big decision is to double down on research, take careful stock of your current situation, check in with your gut, then make a choice. Try not to second-guess yourself or entertain what if scenarios. Just make the best decision you’re capable of making at the time, then move forward and learn from the process.

4. How will I feel about my work in the future?

You can crunch numbers and analyze metrics every day, but none of that will give you an accurate understanding of how your attitude to the work will change over time. As you evolve as a person, so will your needs and wants. What fulfills you now work-wise may not give you the same level of contentment later in life. Conversely, the aspect of your job you like the least when starting out could become one of your favorite parts as time goes on.

Ultimately, you can’t know how you’ll respond to the unique, nuanced course of your career and its inevitable victories, failures, hardships, and joys. Embrace the fact that your perspective will change and make a point to check in with yourself several times a year to ask the hard questions: Do I like waking up for work every day? Am I proud of what I’ve achieved? Am I on the path toward what I want? If not, what can I do to redirect course? Periodic self-reflection will help keep you on the right track, no matter how your attitude on business evolves.


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