5 Questions to Ask Yourself When Considering the Entrepreneurship Path

5 Questions to Ask Yourself When Considering the Entrepreneurship Path

People often come to a crossroads in their career when they must decide between staying with their current employer, finding a new position, or becoming an entrepreneur. While entrepreneurship can be a rewarding decision, it is a challenging path that requires diligence, determination, and grit.

Taking the leap into entrepreneurship involves a wide range of different challenges, and you need to ensure that you’re equipped to mount these hurdles before you decide to become your own boss. When considering entrepreneurship, it’s important to take time to reflect on your own personal strengths and shortcomings.

Some questions that would-be entrepreneurs should ask themselves include:


Can I handle instability?

One of the most important traits of a successful entrepreneur is flexibility. Entrepreneurs frequently find themselves in unstable positions, and they need to be able to handle this uncertainty—and even thrive in it. While the idea of becoming your own boss sounds liberating, the stress involved with having ultimate responsibility for a company can make some people feel more pressured as an entrepreneur than they did in their 9-5 job. If you’re uncomfortable with “the buck stops here” mentality, you may not enjoy entrepreneurship.

Furthermore, entrepreneurs often have to forego some of the benefits of employment, such as 401(k) contributions and vacations, during the early years. If doing so sounds like it would create an unmanageable amount of stress, then entrepreneurship may not be the best path for you. On the other hand, if you enjoy taking calculated risks and can live with some uncertainty, you may thrive as an entrepreneur.

Am I passionate about the idea?

The startup phase of any company is extremely stressful. During this period, entrepreneurs typically ask themselves—repeatedly—if they made the right decision, especially if they feel forced to make continued sacrifices. In these moments, only true passion for your product will give you the determination you need to persevere. During the first years, the hours are extremely long and the income may be nonexistent. If you truly believe in your idea, you’ll be driven to move forward and continue advocating for your product, even when you encounter setbacks, harsh criticisms, or failure. Entrepreneurs are the chief salespersons for their companies, so continued enthusiasm is necessary to get other people excited about the idea and to attract both investors and employees.

How do I make decisions?

Entrepreneurs face difficult decisions on a daily basis. Often, these decisions seem like they will make or break the company. If you want to be an entrepreneur, you need to understand how you make decisions under pressure. Failing to make a decision can lead to significant issues, so if you struggle with indecisiveness, this is a problem you ought to resolve. (For example, you could try giving yourself deadlines, or figure out who or what you can turn to as a sounding board.) On the other hand, rushing into a decision without adequate reflection can be equally disastrous. Whatever the case, you need to understand how you tend to make decisions under pressure, so you can figure out what support you’ll need.


Can I juggle multiple things at once?

While you’ll ultimately aim to build a team that complements your own strengths and weaknesses, you’ll most likely wear a number of hats when you’re getting your company off the ground. When starting out, it is not uncommon for a founder to serve as CEO, marketer, business developer, chief product officer, chief financial officer, and more—all at once. It’s tough, but you need to be able to juggle multiple roles without letting any responsibilities drop, at least until you can afford to build out your team.

Aspiring entrepreneurs who know that they struggle in specific areas can seek out help with those tasks early, but entrepreneurs still need to develop a clear-cut system for prioritizing responsibilities. You may also want to seek out advisors or mentors who can help you with certain responsibilities or tasks before you hire a dedicated professional for the job.

How do I cope with stress and failure?

Among entrepreneurs, burnout is a perennial issue. Entrepreneurs frequently work seven days a week. As mentioned above, passion can be a driving force when it’s crunch time, but entrepreneurs also need to know how to manage stress.

While the perfect work-life balance may be impossible to achieve, it’s important to maintain some semblance of a healthy life, even if that means setting aside just a couple of hours each week for a hobby. Even an hour spent away from your company can be extremely therapeutic. In addition to hobbies, exercise, meditation, spending time in nature, and socializing with friends are among the most effective ways to cope with stress. And of course, never forget the power of sleep. Late nights are inevitable, but try to arrange your schedule so that you generally get enough sleep.

You’ll particularly need some way to de-stress when dealing with failure, whether it’s an investor turning you down, a deal falling through, or an idea for a product that just doesn’t pan out. Failure is part of the entrepreneur’s journey, and it happens to literally everyone who has chosen this path. However, failure can be demoralizing if you don’t know how to cope with it. For this reason, it’s important to frame failure the right way—as a learning experience and opportunity for growth—and to seek support so that you can keep moving forward.

About the Author

Joanna RileyJoanna (Jo) Riley is an entrepreneur, investor, and advocate in technology, and is currently the CEO and Co-Founder of Censia. Jo has a highly experienced background in building and scaling companies, which she attributes to her deep passion for people and building technologies that allow people to be their best selves. She brings her wide knowledge of the industry to better transform the way enterprise companies hire talent. You can connect with Joanna Riley at @joannakiddriley on Twitter or on Linkedin. Read her full bio here.