7 Considerations to Make Before Leaving Your Job to Start Your Own Business


In many ways, entrepreneurship built America. Farmers, ranchers, and artisans nurtured and profited from their skills. Communities supported each other by buying and producing locally.

Therefore, it’s not shocking that Americans still possess an entrepreneurial spirit within themselves. Office work became the norm after World War II when the economy shifted toward government, telecommunications, finance, and real estate industries.

Individuals who have considered leaving their jobs to start businesses are not alone.

In 2023, entrepreneurs can start businesses more easily than they could 30 years ago. Silicon Valley built the infrastructure that made working from home and remotely as employees or freelancers in 2008.

In 2020, video conferencing, virtual workspace, and productivity software proved they could handle large loads and heavy traffic.

Therefore, building a company from scratch is no longer a far-fetched dream.

It’s OK to leap, but it helps to jump in measured and calculated leaps.

For example, entrepreneurs must make several self-assessments, including financial ones. They also must consider their families and loved ones and prepare them for what comes next.

We outlined seven considerations to make before leaving your job to start your own business.

Personal Considerations

Many elements make up the American Dream, and one of them is entrepreneurship. It’s possible to build a company with little to no investment.

However, it’s wise to take some personal components into account.

1. Assess Your Financial Situation

Entrepreneurship is more manageable when individuals have little to no financial obligations. Then, individuals can invest their resources into the ventures.

Therefore, assess your financial situation.

For example, make a list of your financial commitments. Establish how much you need monthly to keep a roof over your head, food on the table, and clothes on your back.

Then, assess if your savings will cover monthly expenses and for how long.=

2. Review Insurance Policies

Some professionals opt to become employees since employers make the benefits packages so enticing. A popular benefit that people enjoy is insurance.

In 2023, professionals can find attractive self-employed health and dental insurance policies. Before making the transition, determine how much coverage you need. Then, prepare to purchase a policy that meets your needs.

Check out this article from Selfgood on employer-sponsored health insurance expiration FAQs.

3. Prepare Family and Loved Ones

Individuals can step into entrepreneurship at any time. However, those who have dependents should consider them before leaping.

Self-motivation is a common entrepreneurial characteristic. It still helps to have support from those closest to you.

Thus, prepare family and loved ones and consider how they’ll react to the news. Consider their needs as you attempt to get a company off the ground.

Professional Considerations

Successful entrepreneurs come from all walks of life, but it helps to consider some professional elements to strengthen success.

4. Assess Your Skills

Some researchers predict freelancers will become the majority labor market group in the next few years. Therefore, the freelance market will see demand for an array of skills.

Small businesses built America. Thus, a demand for their products and services will continue to exist.

Consider how your skills fit into the demand and measure up against those who have been in the market for many years.

5. Assess the Market

After assessing your skills, consider the market that you plan to enter. It’s possible to enter a market that has already experienced saturation. It will simply require more effort and resources to break through the saturation.

The goal is to enter entrepreneurship with a clear view of reality and a level-headed mindset.

6. Assess Your Knowledge of Entrepreneurship

Small business ownership comes naturally to some individuals—most work at becoming successful entrepreneurs.

Before diving in, assess your knowledge of entrepreneurship. The book market has several books on the topic that guide readers through their experiences.

7. Review Local, State, and Federal Regulations

Entrepreneurship requires commitment. It also requires satisfying local, state, and federal regulations. New business owners must obtain licenses and permits, meet zoning requirements, and purchase insurance.

Then, they must pay and collect taxes. Otherwise, owners face hefty penalties and bureaucratic delays.


Professionals transition from employee to entrepreneur daily. Since 65% of new businesses will fail within 10 years, make a few assessments and consider some things before jumping in 100%. By understanding the market and solidifying your financial position, you can weather the initial challenges more easily.

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