Planning to start your own business? Consider these key tips before taking the plunge.
Starting your own business can be an enticing prospect, especially in today’s challenging job market. However, it’s crucial to be well-prepared before taking the leap into entrepreneurship in order to minimize risks and increase your chances of success.
One valuable strategy to test the waters before fully committing to running your own business is to develop a side hustle while maintaining your current job, income, and benefits. According to CBS News business analyst Jill Schlesinger, this approach allows you to explore your business concept without immediately giving up the security of your current employment situation. Schlesinger, who is a seasoned business owner herself, emphasizes the importance of understanding both the potential benefits and sacrifices of starting your own business.
When considering the transition to entrepreneurship, it’s essential to be aware of the benefits you may be giving up, such as employer contributions to retirement plans and health insurance coverage. Opening your own business also entails handling payroll and tax responsibilities, as self-employed individuals are responsible for both employee and employer taxes. It’s crucial to assess the value of employer-provided benefits like legal services, health insurance, and health savings accounts, which may be forfeited when venturing out on your own.
Health insurance is a key consideration for aspiring business owners, and there are several options to explore, including staying on an employer plan through COBRA, switching to a spouse or partner’s plan, enrolling in an Affordable Care Act plan, or investigating association health plans for small businesses. Understanding your tax obligations based on your business structure is also important, as self-employed individuals are required to file their own tax returns and make quarterly estimated tax payments. Different business structures, such as S Corporations or limited liability companies, have their own tax rules and requirements.
Seeking guidance from experts, such as CPAs or Certified Financial Planners, is highly recommended when navigating the complexities of starting a business. Consulting with professionals can help you develop a solid plan and avoid costly mistakes. Schlesinger advises against relying on automated tools like Claude or ChatGPT for business advice, emphasizing the value of expert guidance in structuring your business effectively.
In conclusion, careful planning and consultation with knowledgeable professionals are essential steps to take before embarking on the journey of starting your own business. By understanding the potential risks and rewards, as well as seeking expert guidance, you can position yourself for success as an entrepreneur.


