Money Smart Athlete Blog

The Athlete’s Second Career – Entrepreneurship or Employment?

Is entrepreneurship right for you? 

In your post sports career you will have to decide between two main options:  Becoming an employee or an entrepreneur.  There are two main ways of making money; employment and entrepreneurship, working for yourself or working for someone else. You should focus on choosing which of the two options will make you happier and aligns with your dreams and goals.  

No one but your self can tell you which one is the best option for you, but you can definitely find out which of the two best fits you. Write down your dreams and goals and assess which method will help you the most in achieving them; Entrepreneurship or employment?  There is no black or white answer to which option fits you, as it depends on many factors and nothing will ever guarantee success in either of the two options.  

Some people might be more talented in being entrepreneurs, but no one is born one. People can become entrepreneurs at any point in their lives, no matter what they are currently doing, how old they are, and their level of experience. Being a sports employee for most of your life is something that has given you great experiences that may be a huge asset for you in your future business endeavors. 

If you want to live a comfortable life, you need stability and peace, you hate risk, value your free time and need time to relax, you better choose the employment path.  If you are able to take some risks, you love to work, you want to keep growing, you are ambitious, and you can handle uncomfortable situations then you might as well follow the entrepreneurship path.  Both paths are very different but can be enjoyable depending on your personal characteristics. 


Characteristics of a successful entrepreneur 

Successful entrepreneurs have certain skills and personality traits in common.  Some of the typical qualities of the successful entrepreneur are the following:  

  • They have a vivid imagination and they are creative 
  • They are big picture thinkers 
  • They are self-motivated 
  • They are risk takers and their risk tolerance is above average 
  • They understand their own strengths and weaknesses 
  • They are self-starters, goal oriented and competitive 

In addition to the above, entrepreneurs have the ability to supplement areas where they are lacking by hiring people who are exceptional in those areas, or finding ways to complement and enhance their relevant skills. 

 Athletes should realize that not everyone is cut out to be his or her own boss, but if they find themselves longing to be in control of their lives — and if most of the traits listed above can be used to describe them — then they have what it takes to go into entrepreneurship.  Something very important that all athletes who aspire to become entrepreneurs should know is that most successful entrepreneurs go through a period of struggle before finding and implementing the right business idea that will make them successful. 


The advantages and disadvantages of entrepreneurship: 

If entrepreneurship is the path you have chosen for your post sports career then you should know that it has both advantages and disadvantages.  The advantages of entrepreneurship should make you feel stronger about your decision but at the same time you have to be willing to deal with the disadvantages and not be disheartened when things don’t go as planned.  We list below a few of the advantages and disadvantages of entrepreneurship so that you know what you will have in your plate as a new entrepreneur. 




The personal freedom associated with being an entrepreneur is unparalleled.  You are the decision-maker for everything. You can make your own schedule, make your own hours, and be in control of your own income. 

Choosing Who You Work With 

You can choose the people with whom you conduct business. It’s a great feeling talking business over cocktails at the beach with your friends who are also your business partners. 

Financial Rewards 

As a business owner, you have the ability to control how much you earn. When you want to make more money, you simply work more efficiently or put in more effort.  

Skill Set Growth 

Being a business owner means you are responsible for everything that happens within your company. Consequently, you will be exposed to a lot of new things and you will learn many new skills. 



Financial Insecurity 

You must take the good with the bad, and owning your own business is no different. Being in charge may mean sacrificing the security of a regular paycheck and regular work hours.  You are responsible for your financial security as well as for those who work for you.  That can definitely keep you up at night, trying to figure out how you will meet the payroll at the end of the month! 

Health Insurance 

Employer health plans and other benefits that come with a regular job and which we normally take for granted, are now your responsibility and are likely to have a negative effect on your bottom line.  

Decisions, Decisions, Decisions! 

Although being the primary decision-maker is a key benefit of entrepreneurship, it can also be challenging and sometimes overwhelming, having to make all the decisions on your own.  


Entrepreneurship is not for the faint-hearted, that’s for sure!  Before you actually choose going into business for yourself as a post sports career option, you need to weigh all the relevant factors but most of all you need to be in check with yourself that this is what you really want to do.  For a discussion of the pros and cons of entrepreneurship as a second career and how you can assess whether it is the right choice for you, please connect with us at