From Entrepreneur to Employee: Common challenges and their solutions

If you are returning to the world of work after being self-employed, you will face some challenges as you are not the typical job seeker moving from being an employee in one company to another.  You are essentially changing your type of employment i.e. from self-employed to employee. The good news is that this article will provide you with tips to overcome potential biases, held by employers, against former business owners. It is up to you, as the entrepreneur-turned-job-seeker to present the image that you are not running away from a failed business experience, but have much to offer to the corporate world. The three challenges that you are likely to face when transitioning from self-employment to employee are;

  • The perception that entrepreneurs are hard to manage within a corporate structure
  • Confusion about how to portray the entrepreneurial years on your CV in a manner that makes sense to the corporate world
  • Positioning and selling your entrepreneurial experience to appeal to any role you are applying to, especially if your business was not related to your field of work



Challenge #1: Former entrepreneurs will struggle with authority

Some employers may believe that as a former entrepreneur, who has been operating outside a chain of command, you may not make a good employee. The perception is that you will struggle to accept supervision and authority and this bias may have employers thinking that you are an undesirable hire.

Solution: If you were employed before becoming an entrepreneur, highlight the fact that you have successfully been a traditional employee and operated within a corporate hierarchy before. It would be beneficial to direct the potential employer to your former boss for a reference in order to reinforce this. Additionally (particularly if you have never been an employee) highlight that you consider each of your business clients as “bosses” – as you are required to take instructions pertaining to their individual needs and produce deliverables that satisfy their expectations, similar to a reporting relationship.



Challenge #2: Portraying your experience as a business owner in your CV

It is not uncommon for individuals to venture into a business completely unrelated to their field e.g. an engineer opening a restaurant. As a result, many do not know how to portray the years as a business owner on their CV, in a manner that is both appealing and relevant to employers. In addition, having a title such as Managing Director or CEO may throw off employers as they will not be able to relate your experience to what their business needs.

Solution: As an entrepreneur, you have some flexibility at changing your title in line with the role you are applying for. Do not lie or omit that you were the business owner in your CV. Using titles like CEO, MD, Owner may make you look over qualified if you are applying for lesser roles; use titles such as Managing Partner, Operations Manager, Business Development Manager, Marketing Manager etc. If you ran a business that was unrelated to your field in the corporate world, rather focus on competencies in describing that role – highlighting transferable skills.

For example, if you ran a restaurant and are applying for an engineering manager job, instead of detailing your daily duties at the restaurant, consolidate your experience using competencies (supported by activities) that speak to the corporate world. Think of detailing your experience using categories such as Financial Management, Operations Management, Human Capital Management, Business Development and Strategy, Client Relations etc. as this will appeal more to business and sell your transferable skills.



Challenge #3: You are running away from a failed or failing business

A common reason for entrepreneurs to return to the corporate world is as a result of a business that is no longer sustainable due to economic and other factors. The perception from employers is that you have failed at business and you may be associated with “being irresponsible”, “a high risk taker”, and “operational mismanagement”. Returning to full time employment is a decision entrepreneurs will constantly have to defend and it’s important to frame it in a manner that will make them appealing to the corporate world without misrepresenting anything.

Solution: Even if you were forced to close your business, the experience you would have developed during your entrepreneurial years can be of much value to the corporate world. It is your role to sell that value. Always keep the postmortem about your business very brief, focusing on skills you gained and not what went wrong. The following are examples of what you can highlight as your selling points as an “ex- entrepreneur” in the corporate world:

  • You understand the pressures of meeting payroll and paying bills and have cross functional understanding of business. This gives you a strong appreciation of resource management and allocation,
  • You have a pronounced sense of risk management,
  • In spite of being your own boss, you can still provide references to corroborate your performance using your clients and suppliers – solidifying your credibility
  • You have enhanced creative problem solving skills that a traditional corporate employee is unlikely to have had a chance to develop,
  • Highlight benefits of employment vs. self-employment such as health insurance, paid days off, pension contributions – all in an effort to prove your staying points and address the perception of being a flight risk.


Employers need to think differently about how former entrepreneurs can bring valuable skills when they transition to full time employment. Individuals who have taken the risk, at some point, to trade a steady pay check for self-employment require some credit. Entrepreneurship is often a great developmental experience and comes with many skills, not contained in the repertoire of traditional employees, that can add value to the business.