The Top Five Reasons It Takes a Long Time to Transition From an Entrepreneur to Employee

​Why it can be hard for former business owners to find a new job or career.

​For a variety of reasons, a business owner and entrepreneur may find themselves looking for a job. Sometimes it is right after closing or selling a business, other times it is about a lifestyle change or career pivot, and occasionally it is to find something to do in between entrepreneurial ventures. 

The transition from being a business owner and entrepreneur to an employee is challenging. I know first hand because I’ve been through it. I started and ran a business for nearly 18 years and then had to face what would become one of the more challenging experiences of my life, finding a job. For me, the process took over a year, which is not too uncommon. Understanding these challenges can help you navigate this difficult road.

The top five challenges commonly faced by entrepreneurs who are looking for a new job:

1. Inner Work
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​​After being a business owner, it can be tough to know what type of job you will like doing for someone else. You may have once been the general manager keeping all of the balls in the air. Yet in companies, especially larger ones, they seek out specialists to handle narrowly defined parts of the business. Establishing how your knowledge and skills map to job roles in the market is difficult to do and requires a lot of inner work.

Inner work refers to introspection surrounding three keys areas:

• How are you naturally wired?
• What are you good at?
• What do you love doing?

The place where these three circles intersect is where you should ideally focus your career. There are several ways to arrive at the details to populate these circles. To answer the naturally wired question, take some personality assessments and for the what are you good at or love doing parts, make lists and talk to family and friends. It’s critical to put your time into inner work because if you don’t, you could end up being unsatisfied with your job.

2. Limited Jobs Available

If you operated your business for any length of time, chances are you had a significant amount of responsibility and made good money. To work for someone else with a similar amount of responsibility and compensation, you are looking at higher-level positions in the company, such as Senior Manager, Director, VP, or C-level. There are fewer of these jobs at the higher level. Consider the pyramid in the image below. There are more entry-level lower paying jobs at the bottom and fewer executive high paying jobs at the top.​

You can see that there are fewer seats near the top where you want to be. Further, these roles are highly scrutinized and competitive. Another challenge is that you are not an “insider” who has been climbing the ladder at similar businesses for years. Instead, you’re an “outsider” who ran your own business. To a hiring manager, you’ll appear to be more of a risk as compared to a candidate who currently has the same job title at a competing business.

3. Rusty Job Search Skills

As a business owner, you didn't need to look for a job. The last time you were in the job market things may have been different. There are a ton of new things to know and skills to master when it comes to a job search. If you haven’t had to face it lately, you’ll be on a steep learning curve. 

Some key areas of a job search include:

• Resume, Cover Letter, LinkedIn Profile - Did you keep this information current and updated while you were running your own business? Or is the content no longer relevant to the job you are looking at? These assets need to be on point and specifically oriented to the job you are trying to land.
• Job Search Activity. Are you unclear about what actions to be taking or what combination of tactics to employ? How much networking should you do and what are you asking for exactly? Which jobs should you apply for and how many per week is the right amount? How do you balance all of these activity options and know when to make modifications?
• Interviewing - While you probably have interviewed many people to work for you, when was the last time you were being interviewed? Not only are your interviewing skills rusty, but now you have to convince the interviewer that you will be a good employee and not a lone wolf entrepreneur anymore.​

4. Credentials, Skills, and Knowledge

The things you had to be good at to run your business won’t necessarily apply to the type of job you’re looking for. Experience with a particular software tool is a classic example of this. Your business may have had a CRM tool but it wasn't Salesforce. You understand CRMs, yet deep experience with Salesforce may be a requirement for the type of role you’re seeking and thus you’re stuck. This can apply to certifications like Lean Six Sigma, Project Management Professional, Google Ads, etc. These are things you may have dealt with at your company, but it never made sense to get a certification in any of them. With such fierce competition for higher-level roles, if you can’t check off a certain box for a particular skill or knowledge, you’re much less likely to move toward an interview.

5.  Entrepreneurs Are Misunderstood

Entrepreneurs make up a very small percentage of the world and thus most recruiters and hiring managers have little context for who they are and what value they can bring to the organization. Hiring managers want to hire people that look just like them and their teams who have been in that type of business all along. Entrepreneurs, because they’re so rare, don’t fit that profile. Therefore, hiring managers can’t wrap their heads around their value. 

Classic points of misperceptions include:

• They’ll quit and take our secrets to start another business.
• They can’t work for a boss.
• They’re a loose cannon and won’t follow procedure.
• They must be rich, why do they want this job?

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To break through these challenges you need to work hard on positioning yourself correctly for the role and actively work on downplaying the entrepreneur image and play up your value to their business.

Entrepreneurs are valuable and should be working.

After struggling through all of these challenges myself, I was inspired to create a course just for entrepreneurs transitioning to an employee. Created by someone who has been through the trenches (me!), this course outlines the entire process to help cut down the amount of time it takes to find a new career after being a former business owner.

If you want to learn more about this course, you can get a FREE preview here: oppositeofwork.thinkific.com.

​Entrepreneurs follow many paths in their lives and sometimes that may include working for someone else.

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Bill Ross is a business coach and consultant offering small business owners, micro business owners, and eCommerce business entrepreneurs advice and support to help them achieve their goals. Learn More