How Do You Get a Job After Being Self-Employed for 20 Years?

How Do You Get a Job After Being Self-Employed for 20 Years? was originally published on uConnect External Content.

Self-employment offers many benefits.

Not only can you set your own hours, but you can also prioritize the work that interests you most. However, working for yourself also has its drawbacks. Operating your own business can be risky and unstable at times, too. If your industry takes a hit, you’re left to recoup costs on your own.

So, there may come a time when you want to get a job after being self-employed, sometimes for a decade or more. If you want to re-enter the workforce, what do you need to do to make yourself more hirable? 

Here are our top tips. 


👉 Though you likely wore many hats as an entrepreneur, winnow your job search down to a few roles.

Some entrepreneurs love performing multiple responsibilities; others don’t.

Regardless of your feelings, you likely won’t find a corporate job that will expect you to perform as many tasks as you did during your self-employment. 

With that in mind, identify the types of work you prefer in your self-employment so you can continue them in your new corporate job. That way, you’re not applying widely but can focus on the type of positions that capture your attention. 

“Whenever my clients begin looking for a new job, I advise them to make a list of their negotiables and non-negotiables so that they understand what it is they want to do. This helps them target their job search accordingly,” said Forbes Council member Tammy Homegardner.


👉 On your resume, make it clear that you want to end your self-employment.

Many employers view self-employment and entrepreneurship as a mixed bag.

For instance, they may think that you’re more qualified than other candidates, but at the same time, you’ll be looking for an opportunity to return to working for yourself. 

So, on your resume, make it clear that you want to get back into a 9-to-5 position; you’re not just looking for a temporary situation. 

“I recommend including an end date for your most recent position to demonstrate that you are, in fact, changing your trajectory. I also advise that you refrain from listing your title as the owner or founder and consider a more corporate term, such as general manager, chief operating officer, customer success director, etc.,” Homegardner advised.

This last step makes your resume more compatible with LinkedIn, applicant tracking systems, and corporate recruiters.


👉 Mention the drawbacks of self-employment that have led you back to the 9-to-5 workforce.

In your cover letter, also articulate that you don’t want to work for yourself anymore.

Instead, talk about what you learned in your self-employment before discussing how you’re excited to get back into the workforce. 

This is important because many employers may desire your skills and experience but worry that you’re not in it for the long haul. 

“[Employers] simply aren’t sure how risky you are. Try to highlight this and make them feel at ease. They will likely ask you how you plan on being happy as a team player and content with having a chain of command,” said Levi Swartz, CPRW.


👉 Before your interview, prepare a foolproof “why” describing your interest in working at the company.

Even if you’ve talked about why you want to get back into the workforce in your cover letter, talk about it again in your interview when given a chance. You want to demonstrate your enthusiasm for the job you want to land. So, be prepared with the specifics of why you’re excited about the company, the role there, and your move back to the corporate world. 

What if you’re not excited about a position? You might be applying for the wrong positions. 

“If you do not have the time to research and make an informed decision, everyone is set up for failure. You can’t fake passion. Getting a job is already hard enough without the “red flag” of self-employment. Make sure you are applying to companies that you could be passionate about,” Swartz said. 


👉 If you didn’t have colleagues, per se, use your clients or partners as references.

Some long-term self-employed workers may avoid applying for 9-to-5 jobs because they don’t have supervisors or colleagues who can speak to their experience. But traditional references aren’t the only way you can prove that you’d be successful in the role for which you’re applying. 

Instead, even before you start applying, collect testimonials from your clients and partners. 

“The trick here could be to focus on getting some endorsements and feedback from partners, clients, and everyone that you worked with. Showcase these on your online profiles. Talk about all the new skills you learned and give examples of the most creative work that you engaged in,” advised


How to Get a Job After Being Self-Employed


Some self-employed professionals want to rejoin the corporate workforce after years or even decades away.

If this is you, you may be concerned that companies won’t want to hire you. This certainly isn’t the case. Organizations almost always value entrepreneurs’ skills and expertise; however, they might worry that you’re a “flight risk” who will want to get back to self-employment as quickly as possible. 

So, gear your application materials and interview strategies towards proving that you want to re-enter corporate life. Additionally, articulate that you want to work at the company where you’re interviewing. If you can convey your interest and passion in working for them, they’ll feel confident in assessing your skills and experience and won’t doubt your commitment.