Get All Access for $5/mo

How to Transition Back to Employee After Being an Entrepreneur Being the CEO and the janitor isn't for everyone. Here is some sage advice on how to get back into the day-job routine after working for yourself.

By Carol Roth

Opinions expressed by Entrepreneur contributors are their own.


Owning your own business is tough. It's definitely not for everyone, and even the best business ideas sometimes don't work out. In fact, this happens more often than not. While the numbers vary by study, it's estimated that well more than half of all businesses fail -- or at least fail to succeed.

Additionally, other factors in an entrepreneur's life can change and require them to go back to seek a day job, whether in the corporate world or even with another small business. So, I reached out to my colleague Catherine Morgan, a career-transition coach who works with entrepreneurs and others seeking to transition to a new position through her own company Point A to Point B Transitions, for some suggestions on how entrepreneurs should position themselves when interviewing for corporate jobs.

Related: 3 Tips for Making the Career Change You've Always Wanted

Q: What are some of the common reasons people go back to the corporate world -- or at least working for someone else -- after being an entrepreneur?

Morgan: It's easy to buy into the dream of owning your own business -- and thinking that it will be better than working for someone else. Months or years into business ownership, I have had clients tell me that however many hours they might have to work in corporate, executing on someone else's strategy would seem so much easier than having to come up with the strategy, do the marketing, sell the work and then deliver the work. Being the CEO and the janitor isn't for everyone.

And then, there are professionals who have had personal situations like a spouse losing a job or other life event which may force them to consider full-time employment. And whether it's true or not, there's the perception that a corporate job offers more stability.

Q: When you decide that you are going to hang up the entrepreneur shingle and head back to work, how should you approach figuring out what to do next?

Morgan: Often, professionals will try to go back to the industry or position title they held previously. Or they may take their best skills as an entrepreneur and try to translate them into a corporate setting.

I had a client who had her own business for 20 years with a partner. She was in charge of the financial part of the partnership and felt very confident in her ability to be a controller for another company after she sold her half of the business. We did some interview question coaching and got her really comfortable talking about the skills that she used in her business, and why she wasn't interested in starting another business. After a few rounds of interviews with a prospective company, she was offered a great position.

If the entrepreneur isn't sure how their skills might translate or is at a loss about what they want to do, I always refer them to my eBook, Re-Launch You: Discovering Your Point B and Embracing Possibility.

Q: How do you prepare a resume to highlight your entrepreneurial experience without scaring off potential employers?

Morgan: I encourage entrepreneurs to be proud of their professional accomplishments and describe exactly what they did for their clients or in their business. It's important to list the specific skills used and knowledge acquired, so that a recruiter or human resources professional can make the connection with the job description.

Some professionals will want to explicitly add that they are currently seeking a full-time or contract position in their professional summary, whatever the case may be. Cover letters can be used to connect the dots as well. It's better to address the elephant in the room -- or the big question that you know needs to be answered.

Related: How Quitting Can Get You Exactly What You Want

Q: How do you address the transition in interviews? What about those who ask why you want to be an employee after working for yourself?

Morgan: This is the hardest part -- and it's a bit of a tap dance, to be honest. If you have been successful in your business, people will ask why you don't want to continue. Frequently, my clients want to work on projects that are bigger than they can do on their own. The successful executive turned entrepreneur may miss attending staff and board meetings and creating multi-year road maps.

Professionals who have been mentors and leaders at large organizations may miss building teams and managing people. If that is the case, I urge them to say so. It makes sense to the listener and validates the corporate employment option.

If your business didn't get traction, that's not necessarily a black mark. Frequently, the entrepreneur can get credit for having had the guts to try. They can talk about what they learned in the process. They can talk about how much harder it was than they expected. They can talk about becoming a great time-manager and learning to be self-directed. They can talk about how great it will be to work with a team again after being in a resource-constrained situation.

Or they can talk about being an "intrapreneur" -- bringing their entrepreneurial mindset into a corporate environment. That can be a big plus for some companies! Overall, they should aim to be honest and enthusiastic. Don't apologize. Answer the question and move on.

Q: How do you network to find opportunities?

Morgan: The logical places to start are former colleagues and bosses. Identify companies that are of interest and mine LinkedIn to find people who work there. Try to schedule informational interviews.

Job seekers need to have a clear "ask" prepared, so that they can concisely describe what they are looking for or who they are trying to meet. People want to help, but you have to make it as easy for them as possible.

Q: What are some of the biggest roadblocks that entrepreneurs-turned-employees face in getting hired? What about in succeeding when they return to the workplace?

Morgan: The biggest roadblock for entrepreneurs is their inner game. There is often some shame or sadness associated with leaving your own business. It's important to acknowledge it -- and even grieve a little, if necessary. They may feel like they are "selling out." And they may be afraid that they will lose the friendships they have developed with other entrepreneurs.

Onboarding can be really challenging for former entrepreneurs. The longer decision-making cycles and defined processes and procedures in corporate can seem overly burdensome when you have been able to make quick decisions and change directions easily in your own business. I remind clients to exercise extreme patience -- with themselves and their colleagues.

Going to an environment with cubicles can be hugely distracting at first. Earbuds can help, if you are allowed to use them at work. I remind professionals that they have done it before -- and they can get used to it again.

Also, if they have been working at home or keeping flexible hours, having to go into the office and work a fixed schedule will take some adjustment. I tell my clients that during the first few weeks, they may feel like they have perpetual jet lag. I reassure them that after a while, it will become routine. I ask them to be extra kind to themselves and to make it a priority to eat well, exercise and get plenty of sleep.

If you want to learn more about Catherine and how she works with her clients in career transition, you can find more information here.

Related: 7 Sure Signs Now Is the Time for a Career Change

Carol Roth

Entrepreneur, TV host and small business expert

Carol Roth is the creator of the Future File™ legacy planning system, a “recovering” investment banker, business advisor, entrepreneur and best-selling author. She is also a reality TV show judge, media contributor and host of Microsoft’s Office Small Business Academy. A small business expert, Roth has worked with companies of all sizes on everything from strategy to content creation and marketing to raising capital. She’s been a public company director and invests in mid-stage companies, as well.

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Editor's Pick


ChatGPT is Becoming More Human-Like. Here's How The Tool is Getting Smarter at Replicating Your Voice, Brand and Personality.

AI can be instrumental in building your brand and boosting awareness, but the right approach is critical. A custom GPT delivers tailored collateral based on your ethos, personality and unique positioning factors.

Business News

Is the AI Industry Consolidating? Hugging Face CEO Says More AI Entrepreneurs Are Looking to Be Acquired

Clément Delangue, the CEO of Hugging Face, a $4.5 billion startup, says he gets at least 10 acquisition requests a week and it's "increased quite a lot."

Growing a Business

He Immigrated to the U.S. and Got a Job at McDonald's — Then His Aversion to Being 'Too Comfortable' Led to a Fast-Growing Company That's Hard to Miss

Voyo Popovic launched his moving and storage company in 2018 — and he's been innovating in the industry ever since.

Business News

You Can Now Apply to Renew Your U.S. Passport Online — But There's a Catch

The U.S. State Department officially launched the beta program this week.

Business Ideas

63 Small Business Ideas to Start in 2024

We put together a list of the best, most profitable small business ideas for entrepreneurs to pursue in 2024.

Business News

Apple Reportedly Isn't Paying OpenAI to Use ChatGPT in iPhones

The next big iPhone update brings ChatGPT directly to Apple devices.