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Home > Blog: Job Seeker Tips > Tips for Business Owners Returning to the Workforce

Tips for Business Owners Returning to the Workforce

Harried Business OwnerBeing your own boss is an almost-universal fantasy. Who doesn't dream of being self-employed, calling the shots, never having to ask permission for time off, or being able to fire anyone who pisses you off? Owning a small business can indeed be an exhilarating experience. But it's no guarantee of happiness or success.

About half of new businesses fail within their first four or five years, and others are sold once their owners discover that the entrepreneurial lifestyle has at least as many lows as highs. (Time off? Forget about it!) Whatever the reason, many former business owners, myself included, decide to get the hell out and run back to those long-lost friends: a steady paycheck and employer-paid benefits.

And then comes the dilemma of how to apply for a non-executive position when your last job title was "Owner, Operator, President, and CEO." Having launched, operated, and sold a small business several years ago, I'd like to share what I learned out about the job search when you're transitioning back into the workforce after being self-employed.

Your Cover Letter and Interviews

Remember how I mentioned that being your own boss is everyone's fantasy? That probably includes your future hiring managers, who will likely wonder how you could ever be happy returning to work for someone else after you got to "live the fantasy." (Ha!)

So it's important to convey in your cover letter, and especially in your interviews, that you really do want to be back in the workforce, and specifically, that you want the job you're applying for. Present your business-owning past as a valuable experience that prepared you for the next job, rather than as some boss-free utopia you're sad to leave.

A good way to do this is to prepare a story that communicates three things: 

  1. How good you are at X  [X being a skill that's important in the job you're applying for].
  2. That owning a business prevented you from doing as much X as you would have liked.
  3. You really look forward to a role where you can get back to X.

For example, let's say X = Marketing

"Marketing is one of my greatest strengths and favorite aspects of business, but I wasn't able to focus on marketing as much as I would have liked when I owned my business. There was always a shipping glitch or an accounts payable issue or some other crisis that pulled me away. So I'm excited to get back to a role like this one, where I can apply my marketing expertise to help build your brand and your bottom line."

What About Your Resume?
While the job title President on your resume may be accurate, it's not helpful in communicating your value to your next employer. It might even get you rejected because you appear to be way overqualified.
Since you were your own boss, you can retroactively (and truthfully) give yourself almost any job title, depending on where you want to be next: Marketing Communications Specialist, Customer Support Supervisor, Accounting Manager, Purchasing Agent, Equipment Repairperson, Quality Assurance Specialist, HR Generalist, Event Planner... right on down to Chief Cook and Bottle Washer, as my Irish grandmother used to say.

If you're applying for that marketing job, you could say something like:

Marketing Communications Specialist
Yourname Enterprises, Inc.
April 2006 to July 2009

  • Owned and operated a service business, holding sole responsibility for marketing communications, branding, PR, advertising, search engine optimization
  • Built customer base from 0 to 70 clients, achieving annual gross sales of $150,000
  • Established email marketing campaign that generated an average of 30 leads and 12 new customers a month

As a job seeker, your goal is to demonstrate your value to your next employer, regardless of what your old business card might have said.

These ideas worked for me, but I'm sure there are plenty of others. If you've transitioned from business ownership back into the role of employee, or hired someone who did, what would you advise?

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