are employers wary of the formerly self-employed?

A reader writes:

I’m 35 years old and have been self-employed for the past five years as a sole proprietor. My business entails providing career and educational counseling to students and immigrants. I have a true “brick and mortar,” not a virtual office. Though I have enjoyed the challenges that come with running a business, I’m ready to close up shop and work for a traditional employer.

This job market is particularly tough and I am wondering whether there is a bias against hiring those formerly self-employed. My colleagues have stated that the self-employed are deemed to be too independent to work with co-workers and the perception is that those who now want to work for someone else do so because they have failed in running a business. What is your take on this and what’s the best way to sell myself as a team-player in an interview?

I think this is one of those areas where different hiring managers have different opinions. Personally, I see self-employment as often being a plus: People who have run their own business tend to have strong work ethics, get what it takes to make an operation run well, often empathize with those aspects of management that can irritate other employees because they know all too well the reasons behind them, and so forth. So I like it.

If I’m interviewing someone who’s been self-employed, I want to know things like: Why are they moving out of self-employment? Have they thought about how they’ll adjust to having a boss again, and how do they feel about that? What did they learn from running their own business?

There are good answers and bad answers to these questions, of course, but assuming their answers don’t raise red flags, I lean toward seeing self-employment as impressive.

But as with anything, some others feel differently. But your colleagues claiming that you’ll be branded with a scarlet E (for entepreneur, get it?) that all or even most hiring managers will run from are wrong.

{ 9 comments… read them below }

  1. Anonymous*

    I've been a recruiter for more years than I want to admit. I can tell you from first hand experience that there are a significant number of hiring managers who prefer NOT to hire an entrepreneur. Their logic is that once the economy improves, you'll quit and start up your own company again.
    While employers want lifelong fidelity (and will lay you off when the quarter's numbers don't measure up), don't let this dissuade you. All it means is that you may need to knock on a few extra doors before one opens.

  2. Christine Witt*

    For me, it's more a matter of being able to verify the information on your resume.

    Sometimes, people will fill a blank spot in their resume with "Consultant" and I'm left to try to figure out if they were really consulting the whole time, or if they were having a bit of a break from working full-time.

    Because you had a brick and mortar business, it will be easier to verify.

    Just be prepared to answer questions about why you want to go from running your own business back to working for someone else.

  3. Anonymous*

    Thanks for the comments. I wrote the original question and am wondering what comments would raise red flags during an interview ?

  4. Anonymous*

    I would imagine that if your answers indicate that you would have trouble adjusting to not being the one in complete control, you'd set off a couple warning bells. Some self-employed people get used to not having to answer to anybody, and if you don't show that you're not one of those people you could hurt your chances.

  5. Anonymous*

    From the experience of being in HR, self-employed people often lack modern computer skills, reliable references as well as some soft (social) skills. I would be more interested to know why they chose to be self employed to start from. From experience, many people get frustrated with their management and so they decide to be "their own boss". If that's the underlying reason, then it would be a red flag for me right there in terms of their willingness to accept someone else's management style, having others who's been in the company for a significant period of time, their fit into an organizational culture and respect toward things being done in a certain way, etc.

  6. TheLabRat*

    "Their logic is that once the economy improves, you'll quit and start up your own company again. "

    This one cracks me up because I started my business in response to the bad economy. Had the economy been good, I probably never would have. In fact, I seem to remember a business 101 class that covered entrepreneurs as experiences bumps during recessions.

    "From the experience of being in HR, self-employed people often lack modern computer skills, reliable references as well as some soft (social) skills."

    The computer skills portion of this one also amuses me; again a direct part of why I started freelancing. I was tired of being told by people who don't know squat about computers (and more importantly don't know how to properly use their office software; Word's Style function is your friend kids) that their way was better when I got things done in half the time with fewer errors.

    I totally get what you're saying on soft skills and everything else though. I can work on a team but it's not my favorite thing in the world; years of experience have shown me that there's always one slacker who gets away with it and one person who does all the work and gets none of the credit. While this may be a valid complaint, I can't say my response to this scenario is always appropriate. If that didn't raise a red flag for someone interviewing me I'd be concerned.

  7. Office Humorist*

    I never even thought that employers would have a bias (one way or another) for entrepreneurs (also is a pre-req to being an entrepreneur being able to spell it, because I think i would fail?).

    I guess it makes sense, but I would think the positives of being disciplined and business minded would help–of course if you're bad at taking direction that could cause a problem.

  8. RJ*

    Re the social skills:

    I'm part-time self employed and have taken a job half-time as I had had enough of working on my own, and wanted more dealings with people, and a steady income.

    I've really noticed the poorer social skills of and the lack of a service ethic of the 10 person company I am in now.

    One thing you learn being self employed, and getting income by networking is that you are ALWAYS looking to serve the client, ALWAYS on the job, and ALWAYS need to be super friendly and helpful to people because, when self-employed, you are your brand.

    Social skills are essential for the self-employed, not an optional extra!

  9. Self Employed*

    If you have ever owned a small business then you would know that we have the best “social skills” otherwise we wouldn’t have customers to sell our product to. And, we do everything in our business shipping/receiving, budgets, State/Federal law compliance, Marketing, new product development, Networking, Yes, we are responsible for every aspect of our business. As a divorced parent, I wanted the flexibility of completing these tasks at my leisure. By the way, I also completed my Bachelor of Science in Human Resources and my Masters in Business Administration (MBA) while being self-employed. So your theory of outdated skills is unfounded. Maybe, entrepreneurs have MORE ambition then employees that work in the comfort of a employer 9-5, and only five days a week.

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