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.