Saying Goodbye to Self-Employment? 5 Tips for Getting Hired

in Business, Career, You

goodbye-to-self-employmentShocking, I know. But from time to time, people who are self-employed decide not to be self-employed. Some do it out of necessity, others out of curiosity, others out of financial motivation, and others because they just don’t want to be self-employed anymore. Whatever the reason, finding a new job is sometimes a challenge for self-employed people.

Is Self-Employment Oil to “Regular” Employment’s Water?

It shouldn’t come as a shock, but the idea that someone would leave the utopia of self-employment to go back to working “for the wo(man)” isn’t a popular one. Why it isn’t popular is a blog post for another day. Instead, here we’ll focus on how to go about it, because from first-hand experience I can tell you that it is not easy.

I’m not sure whether or not hiring managers itch out of a psychosomatic allergic reaction, or if it’s just snobbery, but it would seem that self-employment is not widely accepted as valid career experience by those who get to make the life-altering hiring decisions. To give you an example, a few months ago, when I was asked what I did prior to joining a company in a training class with several other people, the manager laughed and made a joke,

“Oh come on. You know you were just unemployed!”

Uh-huh. Aside from misconceptions about self-employment, you will also need to deal with the major change in work environment, work style, and the idea that you will need to ask for time off to go to the doctor or the bank.

Since I’ve made this journey more than once, I assure you that it can be done, and if you are entrepreneurial at heart, you enjoy a challenge anyway. But your first hurdle is getting hired!

5 Tips for Getting Hired

If you’ve made the decision to go back to work for someone else, here are some tips for getting hired.

1. Be Honest About Why You’re Looking for Work

Why are you going back to the traditional workforce? Whatever your reason, be honest.

Include the reason you are seeking employment in your cover letter. Sara Sutton Fell, CEO & Founder of, suggested that being honest and upfront is the best way to accomplish this. “This doesn’t have to be too detailed, but hiring managers will likely look at your resume and wonder ‘Why?’, so it’s best to not leaving them wondering or guessing, just serve it up to them as honestly and positively as you can.”

But what if your “why” makes you look incompetent or weak? What if it was just too much for you to handle? Bill Horne, moderator of The Telecom Digest, and a consultant, suggests giving your hiring manager the benefit of the doubt. “The truth is that running your own business means being ‘good enough’ at a whole variety of tasks,” said Horne. “And managers already know that, so just be honest and say ‘I’m tired of juggling so many hats and I want to do one job that I’m very good at instead of ten that I’m always behind on.'”

2. When It Comes to Titles, Choose Something Recognizable

When you were self-employed, you may have had the flexibility to be creative in how you describe your work. Creative titles help entrepreneurs stand out among their peers. However, when you are trying to get hired, you need to speak a more familiar language and “give yourself a title that is easily translated and transferable to a more traditional organization,” suggested Roy Cohen, career coach and author, The Wall Street Professional’s Guide.

“Without a common language to bridge the two worlds – yours as an entrepreneur and theirs with standards and protocols – you will not be giving them what they are needing and expecting from potential candidates,” said Cohen.

3. Dress Like You Know You Should

I wish this went without saying, but we here at have talked about our tendencies to be sloppy before! Entrepreneurs get to create their own dress code, which can mean pajamas for some people. When it comes to going on interviews, Cohen warns against that and suggests dressing to fit in, rather than stand out. “It’s easy to get sloppy when you work for yourself. Research the company, its culture, and its prevailing style. Every company has either an official or unwritten dress code. Don’t break it or you will look like you don’t belong there.”

4. Use Testimonials to Highlight Your Accomplishments

This is a bit of an insider secret to resumes: don’t talk about what you did; talk about what you got done.

What have you accomplished? Sum up your experiences into a few very special highlights – the positives. Hopefully there are some. “In your resume, highlight your accomplishments and the skills you developed while in self-employment, and how they can benefit a future employer,” suggests Sutton Fell.

If you have been keeping track of client testimonials, this will be easier than you think. Your testimonials are a great source of well-worded accomplishments, because your clients look at the bigger, positive picture rather than the task-by-task daily grind you get used to. You called it “making digital files, tracking results, and compiling reports” and they called it “saving significant time and money by reorganizing their entire accounting department.”

Which sounds more appealing to a hiring manager?

5. Emphasize Your Ability (and Willingness) to Work in a Structured Environment

This point was suggested by Andrew Schrage, Editor at the Money Crashers personal finance blog, and it’s something I think we can all relate to. We spend almost all of our time structured to our own liking – after all, isn’t that one of the major perks of working for yourself?

According to Schrage, “Many people who are self-employed do not work a typical 9 to 5 work day. Perhaps they work more or less, or perhaps they even work on the weekends. Moreover, they’ve likely developed some habits around some of the challenges of working from home. The bottom line is that those who are self-employed have the freedom to work in an unstructured manner according to their preferences and other commitments.”

But when hiring managers consider you for a position within their company, they realize this, too, and want to know whether or not you can adapt well to a structured work environment again. “This can be a concern for potential employers,” said Schrage. “As they think: ‘Will this previously self-employed person be able to conform to our company culture and work in a structured environment and respond to a boss?’

In your interviews and perhaps even in your cover letter, be sure to help ease concerns by expressing your desire and willingness to work with a “schedule and at the demands of others,” said Schrage.

Good Luck!

If you’re getting ready to look for a new job, or are currently in the middle of it, stay focused and persistent. Despite the news, there are jobs out there, even in communities where the economy has taken a turn for the worse.

Be sure to check out two of the sites featured above:

  • An award-winning service for flexible, part-time, telecommuting, and freelance job listings.
  • Money Crashers: Personal finance website that educates individuals in making wise decisions about credit and debt, investing, education, real estate, insurance, spending, and more
Sara Sutton Fell is a online job expert who has appeared in national media ranging from CNN to MTV News, and she recently won a 2011 “Game Changer” Award from Workforce Magazine.

Image: photostock /

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{ 2 comments… read them below or add one }

Raj-PB December 8, 2011 at 3:23 am

I came across a quote which said, “An entrepreneur rejects the 8 hour work day and adopts the 16 hour work day instead”. Getting back to employment or the structured timing it requires is not a big issue for them. The biggest issue is to face the politics and time waster people once back.

Tia Peterson December 8, 2011 at 11:34 am

@Raj-PB Hi Raj! True for some, but not for others. I was only working about 4 hours per day, Monday through Friday. But it’s also true that it was no issue at all for me to go back to working full days, except that I missed my son like crazy and it was very strange not being there for him (even though, truthfully, I really wanted the break)!

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