From Self-Employed to Employed

Dear, Anita,

I’ve been self employed since 1970 but have also held full time positions with other companies at various times, too. From about 1990 to 2007 I experienced so much business that I worked (at home) an average of 12 hours/day, seven days a week. It all came to an abrupt halt when the recession hit. I’m now looking for jobs doing just about anything, but no luck.

I feel my age is working against me but also my many years of experience. I’ve had interviews where the interviewer probably feared I was more qualified than himself. With a resume that shows so many years of self employment I think most employers think I’ll either leave when business picks up or I’ll steal their ideas or their clients. Any advice for switching from self employment to working for other companies?

Dear, Fearful Free Agent,

Entrepreneur PaycheckWith the economic downturn, many entrepreneurs decided (or had the decision made for them) to return to a conventional J.O.B.  Let’s review some of the upsides to “working for the man.” People in your situation can relinquish the financial worries (though the new position may bring apprehensions of its own). There will be a sense of stability that may have been lacking in your recent economic landscape.  Also, being part of a team can be refreshing. Working solo, you sometimes miss people to bounce ideas off of or just to share what you did over the weekend.

That’s not to say the transition will be easy. You may give up the flexibility of setting your own hours for a 9-to-5 schedule. But that means no more burning the midnight oil! And the daily grind may come with benefits like affordable health insurance.

But I’m getting ahead of myself. First, you need to leap over the hurdles to land that position. An employer may have a bias based on age, but if you craft your résumé wisely, you should be able to secure an interview. For tips, check out my post Getting Hired (or not) Based on Age.

While you could be overqualified in your previous area of expertise, you may need to upgrade or learn new skills to broaden your marketability.  Working by yourself, you may not have needed Outlook or other standard office fare. Check out local colleges and universities or Google “job training” to find resources in your local area to shore up your skill set.

When you were self-employed, you were actually both the boss and the employee, so you know a thing or two about wearing many hats and getting the job done. But be sure to nibble on some humble pie. While you don’t want to be modest about your experience and accomplishments during a job interview, your potential employer will be looking for clues that you won’t go rogue. Practice a response to the inevitable question, “Why do you want to work for someone else again?”  Check out my past article, How to Overcome “Overqualified,” for some interview role-playing assistance.

Keep your spirits up during your job search. To help, here’s a humorous music video, “Self Employment Made Harder By Difficult Boss”:

Readers: Have you successfully gone from entrepreneur to company man (or woman)? What was the most difficult part of the transition? What do you like most about having a traditional job?

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10 Comments (+add yours?)

  1. daniel crawford
    Jan 21, 2014 @ 08:40:31

    Dear Anita I’ve been searching work but can’t find any and really need to be employed I have a daughter with a another child on the way.



  2. Anna Rippy
    Dec 09, 2013 @ 01:10:12

    Can you please help me find a job please thanks a lot



  3. Efren Hernandez
    Dec 05, 2013 @ 16:42:12




  4. Roberto ramos
    Dec 03, 2013 @ 14:41:47

    L think it is a Good company



  5. timggrover
    Dec 03, 2013 @ 14:09:34

    I, too, face the same issues. I’m 56, owned a mobile entertainment company for 25 yrs (responsible for over 7000 events!), sold in January. I’ve been working 2 PT jobs since for most of that time. Also, since our DJ biz was seasonal, I did several PT/temp jobs from time to time,. Right now, I’m getting ready to start work tomorrow morning as a UPS holiday driver helper, which I’ve done before. I’ve tweaked my resume many different times and, being a writer at heart, spend a lot of time putting together quality cover letters. Also been doing volunteer work for an unemployed support group, honing my LinkedIn skills.
    One thing I did prior to my last interview was to list all my strengths, which helped me feel better about myself. I also wrote out the typical interview questions with my response, which helped me present myself better, And I emphasized that YES, I was self-employed, and YES, that scares potential employers–but I added that BECAUSE of that, I take ownership of any project I undertake, for better or worse…because that’s what I DID for 25 years!
    Ideally, I’d like to have another biz (alternate career counselling) but wifey isn’t too keen on that. In the meantime, I flail along…
    Hope some of these tips help! Any added advice? Thanks!



    • anitaclew
      Dec 03, 2013 @ 14:18:23

      Tim, listing your strengths and writing out responses to typical interview questions is a great tip for my readers. Thank you for that. I’m glad to hear that you are brushing up on LinkedIn, one of the newer modes of online networking. Since you sold your business, I would be sure to include that fact in your resume, as that is more impressive than if your business closed because of failing sales, the economy, or other less desirable reasons. Let me know when you find a full-time gig (or if you start that new business).



  6. Norshica Jackson
    Dec 03, 2013 @ 08:16:35

    I am looking for a second job but its kind of hard i need help with finding a second job.



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Anita Clew's blog posts are intended for general guidance and should never be taken as legal advice. In all instances where harassment, inequity, or unfair treatment is believed to be present, please consult your HR Department or legal representation.
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