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Self-Employment: How to Get a Job if Your Business Fails

This is a guest post from my friend, the aptly named Your Boss, at What Your Boss Really Thinks. I asked her to write this post because I’m always concerned about how my self-employment would look on a job application if my business ever collapsed. 

Sometimes I wish I could be self-employed. Self-employment has the possibility to be one of the most rewarding experiences. I could be my own boss. I could set my own schedule. I could help people. I could take a nap in the middle of the day. It definitely seems that self-employment could be a good fit for me.

On a different day and, most definitely, on a payday, I think that being self-employed can also be one of the hardest experiences. You never know if you can make enough money. You are almost never sure if your business can last past next month. (Andrea’s note: True story!)

What happens if your business doesn’t make it? You still need a paycheck. So you find yourself in the job market. Again.

However, this time your job search is different. You are worried that self-employment does not look good on a resume. You are getting restless, imagining that your potential employer is asking you the most dreadful question of all “Why did your business fail?” You are ready to burst into tears when someone says “You were not able to run your own business, how can we be sure that you are going to be an asset to our company?”

Different hiring managers have different opinions on the former self-employed looking for a job. I cannot speak for everyone but only for myself.

What to Focus On When Getting Ready for an Interview:

  • A very strong and good reasoning to the question of why you are transitioning from self-employment into a full-time job.
  • Skills you are bringing to a company. I would stay away from discussing benefits, raises, time off. You do need to know all of this but make sure to focus on what you are going to contribute to the company and not what you need from the company.
  • Showing that you are not a failure just because your business did not succeed.
  • Your experience as a business owner. You will be asked why you want to return to salaried employment. This is your chance to show what experience you have gained from being self-employed. This is a very unique angle that you should be able to play to your advantage. Practice!

Tackling Self-Employment on a Resume

I, personally, do not like resumes longer than a page or two. To be honest, I might cringe at a two page resume but I will still look at it.

On a resume I would like to see some kind of explanation of what kind of business you were running. Please do not write a long and passionate explanation why you started your business. However, tell me what skills you have acquired, developed and used during your self-employment period that are relevant to the position you are applying for.

From the top of my head, I can tell you that I would love to see that you are a multi-task expert, a self-starter, and a hardworking person with very strong organizational skills. You can add your specific experience, highlighting these skills.

Insight into Your Boss’s Mind

I want to be honest with you – there are things that concern me about people looking for a job after their self-employment failed to fulfill their dreams.

What Concerns Me:

  • I will have a nagging suspicion that you need a full-time job to transition yourself from your own failed business into another project.
  • I will have doubts about you adjusting to working for a boss. You used to be your own boss for a very long time. Are you going to be okay accepting someone else as your manager?
  • I will wonder how you are going to settle into a fixed 9-5 schedule. It is a big change and, let’s admit it, it is not for everyone.
  • I will wonder what you are not telling me about your failed self-employment. I will question if you gave me a real reason of why you are looking for a job.
  • I will question your ability to work with others. After all, you were on your own for some time. You could have forgotten what it means to be a team player.

In the end it all comes down to your attitude, motivation and confidence. I like confident (not cocky) people. I like survivors and hard workers. Even if I have doubts, it is up to you to prove me wrong.

Andrea’s note: I’m glad to know that all hope isn’t lost if I ever have to apply for jobs again. However, the last section gives me pause – that’s exactly what I’m afraid of. I’ll be honest – if I had to go back to work, in my mind it would be temporary until I could find a way to go back to working for myself. (Unless of course I got burned out and truly wanted a steady paycheck.) I wouldn’t feel comfortable lying to a potential employer, but at the same time, I wouldn’t want to say “I’m just here until my finances stabilize, then I’m out of here!” So for now I’ll just make an effort to keep a list of the skills I’m developing and pray that my business continues to flourish.

Your Boss expresses her opinion and advice on career, job search, management issues and office life at What Your Boss Really Thinks. Your Boss created her blog to help people to better understand their manager and give direction and guidelines on how to navigate the office life. Feel free to ask her about your office or career dilemma by submitting an Ask Your Boss form on her website. 

About Andrea Whitmer

Andrea is a freelance web developer and mom trying to maintain a sense of humor in an otherwise chaotic world. She blogs in hopes of helping others avoid the same mistakes she made in the past. Join in the discussion here on So Over This, or connect on Twitter, Pinterest, Instagram, or Google Plus. You can also subscribe to new posts via RSS so you never miss out!


  1. This is all great to know! Sometimes I think about venturing out into self employment, but always wonder about what to do about if it doesn't work out and I need another job.

  2. This is great! And such a scary thing to think about…

  3. I think depending on the job having self employment experience could be a big help. It just depends on the job you are applying for and the people screening your resume and hiring you.

  4. Pauline @ Reach Financial Independence says:

    I hope I won't have to go back to employment but if I do, I would first try to put the emphasis on my commitment to the company, that I will stay and can bring them a lot of assets. If I see that the person is a bit reluctant, I would try to see how the mission could be filled with a temp or freelance contract and offer that to them, so we get acquainted to each other, and keep a bit of flexibility.

  5. plantingourpennies says:

    I'd add – save lots of documentation. Mr. PoP ran his own hobby business for about a year right before we married, and when he went to work for a big company (the $80K company his post today is about) about 18 months later, he had to account for the period when he was self employed. Well, by then we had shut the bank account that the business was tied to and had to go digging around for stuff since most of it was off the books. It was actually a big PITA and could have cost him the job on a technicality it we couldn't find the stuff. We found it, but lesson learned.

  6. Budget & the Beach says:

    I'm a freelancer looking for a full time job. I don't consider my business as being a failed business, it's just the I prefer the steadiness of a full time job (not that I will necessarily word it that way). But, I do like what you mentioned that someone might be thinking if they were interviewing me!

  7. Great post! As a Recruiter in the past, I've had the same concerns while interviewing someone who was recently an entrepreneur transitioning into employment.

    Depending on the job, it's may even be better to hire someone with that kind of entrepreneurial spirit. Although they may not have had co-workers, entrepreneurs will have had to try to keep their clients happy, they would have had to work with different kinds of people, they would have had to construct a sales strategy, and they would have certainly not been a clock watcher. All good things 🙂

    I agree that a resume that's longer than 2 pages is a drag to read! I've received 8 page resumes! A resume isn't a life story, it's a marketing document and nobody wants to read something so long.

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