Q. Over the last 10+ years or so, I’ve worked only in contract positions (finance and accounting-related).

Part of this had to do with not wanting to commit to the weather in Boston (I used to live in San Diego), and not wanting to commit to a job that I would become bored with. Also, I had no debt and no kids.

Nevertheless, at 50, I am afraid that I have damaged myself such that it will be difficult to find a “permanent” job.

A. Many job seekers look at why they might have trouble getting hired, worry about it, and then do nothing to prepare to overcome the issues. There is a better approach and that is: PREPARE! You need to prepare for the hardest questions, surprise questions, questions you wish you were never asked, and you must have great answers to all of the above. For example – you know (or you do now) that you will be asked some version of tell me a weakness. I asked a person this question today, and her answer was “I am passive aggressive”. I’m sure she is, but I know this isn’t the answer she wanted to give me. She did not prepare for this question so she blurted out an answer which did not make her look good.


Before you get bogged down in “damage control”, review the positives that can be demonstrated on your resume. You have had 10 years of successful employment in a demanding field requiring trust from your employer in your talents, an ability to hold confidentiality, and a commitment to some time period agreed to between you and your employer. There are the ways effective contracts are run. Contract opportunities offered you the flexibility and freedom you wanted, and companies benefit from your availability without a need to make a long term commitment.
You don’t say why, but it seems your needs have changed, and you are now interested in a more permanent job. As with any non-traditional career path, employers want to know why you did what you did, and it has to make sense. You also need to make sure your actions don’t represent you poorly, and that you present as a low-risk candidate. The resumes of people who have had many jobs, or only contracted, appear as though they can’t make a commitment, or there is a performance problem that is not visible from an initial meeting.
You know what people are going to want to know. Prepare the answers to the questions you know will come up. And if you can’t anticipate the questions, then get help in coming up with at least 20 questions that won’t be easy to answer. For example, “Do you get bored easily? Is that why you contracted?”. If you want a permanent job, then this is not an answer that will help you. What you can say is “I took contracts and found that I could gain a great deal of experience from being involved in different financial issues at a variety of companies that I probably wouldn’t have had the chance to do if I had been at one firm. I feel like I continued my education with many classes in each of these contracts, and made significant contributions as well”.
“You haven’t stayed anywhere longer than one year; do you think you can do that now?”. Some question like this will come up. Prepare your answer, and address the fear. The employer doesn’t want to hire you, train you, invest in you and then have you leave. So your answer needs to address these unstated concerns.
So your needs have changed. What is it that the company gets by hiring someone with your non-traditional background? A finance person with broader experience than a traditional 10 years would have provided. A person who has worked at well managed and poorly managed companies and knows how to self-manage and get the job done? Prepare the positives about how the company will benefit. Prepare for positive answers to questions that address your “damaged” career path, and turn the employers view around.

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