Cover Letter Conundrums (Part 3 of 3)

By Mary Carden, CPRW

In the third and final installment of this series, I will review the trickiest circumstances to talk about in your cover letter: risky situations. Although it might feel like sharing these circumstances could start your job search on the wrong foot, that’s not necessarily the case. Here are strategies to address potential “red flag” scenarios without hurting your chances of landing an interview.

11. I’m in the middle of a career change and don’t have a typical background for this type of job.

During and after the pandemic, we at Job Market Solutions have seen a marked increase in people transforming their careers. It’s an exciting, but often very stressful time. It’s easy to worry that your nontraditional background could eliminate you from consideration, especially when more-qualified candidates have also thrown their hats in the ring.

To use a metaphor, the solution is to “build a bridge” that connects your former career with your future career. Try to answer one (or more) of these questions: Which skills do you have that make you a good fit for the job, even if you lack directly relevant experience? How have your prior experiences prepared you for this transition? How will you bring a fresh perspective or unique insight to the team?

12. I have a small business/side hustle and don’t want that to detract from my eligibility for this job.

If you devote any time to a family business, an Etsy store, a freelance role, or casual “gig economy” work, you’re definitely not alone! Many people have started side hustles to generate extra cash or to make ends meet in a challenging economy.

Be aware that your side hustle might make you a less attractive candidate for a full-time, professional role because the hiring manager might see you as someone who can’t give 100% to the company.

However, if your side hustle is relevant to the job to which you are applying, keep it on your resume and add a sentence describing how much time you devote to that venture, especially if it’s only a couple of hours per week. This will help to reassure the hiring manager by showing you’re able to manage your time effectively. Also, if you’re planning to stop the side gig when you start the new job, spell that out in your cover letter.

13. I have a career gap that’s more than six months.

There are pros and cons to bringing attention to a career gap or sabbatical. In general, it’s best to be up-front about the reason/s you were not working and any context necessary to understand what you were up to during that time. Unexplained employment gaps are the ones that raise red flags. Whatever it is, just say it. It’s the absence of an explanation that makes the hiring manager wonder.

The COVID-19 pandemic caused many such career gaps, whether they were caused by professional circumstances (such as a furlough, lay-off, or business closure) or personal reasons (illness, caring for a family member, or bereavement). Everyone was impacted by the pandemic differently, but everyone needed to change their life in some way. The hiring manager will understand that you needed to do what was right for you and your family.

This concludes my three-part cover letter conundrums series. The bottom line: Nobody is a perfect candidate! Almost everyone undergoing a job search has questions, concerns, or special circumstances that they will need to keep in mind as they apply for jobs. Now you have the tools you need to address those issues with diplomacy, present yourself with confidence, and land that interview.

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About Mary Carden, CPRW – Mary Carden is a resume writer and job search strategist. Her clients have achieved professional success securing interviews and job offers in virtually every industry. At the time of writing this blog post, she has written more than 500 cover letters, ranging from entry-level “first job out of college” applications to global searches for chief executive positions at Fortune 500 companies.

Author: Mir Garvy

I’ve written resumes for 2,000+ job seekers just like you—and helped my clients land jobs with companies like Amazon, SAS, Google, Duke University, Travelocity, Cisco Systems, GlaxoSmithKline, Expedia, and IBM.