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This is the latest installment of Tales from the Trenches, a series of advice columns by students for students.

Contributed by Chloe Hilliard (L’22) and Liz Jacobs (L’23), members of the Career Development Student Advisory Board.

Winter break brings time to relax and spend time with your loved ones…but it also brings extensive time spent on applications for summer employment. We are here to tell you to stay calm and organize yourself for the season to come! Here are some tips for managing your job application process over winter break.

Prepare in Advance

Job applications are time-consuming and energy-intensive. Preparing in advance will allow you time to write thoughtful, quality applications. It will also give the CDO plenty of time to review your cover letters and application materials. Expect to submit a majority of your applications either during winter break or the first couple weeks of the spring semester.

“One thing I underestimated about winter break as a 1L was how much time it would take to get materials ready for applications. I would recommend not pushing it all until the end of the break because writing a dozen cover letters in a short amount of time doesn’t give you as much room to be creative and to craft letters based on the position. I tried to write one or two cover letters a day.”
-Emily Casey L’23

Be Thoughtful

As you search for jobs, take time to self-reflect on what you are looking for in a job and why you are the right candidate for a given position. Highlight why you are interested in a specific position, and what uniquely qualifies you for that position, in your application.

“Use your cover letter to tell a story that expands upon your resume – telling the employer something they wouldn’t know just from seeing your resume! This is your chance to shine and tell them why you would be a perfect pick for their summer employment.”
-Jessica Rooke L’23

Apply Broadly

Give yourself options by applying to several positions. You may only be interested in working for a firm or in public interest, but try not to limit yourself to a given sector. The more positions you apply to, the more likely you are to secure a job. You may also discover new interests if you apply broadly.


Winter break is a great time to reach out to potential employers. If you are interested in a given firm or office, don’t be afraid to reach out to someone in that office. Consider reaching out to individuals with shared connections (e.g. University of Richmond alum, or someone who went to your undergraduate institution), or even just someone whose work you find interesting. Start by making an appointment with your career advisor. They can help you identify individuals to reach out to, and can also help you craft the perfect introductory message.

Take a Breather

Job applications can be intimidating, but you’ve got this! Reach out to your career advisor if you need help finding positions, would like someone to review your resume and cover letter, or if you need networking advice. Good luck!


If you would like to write a blog for Tales from the Trenches, please contact Carole Yeatts.