Every graduating medical student must write a personal statement for the Electronic Residency Application Service (ERAS), yet there are no widely available resources designed to aid the writing process, causing stress among applicants. The authors offered every Medical College of Wisconsin senior student in the Classes of 2014 and 2015 a voluntary self-contained two-hour Residency Application Personal Statement Writers Workshop. The session included the selection of writing prompts, speedwriting, and a peer-edit critique. Data were gathered before and after each workshop and at the time of ERAS submission. One hundred nine students elected to participate. Of the 96 participants completing a preworkshop questionnaire, only 28 (29%) were comfortable with creative and reflective writing. Fifty-four students completed a follow-up survey after submitting their ERAS application. Fifty-one (94%) found the session effective in getting their personal statement started, and 65 (70%) were surprised by the quality of their writing. Almost all could trace some of their final statement to the workshop. Forty-six (85%) found working with other students helpful, and 49 (91%) would recommend the session to future students; 47 (87%) agreed that the workshop was "fun." The full workshop will be repeated yearly. Workshops will also be offered to residents preparing fellowship applications. A shorter version (without the peer-edit critique) was used successfully with the entire Class of 2016 to help them reflect on their initial clinical encounters. The authors will seek further opportunities to enhance reflection for students, residents, and faculty with these techniques.