A cover letter for My Destination

9f2a43f1537e42feca3b1c2c5bbd41beIt seems like all I have been thinking about lately is the Biggest Baddest Bucket List competition and scrambling to get votes for my entry.

Though the more I think about it, the more I think of it as a job application because, if I win, it would be a ginormous advancement to my career. It’s no secret that travel is my number one passion. I am constantly devouring travel memoirs and travel magazines, inspired by travel photography and I simply can’t watch a travel show without getting excited at the chance of one day visiting and experiencing it for myself. My professional skills lend themselves to making a career as a travel journalist and I consider this the competition a huge opportunity for me to break into that business.

For that reason, I’ve written an open cover letter to accompany my “application” and I hope that someone from the company will take the time to consider it:

My Destination Headquarters

London, England


Dear Misters Waller and Street,

I saw on your website that you are in search of a creative, independent and passionate candidate to travel around the world for six months and provide video, photo and written content for your website. Based on my professional career in the visual arts, proficient writing capabilities, diverse travel history and experience running and managing my own company, I am confident that I could make a lasting contribution to My Destination and provide quality content while experiencing the Biggest, Baddest, Bucket List.

I have worked as a professional photographer in Chicago since 2007. My work ranges from travel photojournalism, to weddings, to corporate and promotional work as well as fashion photography and portraiture. My diverse photography portfolio can be viewed on my professional website, www.jwinterphoto.com. Images from my travel collections have been published and exhibited in the Chicago area, including a six-page spread in Quintessential New Trier magazine’s November/December 2010 issue.

I also keep an active blog (www.jennwinter.com) that I use to highlight recent photography work, travel writing and ongoing philanthropy work in Kenya. Several of my stories have been republished in online travel magazines, most recently at Bucket List Publications. In addition, one of my stories was published by the Chicago Center of Literature and Photography last summer and one of my travel photographs was chosen as the cover image.

At 24 I took a great risk in launching my own company, J. Winter Photography. It has been a learning experience to say the least, but six years later I am proud of what I have been able to build from nothing. While I have enjoyed the challenge of working with corporate clients and capturing such memorable events as weddings, my first love is travel and I hope to use my writing and photography skills to break into the industry as a travel journalist.

My travel history is as diverse as my photography portfolio, including a semester in Rome (2003,) a summer internship in London (2004,) an 8-month volunteer stint in Nairobi (2006-7) a solo trip to Egypt (2007,) a trek up Kilimanjaro (2009) and a three-week trekking adventure in Peru and Chile (2011.) Travel energizes me and I am hopelessly in love with all aspects of it. I love getting to know locals, trying new foods and customs, exploring cities and countrysides alike and, most of all, challenging myself as I partake in new adventures. Both my successful trek up Kilimanjaro and my trek to Machu Picchu bear witness to my adventurous spirit and ability to push myself to new limits.

I believe that my simultaneous jobs as a photographer, writer, freelancer and webmaster speaks to my day to day flexibility as well as to my time management skills. In addition, my experience at being self-employed shows that I work well independently and am able to meet deadlines while turning out creative and quality content. I am confident that these skills, coupled with my passion and love for travel, sets me apart in this competition, making me an ideal candidate for the job.

Many thanks for your consideration and best wishes.

Jenn Winter


  1. Bravo, as far as I’m concerned you have the job. Of course I’m a little bit prejudiced. Love you Grammie

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