Make Yourself an Offer They Can’t Refuse: Landing a Creative Job.

Rick McHugh is an aspiring pro baseballer turned Senior Vice President, Group Creative Director, and Copywriter at Hill Holliday ad agency in Boston. He scrapped his way up the ladder at agencies throughout the city, including Holland Mark and Greenberg Seronick O’Leary Partners. His work spans the breadth of Dunkin’ Donuts, LG, Kay Jewelers, and Party City; as well as the depths of such creative showcases as One Show, Cannes Shortlist, and Communication Arts Advertising Annual. He is also a staunch advocate of the will to execute a 360, extend one foot, and trek back to the drawing board. Rick McHugh is one Exhibit A in living out the creativity and tenacity required to not only broach, but surmount the advertising industry.

Photo: Tom Perri

Photo: Tom Perri

How did you land your first copywriting job?

I had a few good meetings with a small, creative shop in Boston. No offers but they seemed to like me. So, I met with the CD/owner and said “I’ll work here as many days a week as I can afford - for free, to show you why you should hire me.” Well, when you offer free labor, why wouldn’t they say yes? After I helped win a couple new business pitches, they hired me.

What is an ideal working environment for you?

I don’t know if I have an ideal environment. I do like being able to close a door and get to it. Somewhere you can think, pin up ideas. What’s more important to me is the partner you’re working with. Someone who is talented, of course, but someone who cares about the work and is willing to push until you come up with something you think is interesting and worth someone’s time and attention.

What do you look for in a student portfolio?

Ideas. Big, smart, interesting, memorable, surprising, more-than-one-off ideas. Some craft in writing or design/art direction. A different point of view. An idea of the person’s personality.

What are student books lacking most these days?

See above. Craft is something that is lacking. Writers who can write. Art directors who can art direct. It’s more than just coming up with the ideas. There needs to be an ability to execute.

How can a student best prepare for a job in advertising?

Continuing to work on their portfolio. Always trying to make it better. And developing a thick skin. Creatives are asked to go back to the well and come up with more ideas over and over and over and over. Knowing that many, hell, most of the ideas you come up with will die for a host of reasons. The people who know this are the most valuable.

How do you get inspired when you run out of ideas?

Get up and walk around. Grab a coffee. Look at advertising award show annuals or advertising showcases online. If that doesn’t work, the sheer terror of a deadline or disappointing a creative director should do it.

What’s the best way to get a job at Hill Holliday?

Contacting our creative recruiter and having a great portfolio! Reaching out to creatives here is a good way too.


Hayley Dupree is Junior Copywriter at Dell Blue in-house ad agency who to rewrite likes to different sound sentences so that they. She likes to then recraft writings to spruce up the ear’s experience.