2 Minutes With ... Patrick Holly, ECD at Upwork

Patrick is a multidisciplinary creative whose career has run the gamut from agencies like R/GA and AKQA to brands such Apple and Uber. He even built a content platform with Steph Curry. Patrick currently serves as Upwork’s executive creative director, leading a team of writers, art directors, designers and strategists. Prior to Upwork, Patrick was brand director at Harley Davidson, overseeing content, PR, social and brand partnerships. When he’s is not working, he spends most of his time on two wheels or watching Sex and the City reruns with his wife and dogs in Austin, Texas.

We spent two minutes with Patrick to learn more about his background, creative inspirations and some recent work he’s admired.

Patrick, tell us…

Where you grew up, and where you live now.

I grew up between a small town outside of Boston and Blue Hill, Maine. I now call Austin, Texas, home, but kind of feel like I was meant to be here all along.

How you first realized you were creative.

I think I learned that I was really bad at everything else first. I went to school to be a doctor and while that clearly didn’t work out, it led me to start looking far and wide for a career that sounded fun. After a little while I ended up stumbling into the ad scene in Portland, where I was shocked to find out that pursuing my love for writing could actually lead to something resembling gainful employment.

One of your favorite projects you’ve ever worked on.

Our latest brand campaign for Upwork, “This Is How We Work Now,” certainly takes the cake. It was not only incredibly fun to work on, but ended up being really successful too.

A recent project you’re proud of.

Recently my team decided to find a cure for the “Remote Happy Hour,” an idea that is good in theory, but in practice, it’s anything but. So what we did was make a happy-hour-in-a-box that took all the best parts of a happy hour (meeting people and drinking beer) and literally sent them to your front door. Each box is complete with a six-pack of beer, a special Viewmaster to look at Upwork talent profiles, and a watch where it’s always time for happy hour no matter where you are.

A person you idolized creatively early on. 

My mother. She always had a new creative project or business she was working on. From a painting business to a gift basket service, she always was pushing herself, which I still idolize to this day.

A moment from high school or college that changed your life. 

I had a pretty rough four years of high school, but ended up coming out a more compassionate, empathetic person because of it. So, I wouldn’t say it was a single moment, but more so a series of them that I believe makes me a better person and leader today.

A visual artist or band/musician you admire.

I’ve always admired Donald Glover. He has brought a truly incredible amount of creativity and drive to every endeavor he’s taken on, from music (and music videos), to comedy, to film. His record Camp is also one of my all-time favorites.

A book, movie, TV show or podcast you recently found inspiring. 

I recently revisited Creativity, Inc. by Ed Catmull and reading it in a remote-first world makes it even more interesting. A lot of the ideas he has on making an environment that breeds creativity can translate quite well, in spirit, to the remote world.

Your favorite fictional character.

Mr. Rogers

Someone or something worth following on social media. 

If you don’t follow Pablo Rochat, shame on you.

How Covid-19 changed your life, personally or professionally. 

It’s hard to overstate the impact it had on my professional life in particular—which, in turn, impacts all other elements of my life. It enabled my move to Austin, which, as I mentioned, was my dream city for the longest time. My story probably looks a lot like other peoples’ where the unlocked ability to work remotely ended up changing almost every aspect of my life for the better—and I ain’t going back if I can help it!

Someone else’s work that inspired you years ago.

Years ago, I came across David Neevel’s portfolio. He was one of the first creatives I knew about who went outside the box of “traditional” agency creative: making words, pictures or some combination of the two to go on a screen. He took a fun approach to catching your attention by engineering (and in some cases, comically over engineering) objects that’ll bring you incredible joy through absurdity.

Some of my favorites are …

• Emphasis Bot: a robot that claps with every syllable for added emphasis
• Email Guitar: a guitar that lets you type emails while you shred
• And he even turned all this into his own show on MTV

Someone else’s work you admired lately. 

David Lee and his crew at Squarespace have done a great job making fun, funny, and extremely crafted work with celebrities (something that is no small feat). Although great, my favorite part isn’t the spot itself, but the behind the scenes work that they shoot. Brilliant.

Your main strength as a creative person. 

One of the hardest things in creativity is not just making great work, but selling great work. Over the years, I’ve developed a knack for selling work up the chain.

Your biggest weakness. 

Something that I think plagues many creatives: shiny object syndrome, aka ADHD.

One thing that always makes you happy. 

Throwing spaghetti at the wall with like-minded creatives.

One thing that always makes you sad.

When great ideas die, regardless of reasoning.

What would you be doing if you weren’t in advertising.

I’d probably work construction.