Sai He on Ad Clichés, His Infamous “Dong Draper” Account, & Locating the “Why” Behind Brave Work
Interview by Mike O'Donnell / Editor
At Working Not Working, we’ve been big fans of @DongDraper on both Instagram and Twitter for some time. It’s a satirical send-up of the creative industry (especially AdLand), both funny and often painfully accurate. Armed with the latest meme setups and internet trends, Dong Draper has tackled topics ranging from bad client briefs to too many creative cooks in the kitchen to inescapable creative department clichés. So you can imagine our excitement when Dong Draper revealed themselves to be none other than WNW Member Sai He.
Having revealed his identity to the internet, we felt like the internet should to get to know Sai. It’s also no better time to explore the satirical social accounts and community-connecting work—we could all use a good laugh. Below, Sai shares how working in advertising is a true calling even if the industry is often an easy target, how Dong Draper has opened up doors to interviews at dream agencies and meetings with heavyweights, and why he wants to deliver brave work that serves an actual purpose. “There’s a lot of talk around brave work these days, but we’re fixating on the what — What does it look like? What do we need to make brave work? We’re not asking ourselves why we need to make brave work, and I think that’s because a lot of the motivations are extrinsic.”
We’ve also peppered in some Dong Draper highlights throughout the interview. Enjoy.
Tell me a bit about your creative background. Who is Sai and how did they get here?
I dreamed of becoming a pop star. Growing up, I spent my days writing songs and recording Top 40 covers. I played coffeeshops and showcases and even sang the national anthem before a Red Sox home game. Although my career as a performer peaked then and there, my love of songwriting influences me to this day.
For college, I went to business school intent on working in the music industry. That went out the window my junior year, when I took a marketing elective and our professor showed us The Pitch (the Subway episode with Wongdoody and McKinney). As the creative process played out on screen, I sat in disbelief — brainstorming a breakfast-themed rap song...is a job? I had found my calling.
After that, I stopped taking notes in class and started sketching ads. I taught myself Photoshop and cobbled together a cringeworthy portfolio. I landed a summer internship at Victors & Spoils in Boulder. When I returned to Boston for senior year, I interned at MullenLowe before being hired full-time upon graduation. In the three-plus years since, I’ve traded my Masshole upbringing for stints in San Francisco and New Zealand’s Clemenger BBDO.
How would you describe your creative style? Do you recognize a signature style that links your projects?
I like to take a universal human truth and infuse it with mischief and empathy. Emotional playfulness is at the heart of everything I make.
Oh, and puns. Puns on puns on puns. That’s a direct result of working on JetBlue and having to unlearn many of the Hey Whipple copywriting commandments. One could even say I have a...punchant for wordplay. Sorry.
What do you see as the turning point in your creative development and career so far?
Two years ago, I was at a Starbucks thinking about Wieden + Kennedy — as one does — when a silly thought crept into my mind: how great would it be to have a For Dummies guide to getting a job there? After I mocked up the cover and created an Instagram account to post it from, Dong Draper was born.
Dong Draper is the pseudonym I use to share original memes, musings, and projects with over 15,000 followers in the ad industry. At the beginning, Dong was strictly an outlet for channeling my creative frustrations into shoddy Photoshops. As my audience grew, followers began DM’ing me with relatable #agencylife anecdotes. It feels weird saying this, but conversations with strangers have changed my career trajectory. Many of these chats have blossomed into wonderful friendships. I’m constantly in cahoots with creative idols who challenge me to expand my horizons. Today, I’m incredibly privileged to have no shortage of people I can turn to for support and advice.
“Conversations with strangers have changed my career trajectory. Many of these chats have blossomed into wonderful friendships. I’m constantly in cahoots with creative idols who challenge me to expand my horizons.”
Thanks to the connections made through Dong Draper, I’ve interviewed at dream agencies and met with heavyweights. It’s led to unique opportunities as well. Last fall, I helped cover the annual 3% Conference. Today I’m a Community Leader on Fishbowl, where I support the agency world by facilitating brave, productive conversations.
Using my platform to create camaraderie may sound serious, but I have lots of fun with it. In addition to sharing job openings, crowdsourced advice, and meme submissions, upcoming initiatives include a “What Agency Should You Work For?” Instagram filter and Cannesmouflage, a Chrome extension that replaces Cannes buzzwords with asinine terms.
What’s your creative mission at this stage? What do you feel is missing and what do you want to deliver?
I want to deliver brave work that serves actual purpose. Work that benefits millions by introducing creative solutions to problems big and small.
There’s a lot of talk around brave work these days, but we’re fixating on the what — What does it look like? What do we need to make brave work? We’re not asking ourselves why we need to make brave work, and I think that’s because a lot of the motivations are extrinsic.
Which of your projects are you proudest of and why?
JetBlue — Flybabies
Under the sharp tutelage of Creative Directors Amy Ferguson and Julia Neumann, my partners Athanasia Efthimiu, Alyssa Cavanaugh, and I convinced passengers to cheer for crying babies. Our Mother’s Day campaign appeared on Good Morning America and launched our careers. Flybabies helped cure my imposter syndrome, if only for a minute.
NZ Transport Agency — Let Driving Distract You
Distracted driving is a popular brief that’s inspired hundreds of award-winning campaigns. Which makes it hard to come up with an original idea, let alone a good one. The process was frustrating and brain-melting at times, but in the end we found a fresh angle that subverts category conventions and makes for an unsettling piece of behavior change work.
Dong Draper — I Hope This Email Finds You Hydrated
I thought it would be neat to play with the oft-repeated email cliché, so I turned it into a self-care reminder and asked my followers to join me. It took on a life of its own and is the type of wholesome anarchy I enjoy creating.
Can you walk us through the process of making content for Dong Draper?
Given that it’s a side project without post quotas or KPIs to hit, my process is extremely unstructured. Some weeks I’ll be extremely prolific, while other times I’ll go weeks without posting anything new. It’s really just whenever inspiration strikes.
For example, I was working in a shared Google Doc one day when the three names at the top just so happened to be “A,” “S,” and “S.” It made me laugh, but it also got me thinking about how I could play with that functionality. I immediately related it to a universal pain point around Google Docs — the feeling that everyone is hovering over you watching you work in real time. And that’s how the “ANXIETY” post came to be.
What would be your dream project or job, or is it already on your resume?
I want to direct cinematic and conceptual music videos someday. Other than coming up with ideas, my favorite things about working in advertising are looking at director reels and going on production. I’m honing my filmmaking skills on the side and hope to eventually take what I’ve learned working in this industry and apply it to my musician roots.
Who are your biggest creative influences?
MSCHF
If mischief is my mantra, then MSCHF is my deity. When I’m stuck on a brief I like to ask myself, “What Would MSCHF Do?” I suspect there’s something in the water at their Williamsburg studio. Is it the same water found in their Jesus Shoes? Probably.
The Blaze
The music and video duo are masters of both. “Territory” and “Virile” are captivating, emotional punches to the gut. They’re basically my entire mood board.
Alice Munro
Her Pulitzer-winning short stories demand multiple readings and stay with you long after the last word. “The Bear Came Over The Mountain,” published in the New Yorker, is an excellent introduction to Munro’s multilayered stories that reveal so much about humankind.
What scares you most about making creativity your career?
I’m very nervous about the Tik Tok generation entering the workforce! The ridiculous and delightful content they film using just their smartphones is evidence of serious creative chops.
“I’m very nervous about the Tik Tok generation entering the workforce! The ridiculous and delightful content they film using just their smartphones is evidence of serious creative chops.”
What are 1-3 products or tools that you can’t create without? What’s something you don’t own that would help you elevate your craft?
My Sony A7s is indispensable. I’ve dug myself a hole by praising Gen Z’s smartphone savvy while clutching my full-frame camera, but the Sony’s low-light and video capabilities are unmatched. I take it with me everywhere and use it for street photography and to shoot music videos for my musician friends.
As for something I don’t own, I keep meaning to check out Thomas Kemeny’s book Junior: Writing Your Way Ahead in Advertising. It’s targeted at creatives like myself with a few years of agency experience. Seriously impressive people like Jeff Goodby and Lauren Ranke have heaped praise onto it, which makes me excited to delve in.
Low-light still shot with Sony A7s
What’s your favorite thing on the internet this week?
Amazon Dating is the satirical dating service I never knew I needed, or didn’t need. I’m very torn. Therein lies the genius of this meticulously thought-out project. Every little detail has been considered, leading to countless moments of surprise and delight everywhere you look. It’s hard to pick a favorite detail, but the site’s “Legal” section includes a NGA (Non-Ghosting Agreement) that is hilariously spot-on.
What do you do when Not Working?
I go on freewheeling road trips where the only set destinations are campsites and 24-hour Walmart Supercenters. It’s incredibly liberating to wake up in the back of my car and not know what I’ll see or who I’ll meet that day. These trips give my mind a lot of time to wander, and I always return to civilization rejuvenated and inspired.
I’ve trekked across the US one-and-a-half times. When I moved to New Zealand, I had to learn to drive on the other side of the road. Terrifying, but worth it.
What’s something you’ve learned on your creative journey that other creatives should hear?
Have a strong creative point of view and stick to it.
Not every agency or Creative Director is going to like your work and want to hire you. Don’t take the rejections personally. Learn from their feedback, but don’t take portfolio critiques as gospel. Make what you find interesting, not what others tell you “will get you into [Agency X].” As long as you create for yourself and stay true to who you are, you’ll attract the right people and agencies who value your abilities.
“Not every agency or Creative Director is going to like your work and want to hire you. Don’t take the rejections personally. Learn from their feedback, but don’t take portfolio critiques as gospel. Make what you find interesting, not what others tell you ‘will get you into [Agency X].’”
Who are some other WNW members whose work you admire and why?
I swear I’m not just looking up people you’ve interviewed in the past! I’ve followed Pablo, Brock, and Ani for years and will never not be jealous of them. They’re all peerless in their respective ways, but a unifying thread across their projects is compelling and unorthodox thinking that reaches millions. That’s precisely what I’m trying to do with my career.
What’s next for you? What are you working on now?
Thanks in part to Dong Draper, I have a full-time gig lined up that I’m over the moon about. The leaders are creatives I’ve admired for years. Not only that, but I’ll have the freedom and resources to make big, brilliant, and meaningful ideas. AKA brave work with a purpose.
In the meantime, I’m continuing to build community with Fishbowl. We’re hashing out some audacious event programming and quirky content series going live in the coming months.
Finally, because Dong Draper has given me a voice and opportunities I never thought I’d have, I’m forever keen on using my platform to help a new generation of talent get noticed. I’m beginning to organize and create an initiative for students and junior talent that’s unlike anything out there. Think an unlimited budget version of portfolio night. It might get crazy.
What do you want to see more of in 2020?
The open road. Also plant-based KFC.