Emily McDowell

Tell me about your time in advertising. How did you get started and why did you leave?

In 2002, I was 26, living in Minneapolis, and working for myself as a jewelry designer, selling my work to shops around the Midwest (this was before Etsy). I liked what I was doing, but I’d sort of randomly fallen into it and it wasn’t my passion, and I needed better health insurance. (This was also before the ACA.) I saw an ad in the paper for a scholarship contest at Miami Ad School; until then, I’d never really thought about advertising as a career, and I didn’t know portfolio school was a thing. It sounded fun, so I ended up applying at the last minute and winning the scholarship.

I was hyper-enthusiastic and motivated when I started out, but about two years in, I started feeling increasingly disillusioned and dissatisfied. I moved agencies a lot, thinking I’d be happier if I went somewhere else or worked for someone else. I would eventually realize the common denominator in all those places was me, and that maybe advertising just wasn’t a great fit. But I felt like I’d put in too much time and effort to “start over,” so I kept at it, hoping something would shift, for six more years.

I had a very average ad agency career. I struggled to get good work made, and I won a handful of awards, but nothing spectacular. Five years in, I was laid off from a job I really cared about, and the “work is a family” fantasy bubble burst. This was the beginning of the end for me, in terms of feeling motivated to keep giving so much extra time and energy to my job. Ultimately, I got tired of working all the time with very little to show for it, and I was also pretty over the effort it took to fit into the boys’ club culture of a lot of the creative departments I worked in. 

I’d also started to feel like the clock was ticking. I was a few years older than most of my peers who’d gone straight from undergrad to ad school, and I worried that if I wasn’t on an ECD path by my late 30s, I’d age out. And truthfully, I hadn’t produced the kind of work that would get me there. So in 2011, I quit my full-time ACD job in order to freelance and go back to school for my Master’s in spiritual psychology, primarily to help me figure out what I was supposed to be doing. The personal development work I did in that program helped me launch what became my company in 2012.

What are you doing now? 

In 2012, I founded a stationery company called Emily McDowell Studio. The business started out as me selling prints on Etsy, and eventually became a team of 15 people in our Los Angeles office and our Las Vegas warehouse. Until 2017, I was its CEO, the writer, illustrator and designer of all its products, and the voice and face of its marketing. (This was… too many jobs.) 

In 2018, we merged with a larger, more established indie publisher/gift brand called Knock Knock. With this shift, I became a minority equity partner in the joint company, and we ran both brands under one roof with a shared staff and back end. The merger enabled me to (happily) relinquish CEO duties and focus my energy on building a creative department – taking us from an artist-driven brand to one with multiple creative collaborators, where the work could be executed by a team of people who weren’t me.

In 2020, we changed the brand’s name to Em & Friends; in 2022, both Em & Friends and Knock Knock were acquired by the publishing arm of Barnes & Noble, and I exited the company. I'm now a consultant, advisor, and coach for product-based businesses and the people who run them, a keynote speaker, and author of the Substack newsletter Subject to Change.

Did you always think of advertising as a stepping stone or did something change your mind?

When I started, I thought I’d do it forever; I thought I’d own an agency. 

How did the idea for your new venture come about? 

I ended up taking the advice of an article I read on what to do when you don’t know what you want to do for a living, and revisiting the things I loved doing as a kid. For me, that was writing, drawing, and hand-lettering, which in 2011 was not yet trendy. I opened an Etsy shop to sell prints of my work as a side project, but pretty quickly, I realized there was an opportunity to make greeting cards that felt different from what was out there.

At the time, the big card companies were still making very traditional cards that were more about social convention than about real human connection, with aspirational content – gushing poems for love and Mother’s Day, etc. I rarely connected with these– they just didn’t reflect the reality of my life– and I saw a need for cards that were written for the relationships people really have. 

Creatively, cards were also kind of the perfect match for me, allowing me to combine my writing, lettering and illustration skills, plus my love of psychology and human insights, which was one of the aspects of advertising I liked the most. They were also cheap and easy to manufacture, so there wasn’t a big financial or logistical barrier to entry.

What was your first step in starting your new venture?

I literally just started making stuff. The first card I ever made was a Valentine for the person you’re kind of dating but not “officially.” I put it in my Etsy shop, and then I had the fantastically lucky break of Etsy posting it on their Facebook page. At the time, posts from brands you liked still showed up in your FB feed, so that card got put in front of a ton of people, and it went mega-viral. I shipped 1700 cards one by one from my apartment in a week, at which point I had to cut off shipping because it was February 8th. (First lesson of online sales: put the Valentines in your shop more than two weeks before Valentine’s Day.) I had no idea what I was doing; I didn’t have time to order envelopes wholesale, so I bought out all the PaperSource stores in the Los Angeles area.

I had $15,000 in savings at the time, and I spent half of it launching my first wholesale collection three months later. I had a very clear vision for what I wanted the brand to be, and I built a deck for it as a way to sort of strategically validate the idea. But I didn’t write an official business plan; there were too many variables, and my startup and initial overhead costs were low. My plan was to do stationery on the side while I freelanced in advertising, with the hope of eventually growing it into a full-time job, but it took off immediately, and a week after my wholesale launch, I was scrambling to find a warehouse space and hire employees.

What struggles did you have? Did you have ideas that failed?

Honestly, my biggest struggles in the first five years were what people call “good problems” – navigating extremely rapid growth and demand, while simultaneously learning (through trial, error, and Google) how to run a product-based business with both wholesale and online retail divisions, managing a growing staff and over 100 outside sales reps, writing and illustrating all our products, and being the voice and face of our marketing. I spent six years working nonstop in order to keep up, which ultimately did some real damage to my physical and mental health.

In the absence of a better idea, I’d also impulsively named the brand after myself, which became both a blessing and a curse. It benefitted me personally in terms of ending up with name recognition, and related opportunities that have come along with that, like speaking, publishing a book, etc. But it was ultimately a challenge for the company, in that from day one, the brand was tied directly to me, my personal story, and my personality—for better or worse, I was its name and its public face. Among other things, this made it complicated to hire other creatives, which was necessary in order for the business to be sustainable.

Did you have help along the way?

The stationery industry is the most welcoming, kind group of people I’ve ever met. I was immediately embraced by industry veterans, who generously shared their  knowledge with me despite technically being their competition. This help was critical at different points along the way. I had great emotional support from friends and my partner. I didn’t have outside financial help.

Did you ever consider giving up?

Nope.

What would you do differently if you did it again?

I would deliberately keep the company smaller. Our capitalist, bigger-is-better culture teaches us that if a business works, the natural next step is to grow it – and if you have investors, a company that can’t scale is seen as a failure. But scaling comes with a host of challenges that I didn’t comprehend when I started out. It changed my role and took me away from making the work, which was the thing I loved most. It also required leading, managing and interacting with a ton of people, which turned out to not be my favorite thing, and is hard to do well when you’re doing multiple jobs. 

And, my own personal preferences aside, scaling isn’t always the best strategic path for a business. If you’re selling a physical product, increasing revenue also means increasing overhead costs, which eats into your profit margin. Meaning, after a certain point, growth means adding a lot more complexity and work to your plate for a relatively small increase in profit. If I were to do this again, I’d choose a simpler model with less stress, and be willing to sacrifice the extra profit.

I would listen to my body more (at all!) and make sure my needs as a human being were met first, then the needs of the business, then the needs of our customers. You can skip that step and still be successful according to business metrics, but after a certain point, if you don’t take care of yourself, that success won’t be sustainable.

What advice do you wish you had before you started?

See above – but I’m not sure I would have taken it. Ha ha. The “build your empire” narrative we’ve all been steeped in since the 80s is pretty powerful.

Do you miss your old life? 

I do not.

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