Jessica Walsh can be introduced in many ways: partner at Sagmeister & Walsh, art director, designer, illustrator, one half of 40 Days of Dating, the enviable hybrid of creative / businesswoman, or simply as much shyer than you’d guess. Walsh has won numerous awards for her work, but has perhaps become increasingly well-known for the brave integration of her personal life in public projects. Walsh dropped jaws when she dropped her clothes for the announcement of her Sagmeister & Walsh partnership (at a contrastingly modest 25-years-old), and more recently, for the insanely well received 40 Days of Dating project (the site has drawn over 10 million unique views since it’s launch, and a Warner Bros. movie is in the works.) When asked about how she approaches the professional and personal overlap, she responds: “I think that’s just what happens when you find true fulfillment in what you do.”

“I taught myself to code websites in HTML when I was 11-years-old. By the time I was 12 or 13, I had created a tutorial site with website templates and was making sites for other kids. Google ads had just launched and I had put an ad on my site. I still remember getting my first check in the mail from Google, and thinking, oh—you can actually make money by doing something that’s not a 9-5 job. That was such a revelation to me because my upbringing was very traditionally business oriented—my parents were in the intense early stages of getting a company off the ground and there was a lot of emphasis around money and finance. I didn’t feel like that was the direction for me. Not the actual running of a business, but the finance side never sparked any passion. So this accidental discovery of being able to make money through doing something that I loved was so cool, and I promised myself to find ways to keep doing it from then on.

To keep that promise takes a lot of hard work and persistence.

The whole ‘do what you love’ mantra can be quite dangerous. Of course there is some truth in it: when you do something you love you’re more likely to fully invest yourself in it, and are therefore more likely to succeed in what you are doing. But you can’t expect that solely following your dream is going to guarantee a job, clients or success. It takes so much time to hone your skills. There’s the Malcolm Gladwell rule of requiring 10,000 hours to become an expert in what you’re doing and I think there’s truth to that. You usually have to put in the hours to become an expert at your craft, so you can really excel in your field. I started teaching myself design very young and have put in many hours since then, and it definitely hasn’t been easy to get to where I am now.

Early on I did plenty of jobs I didn’t enjoy, but was willing to do whatever it took. In college and during my first few years in New York I would work crazy hours throughout the night—I’ve always just been so hungry to learn and create new opportunities. My parents really instilled that in me: that you have to put in the time and go the extra mile, that things don’t necessarily come easy. That if you want something, you really have to go for it. I watched them build their business through some difficult times—it was not easy in the beginning for them. But seeing how their perseverance paid off was really inspirational, and it’s something that’s stayed with me ever since.

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I pretty much always have the future in mind. I find that working towards a goal is the best part—it’s way more exciting and interesting than actually getting there. So whenever I do reach a milestone I’ve been working towards, it’s fulfilling momentarily, but then it’s like, whats next? It’s all about the journey of working towards something new. That said, I’m learning to pause and enjoy life more. I didn’t really make enough time for myself in the past, and eventually I got worn out. I now enjoy the little things… like taking time off once in a while with my husband, and spending more time with family or friends. Those moments of getting away mentally or physically, whether it’s wasting a whole weekend watching movies, traveling somewhere new or going out dancing, they’ve become very valuable to me. Especially because generally, the work/life boundary doesn’t exist for me. I like integrating it all. I think that’s just what happens when you find true fulfillment in what you do. The people who I’m closest to are all creative also, whether it be my good friends like Lotta or Tim, or my husband who’s also a creative person.

I bring a lot of my personal life into my projects, so it becomes even more layered in that sense. It’s funny that my personal and work life have become so intertwined, because by nature I’m actually very, very introverted and shy. I was super nerdy as a kid. My confidence has been building over time and hasn’t come naturally for me. When I’m releasing my personal life to the world, whether it’s being in a photo naked or speaking on a stage, these are things that I never ever would have thought I would do when I was younger. I’ve just been so fearful of fear that I’ve been driven to tackle and confront whatever I am scared of.

So all of my life has been an experiment: I try to overcome one fear and based on that feedback, it gives me confidence to do bigger and scarier things.

With the naked photo, I was a little nervous at first but then it just felt so freeing. Like it doesn’t even matter if people see me naked—I’m not sure it’s healthy as a culture to be so prude about nudity. It also helped me become a lot more relaxed about my public image. For example, before that photo or before 40 Days of Dating I had a very curated social media presence. I would only post pretty photos of myself, it was all, oh look how happy I am! And now I’m a lot more honest, like hey guys, I feel like shit today! I think it’s become a problem that we are curating our lives so perfectly, because that perfection is just not a reality and is not a healthy image for anyone. Everyone has ups and downs and is fighting some sort of battle at any one moment, big or small. I’m really interested in breaking those walls down and putting myself out there, but in a way that’s real and open and honest.

40 Days obviously played a huge role in that. I mean, not all the reactions were good—there were people who hated it—but for the most part people responded positively, saying that our writing was very raw and honest. The emails that we got from people were incredible. It has been one of the most humbling and inspiring things ever. In a way, it’s intimidating how huge 40 Days got, because I don’t even know why. We didn’t know what we were doing, we just put it out there.

I think that self-doubt will always be there. But usually, even when things have been horrible in the moment and really difficult to go through, looking back they’ve always worked themselves out. And it’s always been in some weird and mysterious way that really ended up being for the best. So I try to keep that in mind and just keep moving forward. One of my main doubts, actually, is whether graphic design is what I want to dedicate my life to. Is it really enough of a purpose? I can get very existential and over-think everything. I think a response to that doubt is this new direction of exploring more personal projects that integrate design, writing, and life. I want to speak to larger audiences outside of the design world.

I think you have to feel as though you have a purpose in this life to find happiness.

At least for me, that’s a huge part of it. The client side of work will always be challenging, interesting and exciting, and can pay the bills. However lately I have realized that the self-initiated work is the most fulfilling. My new goal is to focus less on form and beauty and dedicate more time to creating work that connects with people, starts important dialogues or touches people in some way.”

Jessica’s #okrealtalk Tips

  • The journey is the best part.
  • All of life is an experiment. Put something out there. See what happens.
  • What is your purpose?
ok

b. 1986

sagmeisterwalsh.com

i. @jessicavwalsh

t. @jessicawalsh


Photography courtesy of Zak Mulligan

As told to Amy Woodside, April 2015