Worn Well

How the Creative Duo, WeShouldDoItAll Unwinds by the Delaware River


Jonathan and Sarah Jackson, the creative couple behind the Brooklyn-based contemporary design studio called WeShouldDoItAll, open up about work, parenthood, and New York. Words and Photos by Kate Rentz.

Back in the day, Instagram started out as a new platform where artists could share their work and lives through tiny square boxes. It was here that I discovered creative directors Jonathan and Sarah Jackson. I was instantly inspired by their cool, simple, and monochromatic style that felt so authentically natural and seemed to bleed into every aspect of their lives, including parenthood.

Jonathan and Sarah own and run a contemporary design studio called WeShouldDoItAll in the Bushwick neighborhood of Brooklyn, New York that focuses on branding, spatial, environmental, interactive, and print projects. Merging digital and in-real-life experiences comes naturally to the couple who first met on MySpace in 2005 and got to know each other through chatting. Their work and personal relationship became interwoven over time—launching a design studio and starting a family together within the past decade.


Jonathan wears the Hurricane XLT2 in Black, Asa wears the Kid’s Ember Moc in Dark Gull Grey, and Sarah wears the Midform Universal in Black Constellation.

Jonathan’s background in architecture and his self-taught graphics instinct comes together with Sarah’s graphics and art history education to craft innovative and impactful projects. They recently launched a traveling exhibition with The Smithsonian titled, ‘Men of Change: Power. Triumph. Truth.’ presenting stories of significant African-American men who stand as national icons.

When they need an escape from the city that never sleeps, they retreat to their renovated schoolhouse along the Delaware River in Sullivan County, a couple hours outside of New York City. Amidst the crisp fall air and changing leaves, I met up with the two creatives at their cozy abode to discuss work, parenthood, and what life looks like in and out of New York City.

Ember Mid

Jonathan wears the Ember Mid in Black and Sara wears the Ember Mid in Deep Taupe for lounging at home in Sullivan County, NY. 

Your design studio is called ’WeShouldDoItAll.” Is there a backstory or special meaning to its name?

JONATHAN AND SARAH: Yes, the name was inspired by a quote from Robert A. Heinlein’s book, “Time Enough for Love.” The quote is: “A human being should be able to change a diaper, plan an invasion, butcher a hog, conn a ship, design a building, write a sonnet, balance accounts, build a wall, set a bone, comfort the dying, take orders, give orders, cooperate, act alone, solve equations, analyze a new problem, pitch manure, program a computer, cook a tasty meal, fight efficiently, die gallantly. Specialization is for insects.” Essentially, the idea is that designers should not be constrained to a singular discipline, but rather practice in a multidisciplinary sense.

What does your workflow look like and how do you get inspired?

JONATHAN AND SARAH: Our workflow varies depending on the day. As creative directors, we balance letting our trusted team do a lot of the heavy lifting when it comes to design, while trying to steer them in a solid direction. Sarah and I are client-facing in meetings but want and need inclusion of the whole team when possible. We seek diverse input and insight. Inspiration comes from all places. Sources within the design world are easy, yet outside sources tend to yield richer results. We tend to think that inspiration comes from the given challenge. It’s about keeping our eyes and ears open and striving to be sponges.

Ember Mid

“The Ember Mid is the perfect go-between comfort shoe where you remain stylish and super comfortable. Most important for me: how quickly I can ease in and go play outside with Asa or run errands.”

Kids Ember Moc

Kids Ember Moc in Dark Gull Grey. 

You live and work in NYC — how do you connect with the city and how has it influenced the work you do and the life you live there?

JONATHAN: New York is like the sun: full of light and an energy unmatched by any other. It shines on us all and we are all grasping at it, trying to get more of its fuel. It keeps us going and its pull is hypnotic — especially for creatives. We connect simply by absorbing all that it provides, trying to filter and separate what is substance and what is waste. I love her and now with age, she wears on me.

SARAH: For me, it’s all about the energy of the people and your community — even the guy at the bodega in the morning or your super who has lived in the hood for 30 years and keeps an eye on things. It’s the connections you can make instantaneously and folks’ no BS attitude. It’s refreshing. The pace of NYC can definitely be exhausting and now with a kid it is certainly a schlep, but there really is no place like it.

Ember Mid

Ember Mid

Sarah wears the Ember Mid in Deep Taupe. 

Speaking of parenthood, how has it changed and shaped you?

JONATHAN: In all honesty, I don’t know if I’ve changed since having our son, Asa, but I have been shaken to my core because of him. Being in my mid-late 30s at the time of his birth, I thought I knew how things worked. I had a fairly good understanding of what love meant and then he came along and shape-shifted that false knowledge to a new level. I discovered a whole new way of seeing life because of him and it feels personally groundbreaking. I discovered a new love that I didn’t know existed.

SARAH: I had a passion for pregnancy and birth for years before Asa came along, but once I went through it personally it was truly eye-opening. That passion has only been amplified. As for Asa — there is simply no other love like it. It also tests you in ways you can’t imagine. I’ve never been so frustrated in my life! Toddler boundary-pushing is no joke. But with those ups and downs comes the strongest relationship you’ll ever fathom, so it’s all part of the process. Parenthood has also put things into perspective. It’s been humbling to say the least. Life is no longer about all that I achieve; it’s about experiences, family, chosen family, and love.

Renovated Schoolhouse

“Setting foot on the property [in Sullivan County] allows us to leave work in NYC and provides complete mental and emotional peace.”

Ember Mid

Jonathan wears the Ember Mid in Black and Sara wears the Ember Mid in Deep Taupe. 

Tell us more about this amazing schoolhouse along the Delaware River in New York! What is your vision is for it?

JONATHAN AND SARAH: Yes! We’re amped about it. It was originally built in 1893 and served as a school up until 1949 when it was sold to become a Baptist church. It was beautifully renovated in 2013, so for us it was mostly turn-key. We have some major goals for it, but more long-term. Essentially, our vision is to make it more cozy as opposed to the hotel feeling it had, as it was previously being used as an AirBnb. We want to maintain some of the school-like environment, balanced with comfy features that will make it personal to us. Some major projects for the future are adding a wood stove and eventually building a space next to the main house for a studio, garage, and third bedroom. We’re certainly taking it slow.

The schoolhouse look and feels like a complete contrast to NYC vibes. Why did this place resonate with you?

JONATHAN: Sarah grew up in the woods of New Jersey and was the main driver for finding something of a slower pace, but I was the one that really pushed for this house. New York is amazing and has been great to us, but we were looking for an escape from the constant hustle. Setting foot on the property allows us to leave work in NYC and provides complete mental and emotional peace. We’ve been extremely blessed and a bit lucky too. There’s also an amazing school closeby that hopefully Asa will go to in the future.

Socks and Sandals

Jonathan’s Fall socks and sandals style wearing the Hurricane XLT2 in Black. 

Kids Ember Mid

Asa wears the Kid’s Ember Moc in Dark Gull Grey, and Jonathan wears the Hurricane XLT2 in Black. 

Midform Universal

“I love the Teva sandals—they bring me back to my preteen years—encouraging me to explore and play like I did back then! They’re so incredibly comfortable and the sparkle pattern makes any outfit feel more complete.”

What cool things have you discovered to see and do in the surrounding area?

JONATHAN AND SARAH: We’re right up the road from the Delaware River where you can kayak, raft, canoe, fish, swim, or just sit and gaze. It’s pretty sweet. There are tons of hiking trails, waterfalls, camping, and lots of foraging. There’s also a great farmers market on Saturdays where there’s always live music and the community comes over to hang. We don’t know a ton about the area yet, but we’re discovering things slowly. It has been nice to take our time and let the area unfold. We’ve honestly had a hard time leaving the house because it’s been so nice being there to unwind!

Midform Universal

Sarah wears the Midform Universal in Black Constellation.

Kids Ember Moc

Asa wears the Kid’s Ember Moc in Dark Gull Grey. 

What is one thing about the other that inspires you?

JONATHAN: Sarah is genuinely true to herself and to what she values at her core. She never tries to be something she is not and in this day and age, that feels rare and refreshing. She doesn’t seek attention or the limelight. She is regal and full of substance and care.

SARAH: Jonathan is the most dedicated and passionate designer I have ever met. He’s so secure in his career path that it’s enviable at times, but mostly I am inspired by it every day. Having a child has revealed another side of him—he LOVES to play! He’s still a child at heart and loves to laugh and be silly and he has no ego. It’s amazing to watch.

Fall Sandals

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