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Back in August 2018, the Designlab team met up for their second ever in-person retreat, in beautiful Breckenridge, Colorado!

Bringing together colleagues from around the world, this was a time of team-building, goal-setting, and future-planning.

Here’s who joined the event:

Designlab Fall Retreat

Patrick Multani
Based in Germany
Designer, Framer addict

Designlab Fall Retreat

Madi Waggoner
Based in Colorado Springs
Director of Operations, extraordinary organizer

Designlab Fall Retreat

Will Anderson
Based in Lexington, Kentucky
Growth lead, lo-fi hip-hop advocate

Designlab Fall Retreat

Daniel Shapiro
Based in New York City
Founder & CTO, Sublime’s biggest fan

Designlab Fall Retreat

Renee Tracy
Digital Nomad
Operations, camping connoisseur

Designlab Fall Retreat

Harish Venkatesan
Based in New York City
Founder & CEO, champion of chill

Designlab Fall Retreat

Teresa Lamb
Based in Tampa, Florida
Front-end developer, knitting ninja

Designlab Fall Retreat

Andrew Wilshere
Based in Lisbon, Portugal
Editor, Rice-A-Roni expert

Designlab Fall Retreat

Sandy Chen
Based in Brooklyn, New York
Mentorship, K-Wave Queen

Designlab Fall Retreat

Lauren Lankford
Based in Brooklyn, New York
Student Success, meme manufacturer

Designlab Fall Retreat

CJ Dreiss
Based in Long Island, NY
Full-stack developer, brisket enthusiast

Designlab Fall Retreat

Manuela Odell
Based in Bend, Oregon
Business Development, secret celebrity

Designlab Fall Retreat

Austin Basallo
Based in New York City
Operations Associate, muscle philosopher


Recent recruits Gina Medranda (Portugal), Josh Parolin (San Diego), and Diego Torres-Galvan (Long Beach) weren’t able to join us this time, but we look forward to meeting up soon!

Designlab Fall Retreat

Designlab Fall Retreat

Designlab Fall Retreat


Purpose of the retreat

As we grow, we’re moving towards holding retreats twice a year. Designlab is a fully remote team, and the opportunity to meet in person every six months helps us to get to know one another better, and maintain deeper connections for the rest of the year.

Retreats are also a chance for us to review company strategy and progress together, to spend time on targeted product sprints and brainstorms, and to share our personal tips and challenges when it comes to remote work and working while travelling—particularly how to stay productive and maintain a healthy work/life balance.

In tune with that aim, we didn’t spend all of our time on work stuff. We reserved about half of each day for downtime, general getting-to-know-each-other, eating out, going on hikes, playing pool, and learning obscure board games (Daniel, our CTO, is OBSESSED).

We also split into two teams for an Iron Chef competition, played a bunch of Nintendo Switch, and drank delicious Colorado beers and ciders (apart from Madi, who’s expecting—congrats, Madi!)

Read on for more details about what we got up to!

Designlab Retreat 2018

Arriving at Breckenridge. Andrew (center) adopts unconventional Rice-A-Roni method, to collective alarm. Photo by Patrick.

Designlab Retreat 2018

CJ and Madi get the brisket ready for dinner! It was prepared abundantly by Madi’s husband (thanks Madi’s husband!) The brisket became a collective emotional focus for the trip. Photo by Patrick.

Designlab Retreat 2018

Here’s where we were staying! Photo by Austin.

Designlab Retreat 2018

At our winter retreat, we had Secret Santa. This time, we shared a birthday party! (Using the Secret Santa method.) Here, CJ admires his Ampersand t-shirt, perfectly kerned by Teresa. Sandy looks on with joy. Photo by Patrick.

Designlab Retreat 2018

We got some pretty stellar views from the cabin. Photo by Austin.

Articulating our company’s work culture

We are still a small company, but feel that in the past couple of years we’ve formed quite a clear picture of the working culture we are trying to build. Here are some of the values we discussed during the trip.

Autonomy. As a distributed team, most of us are working independently. We decide how many hours we work, when we start and stop, and how we organize the time that we’re working. We explicitly value these freedoms, and believe that they empower each of us to work when we’re at our best, to find flow, and to do our strongest work.

Collaboration. Although working autonomously in terms of schedule and hours, our projects are still deeply collaborative, and often involve members of every team—if not the entire company. We value collaborative work and the unique insights and perspectives that each person brings to a project. We do not need permission to give feedback.

Compassion. We talk to each other respectfully, informally, and generously, and welcome inclusive humor as a way to generate the kind of camaraderie and team spirit that can be found in the best bricks-and-mortar workplaces.

Open communication. In a remote team, effective communication is essential. Unlike a regular office, we’re not sharing the same space, or even necessarily the same work hours, so it’s crucial for us to proactively keep everyone updated on where our projects are at.

Radical candor. This is an idea we explored for the first time at this retreat. Radical candor means being honest with one another about what we’re doing well and where we could be doing better. It helps enable us each to do better work, but perhaps more importantly, it means we all feel more secure in our positions, because if there’s a problem, we know that we would hear about it. It is also a principle that doesn’t respect seniority—if a manager isn’t giving their report what they need by way of support or feedback, we are each explicitly empowered to let them know.

Team time. We value non-work-focused time together as a team. Recent cultural initiatives include remote “donut” calls—where we’re connected with a random group of 4 coworkers (by a Slack bot) to just have a donut break together. No pressure to talk about work. We also have virtual happy hours each Friday, and even Mario Kart Mondays! (Mario Kart Mondays actually happen on Thursdays, but “Mario Kart Mondays” sounds better.)

Personal growth. We believe in constantly growing our skill-sets, trying new things, and pushing beyond our comfort zones at work. Every quarter, each of us identifies areas for growth that are meaningful to us as individuals.

Designlab Retreat 2018

We recorded some snippets of the team talking about their experience of working remotely. (They’re coming soon!) Photo by Patrick.

Designlab Retreat 2018

No retreat would be complete without the developers playing Fortnite. Photo: Patrick.

Designlab Retreat 2018

Some of us woke up early... Photo: Patrick.

Designlab Retreat 2018

We had an ideal kitchen for Iron Chef-ing! Photo: Andrew.

Designlab Retreat 2018

Attention was paid to the UX of Iron Chef. Photo: Teresa.

Designlab Retreat 2018

The fruits of our Iron Chef labors. Photo: Teresa.

Designlab Retreat 2018

There were many unexplained things about the Iron Chef judging. Photo: CJ.

Designlab Retreat 2018

Harish and Austin... Photo: Andrew.

Designlab Retreat 2018

...Daniel and Teresa. Photo: Andrew.

Brainstorming the 10-star product experience

One of a number of brainstorming sessions, we spent an hour dreaming up what it would mean for us to have a 10-star experience in different areas of our product.

This idea comes from Brian Chesky at Airbnb. He explains in this piece:

At Airbnb, we strive to have our customers contact the company and demand a 6th star be added to our 5 star review because the experience was so good. Here’s how we think about service past 5 stars:

5 star service — You leave the airport, go to the Airbnb, your hosts are in the house, they let you in. This is 5 star. Worse than this is if your host is late (4 star) and the worst is if your host never showed up (1 star).

6 star service — All of the above + your host picks you up at the airport.

7 star service — All of the above + there is a limo waiting for you at the airport and inside the limo are your favorite chips and coconut water.

8 star service — There is a giant parade when you arrive at the airport and you are honored for coming.

9 star service — The moment you step off the plane there is 5,000 screaming fans holding signs for your arrive — we call this the Beatles check-in.

10 star — I could go all the way up to 30 stars — I won’t, but 10 stars would be when you arrive and a Tesla with your name on it is waiting for you and in the car the driver is Elon Musk, and instead of your Airbnb Elon, takes you to outer space.

So we split into three groups, and each group focused on a different area of the product experience. One was pre-course and onboarding; another was the experience during the course; and the third was the post-course and alumni experience.

This was a great exercise in getting out of our usual way of thinking about product improvements. It’s natural to stay focused on things that are already on the roadmap, but that can quickly mean losing sight of the bigger picture. 

This no-limits 10-star brainstorm reminded us that there are always opportunities to reappraise how we’re doing things, and to make big high-level changes to the experience if we know that those would be beneficial to the user.

Sharing our experiences of working remotely

We’re all working in different places and different ways, with different personal preferences for what life and work should mean. We’ve published more tips from the team in a separate post, but here’s a selection of quotes: 

“One of the challenges of working autonomously and remotely is forcing yourself to switch off and stop working. Going to a coworking space helped me to set a hard start and stop time, which also made me more productive, because I knew that if I wanted to achieve a particular task, I’d need to get it done by my stop time.”

“I’ve been going to the same coffee shop for 5 years, 9-to-5. It works really well for me.”

“I meditate first thing in the morning. It’s also top of the list each day in my bullet journal, so I can start each day by ticking something off, and that’s the beginning of feeling productive.”

“If you’re travelling and staying in Airbnbs, it’s important that they have good wifi and a good desk. Without that, you can quickly get stuck and stressed.”

“I underestimated the language barrier moving to a new country. Without making an effort to learn the language, you can find yourself feeling isolated.”

“Have a backup phone and a backup SIM card. My phone broke while I was travelling and for a few days I was stuck.”

“Working Eastern hours while living in Europe can be draining. In Spain, I had to be proactive with my time in the morning. I really switched up how I was doing my life priorities because of siesta (when everything is closed). It’s also about learning to flex your normal way of being to work with the culture you’re in.”

After the retreat...

After the retreat proper, seven of us went together to Glacier Basin Campground, and spent two days relaxing and exploring the Rocky Mountains. Pro-level campfires (thanks to the fire-building skills of Renee, our Alaskan camping connoisseur) allowed us to serve up delicious burgers and corn-on-the-cob.

We also headed off for a hike (in torrential rain) towards Bear Lake, followed up by delicious New York-style pizza at Antonio’s. All in all, it made for an excellent week of team-building and alignment on our shared goals for work and life.

Designlab Retreat 2018

Heading to Glacier Basin! Photo: Teresa.

Designlab Retreat 2018

Still heading to Glacier Basin. Photo: Teresa.

Designlab Retreat 2018

Setting up the tents. Only one of them blew away. Photo: Andrew.

Designlab Retreat 2018

We saw this blurry guy/gal! Photo: Teresa.

Designlab Retreat 2018

Mandatory “we’re going hiking” shot. Photo: Andrew.

Designlab Retreat 2018

The hike was beautiful, in spite of the rain. Photo: Teresa with Austin’s camera, maybe?

Designlab Retreat 2018

Some nearby Dutch people took our photo on the hike. Photo: Nearby Dutch people.

Designlab Retreat 2018

Post-hike pizza. Antonio’s was amazing! Photo: Andrew.

Designlab Retreat 2018

Glacier Basin gave us some moody weather. Photo: Andrew.

Designlab Retreat 2018

Renee had all the skills! Photo: Teresa.

Designlab Retreat 2018

There was legitimate fireside chat. Photo: Andrew.

Designlab Retreat 2018

There was also a heart-shaped log. Photo: Andrew.

Sneak peeks of what we’re planning

We held a number of structured brainstorms at the retreat around how we could improve the product experience. We’re constantly gathering feedback from Designlab users, which means that increasingly we know what we need to do—it’s just a case of finding the bandwidth to make all the improvements that are in our backlog.

Now that we’re back to our regular work routines, here are some sneak peeks of what we’ll be working on in the next few months...

One of the major outcomes of our retreat was to prioritize an overhaul of our Help Center. Thanks to whole-team collaboration, this project has already started and finished! You can read the launch post, in-depth case study, or just check out the Help Center itself.

In the months ahead, we’re going to be prioritising these enhancements:

  • Better course onboarding, and even better ways to pair students and mentors
  • Major updates to short course curriculums
  • A revamp of the blog

Designlab Retreat 2018

We had ONE SHOT with the timer, because the airport shuttle was waiting. And yes, Harish’s eyes are closed.

Thanks for supporting Designlab. With your help, our aim is to continue changing creative education for the better—through affordable, rigorous, high-quality, mentor-led online courses.

We’re always open to feedback—if you have any thoughts about the plans shared in this post, feel free to take this 2-question survey

author avatar

Andrew Wilshere


Designer, Writer, and Mentor

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