Summer of Sketching Week 9: Taking Risks

Hello from above the clouds!

Hope you had a relaxing weekend. I'm writing to you from a tiny airplane on my way from London to Amsterdam. ✈️

I spent the past 4 days in the UK at WeWork's Summer Camp music festival. I'm not typically much of a festival-goer, but it was nice to hang and celebrate one last time with my NYC / Lunch Money / WeWork family before I head down to South America. Lots of good times and campy lake vibes.

I can feel all of the baggage and stress from the last couple years fading away into the past, and it's incredibly freeing!



Digital Drawing on the Microsoft Surface Studio

Microsoft had a booth set up at camp where I got to try out drawing on their new products including the Surface Studio. I've been curious about this device ever since I saw the commercial last year. It seems pretty ideal for a design studio setup.

It's basically a desktop computer with a massive touch screen on a swivel stand. Overall the hardware felt very nice, but the software I was using was not as intuitive as the iPad. There was also a bit of lag with the drawing and unfortunately I couldn't get the fancy bluetooth knob to work. I posted a little video on Instagram when I was testing it out. Next time I'd like to test out drawing in Photoshop.


Honestly I'm just hoping Apple will make something like this in the next few years (touch screen iMac?) because I have a feeling it will have less kinks.

As much as I still like drawing on paper, I think this technology is the future standard for lettering, illustration and many other types of design. If we're lucky enough to be alive during this technological shift, why not embrace it?

Last week's sketching prompt was TRAVEL

Here's a couple cool pieces from this week's #summerofsketching:

Summer of Sketching Week 9: RISKS

This week's prompt is all about taking risks and living life to the fullest. I chose this theme because I'm essentially working as a "digital nomad" for the next 3 weeks, which is really new and different for me.

Some questions to think about:

What's something that you took a chance on recently? How can we take more risks as designers to create better results / more impactful work? Use these questions as inspiration for this week's sketch and post your work to Instagram with #summerofsketching.


Recording a Podcast - Have Any Questions?

While I'm in Amsterdam this week I am eating a lot of waffles and also recording a long form episode with my friend Femke for her podcast Design Life.

We'll be dissecting this topic of taking risks and we would love to hear your questions. You can send me an email ( or ask on Twitter. I'll share that episode out as soon as it's edited and live.