Joshua Wold


Paired designing

Over the past few weeks I’ve been working with our team on several design related projects. Since we’re all remote, and only get a few opportunities a year to spend time in the same room, we need to find a way to work in collaboration. 

While it’s not quite a perfect system, remote paired designing is pretty amazing! Here’s how it works:

  • Screen share – Using Zoom create a video conference room and share screens with the team member you’re going to design with. 
  • Have a stylus – Connect your iPad (or other stylus device) and share it’s screen as a secondary device, then you can sketch live and wireframe while you talk through the problem with your team member. 
  • Use Balsamiq in the cloud – If you go past sketching jump into something like Balsamiq and start throwing boxes and arrows around while you’re both talking and working through the design problems. 

Beyond that there’s some other interesting options out there: have a camera pointed at a whiteboard, use InVision Freehand, or similar. 

It’s great if you can have two people sketching at the same time or whiteboarding, or wireframing. But in practice I’ve found it can be a bit messy. At the moment it feels best to have one person do the majority of the sketching or wireframing, while both (or more) folks discuss together. 

Doing too much

It’s a bit of a circular game. You’re available to do stuff, so you say yes, and yes, and yes some more. Then pretty soon you’ve taken on too much, and things start to slip.

At first it’s just a little, barely noticeable. 

Then, over time you get used to it. The slipping becomes normal. Now you’ve gotten comfortable with medocrity in a bunch of areas, versus excellence in a few. 

Be kind to yourself

You’re generous, understanding, and forgiving of your best friends. You understand when they mess up and aren’t able to meet everything they thought they could.

You’re there for everyone else, you’re making a difference for others, giving consideration for when things just couldn’t quite come together, and recognizing the frailty of humanity. 

So, why aren’t you doing that for yourself? Give yourself a bit of a break on things. You’re trying, you’re doing, you’re awesome and making a difference. Recognize that, celebrate it, and be as kind to yourself as you would be to your dearest friend. 

The Best iPad Pro Drawing App

Updated June 6, 2018

TL;DR: Paper 53 is the best all around drawing app for sketching, illustration, and wireframing.


Pen and paper offer endless opportunities to create anything your mind can imagine. Throughout my life I’ve always been drawing. This led into a career in design and business. As a result I’ve spent a lot of time creating sketches, drawings, diagrams, and wireframes.

Over the past two years I’ve been using the iPad Pro, with an Apple Pencil, to mostly replace my day to day drawing. As a result I’ve tried almost every drawing app there is. This doesn’t mean I don’t still enjoy actual analog devices, but for my purposes it really does what I need.

At the end fo the day I really only use two apps for 95% of my drawing and sketching. Yes there’s a lot of other decent options available, and some with tons of features; but most are too complex, ugly, or unnecessary for what I want to do.

My main pick

Paper 53 is simple, but not simplistic. It offers a few tools for drawing, an eraser, ruler of sorts, scissors, etc. As you dig into it you’ll find that there are additional features that work without making the app feel busy.

It’s only been in the past few months that they’ve allowed multiple brush sizes, and they found a way to do it that without adding complexity to the interface.

Whenever I want to take notes, or just sketch out an idea, I open Paper 53 and jump right into it. It has a layout that just begs for you to start drawing.

One of my favorites combinations is line drawings combined with watercolor backgrounds.

What do I like the most?

  • Simplicity – just a few tools, and covers most of my use cases
  • Natural feel – all of the brushes seem to cover the page at about 90% strength, which means you can go over the same spot again and get a dual toned sketched look. I’ve found this adds a touch of sketchiness to the drawing, and makes it look less like it was done on a digital device.

What could be improved?

  • Copy paste – It works, but it could be better
  • Layers – this might go against the core of what the app intends, but there are times where I wish I had just 2-3 layers to work with. Technically you can draw in layers by using the pen tool for line drawing and the thicker marker tool for background drawing (it draws behind the pen tool).
  • Rotate and resize – There’s been many times that I’ve wished I could shrink or rotate something.

The runner up

Linea Sketch is quickly becoming an app I turn to more and more.

The team creating it has been careful to add features without adding complexity, much in the vein of Paper 53. There are a few things I can do with this app that Paper doesn’t allow, but also a few things I wish it had.

What do I like the most?

  • Rotate and resize – It works. The rotating touch area is a bit too small, but you can work around it.
  • Layers – Love the 5 layers. They are not to complex, and you can change the opacity to hide them.
  • Backgrounds – Their blueprint background is nice. That, along with a simple white grid makes it easy to sketch out ideas for floor layouts and diagram physical objects.
  • Simple – It feels simple to use, with only a few drawing tools available, so you spend less time tweaking, and more time drawing.

What could be improved?

  • When I draw I want the artwork to have a rough sketched out feel to it. The pencil and pen tools do this well, but the marker tool isn’t great. It tends to give my artwork a flat vector look. If they could tweak it so you had a thicker brush tool that gave off a gauche feel, or a watercolor brush, then I’d seriously consider making this my main choice for the iPad.
  • Other than that? Not much else, I’m pretty happy with it and looking forward to seeing how they improve its features in the months to come.

If you need more features

Procreate is the best full scale drawing app I’ve used. You can do almost anything with it. It offers custom brush options, along with very fine tuned adjustments. You can sketch, draw, and paint in a way that is natural and elegant.

I keep it around just in case, but since most of my drawing is sketches and wireframes it feels like overkill.


My son is five years old.

I’m busy. Life gets in the way. Work is always there, another conference call, another task, just one more email.

It never stops. It’s easy to keep going, to tell yourself that an extra couple of hours in the evening will make a difference.

But then my son sits there waiting. 

“Will you play with me now daddy?”

No, not right now. I need to take care of this thing that’s really urgent. 

Right now I’m a key figure in his life, and all he wants to do is spend time with me. He’s not asking for much.

One of his favorite times of the day (at least on days when he’s home from school) are the few minutes I can disconnect and play with him. 

It’s almost instant, his eyes light up when I tell him I can now play with him. 

How do I make sure I don’t miss this? How do I make sure I’ll be there for this? 

It’s hard. It’s a struggle. I want to spend time with him, and yet so many other things beckon for attention. 

What I’ve finally realized in recent months is that a daily habit is more important than grand gestures every few months.

Spending a few minutes in the evening, right before bed, is one of the easiest ways to make sure we can connect and do something together.

This is so easy, and I need to do it more.

I write this more as a note to myself. 

Today we spent 15 minutes playing a game together on the iPad. It’s not ideal, but it’s time together, and he loved every moment of it.

Your voice matters

Is there something you care deeply about? 

Do you regularly find yourself frustrated with how things work?

Are you constantly thinking about ways to make something better?

Your voice should be shared. 

Even if you don’t feel that you’re the most qualified (hint: you rarely feel qualified), the impact you can create by sharing cannot be fully measured.

Recently a colleague of mine gave a talk at our company about an important topic related to privacy. We discussed the talk and the impact it made; taking a topic that some might not have paid as much attention to, and finding the angle to make it interesting and relevant.

I suggested he speak at public events with this topic. Initially he hesitated, citing some valuable reasons I can’t quite remember. 

What I felt impressed to do at that stage was push a bit harder and suggest he do the talk

He applied and was accepted.

Now, I know that I wasn’t the only reason for this happening, but I do recognize the value in personal connections and encouraging others to share their voice.

Slicing bread

There’s a passage in the Bible where Paul, one of the early church leaders, talks about a problem in a community (1 Corinthians 3).

Apollos and Paul, two preachers who loved to share with others, were both teaching and preaching in the same general area. As a result some people started calling themselves followers of Paul, while others said that Apollos was the one they followed.

Paul’s counsel was to not call yourself a follower of either. Neither he nor Apollos could take credit for helping to share their belief, it was a slow process that took time. He said (my paraphrase) that one person could sow the seed of information, and another might come along and add water to help it grow. 

This reminds me of a situation I’ve run into often over the past few years.

Let’s say I have an idea that I want to share with a friend. I’m really excited about a new way to slice bread that I just read about. I tell my friend about it and try to convince them to try it.

A few months later my friend starts slicing bread the way I described.

Naturally I’ll be inclined to take credit for it.

However, what I could easily miss is that I was only one small step in her journey toward choosing to slice bread that way. I didn’t see the conversations she had with another friend about it, the time she looked it up and read about it on her own, and the fact that heard it mentioned two years before I said anything (but decided it wasn’t for her yet).

This is where humility should come in. My natural inclination is to get excited about something, and then share it with others. Over time I start to see results where friends adopt some of the ideas I’ve been sharing. While I may absolutely have been instrumental in their reasons for changing, I don’t know the whole story.

Ultimately it has to become the idea that my friend chooses to own themselves, and they likely came to that decision with lots of factors involved, not just my telling them.

So I’ll keep sharing about the new method of slicing bread, but with an understanding that I’m not the only one involved. Other people are also sharing things they care about!

Four day trip with the Goruck Bullet

Eureka! The perfect backpack exists, for me at least. Ok, I’ll try not to get too hyperbolic.

Choosing Goruck as a brand

I’ve researched a lot of ways to carry my stuff (junk?) from point A to point B. As a result I settled on wanting a somewhat small backpack as the sweet spot. That doesn’t mean a bag with wheels is out of the question (I love my Travelpro that I found on Craigslist). But it does mean I need a good bag to throw on my back when I go on a trip.

Picking the right size

Thanks to Ben from Brooks Review I was convinced Goruck was a solid choice. A backpack should be sturdy, have a small profile, and be visually understated. I ordered the GR1 and the Echo. The GR1 is a great midsize backpack that can carry a laptop and several days worth (easily) of clothes for a trip.

The Echo is like the GR1, but it’s short and squatty, like someone took the bottom and chopped it off. Since I’m 6’ 2” tall I decide the Echo would look too small on my back and returned it. I used the GR1 for a trip to Amsterdam and found it a nearly perfect fit for bringing a decent amount of stuff: clothes for 4-5 days, my DSLR camera, an iPad Pro and my MacBook Pro (along with other odds and ends). It’s just small enough that I can shove it under an airplane seat if absolutely necessary. However, in situations where I can pack lighter (Summer time), it’s too big for my needs.

Trying another size

So I decided to try the Goruck Bullet. I tested it on a cross country trip for 4 days. I found that it fit my MacBook Pro (13 inch), iPad Pro, clothes for the trip, and a few accessories. The trip wasn’t quite perfect. I ended up tossing my clothes into a collapsible tote bag on the second day to make it easier to split up things during meetings. However, it was small and light, fit well under the airplane seat, and didn’t look silly on my back. It’s really perfect for specific situations.

GR1 is perfect for trips where I have to make compromises and bring more than I want. The Bullet is perfect for times when I can simplify on clothing and not bring a ton of electronics.


What I actually packed
(Minus what I wore to take the picture)

  • 1 MacBook Pro (13 inch)
  • 1 iPad Pro (12.9 inch)
  • iPhone
  • Cords and accessories for all three
  • Small battery charger for the iOs devices (didn’t end up needing it)
  • 1 pair of pants
  • 1 pair of shoes
  • 5 shirts
  • 1 pair of shoes
  • Running shorts
  • Cubes for sorting clothes
  • Belt
  • 5 pair of underwear
  • 3 pair of socks
  • A few small food related items
  • Glasses case
  • Small quart ziplock with toiletries
  • Wallet
  • AirPods

Downsizing from here?

For my next trip I want to reduce the number of shirts I bring (Wool & Prince, 2 pair total), and find a pair of shoes that fit well for running and business casual. I’m also interested in only bringing my iPad (or getting a smaller iPad) or laptop, not both. I almost brought my Patagonia down jacket (it collapses into a small pouch), but decided Florida should be warm enough without it. I also left my water bottle at home.

Universal notes

Evernote, Apple Notes, Simplenote, TextEdit, Notepad++, Field Notes, Google Docs, Confluence.

Over the last decade I’ve tried out a lot of options for capturing notes. My perfect notes doc would:

  • Be universal – It’s always with me, or easily accessible. This doesn’t necessarily preclude an analog option, such as my beloved Rhodia notebook, but it’s not going to always be with me.
  • Fast – I should be able to start taking notes within a few seconds.
  • Pastable – I write in one doc and have to paste in WordPress or Google docs. What does that look like?

So far I’ve never found the perfect solution. However, Bear is very nearly the closest to perfect I’ve found so far. Now if only Markdown was truly universal.


The value of design

Earlier today I attended a talk by Adam Morgan, a senior Creative Director at Adobe. He shared why creativity and design matter, and why they deserve a seat at the table alongside logic and data.

The question that started the talk was, “do creative ideas work better?”. To find out the answer he discussed the differences between logic and emotion, the subconscious decisions our brain makes vs the conscious decisions, the linear vs connotational way of thinking, and the frontal lobe vs the rest of your brain.

Decision making

All of this led to the importance of considering both logic and emotion when making decisions. For example:

A logical decision

If you need to buy a potato peeler – you make a quick logical decision based on a few points of data. It’s that that difficult. 

An emotional decision

However, you’re going to buy a house, there are literally thousands of data points to consider that will make up your final decision. Is the crown molding the kind you want, is the location correct, how about the size of the lot, color of the walls, which direction does it face on the compass, do you have a good view of the sunset, is it an open floor plan, do you like the pain color, tile selections, the list is endless.

Your brain will take all these questions and work through reams of data in an instant. From all that data, which is really just 1s and 0s, you’ll make a “gut” decision on whether you like it; an emotional decision.


Our brains run on autopilot much of the time. Consider your daily commute. You probably don’t remember anything from the time you hopped into the car until you parked in your garage. But the moment you spot a car accident, your brain flies out of auto pilot and the command center takes over.

Our brains focus on anomalies in and fill in the rest of what we see what predictive models. In other words, you’re not really “seeing” most of your daily commutes, your brain is filling all that in and letting your run on autopilot.

Your brain has 86 billion neurons holding data, and that data is locked in with emotions. You can bring your brain out of auto pilot, in theory, with a logical data point. However, the best way to get all the neurons firing is to force an emotion.

If you see a red flame your brain checks its database to decide what that means, it finds a data point – hot fire, OUCH! – and uses that to help you decide you shouldn’t touch it. An emotion helped lock in that data point and helps make it easier to recall.

If you see a blue flame your brain might not have a data point to check against, so it flags it as an anomaly. It will then report that back to your command center to decide what to do with. Once you decide – yes it’s still hot, it’s similar to a red flame – it will burn a new memory to lock in later.

Emotions are powerful things! They create memory traces. If you want someone to remember your the work you’re creating, you can use emotion to help lock it in or retrieve it. Consider likability (versus negative advertising) and nostalgia for encouraging decisions.

Logic and emotion

Some decisions require logic, while others require emotion. This is where creativity needs a seat at the table; if you want to understand how the human brain makes decisions then you need to consider how emotion and anomalies fit into the picture.

The marketing gut is not dead. At Adobe they champion analytics through their own product, but they still use their marketing gut, along with the repository of past data, to help make decisions.

When you’re trying to decide what features or user interface to implement into a product, you should definitely consider all the data you have available. But don’t ignore the value of your own experiences and emotional feelings.

When it comes to measuring your creative ideas you should use data and logic to provide insight into where you’re going with the decision. From there focus on creating an experience and measure whether that experience hits the trigger for decision making with your audience.

Many companies are afraid to be creative and say they only make logical decisions. This is a fallacy; emotion is involved in much of our decision making at a subconscious level.

By avoiding creativity a company risks not connecting with their audience.


Companies are either relationship driven, process driven, or focused on product innovation. If your company is process driven then creativity will likely not be needed. But if you’re a product innovative company (like Adobe) or a relationship focused company, then creativity has the opportunity to thrive.

If you want to learn more, feel free to visit; Adam will be publishing a book soon to expand on this topic!