What do you do with the insanity?

Five projects are due next week. You’re a blocker for two teams across four of those projects. You need to hire three new team members to handle all the work going on, but you have no time to find that hire. 

What do you do?

You could work 12-15 hour days. You could find a new place to work. Or you could ignore most of what’s going on, focus on one or two things at a time, and deal with the fallout. Sometimes that last option is a decent one.

Here’s the thing. There’s not really a great answer. We all find ourselves in situations where there’s too much to do. In no particular order, here’s how I’ve found ways to deal with the insanity:

  • Take a break – Every seven days, on Saturday, I completely disconnect from work. That means I won’t check my work email, Slack, Github issues, design updates, attend business calls, business conferences, etc. It’s a solid rule I’ve made for my whole career, and it’s one of the reasons I’ve kept from getting fully burned out. At times I’ve gotten close, but there was always knowing Saturday would come and I could disconnect for 24 hours. 
  • Get help from your team –  It’s tempting to think we’re the only person in the world who can solve a problem. That’s not the case, not at all. If you work with others, or even if you’re completely on your own, chances are there’s someone out there who can help you. 
  • Force constraints – Find a way to shrink the amount of work. There’s usually somewhere that fat can be cut without compromising the integrity of what you’re building. 
  • Don’t overwork for too long – We’ve all done it where we worked a ton of hours for an extended period of time. The reality though is the quality of work absolutely suffers the more time we put in without rest. Sometimes it means deciding you’re done for the day and getting a full night’s sleep to tackle the problem with a fresh set of eyes.
  • Be nice to yourself – You’re amazing. You’re doing wonderful work, you believe in what you’re building, give yourself a bit of a break. It’s going to be ok. 
  • It will be ok – Yes, this is worth repeating. You’ll get through this. Keep up the great work!

Getting away

On Friday I stepped away from work. Lots going on, but I had done what I could to get things in place for Monday. And with that, for the most part I was off until Monday morning. 

On Saturday our family spent some time in the afternoon hiking with friends out in nature. Part of that hike involved walking out onto a walkway into a marsh. It was beautiful.

The smoke (it’s getting better) in Washington lent a hazy yellow to the atmosphere, dulling the colors and adding a feeling of warmth to everything.

Looking back I have some wonderful photos of the kids, and a feeling of just getting away and taking a break. 

That’s important. We need times like this. 

Stay low fidelity

If you’ve ever try to build something, at some point you’ll need to figure out what it should look like. As a result you’ll probably turn to creating a wireframe or prototype.

That’s a good thing. Try to get it into a visual medium (a sketch, a cardboard prop, a whiteboard diagram).

However, as you do that, always shoot for low fidelity. Meaning, keep it as rough and simple and quick for as long as possible. 1 minute invested into a napkin sketch means only 1 minute lost if you have to change plans. 10-20 minutes invested into a wireframe can just as easily be thrown away for a new idea. Once you spend the time to really get into the details and create a fully flushed out visual prototype you’ll quickly find you’ve become attached to it. At that point scrapping the whole thing is hard, almost impossible.

Try to stay simple and quick for as long as possible. 

Fear from too much

There are times where we may feel that we have a bit too much going on. That might mean having a bunch of unactioned emails, unmarked todo list items, unread Slack messages (marked that way after taking a peak), or handful of text docs floating around.

At these times it’s easy for paralysis to set in. It’s impossible to take care of everything, so maybe we should just do… something else, instead of that. 

At times like these there are ways to prioritize, triage, and focus. The big thing to keep in mind is a correlation between how big a task looms in our mind based on how long we’ve held off on doing it. When that happens sometimes it helps to promise yourself that you’ll only spend 5 minutes on it, just to get started. 

Having a good day

Sometimes there are days where you’ve done it. You accomplished a herculean task. You got all the way through and by applying every last bit of energy you pulled off the impossible.

Days like that are magical, and unfortunately, can be rare. If you’ve reached that point in a day where it’s all come together – you’ve hit that deadline, delivered that project, solved that challenge – then give yourself a bit of a break. 

Take that time to count your victories, and celebrate. 

Just read a great idea to create sticky notes documenting your wins. 

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.