An Exercise for Professional Clarity

Isaac, Praxis’s founder and CEO, had me do an exercise today that helped me clarify what the education part of our product is and how we expect customers to use it.

Think about what you do at your job, why you do it, and how you do it. Or even better, what your company’s product or service is, what need you are trying to fill, and how your product fills that need.  If you are a department head or team manager, focus on what your team does, why and how you do it, and how it fits into the overall company. Turn this into a 5 minute video.

It took me a few hours of thinking about it over an evening and the next morning, then 3 different takes:

  1. First cut, 10 minutes long, awkward phrasing as I figured out what I wanted to say.
  2. A tighter 6.5 minute version with two areas that were solid and one area that was too detailed in some areas and too light in others.
  3. A third and final take that was 4.5 minutes long that was clearer in almost every way. The only thing I’d add if I chose to shoot it one more time is a better 20 second conceptual framing of our why at the beginning. It was sprinkled throughout, but not laid out in one statement.

This helps you take a 10,000ft view of what you do, figure out your part in the organization, learn how to present your role in a coherent way, and figure out where you need to do some work. 

Share it with your team and see what they come up with, too.

Three Weeks with the 10.5” iPad Pro

I bought the 10.5” iPad Pro the day it was announced and received it the following Monday. My old Gen 3 iPad didn’t support multitasking, Touch ID, iOS 10, or True Tone. Basically nothing that makes an iPad awesome for work. It was getting pretty slow and desperately needed an upgrade. I’m super happy with the new iPad Pro. Here’s what I love about it after the first three weeks of use:

  • It is really snappy. I mean really snappy. Even faster than the previous generation.
  • Multitasking and split view is wonderful. I take notes while reading, do research while chatting with my coworkers on Slack or answering questions on Facebook Workplace, grab links while I write blog posts, and pop out videos to watch while I open brainstorm in another document.
  • Using Touch ID to unlock my iPad and authenticate 1Password on it really speeds things up. I didn’t realize how much I used it until I switched back to my old iPad and went without it for a bit.
  • The Smart Keyboard is very easy to type on. It took all of an hour to adapt to. I love it.
  • True Tone makes it possible to use this screen outside, even in the sun. I’m sitting out at a park right now writing this. As someone who works from home, this is a game changer. I now work outside for multiple hours each day, weather permitting. My old iPad and my MacBook Pro are almost unusable outside.
  • Swift Playgrounds is a fun little puzzle game when I need a distraction.
  • The speakers in this are great. They blow my previous iPad out of the water.
  • iOS 11 (I’m on Public Beta 1) really does make iOS easier to navigate and use. The new task switcher screen, control center, and dock make flipping between apps and navigating around the system a breeze. 
  • Taking screenshots and being able to mark them up or use them immediately is super useful. 
  • The slide down for numbers/symbols on the on-screen keyboard is very intuitive and easy to use. That said, I primarily use the Smart Keyboard.
  • I love the trade off between portability and how much I can get done on this device. The Tom Bihn Small Cafe Bag fits it perfectly with enough room for an Anker battery pack, a notebook, my Kindle, and my keys. This setup is an order of magnitude lighter than my backpack and MacBook Pro, making walking around town and finding a place to work easy and sweat-free. 

iOS 11 is pretty sweet. That said, Public Beta 1 is still pretty buggy. Apps crash a lot when launching and closing split view, the multi file selection is really buggy and doesn’t really work on springboard yet, sometimes I can’t get split view to launch, launching Notes from the lock screen with the Apple Pencil doesn’t always work for me, and I’ve had to reboot my iPad a few times because it became unresponsive. I can’t get TextExpander to work with the Smart Keyboard yet, which is annoying. iOS 11 is also a huge battery hog. I’ve been using my iPad for three and a half hours this morning and I’ve drained 61% of my battery in that time. I’m sure it will get better over time. 

I don’t use the Apple Pencil as much as I thought I would. It is super fast on the screen with the recent updates. I plan on taking a course on Procreate soon, which might spur more Apple Pencil usage. I was really excited to use Paper by 53’s diagramming features, but the shape recognition and Apple Pencil calibration severely lacking. Linea is awesome, but I just don’t draw very much. Perhaps that will change over time. The handwriting recognition in Notes is pretty good all things considered, but my handwriting sucks, so I prefer to type. 

I could work on the iPad most of the day. There are still a few things I find it easier to do on macOS, but the list is much shorter than on my old iPad. The tasks I’ve had to switch back to my MacBook Pro for are:

  1. File conversion. I had to convert a bunch of videos from MOV to MP4 for a coworker. There is probably an app or Workflow out there to do this, but downloading and manipulating a bunch of 500MB+ files is just faster and easier on macOS connected to Ethernet.
  2. Local web development. I prefer to develop in a virtual machine powered by Homestead. There is just no iOS equivalent right now. This isn’t a dealbreaker because I have options: Connect to a remote server and use Coda to pull down files, edit them, and push them back up to test. Or I could set up a system to remote into my home computer. These are fine for hot fixes, but spending a few hours working on and testing updates is just easier on my Mac with the second 27” screen and full local environment.
  3. Meetings. Regular meetings are fine on the iPad with apps like Hangouts and Zoom, but there are two big things missing: Screen sharing and splitview while on video. If I could take notes or look at documents in splitview while on video, I’d probably do 3/4 of my meetings from my iPad. Currently, I prefer to use my Mac so that I can open multiple docs and share my screen during meetings.
  4. Updating my Jekyll site. There are a few hacky workarounds people have made to kick off Jekyll builds from iOS using git repos, but my build and deploy system is super smooth on my Mac. I’ll probably just write posts in markdown on iA Writer on my iPad, then just switch over to my Mac to build and deploy. That said, I’m probably going to switch my site back over to WordPress again soon anyway.
  5. Creating, editing, and using CSVs to move data around. I export a decent amount of stuff from our CRM to use in other systems. I almost always have to manipulate the CSVs first with bulk find and replaces before uploading. I could probably hack something together with Pythonista, Workflows, and regex if I needed to, but I prefer to just use my Mac.

What all of these things come down to is that I prefer my Mac for these particular tasks, but I’m not chained to it. I’m completely fine traveling with just my iPad for a few days. But if I’m gone for more than a few days, I’ll take my MacBook Pro. As-is, my Mac usage has dropped by at least half most days, some days more than that.

In short, I love it.

Using Walks, Drives, and Commutes For Work

I used to think that walking, driving somewhere, and commuting were things that we fundamentally opposed to work. Complete downtime. Even using them to listen to podcasts isn’t working. It is a good use of the time, but it isn’t working.

I now regularly go for walks throughout the workday and take time commuting between my house and coffee shops without stress because I’ve learned how I can best use those periods of time productively for work: I use them to think about a specific problem.

We all think when we walk, drive, and take public transit, but the key is using that time to focus solely on one problem instead of just letting our minds wander. It is tricky, because unlike working at your desk or diningroom table, driving, walking, and commuting are full of opportunites for distraction.

Here is what works for me:

  • I define the problem I’m trying to solve, give it parameters, and write it down in my notebook.
  • I go over the relevant research I’ve done previously. It usually takes me no more than 15 minutes.
  • I forego podcasts and most music. If I’m on the train, sometimes I put instrumental music on to block out the surroundings, but if I’m walking or driving I leave my headphones in my bag. If your mind wanders, notice it and pull it back to the topic at hand without judgment.
  • I have a notebook ready to take notes. If I’m driving, I usually wait until I get to my destination. If I’m walking or taking the train, I can take notes immediately. I used to take notes on my phone, but I find the allure of apps and notifications too distracting, so now I opt to leave my phone in my pocket.

Here is an example from earlier today. I wanted to go work from a coffee shop for a while because I needed some coffee. Here is how I used my time driving there and back:

  • Defining the problem: I have three months of curriculum content to decide upon with TK in a meeting this afternoon and 6 topics to choose from. What best flows from what already exists and how can it be used?
  • Research: Going over the existing 6 topics to choose from and the curriculum elements we’ve already decided on.
  • Today I was driving, so I left podcasts off and just thought as I drove. When my mind wandered off, I noticed it and gently shifted my focus back to the curriculum, just like I’ve been learning to do with my daily meditation practice. (I use Headspace.)
  • When I got to the coffee shop, I wrote down the ideas I had and took a few minutes to refine them.
  • I worked on something else for a while, and then got ready to go home. I reviewed my earlier notes and asked myself, “Where are the holes in this plan? What would make this better?” That is what I focused on while driving home.
  • When I got home, I had 15 minutes to write down my notes and get ready to talk to TK about them.

I do this all time time now, especially on my walks. It is amazing how much framing a specific question before leaving and focusing on that can turn something we usually squander into useful time.

Two questions to ask when you are stuck on a project

  1. What is this project about?
    This is sometimes a tough question, but figuring it out makes all the difference. If you figured it out at the beginning of the project, simply reminding yourself what the goal of the project is and what the core parts of the project are can be enough to get you back on track. If you haven’t answered that question before and are doing it for the first time, start broad, then keep refining it and narrowing it down. Don’t throw in the towel just because it is tough. When you come out on the other side, your project will be much clearer. Don’t do anything in your project that doesn’t lead directly to the main theme of the project.
  2. What’s missing?
    Once you’ve figured out what the project is all about, ask yourself what is missing. What does your still need in order to reach its stated purpose? Write those things down and start working down the list.

This is paraphrased from Steven Pressfield’s Do The Work.

Ted Kooser on Writer’s Block

Writing Routines, a great new sites that gives behind-the-scenes look at the daily habits of writers and authors, has an interview with Ted Kooser, a former US Poet Laureate. I love his answer to a question on writer’s block:

William Stafford, one of our great poets, said that the best thing to do about writer’s block is to lower your standards, and it’s the best advice to give someone who’s stalled.

Two Ways to Handle Client Requests

There are two ways to handle client requests:

  1. Build the request exactly to the client’s specs and deliver it on time.
  2. Take a step back and figure out what the client’s end-goal is, regardless of what their stated specs say. Then architect a solution that you think best fits their goal and pitch that to the client. Then build it.

In my experience, clients often tell you how they’d solve the problem instead of telling you what the problem is first. The issue is that since your clients are hiring you, they rarely know the entire realm of options when it comes to solving the problem. If you are the one doing the work, you probably have a better big-picture view.

I once worked on a project that we built exactly to client specs because the client was insistent that we start immediately. It looked great from the surface, but a number of backend systems were tedious to use, didn’t connect, and missed some clear feature opportunities because the client wasn’t a system architect and hadn’t thought them through. We were technically in the clear because we followed instructions to a T and delivered on time, but the client was still frustrated and we ultimately had to fix the issues to keep the client. We should have pushed back and architected it in the first place. It would have saved time, money, and frustration for both parties.

If you build it to the original client specs, you miss an opportunity to be the expert that helps solve problems and sets your clients up for long-term growth and success with the things you build. Handling requests like a consultant makes for better solutions that are more flexible and scalable in the long-term.

I think the second route is best. That is the way I approach all client requests, no matter what size, or who the client is.

Developers who think for their clients and write the code keep their clients coming back. Developers who just write code are a dime a dozen.

I’ve been feeling stuck with some creative issues at work and decided to try a new tactic today: 

  • I spent 30 minutes digging into what specifically I was stuck on instead of just the general “I’m Stuck.” 
  • I picked one of the items on that list and turned it into a question. 
  • I wrote that question down and repeated it in my head a few times. Then I grabbed my notebook and a pen and went for a walk. 
  • I thought about the question while I walked and stopped along the way to write down what I was thinking. The ideas started flowing and I got a whole notebook page down about that particular question. 

I go for a walk every day, but I usually listen to a podcast instead of using it to focus on a particular question. Defining the question beforehand and leaving my headphones at home allowed me to focus without my mind turning to whatever the podcast was about. 

What to Do When You Mess Up

  1. Own up to it and take responsibility for it.
  2. Fix it immediately.
  3. Put a system in place to make sure it doesn’t happen again. Could be a checklist, could be checks by multiple coworkers before something goes out, etc. Whatever works best for you and your team.
  4. Remember that feeling bad about it helps keep it from happening again, but don’t dwell on the mistake for multiple days. Make the necessary changes and keep working.
I once messed up a routine server update without doing a backup first. It froze in the middle the and an entire school district lost access to their email. My boss graciously took the angry phone calls and I stayed up all night learning how to rebuild the mail server from various online documentation. I finally got it back up and running with messages restored.
The only thing that my boss said when he came in the next morning was, “Now you know why I stress the importance of backing up before every update, no matter how small. I trust you’ll never make a mistake like that again.”
He was right. I’m now a fanatic about backing up. My failure got me to institute a process that I’ll rely on for the rest of my life.

The Most Important Thing About Creative Work

One of the things I’ve had to learn about transitioning into a more creative and visionary role with my new job is to change the way I think about when and where work gets done.

The most important thing about creative work is that it gets completed by your deadline. Everything else is secondary.

I’ve always worked remotely, but in my past two jobs, my remote work required me to be at my desk to handle incoming requests. Even going out to lunch was stressful because I didn’t want to have to take a Skype call from a client at the local sandwich place. When 5 years of working means 5 years of being at your desk from 9am to 5pm, this is a difficult mentality to break.

I started out the day being unable to focus. By lunchtime I was getting worried and feeling bad about not getting enough done. Then after lunch I asked myself a question: “Do I need to be at my desk to get this planning done?”

No. There was nothing keeping me at my desk but my own mind. So, I turned off my laptop, grabbed my notebook, pen, phone, headphones, sunglasses, and keys, then walked out the door.

I’ve gotten more outlining done and more clarity about what I need to do for the next few weeks in the past hour and a half at a dirty picnic table in the park down the street from my apartment than I have in the last two days at my desk.

Giving myself permission to step away from my desk over the past two months has been wonderful. My fears of missing something were unfounded. I’m able to take a phone calls with minimal distractions and I’m still able to answer questions on Slack from my coworkers. The biggest step I took in that direction was setting the expectation of not being constantly online, but checking in every few hours instead. I’m still reachable if something is urgent, otherwise I get up to speed and weigh in every few hours.


Realizing that work doesn’t have to be done solely during the traditional 9-5 schedule has been crucial for me, too. This statement actually has two parts:

  1. Working outside of traditional hours is okay.
  2. Not working during traditional business hours is okay, too.

Before this job, I understood #1, but I never gave myself permission to not work during business hours.

The most important thing is that a task gets done by its deadline, not that it gets done between 9-5.

If getting up early, working for an hour or two, then making breakfast and reading or walking for an hour allows you to stay focused for the rest of the day, do it.

If going home at 4pm and doing those invoices after dinner will reduce your stress levels, do it.

If staying offline for a few hours reduces distractions and allows you to get important work done, do it.

If researching new tech platforms is easier with a cocktail after 10pm, pour a drink and do it after 10pm.

If taking off Friday to spend the day with visiting friends and completing your tasks on Sunday after they leave works best for you this week, great!

Do what you need to do in order to get your work done in the best way possible. Everything else is secondary.

What assumptions are you making about how your work must be done? Question them. Try breaking those assumptions and see what happens. The downside might be smaller than you think. The upside is a better life.

Integrating Care into the Customer Experience

I was at an Intelligentsia coffee shop in Venice, CA, a few weeks ago. I ordered an espresso. As my order came up, I watched the barista. He pulled the shot, and as I was ready to take and enjoy it with the side of sparkling water they include, he paused before he gave it to me. He took the towel tucked into his apron and carefully wiped off the few tiny splashes of espresso that ended up on the rim of the cup and around the saucer.

He could have easily given it to me as-is and I would have been happy. But he took that extra step. And I noticed.

This is one of the reasons Intelligentsia is so successful: They’ve integrated care into every part of their customer experience.  That isn’t necessarily the kind of thing that gets people in the door for the first time, but it is what keeps them coming back again and again.

There is no right time to quit a job, have kids, or start something new. If you want something, you have to take the first step immediately and figure things out along the way. The right time will never come. Jump now.

Ignore the Rules and Be True to Yourself

“Writers write every single day.” “If you aren’t writing code every day, you can’t call yourself a developer.” “The best in every field get up at 4am and start working by 6am after a workout and an hour of reading.”

Rules are so fun to state. They make you look hardcore, driven, and disciplined. But if you are on the other side of that exchange and are the one hearing those rules, ignore them.

Seriously, fuck those rules.

Don’t get me wrong, I love hearing about people’s processes. I love reading books like Daily Rituals. But you won’t get anywhere by worrying about following someone else’s process. You have to figure out with works for you and be ruthless in following it.

I personally see a lot of benefits of showing up and doing things daily. I don’t wait for inspiration to find me, I spend time consuming great stuff and thinking about it. I’ve recognized that I need space to think, walk, read, and listen. Inspiration always comes, and when it does, I’m ready.

That said, I don’t stress out too much over it. While I do get stuff done every day, that isn’t necessarily when my best work hits me. Sometimes I’ll have weeks where I get tons of ideas and am excited to work on some cool stuff. For example, I had the idea to build this WordPress theme this week. This is the first full WordPress theme I’ve done all on my own. I couldn’t get it out of my head until I got the templates done and shipped it. My Jekyll blog template was the same way last year. So was the Sol LeWitt project, the Slack Toggl slash command, the Apple Photos analysis project, and the Cocktail library.

Other times I’ll go a few weeks without being moved to do anything beyond the daily tasks I’ve set for myself. I’ve learned to be okay with that. Fuck what works for other people. These are my projects.

What I can never forgive myself for, though, is not doing the work when I feel the call.

Not following the traditional rules is totally fine. What is inexcusable is not staying true to your own terms and getting your work done.