‘Embrace procrastination’: itr8group cofounder Rory Laitila on getting things done

Rory Laitila and his business partner Adam Steele work more than 1,000 miles away from each other.
But that didn’t stop them from creating itr8group in June 2014. The duo works with a client’s executive team to develop internal software, build and train software development teams and improve business processes through data, analytics and custom software solutions.
Steele, who is based in La Crosse, Wis., and Laitila, who works from The Loft in Wilmington, launched their new brand and website last week.
“Whereas there are of course a lot of creative agencies that can build web products, we really focus on using custom software to solve complex business problems,” Laitila said.
Laitila also created and managed Doughnuts and Demos, an regular event at The Loft that gives each coworking member the space to share what they’re working on in a collaborative environment. Doughnuts and Demos is still held occasionally; Laitila said he is having more success strategizing with a few business owners from The Loft each week to discuss business-specific challenges and provide advice to one another.

Here’s how Laitlia gets work done five states away from his business partner.

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What’s the first thing you do every day before doing any job-related work?
I make a cappuccino and read: A lot of Reddit (r/programming, r/economics, r/Delaware, r/business, r/entrepreneur, honestly very little of r/funny usually), Hacker News, technology Google groups. There is so much going on with new technologies, I need to do this just to keep up. It’s impossible to learn how to use everything, but I like to know a lot of what is out there so that I know where to look if I come across a new problem.
How often do you check your email, and do you use any program to get to ‘Inbox Zero’?
I pretty much check every message that comes in, unless I am programming which then I turn it off (with programming one needs a lot of uninterrupted time). I use a combination of inbox zero, and I wrote a custom GTD-style task tool called Thread (now in private alpha), which makes it easier to manage diverse contexts of work as a business owner. The hardest thing about what I do, is that I am operating at all levels (customer communications, programming, accounting, marketing, team management). These things don’t always fall into clear “tasks” or units of work. I needed a tool which gives me the long and short term in one “inbox” and allows me to “context switch” without mental overhead, so I wrote that tool.
When you need to take a break, what are you turning to?
I’ll go back to my normal reading previously mentioned a lot of times. I also like to walk back home (I live two blocks from The Loft), have a cup of coffee, take a “coffee nap,” and then go back to the office for a second session of work.
What’s one way in which you believe your day-to-day work is better now than it has been? Is there something you do now (or don’t do) that you didn’t do before (or did) that has made a big difference?
I focus on the task at hand and don’t let myself get stressed by having a lot of deliverables.
Using Thread helps a lot with this because it manages my mental contexts for me. Before using such a tool, one tends to get stuck in continually reviewing their email list, or with a traditional task list you may find yourself staring at it, thinking: “What should I work on next?” You can waste a lot of time this way. Inbox zero combined with Thread has made a big difference in keeping on task.
Anything else?
Embrace Procrastination
I’ve also learned to embrace procrastination.
There are two types of procrastination to me: 1) Not doing something because it is dull or tedious, and 2) Not doing something because you are not yet ready to produce it.
On No. 1, a good task system helps you get those tedious things done, with a “just do it” attitude. For No. 2, I put the task off until I am better suited to produce it. In creative work, my motto is: “Why do today what you can put off till tomorrow?” Your subconscious works on problems for you, and by the time you do them, having waited a little longer, you will often do them better and faster. For creative projects I think this saves a lot of time as I am not spinning my wheels, I rarely have any kind of “writer’s block” symptoms with this method.
Coworking Helps
I also think that The Loft helps a lot. The different people there often lend little pieces of advice that can break you through a rut in a project.
Whereas when working in a traditional office environment, you tend to get the same opinions. I’m much more likely to find a contradictory or novel idea from my colleagues at The Loft that helps. Sometimes the activity at The Loft can be distracting, but I think on balance, coworking is valuable. I even wish that traditional companies would embrace coworking and cross-office work environments and be less siloed and protective of their ideas. Open collaboration is greater than the sum of its parts, I believe.
Choose Projects Wisely
The key to productive creative work is low stress, or getting into “flow;” the key to low stress and flow is working on projects which your skills are well suited for, and which there is a lot of mutual trust and respect between client and vendor.
I only take on clients which can come together in an attitude of “partnership” and reciprocity. Being able to take on the right clients means knowing when to turn down the wrong ones. Being able to turn down work requires frugality and thrift, and frugality requires self-awareness of what your goals in life are and what is truly important to you. Knowing what is important to you requires introspection. For me, I like to improve introspection skill by reading classic philosophical texts, particularly the Stoics and the Taoists. My time is only truly productive when the product produced accords with what I consider purposeful in my life. Everything else then is busy work, and a lot of people can confuse these two concepts.