Digging into Deep Work

My college major was Industrial & Systems Engineering. I was trained to analyze systems and adjust them to seek optimal outcomes.

I don’t work on industrial applications, but the greatest system I have access to today, where I have direct control, and the capability to have an enormous impact, is my own system of how I work.

I realize now that I’ve gone years with limited stints of deep work. I have waded in the shallows, exhaustively, for the vast majority of my work efforts — constantly shifting from one work arena to another, rarely giving my mind time to properly engage an important task.

Cal Newport won’t blow your mind with the definition of deep work itself — which is pretty self explanatory. What I like is, within his book, he both makes the case for deep work, and also establishes example routines for sensible, achievable levels of deep work (while leaving the door open for more extreme variations).

My own deep work, I realize in retrospect, has usually been either deadline or panic driven. Unmissable deadlines (self set or otherwise) or panic work sessions in rapid bursts of hard-spent energy (almost always at non-ideal times, like late at night or a weekend) have been my primary avenues of deep work. I can do better! Deep work is something I should be accomplishing in my regular routine.

Excuses to work shallow

I use social media for work. It has, in no small part, been the responsible venue for my ability to create multiple brands that turned into spheres of influence, income streams, and new friendships.

But my ever-present engagement with these platforms is not effective for helping me grow — either those brands, or in my own work capacity. They are still useful, but they are not necessary to be fully immersed.

I can do better work for myself, my clients, and those same social audiences, if I tone down how I interact with social media (primarily Twitter).

My default work “break” has long been to pop open Twitter and see what’s happening, which then sometimes can translate back into content that I put out via newsletter, analysis, conversations, etc. But for a long time now, the payoff in what Twitter creates via serendipity is not worth the cost: significant distraction from what’s important for me to accomplish.

Newport’s book doesn’t just focus on social media, though it’s absolutely a key platform for distraction and common reason people avoid deep work. He also talks about the regular ebb and flow of most businesses, and how many are structured in a way to prevent deep work. I have done this in my own work, in how I (poorly, often) balance between three different work endeavors.

I have already made several adjustments over the past year or two in how I work. Something led me to read this book, after all. I already acknowledged I needed change, and have experimented. It was a start. Now, my aim is to execute with a better plan, and not haphazard experiments.

In response to what I’ve taken away from this book, I’m making personal changes which, I hope, I will stick to better by writing them down here đŸ™‚

Changes on social media usage

I’ve deleted Twitter from my phone. I manage my personal account and two brand accounts — all of which are active. I felt a sense of abandonment within about 10 minutes, not being able to read my timeline.

I know myself. My problem isn’t that sharing is distracting, it’s reading (primarily on my phone) that’s distracting. So I’m tweeting still, but using Buffer to maintain my social posting, limiting my ability to engage by phone.

Now, if I’m to engage in other things (checking notifications, reading my timeline), I have to purposefully open the app on a desktop, and have a work purpose to do so (much like I’ve somewhat achieved with email). I do have legitimate work purposes to do this, so it’s still an important part of what I do, but this should create significantly more balance and barriers in my social interactions.

Changes on chat management

As a remote worker, chat can eat into my day like nothing else. In the web landscape, I use Slack to talk to customers and friends. For SkyVerge, we use it for company chat. For crypto, I use Telegram to talk to friends, other traders, and other relevant contacts for things like my podcast.

All of these options for chat take away from deep work opportunities, and introduce plenty of variables that increase the probability my day gets sidetracked. And I know very well how to give into them.

I manage thousands of online relationships. Many of these are important. Cumulatively, they should not take over my life.

Over the past year, I’ve gotten better about limiting my chat usage in Slack, but I’m very good at replacing one bad habit with another. I transitioned some of these broader big-group chats into just as distracting small-group chats.

Chat groups for me are a huge distraction. They are important, but they need better management.

  • I keep chat apps closed on my desktop unless I need to send a message or have a planned session for managing chat. It’s never casually open.
  • I turned off all notifications for Telegram (crypto stuff is not a priority communication channel and needs should be relegated to leisure time).
  • I only enable Slack notifications for work-sensitive channels, and only via direct mentions and DMs.
  • I quietly removed myself from many, many chats that don’t meet my primary goals.

Tracking my habits better

I’m tracking things using the Tally app. I’ve been doing this all year, but I added a category for deep work tracked by hours in a week. I haven’t yet set a target (an option inside Tally) as I want to see what I tend toward naturally. I’m hopeful I can get at least two hours per day; Newport advises that 4 is a pretty high bar for most workers who have a significant amount of shallow work required.

I’m already using Tally to track other things:

  • Physical things: Tracking workouts per month, coffee drinks per day (just to know), alcoholic beverages per week, standing work hours per week, how many times per month I’m later than my goal dropping my kids off at daycare.
  • Knowledge things: Books per year, good reading sessions per week (the bible, something where I am enriched by reading, etc), personal blog posts per year, and now deep work hours per week.

I like Tally because it’s easy to use and offers a good overview of how I’m accomplishing what I aim to accomplish. It offers a dose of reality to my ambitions.

Newport logs his deep work hours via tick marks on a paper near his computer. I know through my 70 or so days of Tally-ing that Tally gets the same job done for me: personal drive and satisfaction in ticking the boxes and seeing my progress (or accountability in lack thereof).

Time logging and schedule blocking

I’ve been using Toggl to track the time I bill to SkyVerge, where I contract regularly. I have other categories (I tracked how many hours I spent working toward my new partnership for Post Status, for example). But I haven’t been a great time tracker for other work — especially shallow work.

Two of my most productive friends — Syed Balkhi and Brian Richards — have recommended detailed time blocking to me. Cal Newport also recommends it in his book, via planning sessions of both shallow work obligations (email, data entry, admin stuff) and deep work routines (write long form content, research an important project, write code, etc).

I need to divide and conquer my week amongst three focus areas: SkyVerge, Post Status, and Ledger Status. These three focus areas are not equitable distributions, but if I don’t time block them, it’s easy for me to spend more time than I intend in an area I shouldn’t.

If I plan my week through detailed time blocking, and then blend this with time tracking, I can better know both my plan and my execution.

Newport explains a nice hack on this as well: he understands that a schedule can change. He describes the process where he evolves his time blocks as it inevitably changes during a day or week. It accepts that adaptations can be made while maintaining a commitment to blocking time.

I know this will be hard for me. I’ve tried it before (but without allowing for block-evolution). I look forward to trying this method, which may require I shift from a calendar centric method to old fashioned pen and paper as he recommends.

Saying no

I say, “yes” too often. It usually leads to later saying, “I’m sorry.”

I love saying, “Yes!” And I don’t want to stop saying it. I just want to start saying yes to the things I love saying yes to, and saying no, ruthlessly, to everything else.

I get so many inbound contacts: via website contact forms, email, Twitter, Slack, chat, wherever. All the time. I’m pretty good at ignoring the least of these. I’m pretty good, unfortunately, at ignoring the more important ones too — particularly through email. Because I’ve been very bad about managing chat well, I have too often ignored more important asynchronous communication.

I want to say yes to things like:

  • Building small websites for friends or organizations it would benefit enormously
  • Helping mentor or consult someone in my industry who seeks my advice and has great potential
  • Volunteering in my community, for my kids’ activities, or for my church

I must say no much, much more than I do now. No to synchronous requests, and no to things that I know don’t fit the bill for accomplishing my goals.

One of the things Newport did that I’m absolutely following through on is to establish more friction in cold outreach channels (like my contact form). I want someone to really want to get my attention before I give it my attention. Not because I want to be rude, but because I want to be great for the things I prioritize as my yesses.

A deep work benchmark

Systems can be stochastic or deterministic. The way we work is a stochastic system: our work is subject to many variables and probable outcomes as a result of choices made along the way.

How we implement our system of work will give us a greater probability to do more high quality work.

I’ve been on a journey to better my work. What Deep Work has helped clarify for me is that deep work can be a difference maker in actually bettering that work.

If I prioritize working deeply, I can accomplish several of my goals (things I want to optimize for):

  • Do better work across multiple disciplines
  • Effectively balance multiple business endeavors
  • Get more stuff done that matters over a long period, rather than just get done what matters near term
  • Keep work at work and have better presence with my family

I use to manage by using “10 to 2 time” — late night deep work sessions to make up for a day in the shallows. Now? I have two kids. I’m too exhausted for that. I have to have a better system.

Newport’s book covers a lot of things I didn’t talk about here. His book helped clarify how to go about my work in a systematic way that gives me a higher probability of achieving my goals.

If you feel like you’re consistently in the shallow end of your work potential, give it a read.

I’ll try and keep you updated on the evolution of my work systems. Meaningful blogging, after all, is one of my goals. Now if you’ll excuse me, I have to go, because I’m excited to tap this button for my first logged hour of deep work.

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