Fri-Oct-28 Deep Work for Bootstrappers: How to Double Your Productivity

One of the perennial discussion topics at a Bootstrappers Breakfast is “time management.” At today’s Bootstrappers Breakfast in Mountain View, Steve Kim of gave a great briefing on Cal Newport‘sDeep Work” and shared some of his lessons learned in applying it to bootstrapping his startup. Here is an HTML version of the handout he gave to breakfast attendees this morning with some hyperlinks added.

Deep Work for Bootstrappers: How to Double Your Productivity

Friday, October 28, 2016
By Steven Kim, Founder of


  • About me and bootstrapping
  • How I doubled my productivity

Bootstrapping Challenges

  • The multi-hat problem; too many things to do, and lots of different kinds of tasks
  • The biggest constraint is time

Overview of Deep Work

  • Definitions
    • Deep work: “Professional activities performed in a state of distraction-free concentration that push your cognitive capabilities to their limit. These efforts create new value, improve your skill, and are hard to replicate.”
    • Shallow work: “Noncognitively demanding, logistical-style tasks, often performed while distracted. These efforts tend to not create much new value in the world and are easy to replicate.”
  • Examples:
    • Deep work: coding, engineering, writing, design, certain kinds of strategy
    • Shallow work: emails, social media interactions, certain kinds of customer support
    • In-between: marketing
  • Evaluating the depth of tasks:
    • How important is it to your business?
    • How hard is it?
    • How long does it take (minutes, less than 30 minutes, or multiple hours)

How to Improve Deep Work

  • The law of productivity: High-Quality Work = Time Spent x Intensity of Focus
  • 3 areas of Deep Work:
    1. Increasing endurance (more time spent, going deeper)
    2. Increasing mental focus and attentional control
    3. Avoiding multi-tasking and distractions
  • Multitasking has high switching costs which drains willpower. This is especially true for hard, complex problems with lots of “overhead”
  • Attention residue: when switching tasks, part of your attention remains stuck on the prior task, resulting in worse performance on the next task
  • Zeigarnik effect: mentally exhausting to keep thinking about incompletes
  • No wins instead of small wins; lesson from Lean Kanban (c/f The Lean Startup)
  • Willpower is a limited resource; successfully resisting temptation still reduces the reserve of willpower, thus leaving a person more susceptible to the next temptation and with less willpower to apply to work

Bimodal vs. Rhythmic Deep Work

  • Bimodal: switching between periods of isolated deep work (at least one full day) and periods of being available to interact with others / shallow work.
  • Rhythmic: habit of performing deep work daily, ideally at the same time and place and for the same duration.
  • What to do with Shallow Work: eliminate, outsource, bulk-process, do when “low energy”

Deep Work Habits

  • Quick overview of habits (c/f The Power of Habit)
    • The habit loop: cue, routine, reward
    • 5 types of cues: location, time, emotional state, other people, immediately preceding action
    • Internal vs. external triggers (c/f Hooked)
  • Build a deep work habit
    • Same time, place, duration
    • Leverage a starting ritual
  • Eliminate the “distraction habit”
    • Cue: feeling bored, tired or frustrated
    • Routine: switch to Internet distraction
    • Reward: feeling of relief, fun, stimulation and social validation
  • Common online distractions: social media, email, instant messaging and chat, videos, news, games; same rules apply to offline distractions

Deep Work Tools and Tactics

  • Online / offline time blocks
  • Internet blocking tools
    • Category blocking: K9 Web Protection, OpenDNS
    • Scheduled blocking: Freedom, Cold Turkey (Windows only)
    • Interval blocking: Freedom (get 50% off)
  • Device management
    • Separate devices and locations for work vs. play
    • Turn off all notifications during deep work except emergency notifications (external triggers) this includes sounds, noises, vibrations, popups, badges
  • Space management
    • Separate space for deep work to build habits
  • To-do list management (comprehensive list vs. focus list)

Recommended Reading List

Productivity and Habits

Startups / Bootstrapping

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