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The Jungle Gym - March 2019

Friends– Thanks to those of you who shared feedback on last month's newsletter. Your comments were re
The Jungle Gym
The Jungle Gym - March 2019
By Nick deWilde • Issue #2 • View online
Thanks to those of you who shared feedback on last month’s newsletter. Your comments were really encouraging and left me excited to keep this going.
If this is the first issue you’re seeing, it either means we just met in the past month (👋) or I somehow forgot to include you last time (sorry 😔). To get a sense of what this is all about, check out the previous edition here.
After several conversations with friends, who didn’t realize they needed to sign up to get future emails, I decided to tweak my plan for who to keep on the list. Without going into all the details, I decided to retain anyone who:
  • Signed up on the form
  • Shared positive feedback on the first email
  • Missed opening the first email
  • I know well enough to not be concerned about spamming :)
With that said, I’ll be completely understanding if you decide this email isn’t for you and want to hit the unsubscribe button at the bottom.
While I’m not making an active effort to spread this newsletter beyond my own personal network, if you have someone in your life who you think might enjoy it, please feel free to forward it along (here’s the link to sign up for future emails). The only caveat is that the offers I make, at the bottom, are meant for people who I can personally vouch for (that said, I’m always open to meeting new people).
I’ll include a few more housekeeping notes at the end, but for now, let’s get into the good stuff.

Increasing Your Personal Output
Over the past month I’ve gone deep on the topic of personal productivity. I’ve implemented a bunch of systems and tools into my workflow that already seem to be positively influencing how much I get done and how I feel at the end of a workday.
Here’s the general structure for how I’m currently thinking about productivity:
  1. Task Management helps you capture, retain and prioritize what to work on
  2. Time Management allows you to create space in your life to accomplish the tasks you’ve prioritized
  3. Energy Management ensures that when you sit down to work that you can actually focus on the task at hand and finish it in the time you’ve set aside
For the sake of not turning this email into a novel, I’m only going to cover my learnings in the first two sections, but if there’s enough interest I’ll cover energy management at a later date.
Task Management
The best advice I’ve read on task management comes from David Allen’s book: Getting Things Done. While the whole book is great, I think the first two steps of his process are the most impactful: capture and clarify.
Capture Everything
Rarely do tasks start out as actionable units of work. They originate from a variety of sources (your significant other, boss, an author, etc.) through multiple channels (conversations, email, mobile messages), and without appropriate context for how to take action. These same channels also contain plenty of irrelevant information that, at first glance, can be mistaken for a potential task. Since it takes time to separate the signal from the noise, your job, when something captures your attention, is to write it down immediately
While some object to the idea of quick capture as an act that pulls you out of the moment, the alternatives are much more mentally taxing. Picture yourself at dinner with your friends and you suddenly remember that you have a presentation due next week. In this situation, you have three choices:
  1. Do nothing – without expending some mental energy chances are that you’ll end up forgetting all about the presentation and suffer the consequences.
  2. Become preoccupied – by devoting your cognitive energy to retaining this thought you’ll inevitably lose focus on what’s going on around you
  3. Quickly capture it – record the thought and worry about it later so you can engage with your surroundings
Personally, I’ve found that having the peace of mind that all my potential tasks are safely stored has allowed me to be much more present in everything I do.
Which tool you use for capture will depend on your own personal habits. Some people like paper notebooks because of the freedom they offer. I find that since my mobile phone is always an arm’s length away, it’s my most reliable capture device for my workflow. I adopted a task tracker called Todoist which I like because it’s easy to capture things quickly, has a mobile app, a desktop app, a Chrome extension and even a Gmail plugin. I’ve enjoyed it to the point that I’ve already signed up for the premium version (here’s my referral link if you want 2 months free).
If you choose a task tracking app you’ll also want to make sure you have solutions for where to store articles, long-form notes and PDF files. I’ve been using Notion for this, which has been great so far (if you want some credit, here’s my link). That said, there are also plenty of other good solutions for tools. If you use anything great, I’d love to hear about it.
A note on email: unless you’ve already have a good system for it, I’d strongly discourage using your email as a capture device, since so much information already flows through it. That said, it’s definitely a good idea to have a capture tool that is only a few clicks away from your inbox for when you need to store something relevant.
Not all the items you’ve capture are destined for your to-do list. Your next step is to take each one and determine where it belongs. Any item capture should go into one of the following buckets:
  1. Archive or Trash – the place to send any items that you don’t need to interact with anymore
  2. References – for any information that isn’t directly actionable, but that you don’t want to forget (a quote, a manual, a presentation deck, an interesting statistic) you’ll want to put in a file system where you can store it and easily find them later (this is what I use Notion for).
  3. Later list – a place to store items that might require action in the future, but don’t have enough urgency to handle in the near-term.
  4. Waiting list – if you’re waiting on somebody else to accomplish something, this is a good place to record it
  5. To-do list – for items with clear next actions that you’re not ready to do immediately
  6. Calendar – for items that you’ve committed to doing at a certain time on a certain day.
  7. Project list – If something has multiple steps that may span the length of more than one working session it should probably be designated as a project
To help determine which bucket an item is meant for it’s helpful to ask yourself following questions:
Is it actionable?
Is this something you need act on? If the answer is no, then it’s probably meant for one of the following destinations:
  • Archive or trash – if you don’t need to act on it
  • References – If you want to hold onto it for the future but can’t think of when you’ll use it
  • Later list – If it’s something that you may want to act on in the future
What’s the next action?
If you’ve determined that an item is actionable, your next step is to decide what that action should be.
A good next action should be physical and visible. For example, “figure out job requirements” isn’t physical or visible action but “drafting requirements for a role” is.
Do it, delegate it, or defer it?
Once you know the next action you want to take, you have three options
  1. Do it. If an action will take less than two minutes, go ahead and do it, since the overhead of tracking in your to-do list will likely take longer than two minutes.
  2. Delegate it. If you’re not the right person to do it delegate it to the appropriate entity.
  3. Defer it. If it takes longer than two minutes, and you’re the right person to do it, then it’s likely a good candidate for your to-do list
A Note on Email
Email was my productivity kryptonite. I found myself sometimes dipping into the email slot machine every thirty minutes. I desperately needed some way to process my email quickly so I could get onto more important things. I set up my email using this workflow, that Tiago Forte recommends and it’s been a lifesaver. If you find yourself in a similar situation I highly recommend it.
Review & Prioritize
Just because a task appears on your to-do list doesn’t mean it’s necessarily worth prioritizing. Certain tasks demand to be finished immediately while others can be put off indefinitely. Whether or not you make an active effort to prioritize your tasks, you will inevitably end up spending more time on some than others. Rather than leaving it up to gut feel, it’s worth spending the time to review and rank what’s most important.
I’ve been doing my weekly review on Sunday, before the week kicks into gear, and people start making asks of my time. The goal of this process is to consolidate my tasks into one place and end up with a ranked list of what I should be spending time on. Here are the steps I take (under ideal circumstances):
  1. Audit my previous week – Did I get everything done that I committed to? If there are any tasks left over, I add them to your list of potential tasks for the upcoming week.
  2. Perform a brain sweep – Even though I’m pretty good at capturing items when they arise, I often still have a few stray open loops in my head. I try to give myself some time away from distractions to get them all on paper.
  3. Review my projects – I look through each of my projects and areas of responsibility to determine what progress I want to make over the next week. Then I add any tasks that might be required to get me there.
  4. Glance at my “later list” – Next I check to see if any items on this list have risen in importance and may make the cut for something I want to accomplish in the near future.
  5. Consolidate potential tasks – If I have items in multiple places, here’s where I’ll consolidate them in one location alongside anything that came up during my brain sweep. It’s a good idea to pick one system of record and make sure everything eventually finds its way in there.
  6. Clarify any outstanding items – This is when I clarify any items that I’ve captured but haven’t tagged with an obvious next step, using the process we just covered.
With all my potential tasks clarified, and in a single place I can now determine which ones are worth spending time on this week. Here are the criteria I use to prioritize:
  • Value – What are the the consequences of completing that task multiplied by the probability that those consequences will be realized?
  • Urgency – Do I stand to lose a lot of potential value by putting this task off?
  • Leverage – Will completing this task make my other ones easier?
  • Investment Required – How much time, energy, money will this task require from me?
  • Dependencies – In order to complete this task am I waiting on someone else?
  • Constraints – Will doing this improve the throughput of the system as a whole or am I just putting more stress on the bottleneck?
  • Stakeholder Demands – Who’s asking for this?
This list is exactly MECE yet. Nor have I figured out the correct weightings, but it’s a good start.
The result of it is a stack ranked list of my tasks. The next step is scheduling, which is where time management comes into play.
Time Management
I’ve dug into lots of articles and books on Time Management. Here are some of the most helpful principles I encountered:
Design Your Day
If you want to ensure your time is being allocated towards the right things, start by adding them to your calendar. By blocking off periods of time to accomplish your priorities you make a commitment to yourself that you’re actually going to do them.
I’ve been scheduling every minute of my workday. Do I always follow the plan? Nope. But I try my best, and usually I end up completing what I committed to that day.
One objection people have to scheduling is that they hate feeling like they’re controlled by their calendar. While your calendar may remind your of things, it’s ultimately what shows up on it is up to you. By scheduling each minute you’re allowing your responsible reflective self– the one who has your best long-term interests at heart– to take the control of your most valuable resource from your impulsive self.
Fix the length of your workday
Along with scheduling your working hours, it’s also helpful to fix your workday to a certain length. How many hours you set aside each day may vary and depend on your specific goals and situation but the principles are the same:
  1. Choose a schedule of work hours that you think will allow you to best accomplish both your personal and professional goals
  2. Do whatever it takes to avoid violating this schedule.
The reason this is helps your productivity has to do with a time management principle known as Parkinson’s Law, which states that, “Work will expand to fill the time allotted for its completion.”
If you don’t fix your schedule, it can become easy to goof off and waste time. Your work will end up taking longer and naturally you will need to pull from somewhere which can deteriorate your health and relationships over time.
Maker vs. Manager Activities
Certain types of tasks require different amounts of energy and time. Activities like meetings, calls, or email management lend themselves to shorter 30-60 minute windows.
Tasks that involve creative heads-down work, are almost impossible to complete in short windows of time. Instead, they require long 2-4 hour windows of uninterrupted focus.
This distinction is what Paul Graham refers to as maker vs. manager time. Manager time is divided up into short windows to deal with issues and put out fires whereas maker require long stretches of deep work. When scheduling tasks, be mindful of what kind of task you’re trying to accomplish and how much time it requires.
Bulldoze Your Calendar
When you first encounter your schedule you’re likely to be confronted with a bunch of appointments that don’t reflect your priorities. If you leave them where they are you won’t be able to make room for the larger blocks of time you’ll need for generative work. Take the advice of Make Time’s authors, Jake Knapp and John Zeratsky and bulldoze your calendar:
“Imagine a tiny bulldozer driving through your calendar, pushing events around. The bulldozer might compress one meeting by fifteen minutes and another by thirty. It might shove your one-on-one from the morning to the afternoon or push your lunch back by half an hour so you can get a full two hours of generative work done. The bulldozer could even stack all your meetings on one or two days of the week, freeing up the other days for solo work.”
This can be challenging to do if you don’t have much autonomy over your schedule. If you’re in this situation I’d recommend trying to lobby for at least one day each week that you can clear for generative work.
The Scheduling Process
With these principles in mind, you can now go about scheduling the tasks you’ve prioritized on your list. The scheduling process is often most helpful when it follows your weekly review, but it can also be done separately. You’ll want to start from your highest priority task and work your way down, taking the following steps:
  1. Ensure tasks are properly scoped – the more you can downscope a task into smaller parts, the easier it will be to fit into various blocks of free time. By turning one large task into a series of smaller deliverables, you can create momentum and allow yourself to ramp back up into a task after an unwanted distraction.
  2. Estimate task times – if you haven’t already try to estimate how long each task should take. Try to give yourself a bit of buffer so you don’t end up driving yourself crazy.
  3. Bulldoze your calendar – take a look at your schedule for the week. Is it already filled with meetings and tasks that don’t accurately represent your priorities? This is your opportunity to move things around.
  4. Add anything that must be done at a certain time – If you have a morning routine, you’ll need space for it when you wake up. Most standing date nights, need to happen in the evening. If an activity requires transit from one place to another this is a good time to slot it in.
  5. Find space for what matters – here’s where you’ll start actually inserting your most important tasks into your schedule.
With your schedule all planned out, the final step is figuring out how to manage your energy and attention so that you can actually get the work done.
As I mentioned above, since this email is getting long, I’ve decided not to cover energy management. If this topic generates enough interest, I’ll cover it in a later issue.
Reading Recommendations
Every time I dig into project management principles I find something I wish I’d known a decade ago. The concept of cost of delay definitely falls into that category. Essentially, it’s a framework that covers how to prioritize competing projects and initiatives. I linked to the first article in the series (since it’s got a nice explainer video), but I’d recommend reading them all.
The part I’ve found most actionable is the way he defines urgency. Essentially he says that the urgency of a project tells us how much value we stand to lose out on based how long we delay taking action. When defining the urgency of one thing over another, there are two variables to consider:
  1. The length of the lifecycle of benefits (how quickly the benefits ramp up and down)
  2. Whether the peak is affected by delay or not.
He goes on to explain three common urgency profiles to look out for:
1. Short life-cycle; Peak affected by delay
  • Deciding whether to make a trade on proprietary information before the news becomes public
  • Trying to launch a marketing campaign based on events in the news cycle
2) Long life-cycle; Peak affected by delay
  • Trying to get first mover advantage into a new market
  • Deciding to learn a new and promising programming language (since learning compounds)
3) Long life-cycle, peak unaffected by delay
  • Canceling a subscription to a service you no longer use
  • Automating a process at work
There’s lots more good content in these posts. Highly recommend you give them a read.
Last time I included Simler’s article on “crony beliefs” and what sort of incentives might cause us to adopt them. I think the ideas in this post are an important piece of the puzzle.
The post characterizes simulated thinking as the habit of following pre-defined scripts in response to environmental triggers (think of your friend who launches into a scripted diatribe every time someone mentions the word “socialism” or “capitalism”). It suggests that beyond the social rewards for retaining crony beliefs, there also exist rewards for practicing the type of thinking that perpetuates them.
For example, consider the political debates you’ve witnessed. Who tends to look better: the debater who can quickly rattle off facts and figures in response to arguments or the one who attempts to employ reason and make sense of new information? The former, often ends up looking much more elegant and desirable whereas the person thinking in public tends to look awkward.
Given our media consumption habits and education system only further incentivize this behavior suggests dire prospects for true thinking. Fortunately, thinking has reality on it’s side:
“The more reality drifts from the environment that the scripts of simulated thinking were designed for, the more errors the simulation will throw. The glitches in the Matrix will become both more obvious and more egregious. By contrast, as thinking starts to get itself sorted out, it becomes more adaptive to changing reality. What first looked like error starts to look more and more like insight.
And thinking has nature on its side. Explore mode is a fundamental part of our human toolkit. We all start with it. And while our environment can separate us from thinking, it can’t remove the capacity altogether. Anyone who chooses to can re-learn learning. Not without effort, and until there is a critical mass of other folks taking the same journey, not without social consequences. But it can be done.”
Let’s hope.
Whenever I meet someone new, I can’t help but ask about their work. Yes, I recognize that a person’s identity is more than just their profession. But, without knowing how someone spends their time, it’s hard to get a sense for who they are. Time is our most precious asset, as it’s the one thing we can’t replenish. How we spend it says everything about our priorities. Since, outside of sleeping, work gets the largest allocation of time, from most people, I think it makes for a worthy opening question (Side note: I actually think the problem with this question is what people ask next, but that’s another post).
I started thinking more about this after reading this thoughtful article about how Americans (particularly millennials) have been searching for meaning in their work, and coming up short. The author, who dubs this practice as “workism,” defines it as:
The belief that work is not only necessary to economic production, but also the centerpiece of one’s identity and life’s purpose; and the belief that any policy to promote human welfare must always encourage more work.
Other recent articles have demonstrated how this practice is leading many to burnout and even the most successful of us to misery.
While I appreciated these articles, I couldn’t help but feel that there was a more nuanced explanation for why we aren’t finding meaning in our jobs. That was when I stumbled on the title post by Rusty Guinn, who filled in the missing piece:
We are a nation full of people doing jobs where the real job is to look like you are doing the job.
At least for most knowledge workers, I suspect that what’s making us miserable is not the nature of our work itself, or the longer hours we are spending getting things done. Rather, it’s the time we waste signaling to one another about how productive and useful we are. Guinn ends the piece with a sentiment that resonates:
Hear me again: your work is holy.
No I don’t mean your job. I also don’t mean your passions. Your life’s greatest work may never be a passion. And no, this isn’t another paean to artisanry, crafts and trades, although these are perfectly legitimate paths to meaning, too. I mean your work: what you make. When you set your mind and hands to work, what do they produce? Does your labor result in knowledge, happiness and health, beauty and wealth, for yourself or for others? Even if you manage to reserve a good amount of time for leisure with friends and family, make no mistake: Your work will still matter to your happiness.
The form work takes for you will differ based on the talents you have. Whatever it is, there is no substitute for it. If you reduce your work-less job from 70 hours to 55, you will still be unhappy. If you are able to find relationships and connections and even follow your passions at your job, if it is not work, you will still be unhappy. If you are retired early, sedentary and wealthy enough to do nothing for as long as you want, you will still be unhappy. Good people are wired to be productive, to contribute and to give more than they got.
For what it’s worth, my advice is to spend your precious time creating real value for others, including family, friends, customers and colleagues. If your job too abstracted from that value, find ways to glimpse it and remind yourself why you do what you do.
If after searching you can’t find any meaning in your work, drop me a line, and we can talk though what you should be doing instead.
Like I mentioned last time, one of my goals for this newsletter is to find out what challenges you all are facing and help where I can. To that end, here are a couple of offers:
Note: If you’re one of the few people getting this email who I haven’t met personally, I’ll need to get to know you a bit better before I feel comfortable recommending you. A good way to start is by dropping me an email to introduce yourself.
If you’re hiring, share some info about what role you’re looking to fill, and I’ll try to pass it along to the right people.
If you’re looking for your next thing tell me a bit about what kind of role you’re looking forand I’ll keep my eyes peeled for interesting opportunities.
If you want to grab coffee with someone in a similar role, let me know and I’ll try to match you up with a peer.
Lastly, if you have any thoughts on the general format of this email, and how it can be improved, I’d love to hear what you think.
Until next time,
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Nick deWilde

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