Managing Extreme Personal & Professional Complexity
Whether personal, professional, entrepreneurial, or creative, when pursuing a complex, ambitious, or long-term goal, you face several needs, among them:
Understanding your motivations so you can refer back to them when you face challenges
Refining your goal and creating boundaries around it
Managing complexity
The first point is discussed in Foundational Wealth and CMV, and the second in M-SMART Goals, so you should read those first, if you haven’t already. This final point is the one I'll be writing about here. In my book, Foundations of Execution, I cite managing complexity as one of the three behaviors that separate those who consistently execute from those who consistently fail. But what does complexity mean in this context?
Learning a new skill or volunteering for a cause you care about is harder than sitting on your ass and watching TV. Just like having the tough conversation and moving all your stuff out is harder than staying in a bad relationship. These actions are harder not just because they involve work or emotional strain, but also because they introduce complexity to your life—they introduce unknowns and potential problems, anxiety and the possibility of regret. There’s complexity in the unfamiliar and the risky, and haven from complexity in familiar routines and paths well traversed.
With very few exceptions, anything ambitious introduces complexity to your life. Think about it: adopting a pet, starting a new workout routine, or even traveling to a new location all introduce some degree of newfound complexity. Whether or not they’re enjoyable, fulfilling, or worthwhile, embarking on them is always more complex than the alternative.
What about starting a business, reconnecting with an estranged loved one, pursuing a new career, taking on a creative challenge, committing to a lifestyle change, or working toward a professional goal?
Complexity. Complexity. Complexity.
You most likely never learned to manage complexity properly — it’s simply not something we’re taught — so you never learned to manage ambitious goals (which are inherently complex) properly. And yet, you’ve doubtlessly heard the same advice from gurus, loved ones, colleagues, and inspirational memes scattered across social media: get out there and begin working on your goals today. Unfortunately, this is no different than telling you to start building the walls of your dream home without first laying a foundation. As goals evolve and progress, tasks and responsibilities begin to pile up, and anyone who lacks a concrete framework for prioritizing and organizing them is going to quickly become overwhelmed.
The overwhelmed tend to suffer. And those who suffer — especially before seeing benefits — tend to quit.
Moreover, complexity doesn’t emerge only from your ambitions, but from all aspects of your life — whether interesting or mundane — and you need to learn to manage complexity in all of its forms. Luckily, managing complexity doesn’t have to be complex. You can build a framework that leverages basic organizational skills and simple technologies. Managing complexity requires you to answer three questions:
How? — How will you organize your goals?
When? — When will you address your goals?
What? — What tools will you use to record/represent your goals and the time you’ve committed to addressing them?
Here, we'll answer the first question. The second two are covered in The Franklin Principle: A New Definition of Time Management and The Three-Tool Execution Ecosystem, respectively. The short answer to "How?" is: Become accustomed to creating Scripts and Hot Lists.
Scripts
A Script is a simple, ordered, linear process that you follow to keep yourself on task whenever it’s time to work on something. Your Scripts shouldn’t change much from day to day — you won’t be deleting or editing items (at least not often).
To illustrate this, imagine that you’re a professional with an office job. You come into work in the morning and pull up your work Script:
Check your work email and voicemail and reply as needed
Assess any new items you need to keep track of and add them to your to-do list
Check your calendar; review the day's meetings and prepare notes for each
Perform daily repeated tasks
Address your to-do list
I call this type of Script a Daily Script. Once you arrive at work in the morning and get settled, you know it’s time to refer to this Script. A Daily Script can work for a job, a morning routine, or even as a way to provide structure upon retirement.
A Script like the one outlined here may seem insultingly obvious, but it exemplifies a habit I reinforce time and time again whenever I help someone manage complexity: the habit of recording every remotely complex process you perform. I have dozens of multi-step processes I need to follow in all aspects of my life — some of which I only have to reference a few times each year. Do you think I want to have to remember every step of each? No — I don’t want that burden or the stress that accompanies it. Personally, I’ve used Scripts for opening a pool, collecting materials for taxes, intonating a guitar, assembling children’s school lunches, and dozens of other multi-step, repeated processes. Professionally, I’ve used Scripts for performance evaluations, root cause analyses, new staff onboarding, financial forecasts, process audits, training, technical security reviews, and more.
Note that the item Perform daily repeated tasks in the above example could refer to anything applicable to your specific job. Think of a job right now — either your current job or one you’ve had in the past. If you’re in IT, you may need to review technical logs every morning; or maybe you’re a retail manager who needs to look at the night shift’s final tallies. Maybe you’re a competitive athlete who performs visualization exercises before starting your daily training regimen. Maybe you’re a contractor who needs to clean your tools and stock up on materials for the day. Do you change ink cartridges, check tire pressures, manage your stress with mindfulness practices, or feed all of the animals in a shelter? Do you order new inventory? Almost everyone has things they have to do or check every day, and there’s value (and often safety) in organizing them and articulating them outside your head as opposed to relying on your memory, which can be affected by countless factors.
Creating a reliable, meticulously organized, and consistent ordered process for any multi-step task not only helps to reduce oversight, but also the anxiety that often subconsciously accompanies the fear of oversight.
“Shit — did I skip a step in opening the pool and damage my pump?”
“Shit — I feel like there was one more item I collected for my taxes last year. What was it?”
“Shit — this kid’s lunchbox looks kind of empty. Am I missing something?”
Avoid the shits.
The examples given so far have focused on tasks and processes, but Scripts really shine when it comes to goals. Consider a personal goal: imagine that you’re learning to juggle and set aside two dedicated thirty-minute practice sessions each week. What could a Script look like for each chunk of Blocked Time?
Locate your juggling materials (1 minute)
Set up in a quiet place; mute your phone (2 minutes)
Stretch (2 minutes)
Review fundamental exercises (5 minutes)
Review most recent exercises (15 minutes)
Study new exercises (5 minutes)
I know nothing about juggling, but I think that’s probably a decent guess (and I’ll wait for a professional juggler to correct me).
For some Scripts — especially those that relate to skill acquisition, like juggling — adding time limits to each item may make sense. In other cases — such as in the Work Daily Script above — you may simply want to work through each item until you’ve completed it. Use your judgment given the nature of the Script.
What would a Script look like for learning sign language or how to play guitar? Pick one of the two (or any practice-oriented discipline with which you’re more familiar) and create a Script for it. What would you do consistently during each session? Remove as many decisions as possible from your workflow. Mindless process is the name of the game; imagine that these instructions were written for an understudy who lacks the context to make educated assumptions.
Once finished, look at the Script you just created and take a moment to consider what you’re doing here; you’re outsourcing a process from your brain to an external artifact. The steps you go through during each practice session for guitar or sign language may seem obvious, but in providing yourself with ordered instructions, you’re assigning intentionality to the time you spend working on it. It’s becoming structured. It’s becoming something you’re taking seriously. This level of organization, applied to seemingly inconsequential processes like these, creates a shift in mentality that will prepare you for the complexity you’re going to face when addressing much more complex goals.
Hot Lists
A Hot List is a simple, constantly changing, text-based list of prioritized tasks. It isn’t just a to-do list (otherwise it would be called a to-do list). To-do implies items that — once addressed — can be removed, and that’s not necessarily the case with Hot List items. While there may be to-do-style items on a Hot List, it may also contain items to which you need to continue paying ongoing attention.
Since we were introduced to Scripts through an office job example, let’s do the same in order to become familiar with Hot Lists:
Follow up with the legal team about the wording of the new advertising posters. Last contact: Frank Doe (phone), 2/6, 5:39 p.m.
Talk to the recruiter about filling the sales position. Last contact: Lara Gupta (email), 2/7, 3:11 p.m.
Schedule time with the boss to talk about next year’s goals
Get Dave White access to the new project management tool
Schedule a meeting with the design team to discuss the new branding guidelines
A few things to note here:
First, the more important or pressing an item is, the higher it is placed on the list.
Next, you’ll notice that certain items are nice and simple: Get Dave White access to the new project management tool. This is a classic to-do list item: you do it, it’s done, you cross it off, and move on. However, not everything is like that. Some items require ongoing attention. Take a look at Talk to the recruiter about filling the sales position and note the comment at the end: Last contact: Lara Gupta (email), 2/7, 3:11 p.m.; this serves several purposes. First, if Lara claims you never contacted her about this topic, you can correct her, citing the day and time without second-guessing yourself or having to dig through your records. We communicate through multiple channels — in person, via email, over the phone, via text, or through messaging apps — so it’s useful, in many cases, to note the channel through which the contact occurred so you have the option of quickly pursuing more detail should the need arise.
More importantly, recording the last contact gives you an idea about when you should follow up next; this makes it easy to stay on top of things and remain effortlessly responsible. To illustrate this, consider the first item, Follow up with the legal team about the wording of the new advertising posters. Note the last contact comment next to it.
Imagine that you and Frank from the legal team have gone back and forth several times about these posters, and now the ball’s in his court — he has to make some changes and get them to you for review. Technically, at this point, you’re absolved of responsibility; Frank is a grown man who’s accountable for his own promises.
However, a simple note like this gives you the opportunity to showcase a heightened sense of ownership — to go above and beyond the call of duty. As you can see, your last contact with him was on February 6. When you come upon this item in your Hot List on February 7, you can say to yourself, “It’s only been a day, so I won’t bother him yet,” and move on to the next item. The same can be said for February 8, February 9, etc. However, a week later, you may say, “You know, it’s been a week, and I probably should have heard from Frank by now. I’ll follow up to make sure he didn’t lose track of this.” You would then follow up and update the last contact comment. Updating the comment is simple, painless, takes only a moment, and removes a lot of ambiguity; you’ll now know for a fact when your last contact was and can reference it almost immediately.
I can’t tell you how many times over the course of my career and personal life I’ve heard, “Oh, I totally forgot about that—thanks for following up.” Our lives and workplaces are awash in a sea of individuals for whom the volume and complexity of responsibilities have slowly grown over the course of years, and now find themselves drowning in a seemingly endless backlog and with no process with which to manage their workloads. Oversight, mistakes, and slippage have become the tolerable norm. However, amidst this chaos, here you are, cool and collected. This little trick can drastically change the way people perceive you, because it can make you seem more responsible and reliable — and that’s not just perception; that’s reality. That is you being more responsible and reliable. That is you staying on top of things. That is you inspiring trust. It just doesn’t need to all be in your head — you can outsource the work and stress of remembering to follow up and have technology track it for you. You don’t get an award for doing this without tools, and in The Three-Tool Execution Ecosystem, you’ll learn what types of tools are best suited for building and maintaining Hot Lists.
This isn’t a wild, innovative secret, and yet almost everyone fails to take advantage of this type of simple behavior. Those who struggle often assume the successful and organized are simply gifted and keeping all of their responsibilities in their heads; most of the time, that’s simply not the case. I consider myself responsible and reliable — I pride myself on being so — and I can assure you my tasks, responsibilities, and commitments aren’t all stored in my head. Far from it. I promise you that the dozens (sometimes hundreds) of last contacts I may need to reference in the coming weeks are captured digitally, and I’ll be the first to admit that I’d be an absolute disaster if I wasn’t employing these types of behaviors.
You’ve already come to understand how Scripts can reduce the anxiety that often subconsciously accompanies the fear of oversight; the same is true for Hot Lists. If utilized properly, you no longer need to suffer from the uneasy feeling that you’re forgetting something at work or home. The 2 a.m. realization that, “Shit — I just realized I forgot to respond to so-and-so,” or “Shit — I never booked a rental car for the trip,” or “Shit — I just remembered I have to schedule blood work before the Tour de France” can become a thing of the past. This “shit reduction” is an important by-product of becoming organized that people often overlook. These behaviors help battle one of the most pressing and constant sources of anxiety we face in the modern world: the shapeless weight of collected responsibilities.
If you were to suffer a blow to the head and become an amnesiac tonight, but have been following the processes you just learned, you should be able to look at your Scripts and Hot Lists after leaving the hospital and continue on with what you were doing without a single responsibility getting lost. And while amnesia is, of course, unlikely, consider that you can go on vacation for several weeks and come back knowing exactly where you left off relating to everything you were working on. I’ve also shared this process with employees who go on maternity leave or sabbatical. They hand off their Hot List to a peer with a little contextual explanation, and the delegate knows exactly what’s already been done and what should happen next.
In order for this framework to be effective, however, you need to be diligent about truly recording every item that needs tracking and include enough detail to ensure that each is actionable. If you begin to miss things or let things slip, you’re defeating the purpose, you’ll lose faith in the process, and the whole system will go to hell. I’m personally diligent about my Hot Lists and prefer the negligible work of staying organized to the immense work and stress that accompanies inconsistency and failure. Any task or communication that requires action or follow-up — pretty much any worthwhile personal, professional, or creative task — is captured in an appropriate Hot List.
It can be strange to approach aspects of your life — your personal life, especially — with this level of organization, but I assure you that these are processes worth adopting and are non-invasive once you become used to them. And again, this will all translate from the day-to-day minutia you’re learning about here to big goals. Simple behaviors like this, repeated until they become habit, fundamentally change how you operate.
Hierarchical Thought
You learned how Hot Lists can help you organize processes, multi-step tasks, and simple goals, but before you can apply Hot Lists to larger, more complex goals, you need to better understand how you handle information in general.
Even as infants, we manage complexity by categorizing and placing things within hierarchies; it’s a natural human tendency. The universe is comprised of objects, places, times, events, actions, and ideas that — while complex — relate to one another in consistent ways, and being able to use these relationships to predict future events and risks has immense evolutionary value.
This is so obvious and ingrained into the way we operate that it seems silly to think about (though doing so is the foundation of a serious field of study called ontology).
As a quick example of hierarchies, consider the following list of items:
John Wick
Incredibly irritating songs from the 1990s
Rambo
Rednex: “Cotton Eye Joe”
Entertainment
Films
EMF: “Unbelievable”
Music
Action movies
Given only a few moments of sorting, you’d most likely be able to turn the above into the following hierarchy of nested items/lists:
Entertainment
Films
Action movies
John Wick
Rambo
Music
Incredibly irritating songs from the 1990s
Rednex: “Cotton Eye Joe”
EMF: “Unbelievable”
Each item — other than the broadest — represents an instance or example of its immediate parent item (the one above it). Looked at another way, each item — other than the most detailed — describes its immediate child items (those below it). Once you begin to apply this somewhat obvious mental model more intentionally to increasingly larger and more multifaceted things, you’ll begin to manage complexity in a more scalable and sustainable way that will serve you well when the time comes to tackle large-scale or long-term goals.
While an item may have multiple child items beneath it (for example, there are several films listed under the Action Movies item), an item can be associated with only one parent item (for example, Coffee couldn’t be beneath both Things I like and Things that are hot without being duplicated). This is a limitation to two-dimensional mental models like this one, but it’s an important benefit; this limitation will actually force you to keep things simple in a way that will prove useful.
To illustrate how you could apply this model in the real world, let’s look at a fictitious person’s entire personhood — a collection of her actions, how she spends her time, and the things she focuses on.
We’ll call her Jackie. Like you, Jackie is dynamic and multidimensional, so she may choose to mentally organize her life such that the broadest practical distinction she can make separates her personal and professional interests.
Personal
Professional
She could then expand these top-level items to think of her life as a whole: The catering business owner Jackie; the parent of three Jackie; the business student Jackie; the weekend acapella-techno DJ Jackie.
Personal
General to-do list
Parenting
School
DJ/Music
Health and fitness
Professional
Work to-do list
Work meeting notes
To-do list to prepare for upcoming vacation
However, Jackie doesn’t always want to look at her life as a whole. She wants to be able to mentally “zoom in” on a distraction-free view of a single theme or specific undertaking — to compartmentalize. For example, drilling down within the Health and fitness item in the above structure should bring her to deeper items nested within it and push everything else out of view:
Health and fitness
Soccer
Gym
Then, drilling down into the Soccer item should show her even further nested items:
Soccer
Ball control drills to work on
Research stretching routine
We do this naturally, but it’s useful to think about it intentionally because we’ll be using this type of structure to organize more complex and large-scale undertakings.
With this mental model in mind, let’s dig into Hot Lists a bit deeper.
Almost everything you’d ever want to accomplish, no matter how large or small, can fit under some sort of theme or heading. Embracing this approach — understanding where your goals fit within your life, as a whole — is key to managing complexity. Like Jackie, create separate Hot Lists for each such theme/heading in their appropriate place within an overarching hierarchy that loosely reflects your life. Examples of Hot Lists within a Personal list could be Home improvement, Books I want to read, Things I want to learn, or Model airplanes to build.
Professional
General work Hot List
Career growth Hot List
Personal
Home improvement Hot List
Books I want to read Hot List
Things I want to learn Hot List
Model airplanes to build Hot List
What about things that don’t really fit into a project heading quite so cleanly? Something like Scan old childhood photos is unrelated to any project, so where would you place it? For these, a Hot List entitled General personal Hot List could work.
Professional
General work Hot List
Career growth Hot List
Personal
General personal Hot List
Scan old childhood photos
Look into helicopter lessons
Get tattoo of Nicholas Cage as his character in Con Air
Home improvement Hot List
Books I want to read Hot List
Things I want to learn Hot List
Model airplanes to build Hot List
You can then prioritize the items within that specific Hot List in relation to one another.
Handling Slightly Larger Goals
Even though they can seem intimidating, larger goals are really just comprised of a series of smaller tasks that share something in common. That sounds ridiculously, dismissively simple, but really think about it. Both the Manhattan Project and Napoleon’s plan for invading Russia were really just collections of a staggering number of individually actionable tasks that shared a mission and were placed in a logical order.
Above, there’s a Things I want to learn Hot List underneath the Personal theme. Imagine that it contained the following:
Things I want to learn
Real estate investment
How to speak Brazilian Portuguese
How to snorkel
See the first item? Real estate investment. Imagine that you’ve always wanted to learn about real estate investment, but that isn’t exactly a simple, cut-and-dry topic you can master in an afternoon. You can put aside time each week for this goal, but when those sessions of Blocked Time arrive, you may find yourself asking, “What do I actually do?”
First, you need to perform some research. Learn a little bit about the subject matter, refine the goal, and decide on a series of smaller tasks that will culminate in your reaching the larger goal. When it comes time to work on this goal, you should follow a Script, which should eventually send you to your Hot List. An example of your Real estate investment goal in your Things I want to learn Hot List could, therefore, look like:
Real estate investment
Read Real Estate Investing for Dummies (Eric Tyson and Robert S. Griswold)
Read Property: Examples and Explanations (Barlow Burke and Joseph Snoe)
Read about Internal Revenue Code 1031 (online)
By the time you actually begin working your way through this Hot List, you should be confident that it’s well-researched, prioritized, and placed in a logical order; if so, you can focus on the first task (in this case, the first book you want to read). Once you finish the first task, you would know to move on to the second:
Real estate investment
Read Real Estate Investing for Dummies (Eric Tyson and Robert S. Griswold)
Read Property: Examples and Explanations (Barlow Burke and Joseph Snoe)
Read about Internal Revenue Code 1031 (online)
Think of this as though you were serving three roles in a small business dedicated to this goal: you act as the researcher, the project manager who organizes the goal and ensures progress is being made, and the individual performing the tasks.
Here, we've taken a goal — learning about a complex and multifaceted subject matter — and broken it down into several smaller, more manageable tasks (reading three books). We’re going to call the larger task a Major Task, and the smaller tasks that comprise it Minor Tasks.
Let’s explore a slightly more complex example: imagine that you need to plan your wedding, and this is the top item in your General personal Hot List. This is certainly a Major Task, because it isn’t something that can simply be done all at once; it’s comprised of many Minor Tasks. They include:
Plan wedding
Select venue
Select date
Select theme
Invite guests
Select DJ
Get tuxedo (or dress)
Let's imagine that you’ve finished the first three Minor Tasks and need to begin the fourth, Invite guests. This is a Minor Task, because it’s a component of the Plan wedding Major Task, but it doesn’t tell you what actually needs to be done; it’s not itself actionable. In reality, it involves several even smaller Minor Tasks, which can themselves involve even smaller Minor Tasks. As a result, there’s no steadfast rule about what you’d consider a Major or Minor Task except in relation to its respective parent and child tasks. All but the highest- and lowest-level tasks are going to be both Major and Minor, depending on what level of detail you’re focusing on. Let’s expand the final three items under Plan wedding.
Plan wedding
Select venue
Select date
Select theme
Invite guests
Create an ideal, unedited list of prospective guests
Reduce the number of guests to comply with seating limitations
Locate contact information for all members of the final list
Purchase invitations, envelopes, and stamps
Address, stamp, and mail invitations
Select DJ
Research DJs online; make a list of prospects
Call each, interview them, confirm availability, and collect quotes
Decide on a DJ and book the engagement
Get tuxedo or dress
Research tux rental services or dress shops; make a list of prospects
Decide on one
Go into the shop, get fitted, discuss details, and finalize order
If you think about it, this looks like the outline of a book: Major Tasks like Select venue and Select date are like sections, the first sets of Minor Tasks like chapters, and any deeper Minor Tasks like paragraph headings. While a Hot List can refer to even simple collections of tasks, when we’re talking about a single goal broken down a few layers deep in this way, resulting in what amounts to an instruction manual for end-to-end execution, I call this a Goal Scaffold.
In many ways, we already do this in our heads all the time, even though we don’t necessarily use this terminology or subscribe to the same level of detail. Think about it: isn't a grocery list simply an array of Minor Tasks that exist under the umbrella of the Major Task, Go food shopping? Organizing this way, you can break your grocery list down by store section, reducing any need to backtrack through the aisles.
Go food shopping
Dairy
Milk (skim)
Almond Milk (vanilla, unsweetened)
Yogurts (Greek, raspberry)
Fruits and veggies
Eggplant
Sure, it may seem a little over the top to organize your grocery store list this methodically, but it’s perfectly sensible to apply this model to more complex aspects of your life (like big goals).
As an exercise, break the Major Task, Make a peanut butter and jelly sandwich, into at least seven Minor Tasks. Imagine that this is a set of instructions not for you, but rather for someone who has never made any sort of sandwich before. The more detailed you can be, the less likely they’ll be to miss a step or forget something.
Really do this. Take your time and continue when you’re done.
How far did you break it down? How many layers? A preparation/set-up section, during which you check your bread, peanut butter, and jelly inventories, get everything out, and locate a knife and a plate? A sandwich construction section? A clean-up section?
Ask yourself if you could have broken things down further. This exercise may seem silly, but it serves to build a skill you’ll need when it comes time to make sense of and tackle incredibly complex, daunting, multi-month or multi-year goals. Detail is your best friend.
With the PB&J example fresh in your mind, break down the Major Task, Throw a birthday party for a five-year-old, on your own however you see fit. Spend the time to organize it as clearly and logically as possible.
A Quick Note About Priorities
The order in which you need to execute on tasks is sometimes obvious. Consider the example of a screenplay’s life cycle — Brainstorm screenplay, Outline screenplay, Write screenplay, Edit screenplay, and Sell screenplay. By nature, you don’t really have too much flexibility in that order, as each Major Task has a dependency on the Major Task before it. In the same way, you would need to decide on the guest list for a wedding before sending the invitations. However, when it comes to independent tasks (such as Paint the basement floor and Clean the shed), an order may not be quite so obvious. Likewise, it can be difficult to prioritize unrelated tasks within a single goal when no dependencies are involved.
The best thing you can do to simplify prioritization is to build highly detailed hierarchies within your Hot Lists and Goal Scaffolds. If more than a dozen Minor Tasks exist within a single Major Task, consider whether the Minor Tasks share attributes that make them candidates for further grouping.
Imagine that you were an individual who was starting your own knife-sharpening business, and your Hot List looked something like this:
Decide on company name (Lookin’ Sharp? Knife to See Ya?)
Sharpen the knives dropped off by Samantha G.
Buy a new sharpening kit
Take photos of recent work for website
Sharpen the knives dropped off by Garrett T.
Open a credit card in the business’ name
You have six items competing for priority. However, if you refine it a bit, you may end up with:
Company formation tasks
Decide on company name (Lookin’ Sharp? Knife to See Ya?)
Take photos of recent work for website
Open a credit card in the business’ name
Current sharpening work
Sharpen the knives dropped off by Samantha G.
Sharpen the knives dropped off by Garrett T.
General
Buy a new sharpening kit
This way, you now only have three Major Tasks competing for Priority, or which — in cases like this — can be treated like independent Hot Lists and addressed during different sessions of blocked time dedicated to each. Within each of these three Major Tasks, three or fewer Minor Tasks compete for Priority. Organizing with this level of detail helps make prioritization simpler, but you still need to prioritize the most granular, actionable Minor Tasks: how do you decide whether to sharpen Samantha’s or Garrett’s knives first?
At its simplest, Priority is the recognition that some tasks need to be completed before others due to factors like deadlines, financial considerations, and risk. While you certainly shouldn’t overthink Priority, it’s valuable to have a thought process at your disposal because winging it can cause you to miss such factors and, therefore, prioritize poorly.
Bullshit alert: If you perform an online search, you’ll find hundreds of prioritization systems out there. Some of them are incredibly complicated, with more extreme examples suggesting you label tasks by urgency and importance, rank them numerically, sort them by the estimated time necessary for completion, and use this to form a Priority matrix. While I appreciate the intention, such approaches are unnecessarily convoluted, even for prioritizing complex goals. Don’t fall into the trap of organizational fetishism. You’ll spend more time organizing your tasks than you will executing on them, and this can foster a false sense of accomplishment.
Here’s a simple and effective thought process: If something new requires your attention and you need to fit it within a Hot List or Goal Scaffold of related tasks — and there are no dependencies involved — place it at the very top, compare it to the task below it, and:
Ask the question, “Which, if any, has a more pressing deadline?” Maybe Samantha is competing in a knife-throwing competition next Thursday, while Garrett simply wants to refresh all of his high-end kitchenware.
Ask the question, “Which, if any, could cause potential problems if put off?” To use an example you might find on a General personal Hot List, you probably want to fix a broken window before it rains in lieu of shopping for a new bowling ball.
Ask the question, “Which, if any, involves financial considerations? What are they?” If you don’t pay the bathroom floor contractor on time, you may incur a late fee. If you need to decide between that and buying a fancy new coffee maker, the priority becomes obvious.
If it makes sense at the top, leave it. If you had to perform a swap, repeat the same comparison along with the next peer task, over and over until the new one lands in an appropriate place. Once it has, review the entire group of tasks to ensure the overall order still makes sense after introducing the latest item.
Hot List Maintenance
Hot Lists need to be curated occasionally; sometimes tasks age out after being pushed down a few times by more pressing items, so don’t be afraid to dump tasks you’re probably never going to get around to—tasks that provide no value and for which dumping would introduce no risk.
Consider this example: A few years ago, I was suddenly reminded of a lunch pail full of cassette tapes I always listened to as a kid, including some carefully curated mixtapes I made of all of my favorite music. Overcome with nostalgia, I resolved to find them. I was sure the lunch pail was in my basement or attic somewhere (or maybe my aunt’s), and before I forgot, I placed this item in a General personal Hot List. It was low-Priority because, as you can imagine, it was in no way urgent—no deadline, no problems introduced by putting it off, no financial considerations, etc.
After about a year, this item was still hanging out near the bottom of the Hot List, constantly displaced by higher-Priority items. Finally, I just got rid of it. Sure, it wasn’t causing any harm aside from cluttering up my list, but it’s a good idea to ask yourself now and again if a lingering task is really going to provide any value, or if its presence is devaluing the rest of the items on your Hot List. I asked myself, “What would happen if I just deleted this?” In the big picture, the answer was, “absolutely nothing,” so I dumped it and never looked back. If I really want to take a trip down memory lane while blasting a grainy cassette version of Poison's “Cry Tough,” I can certainly reconsider at a later date.
Use your head, and most importantly, respect your Hot Lists by ensuring they’re not polluted by low-class citizens—forgotten stragglers and relics of intentions and whims past. Your Hot Lists are not journals or reminders; they’re a record of your intention to act.
Earlier, we discussed how managing complexity requires you to answer three questions:
How? — How will you organize your goals?
When? — When will you address your goals?
What? — What tools will you use to record/represent your goals and the time you’ve committed to addressing them?
We just addressed How? Next, explore When? by learning about The Franklin Principle: A New Definition of Time Management.
Resources
If you’re a Workflowy user and want a jump-start, you can copy my template, which is pre-populated with a few example hierarchically organized nodes.
Worksheets
Get your hands dirty! Check out a comprehensive (and free) worksheet to help you make the most of this specific Foundations of Execution strategy.
Managing personal and professional complexity is just one of the fundamental concepts I explore in my book, Foundations of Execution.
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You’re ambitious. You’re driven. You’re creative, believe in your vision, and know what you’re capable of. But like most, you often find it difficult to make progress toward the things you value.
When it comes to accomplishing personal, professional, entrepreneurial, and creative goals, the world is bombarding you with bullshit guidance — coddling mantras of positivity and motivation devoid of practical action. Bullshit sounds good. Bullshit feels good. But bullshit will fail you in the long run nearly 100% of the time.
No more bullshit.
Let’s change tactics. Foundations of Execution won’t motivate you; it will give you the tools you need to execute despite the lack of motivation that will inevitably befall you. It won’t train you to abstain from excuses; it will give you the tools to strip all power from the excuses that will inevitably bubble to the forefront of your consciousness. It won’t argue the same tired case for self-discipline and convince you to work against your nature; it will show you how to circumvent your nature when it undermines your interests.
As shockingly simple as it may seem, three behaviors tend to separate those who struggle from those who consistently execute on their goals; and by the time you’ve finished reading this book, you’ll have mastered all three. You’ll come away with repeatable habits that address not just how you tackle complex undertakings, but also how you think, behave, and approach problems in all aspects of your life. It’s an irreverent, philosophy-first, whole-self approach to execution that will change you forever.
Paperback & Kindle
181 Pages