Part 5 (Productivity): Objectives and Plans That Don’t Suck


We’re finally ready to dive into the first part of the productivity system. First, a quick overview of where we’re going: we’ll take an objective (which can either be specific or very general, like “write a 60,000 word novel” or “be able to move with fluidity and no pain”) and reverse-engineer it back into the small but meaningful daily habits that will bring you there. This avoids the problems presented by setting lofty goals, then having no actionable steps to get you there besides “do stuff.” If you look carefully, you’ll see that this system is fractal (the parts are like the whole; for example, a puddle looks like a lake, which looks like an ocean). Your daily habits, then, are the true objective in a very real way (not just as an abstract, process over results type of way).

Therefore, success is simple: doing your daily habits.

And failure is equally simple: not doing your daily habits.

And on that note, let’s start by talking the driving mindset behind this system.


I want to revisit two key principles for a moment: compounding and progressive overload.

Compounding demands long-term consistency. People tend to massively underestimate the power of consistency (both negative and positive). Consistency is like showering: what you did yesterday matters very little. Progress tends to evaporate if you stop and start. That doesn’t mean you need to be perfect, only that you show up often enough to reach the inflection point, which is the exponential growth phase where you suddenly see massive results. The key to consistency is adherence, which demands making our habits easy enough to accomplish each day (or as frequently as necessary).

However, making our habits easy enough to maintain consistency appears to be at direct odds with the principle of progressive overload, which demands pushing ourselves. To maximize our rate of compounding, we need to be working with enough intensity to produce neural adaptations. This requires working at or just beyond the edge of our current ability.

Thus, it would appear we’re at an impasse, where we can either settle for small daily habits that barely move the needle, or rely on super intense bursts of activity that inevitably peter out. The end result being the same: minimal results.

This, fortunately is not the case. For there are two components undergoing neural change: the habit and the skill itself. Enter an approach I call start small, then scale.

  1. PHASE 1: you start by building the neural circuits associated with the habit itself. Thus, doing 1 pushup a day, or writing 20 words a day, while rarely intense enough to build skill or produce results, can be difficult enough (depending on your level of habit in these areas) to create changes in your brain. The objective here is to burn in the habit by matching it to your current level of ability. In areas where you struggle, this is likely much lower than you’ve previously tried. Performing such inconsequential tasks may seem pointless; which it is, if you’re focusing on the results side of the equation. But when viewed from a habit perspective, it’s crucial, because you’re building an entirely different skill: the skill of showing up.
  2. PHASE 2: scale. Once a habit’s neural grooves begin getting etched into your brain, you can focus on building the neural circuits associated with the skill itself, by ramping up the intensity. 1 pushup becomes 5, becomes 5 pushups + 5 chinups, until suddenly you’re working out 3 – 4 days a week with a complete program. Note that each habit seems to have a limit to how far you can scale it.

In short: worry about showing up first, then worry about getting good.


Humans are bad at setting goals.

This is not news. Most goals are wishes coupled with an unrealistic deadline.

What’s shocking is that despite the writing on the wall, people keep going back to the same tired well. This is a recipe for self-loathing and failure, not progress. There are two key problems with traditional goal setting:

  1. Goals are focused solely on outcomes. The real benefit of completing a goal is not the result, but the skills and habits you build along the way. Most people wind up focusing on the finish line at the expense of the day-to-day process. This leads to one of two scenarios: quitting after a few days of misery when immediate change isn’t imminent OR succeeding, but adopting strategies that don’t actually build solid skills or habits.
  2. You have relatively little control over your rate of progress. Depressing to everyone who wants to get ripped in 90 days, no doubt, or believes in the transformative power of the grind (note my sarcasm). We all learn different subjects and acquire skills at different rates. Fundamentally obvious to us as children—one kid will be burning it up in math, the other reading Dickens by the age of 6—but somehow lost amidst the chorus of pseudo-egalitarian, “just try harder and want it more” mantras we encounter as adults. Furthermore, here’s the real kicker: within a given subject, the same individual will learn different units at vastly differing speeds. Take English: someone might kill it at reading, but slowly learn handwriting, then be a savant at essays but take years to internalize basic story structure. Your rate of progression is impossible to predict beforehand, and occurs on an individual basis. As such, goal deadlines—which are almost always overoptimistic to begin with—are simply flights of fanciful fiction.

My approach is different. I refer to goals as objectives, which seems like a pedantic difference in terminology. Effectively, they’re the same thing: something you wish to accomplish. But the underlying process is vastly different, and I feel it’s important to mentally disassociate the two from one another. Traditional goal-setting is hyper-focused on rigid, arbitrary end points that are often near-term. Objectives, by contrast, are not about achievement, but building long-term skills. They are simply a North Star by which to chart progress. Generally speaking, the objective is not the end game; it simply gives you a framework through which to channel your efforts.

Most goal-setting guides recommend you look at your goals, review them constantly.

Those in the corporate world will note that this system is pretty similar to OKRs, which stands for Objectives Key Results. While the framework shares many similarities (breaking down a large project into smaller action items/milestones), the mindset is immensely different.

I don’t give a shit about my objectives once I reverse-engineer them into habits. As previously mentioned, at this point, those habits are effectively my objective. And, what you’ll find going through the daily process is this: the objective probably isn’t what you really want, anyway. It’s just a guidepost to get you pointed in the right direction.

There are three types of objectives:

  1. Core objectives. These tend to be general lifestyle things, but they can be relatively specific.
    1. Ex. Make $100k/yr while working from home
    2. Ex. Be a full-time writer
    3. Ex. Spend more engaged quality time with your kids
    4. Ex. Get a six pack
    5. Ex. Be lean and strong
    6. Ex. Teach dog more tricks
  2. Projects. These are similar to traditional goals and challenges, in that they generally have a clear failure/success criterion, and are specific; they may also have a deadline, though not always (e.g. revise my website by end of Q1). However, the system below completely changes the focus from getting the end result to cultivating habits and skills that will get you that end result. This has two advantages: one, it focuses on building skills that will remain with you after the project’s completion, and two, it vastly increases your chance of actually completing the project at all. A focus on results often leads us to sandbag or take shortcuts. A focus on process (quality habits) ensures that a project is not a one-off thing we brag about on Instagram, but instead something that leads to permanent growth.
    • If you are using projects, keep them sharply defined. Make sure you understand the specific skill you’re trying to train. “Doing hard shit” because some internet blog told you to is pointless.
  3. Tasks. These are smaller than projects, perhaps taking a few hours to a day. The idea here isn’t to turn them into habits, but use the same reverse-engineering process for intransigent (but necessary) tasks that seem to have stuck on your to do list for weeks. By breaking them into smaller parts, you can get started and build inertia. Not used often, but useful for things that just won’t get done.

I like more general objectives, even though that flies in the face of “good” productivity technique. Here’s the reason: obsessing over a specific outcome leaves you in a state of failure until you cross the finish line. This is demotivating, lowering your chances of success.

But the real reason I don’t tend to worry about specific outcomes is this: you probably don’t know what you actually want.

As an example: you may see a one-arm pushup on YouTube, and say that looks cool. It may even be motivating enough to start exercising. But you may find, two months into training, that your priorities shift toward simply getting in shape. Or you want to bench press. Or explore any of the other dozen things you’ve learned since starting from Square 0. A rigid objective gives you something to aim for, true, but it’s at the expense of pivoting toward something better that you find along the way. Yes, this prevents shiny object(ive) syndrome, but it also stifles innovation and evolution. You may hit your target, but be blind to an opportunity that’s 10x more satisfying.

Let’s work our way through two objectives, so you can see exactly how this works. One will be more general and long-term, and one project-based:

  • GENERAL: lean, strong, and pain/fatigue-free
  • PROJECT: publish a 60,000 novel.

From here, we need to break our objective into a plan.


Planning usually devolves into fictitious exercise where we attempt, unsuccessfully, to play Nostradamus and divine the future.

I am not advocating five year plans or carefully bullet-pointed sixty-seven page documents.

No such nonsense plans will be formed here. This takes 10 – 15 minutes, it’s painless, and it will save you weeks or even months of wasted time on the back end.

A plan is not meant to anticipate every contingency or obstacle. Nor is it an attempt to predict the future. Both endeavors are impossible and pointless.

Good planning is about eliminating unforced errors by addressing obvious challenges beforehand. We often fail at changing our behavior because we don’t think the problem through or fail to assess our current resources/abilities. Instead, we start, fall once, and then say well, that didn’t work.

A plan simply breaks your objective into smaller milestones, which are simply smaller objectives. You can track these milestones and check them off as you accomplish them if it’s helpful for keeping you on task, or simply use them as an exercise. I do the latter and toss the plan once I’ve reverse-engineered the habits. I don’t want to be distracted from the day-to-day or demoralized by how far I have to go.

Finally, we break those milestones down into daily habits that are 5 – 25% beyond our current level of ability OR are so small that they’re impossible not to achieve.

By working through this process methodically, we can identify breakdowns in our thinking and also sticking points.

Let’s go through the process, starting with a general objective: becoming lean, strong, and pain-free. We could take two approaches here: we could either make it more concrete and rigid (e.g. be able to do a one-arm chin-up, which you can only do if you’re strong/in good shape) or keep it as-is.

Concrete objectives make reverse-engineering a matter of arithmetic.

More general objectives require more of an idea-based approach.

As outlined above, I prefer general destinations, largely because they unlock a variety of potential strategies. Let’s take our objective of being lean, strong, and pain/fatigue-free. To get here, I can lift weights, I can do calisthenics, I can mix both; this flexibility allows me to tackle plateaus and problems in unique ways as they arise. It’s important to note that while reverse-engineering seems like a linear process, it’s not; it’s an exercise in critical thinking to generate solutions.

From our objective of being lean, strong, and pain/fatigue-free, here’s (my actual) plan:

  • STICKING POINTS: don’t want to go to the gym, eat too many candy bars
  • EXERCISE STRATEGY: resistance-based calisthenics, because I can do them from home; this increases adherence and decreases workout time
  • DIET STRATEGY: balance of foods that I enjoy and healthy foods that I enjoy (or can tolerate), removing junk food from house, eating enough protein so not hungry, tracking via MyFitnessPal
  • ONE-OFF TASKS: ordering bands
  • HABIT: working out six days a week to burn in habit (now five), varying intensity to prevent over-fatigue. 50 – 100g protein shake daily.

It’s important to note that this is not where I started; this is what has evolved over the years. And it’s nowhere near final. I run through this planning process whenever I’m considering making big adjustments to my routine. It’s mostly automatic at this point; I just apply it to a situation by essentially looking at where I want to go and saying how do I get there? This is the true beauty of reverse-engineering: it becomes a mindset and skill where you can quickly break very large things into manageable chunks.

Remember: start small, then scale.The important thing is not where you currently are; it is meet yourself there, then build on it.

For concrete objectives or projects, reverse-engineering looks like this.

First, we start with the objective, which was publish a 60,000 word novel. Then, we look at our historical daily average word count, which might be 700 words a day. If we’ve never written a novel before, then we could either track our words over the course of a week to get an idea of our pace, or simply estimate. If you haven’t done something before and have no historical data, then I’d underestimate your own output and overestimate how long it will take. In other words, be conservative and take things slow. You can always scale up your habits rapidly if you find things are too easy. But it’s far better to build momentum and actually show up than to make it onerous and quit.

Taking our historical daily word count of 700 words/day, we estimate a completion time of around 86 days. Done, right?


Remember our sticking points above? Accounting for these is the most critical part of the planning process. We tend to plan for the unicorn, totally smooth, maximum motivation scenario. Surprise: this never happens. We need to incorporate slack—and lots of it—for various things like:

  • Revision. Because gremlins won’t take care of it.
  • Days off. Your dog is gonna get sick. Friends are going to invite you out for a beer. In short, no matter how bulletproof your habits and routine, something will disrupt them. Some of those will be distractions, but some of them will be worthwhile. Becoming an automaton is no the answer.
  • History. If you haven’t written 85 days in a row at your average pace before, you’re not going to magically make the leap. Your plan needs to be based on historical output, not Narnia fantasies. It can and should push the boundaries of your current output, but if you’ve only written on 70% of days in the past, it’s unrealistic to see that number jump to 95% in three months.
  • Proofreading, covers and formatting. Remember, I said publishing a novel. The freelancers you hire need time to pull these elements together.

As you can see, by ignoring these realities and simply “jumping in” with the writing, we’re setting ourselves up for failure the minute we get started. Instead, if we account for these other aspects of the publishing process in our plan, we’ll get something like this:

  • Draft 1: 60,000 words. Historically, in this example we write 70% of the time. We’ll use that as a baseline, with 750 words a day (up from 700) as our pace to push our skills forward, while still being realistic. Total time for Draft 1: 80 days.
  • Revision: historically we’re a bit faster with this than the writing process, maybe, so we’ll pencil in 2 weeks.
  • Slippage: remember, life will intervene. We want to build a series of wins, rather than losses. We’ve already accounted for the fact that we don’t show up 30% of the time, but we still need more slack. 6 days.
  • Then we have the formatting + copyediting + proofreading. That’s another 3 weeks. The cover can be contracted while writing the first draft (maybe on one of those days where you’re not feeling it at all).
  • Publishing date: 121 days (17 weeks, or about 4 months)

Thus, we end up with this:

  • OBJECTIVE: publish a 60,000 word novel.
  • MILESTONE 1: 25% of draft complete by 24 days.
  • MILESTONE 2: 50% of draft complete by 45 days.
  • MILESTONE 3: Draft 1 complete by 80 days.
  • MILESTONE 4: Revisions complete by 94 days and send to copyeditor.
  • MILESTONE 5: Copyedits received and reviewed by 105 days, and send to proofreader.
  • MILESTONE 6: Proofreading completed by 112 days, and send to formatter.
  • MILESTONE 7: Formatted manuscript received, publish on Day 121.

And all of this is achieved by the simple habit of writing 750 words a day.

We can now hopefully see to things: one, our original projected finish date was off by over a month. Had we succeeded in writing our novel in 86 days, we still would have been deflated upon realizing that all the production (copyediting et al) lay ahead. That can be enough to derail the whole thing, especially if pushed ourselves way beyond our current capacity just to get the thing done. Thus, that manuscript might get done in 86 days, but not actually be published for another six.

That’s not what we want. Accounting for everything may be discouraging at first, but it saves you time and frustration in the long run.

Two, small habits produce massive results. Because this translates to three full-length novels a year, which is sufficient production to become a full-time author (if sustained over 3 – 5 years).

Before anyone screams but it’s possible to write much faster immediately if you push yourself, yes, you are correct.

Let’s talk about that.


I doubt the above system is how you approach projects. Many people use a different strategy I call sprinting. This is very simple; it’s the same idea as cramming for a test or doing a paper the night before. You consolidate all of the work into a massive, all-out flurry of activity, accompanied by a hard deadline.

So, taking out 60,000 word novel, we might write it in 8 days because our release date is approaching. That would massively outstrip our average pace of 700 words a day by 10x.

Success, right?

As with anything, there are positives and negatives.

The good: the project gets finished.

The main problem: this does not form solid habits. That’s fine for one-off tasks that just need to get finished (not everything needs to be a habit). But when you’re attempting to achieve a professional level of output or practice time in a field that demands consistency over time, these random spikes of activity, when repeated too often, raise the intensity too high. Far exceeding your current production capacity on a consistent basis often leads to burnout.

So yes, you can certainly complete a novel by sprinting your way to the finish.

Once or twice. Maybe even ten times.

But each time tends to get more difficult. More of a slog.

And eventually you hit a breaking point where production ceases all at once.

We do not want this. Working ourselves to exhaustion in pursuit of the mythical “grind” is beneficial for neither skill-building nor results. Ignore all idiots who claim otherwise.

That being said, sprinting can be a fantastic way to break through production plateaus or get things finished when you’re plagued by fear, analysis paralysis, or perfectionism. The hard deadline and flurry of activity drown out thought and use different neural pathways. Thus, in certain specific cases, a mad dash to the finish may be exactly what you need. But as someone who tends toward boom-bust cycles of activity, a word of warning born of experience: it’s very difficult to build a long-term writing career solely in this fashion. Further, some areas, such as health and fitness, do not lend themselves to sprinting at all; crash dieting, for example, is devastating for one’s long-term health and simply isn’t a viable approach. And you can’t build muscle with 10 days of super hard workouts, then nothing.

Subsequently, I’d recommend employing this strategy as a break glass in case of emergency tool in appropriate fields only. You may still sprint more than other people (this is probably somewhat innate; I’ve done this since I was pretty young), but cultivating good habits reduces the intensity enough to avoid burnout. And we want to avoid that at all costs. Because you want to know the true secret of productivity? Longevity. Working like a fiend for five days gets all the blog clicks and Instagram clicks, but working consistently over five years gets you the actual rewards.


In Part 6, we’ll talk about how you can deliberately design habits.


  1. Write down one general objective, then sit a timer for five minutes and reverse-engineer a plan and daily habit.
  2. Write down one project, then set a time for five minutes and reverse-engineer a plan and daily habit.
  3. Write down one task that has been sitting on your to do list for multiple weeks. Reverse engineer it into its component parts, then start with the smallest possible action.
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