The Write to Roam

The Personal Blog of Ethan Brooks

The Art of Setting Effective Deadlines

Everyone has a story about a time when a deadline loomed, and they performed near-miracles to get a project finished. Similarly, we’ve all got a laundry list of things that would be nice to do someday — paint the trim, start that blog, try that Indian restaurant down the street — things which wouldn’t take much time at all, but remain undone because they’ve never been “a priority”.

Deadlines help to create priority.

For people who buy into the D.A.M.N. Goal Framework, the question is not whether to set a deadline, but what deadline to set. The purpose of this article is to offer a few concepts which I’ve found helpful in setting high performance deadlines for ambitious goals or projects.

First Things First — Two Deadlines

When they think of deadlines, most people think of just one kind: the end deadline, the date by which something is due.

But there’s a second deadline one must take into account as well: the starting deadline or the date by which you will begin taking action.

Could you imagine a race without the starting pistol, or a year without new years eve? Clearly defined start times help us understand that something important is about to begin.

They also help us clearly track progress. It’s easier to measure the success of a given course of action when you’re looking back at a clearly defined beginning and ending.

So when you’re defining a goal, be sure to include start and stop dates.

But how do you decide on either? For that, we turn to a humorist who accidentally did something useful.

Parkinson’s Law

In the nineteenth century a humorist named Cyrill Northcote Parkinson penned the words “Work expands so as to fill the time allotted for it.”

He was writing about his experience with bureaucrats, but the idea turned out to be so universally true that it has since been coined Parkinson’s Law and applied to a wide range of industries.

The idea behind Parkinson’s Law is that projects tend to take up however much time you give them. As Tim Ferriss wrote in The 4-Hour Workweek, projects also grow in perceived importance and complexity along with the time given for their completion.

In other words, the longer you have to do something, the bigger and more complex the project seems and the longer you will likely take to finish it.

Think back to high school where you were given weeks or months to research and write a ten-page paper. If you were anything like me, the project went something like this:

What’s interesting about this cartoon is that the only time actually needed to do the project was the green bit at the end. So why didn’t we just do that in the beginning, get the task off our plate, and spend the rest of our time watching cat videos on Youtube?

Parkinson’s Law in action.

What would have happened if our teachers assigned the same project over the weekend? According to Parkinson’s Law, there may have been more grumbling, but there’s no reason to believe it wouldn’t have gotten done.

I wrote about this extensively in my article on how to fit three semesters worth of classes into four months.

This idea has proven to be so wide spread, so universal, that it’s even coined a number of corollaries including the Horstman’s corollary that “work contracts to fit the time we give it” and the Stock-Sanford corollary, “if you wait until the last minute, it only take a minute to do”.

Parkinson’s Law Forces Priority

Simply put, short deadlines force you to focus only on what’s important. But how short should we go?

It’d be impossible to give a one-size-fits-all answer here, but the practice I recommend is as follows:

When you’ve scoped out the project roughly, ask yourself where you would instinctively place the deadline.

Your first answer will almost always be overly conservative. So, as a thought exercise, proceed to ask yourself, Is there any law of the universe keeping us from getting it done in half the time?

If the answer is no, set that as the new deadline and ask the question again. Keep going until you come up against a real barrier.

In his article on ruthless prioritization, Brandon Chu writes that “there is always always a way to accomplish your goal faster than you currently plan to. Always. You just have to find it.

If you allow your deadline to help determine the action you will take rather than the other way around you will find that you’re often able to accomplish large things much faster than most people think is possible.

Sprinter or Marathoner?

Early in her podcast series, Gretchin Rubin talks about different working personality types known as Sprinters and Marathoners.

Sprinters are people who work best under tight deadlines. They get a rush of adrenaline and feel most alive when a project is compressed into a short period of time.

Marathoners on the other hand feel very uncomfortable with a looming deadline of any kind. Slow and steady is their preference, and if given a long-term project they will tend to do a bit each day, often finishing well ahead of schedule.

What’s interesting is that both groups need a deadline of some sort in order to do their best work. But the type of deadline set for each will be different, and it’s important to take this into account when planning.

Caveat Emptor on Parkinson’s Law

Tight deadlines alone are not enough to guarantee success. As with all things, there is some finesse involved, especially if you’re working with multiple people.

First, while a deadline can be ambitious, it also has to be believable. It doesn’t have to be comfortable, but people need to think there’s some way to get it done otherwise it can have the opposite effect and rather than spurring meaningful action, people will simply throw their hands up and ride out the project calendar knowing they are doomed from the start.

Second, whether it’s you alone or a team, everyone involved needs to understand why the deadline is what it is.

Is it because there are other things hinging on this goal, and failure to ship by a certain date will cause massive, irreparable harm? Is it because you truly know this project is not that much work, and you want to avoid psyching people out by allowing too much time for its completion? Something else completely?

It’s important to be clear about this, otherwise a deadline can begin to seem arbitrary, uninformed, or worse… selfish.

Finally, I’ll say that there seems to be a maximum capacity on short deadline work. Interest and energy are cyclical, and while you can accomplish quite a bit in a short period of time, you should remember to balance intense work periods with plenty of rest.

Operating on tight deadlines can help to ward off burnout because it avoids the long drawn-out spells of meaningless meetings, email-checking, and web surfing which are tiring but not productive. But jumping from one red alert situation to the next too many times without time off for a break is a recipe for ultimate overwhelm.

Action Questions

Use these to help define meaningful deadlines for your project:

* When should we start? Is there a date that would be best strategically?
* When should we end? Is there any law of physics keeping us from doing it in half the time?
* Why are these deadlines important?

How to Set a D.A.M.N. Goal

Back when I was designing and building websites for a living, I used to start each meeting with prospective clients by asking what their goal was.

It doesn’t matter if you’re a designer, a developer, a photographer, or any other kind of —er, as a freelancer you’re paid to help other people achieve their goals and your long term success hinges on your ability to make your clients feel like they got more than they paid for.

To do that, it’s crucial you know what they’re actually after. Hence, the question.

Answers varied from project to project, but generally sounded something like “We want to build a larger online business” or “We just want a better looking website”.

I came to call these V.A.N. Goals because they tend to follow the same verb-adjective-noun structure


If you set goals like these, you end up living in a van down by the river. They don’t work.

They’re too vague, too subjective, and don’t offer a clear path forward.

If the business grows, but profit margins disappear, will you feel you’ve gotten your money’s worth? Who decides what “better looking” means anyways? Me? You? Your customers?

I needed something to help my clients think through their projects more rigorously, something that would lay the foundation for a solid plan, and strong likelihood of success, ideally something that would allow me to swear at them while appearing to be helpful.

And so, with this in mind, the D.A.M.N. Goal Framework was born, and I turned it into a free online course. While the course is complete with videos, worksheets, and external resources, this is the first time I’ve written about how to set a damn goal from start to finish.

I’ll be the first to say that I’m no success guru, and while it’s an extremely effective way to boost the likelihood of success for any undertaking, the framework is no silver bullet.

More than anything it’s a method for asking important questions and clarifying your thinking and it can be used for everything from business to education to fitness goals. The idea is that for any given project, your odds of success dramatically improve if you have:

  1. Deadlines
  2. Action Steps
  3. Measurable Benchmarks
  4. Negative Consequences for Failing to Follow Through

For the remainder of this piece, I’ll show how these ideas can be applied to turn a simple V.A.N. Goal into an effective D.A.M.N. Goal. Let’s start with this:

I want to become a good guitarist


Why is it that we find time to do our taxes every year, but not to pursue our dreams? If you ask me, deadlines play a role. You know when your taxes are due. Surely, the process of filing them is less enjoyable than following your heart’s desire. But you’ve got all the time in the world to do that, the taxes have to be done now.

Simply put, deadlines drive action. A well-structured goal should have two deadlines – starting and ending.

The first is the starting deadline; the day upon which you will begin work. It carries with it two primary benefits:

  1. It gives you time to plan and do research before taking action
  2. It protects against analysis paralysis

Most people never set a starting deadline. Instead, they either begin work immediately or never begin at all. For projects that really matter, both are a mistake.

To begin right away leaves no time to do research or figure out the most effective path forward. Instead, you rely on your current knowledge, and rather than learning from those who’ve gone before, you’re forced to throw a lot at the wall and see what sticks. Not only is it time-intensive and resource-intensive, but the potential for failure skyrockets along with the likelihood that you will get fed up and quit.

Better to take some time to research the paths available, look for people who have achieved what you want to achieve, identify the resources and tools which will be most helpful and find the potential pit-falls others have experienced.

Of course, you can’t spend too much time researching. That can lead to analysis paralysis; inaction caused by too much thinking.

Give yourself some space, but set a date upon which you will take the first step.

The second deadline is one people are more familiar with, the ending deadline or the day upon which you want work to be finished. Not only does this spur action, but it also gives you a concrete day upon which you can check in and assess whether what you’re doing is working.

Learning to set these deadlines effectively is an art, and something I’ll discuss further in other articles. But for now, think about your goal and ask yourself whether you know what your exact deadlines are?

When it comes to our sample goal, you will see that the addition of a starting and ending deadline quickly make it more tangible:

Between March 1st, 2018 and March 1st, 2019, I want to become a good guitarist.

It’s still not great though. We know more about when we want to do our work, but still have no idea what we’re going to do. That is where the next piece of the equation comes into play.


Rarely is the work of a project actually the most difficult part. It’s sitting down to do the work that kills us. Procrastination is the enemy of progress. In The War of Art, author Steven Pressfield gave this enemy a face and a new name, calling it Resistance.

Most of us have two lives. The life we live, and the unlived life within us. Between the two stands Resistance. -Steven Pressfield

After a few so many failures of my own, I can say for certain that Resistance is real and in those cases where it has kept me from pursuing my calling — whatever the calling might be — it’s often because I don’t actually know what my next steps are.

So these days when I’m thinking about a goal or project I’m careful to focus not only on the desired outcome, but also on the specific action I’ll take in order to get there. This specific action must be written into the goal so that I am reminded of it each day.

It’s important to be able to identify actions which have a high probability of driving success. You shouldn’t hold yourself accountable for meaningless work. Learning to recognize high-leverage opportunities is a skill all it’s own, and something I’ll write about in more detail later. But for now, you can check your goal by asking either or both of the following questions:

  1. Am I focused on action, rather than outcomes?
  2. Do I actually control this? If not, what can I control?

Let’s take a look at how this applies to our sample goal:

Between March 1st, 2018 and March 1st, 2019, I want to become a good guitarist.

The questions above reveal a couple of interesting issues.

Am I focused on action rather than outcomes?

Clearly, no. There’s no specific action mentioned above, and the goal is built almost entirely around the subjective outcome of “becoming a good guitarist”.

Do I control this? If not, what can I control?

If you ask a dozen people who they think the best guitarist in the world is, you’ll probably get a dozen different answers. That’s a problem when it comes to our goal. I can’t control whether other people think I’m a good guitarist. It’s completely subjective. Therefor, there’s no way to say when we’ve been successful. No bueno.

We can address both of these issues by choosing to focus on an action that we can control, and which we feel has a strong probability of leading to the outcome we want. In this case, I think it’s practice.

Between March 1st, 2018 and March 1st, 2019, I will practice guitar.

That gives us a starting and ending deadline, and an action we can control. The next step is to set ourselves up for success by getting even more specific.


What gets measured gets managed, or so the old saying by Peter Drucker goes. There are two ways that measuring helps us to manage our goals.

  1. Specificity – It helps us to be more clear about the action we’ll take
  2. Progress – It helps us to see how far we’ve come since starting

Recall that the great hurdle for most goals is sitting down to do the work. The more specific we can make our action step, the less thought required when we’re deciding whether to sit down. By adding measurable components we remove obscurity and make it easier to take action.

In the case of our sample goal:

Between March 1st, 2018 and March 1st, 2019, I will practice guitar.

We can make this more measurable by adding some detail to our practice schedule. For instance, how long will we practice and how often? The result may look something like this:

Between March 1st, 2018 and March 1st, 2019, I will practice guitar for one hour each day.

We could get even more specific by listing the individual components of our practice schedule, or committing to a certain number of reps. Use your best judgement here, but know that the more concrete your action plan is, the easier it will be to sit down and do it when the time comes, and consistent action is key to success with any goal.

There’s something else we can do to help ensure we stick with our work… Track progress.

Tracking progress is important for two major reasons. First, it allows us to be held accountable for our work. And second, it allows us to see how far we’ve come, which in turn helps keep morale up when things get difficult.

So, it’s important to take a second look at this goal and make sure that some aspect of it will allow us to track progress. Examining our goal above:

Between March 1st, 2018 and March 1st, 2019, I will practice guitar for one hour each day.

We can track the number of times we practice, but unless we spend that time with someone else, we can’t actually prove we did the work. There’s no accountability baked in. And while counting practice sessions might help us keep track of how much work we’ve done, it won’t allow us to concretely see how our skills have progressed.

There’s a simple fix though. We need a record of some kind.

We could use a simple computer application or smartphone to record a song or practice session once a week. The number of recorded sessions becomes our accountability criteria, and by going back to listen to the old ones, we can clearly hear how we’ve progressed.

The sound quality of the recording is not what matters so we don’t need fancy equipment. What matters is that we have a way of proving our output and that it allows us to go back and see how far we’ve come.

With this in mind, the new goal might looks something like:

Between March 1st, 2018 and March 1st, 2019, I will practice guitar for one hour each day, recording one session a week.

Speaking of progress, let’s take a second to see just how far we’ve come with our goal. We started with the very vague V.A.N. goal of:

I want to become a good guitarist

By adding clear starting and ending deadlines, and measurable action we’ve come up with:

Between March 1st, 2018 and March 1st, 2019, I will practice guitar for one hour each day, recording one session a week.

This is much better. But what’s to ensure we actually follow through? That is where the next and final piece of the equation comes into play.

Negative Consequences

This is by far the most difficult part of the process, and it’s also the one which drives the biggest difference between those who are successful and those who never follow through.

The idea is simple: You set up negative consequences for failing to follow through. Rig the game so that if you reach your deadline and have not certifiably completed your measurable action steps, you stand to lose something you don’t want to lose.

The power of this is based in a principle called Loss Aversion. Simply put, people are very very motivated to avoid losing things. The perceived pain of a loss is significantly greater than the perceived pleasure of a gain. So people will often work harder to avoid losing something than they will to gain something of equal or even greater value.

By itself, this can make us risk averse and keep us small, but we can use it to our advantage.

By rigging the game so that failing to follow through guarantees we’ll lose something valuable, we give ourselves the nudge we need to stick to our guns even when it’s difficult or inconvenient.

Now, there are a lot of ways to do this, but each one basically involves choosing collateral and finding an accountability buddy who will take it from you if you can’t provide proof that you followed through on your action steps.

There are only three rules in order for this to work:

  1. You must be sure that your accountability buddy will not cut you any slack
  2. You must really really not want to lose the collateral.
  3. You must provide the collateral up front

Beware of your brain on this one. It is programmed to help you avoid losing things you don’t want to lose, so your first instinct will typically be to either choose an accountability buddy that you know will go easy on you, or else choose collateral that you don’t really care about losing.

Similarly, you provide the collateral up front so that your accountability buddy has control of it while you’re working. That way you can’t worm your way out of the deal.

The end result is that something you care about is in the posession of another person and you are going to lose it unless you are able to prove you followed through on your plan.

As a rule, you should not choose collateral that you can’t afford to lose. In other words, don’t bet the deed to your house on your new diet plan.

But do choose something that is large enough or special enough to sting. If you feel an instinctive cringe when you think about losing a thing, you know you’re on the right track.

Once you’ve decided on your collateral and your accountability buddy, you structure the deal something like this:

If by [End Deadline] I can’t deliver [Measurable Proof of Action] then [Name of Accountability Buddy] will [Sell/Donate/Burn/Etc] [Insert Collateral Here]

In the case of our goal, perhaps we have a record collection with a vintage vinyl that we love from one our favorite guitarists. Our Negative Consequences might look like this:

If by March 1st 2019 I can’t deliver 50 recorded practice sessions then Danny Dayruiner will donate my vinyl to the local thrift shop.

Note that this says nothing about “being a good guitarist”. I’m not being held accountable for any level of skill, just for taking the action that I committed to.

Note too that the Negative Consequence is not harsh enough to ruin me. We could probably buy the record back from the thrift shop if we wanted to, but it would be inconvenient, possibly expensive, and there’s a chance that someone else beats us to it. The goal is not to do harm, just to inject enough pain that the thought of practicing seems small by comparison.

In the past I have used everything from money posted as collateral, to small inconveniences, like having my accountability buddy promise to shred my debit card if I couldn’t wrap a project up in 24 hours. In that case, you don’t lose actual money. But replacing the card is enough of an inconvenience to make you knuckle down and focus for a day.

Notice, we chose 50 recorded sessions because our goal is to record one session per week so delivering 50 would be measurable proof of our work. This allows a bit of flex too so that if we happen to miss one recording session we don’t get overwhelmed and quit. You could adjust as you see fit.

Might it be possible to cheat and sit down to record fifty sessions the week before our ending deadline? Sure. But even if we let it slide to the last minute and then recorded fifty hours of practice sessions last-minute, we would probably see a significant increase in our baseline ability, which is the ultimate goal.

There are other subtleties to choosing effective Negative Consequences, and I will cover them at length in a future article. But for now, let’s add this to our goal and see where we stand.

Remember, we started out with:

I want to become a good guitarist

It was vague and had little chance of success. With a few simple changes, and the addition of deadlines, measurable action steps, and negative consequences for failing to follow through, we ended up with:

Between March 1st, 2018 and March 1st, 2019, I will practice guitar for one hour each day, recording one session a week. If by March 1st 2019 I can’t deliver 50 recorded practice sessions then Danny Dayruiner will donate my vinyl to the local thrift shop.

It may not guarantee success, but in my experience starting with something like this offers a damn good shot.

Like SMART Goals, But Smarter: How DAMN Goals Became a Thing

“So… What makes D.A.M.N. goals better than S.M.A.R.T. goals?”

This is usually the second question people ask when they hear about my damn goal course, the first question usually being a chuckle followed by “What’s that?”

I have an answer, but first, a caveat: The best system for goal-setting is the one you use consistently. If you’re already using smart goals and you’re happy with your results, damn goals might not be better.

I’m familiar with smart goals and used them myself in the past. I even taught them to clients back in the early days. They can work well.

That said, there are a number of things which I found frustrating about the “smart” framework, and which ultimately led to the creation of the damn goal methodology.

Too Many Cooks

To begin with, there is no common definition for what each letter of S.M.A.R.T. actually stands for. When the framework was first introduced in a Management Review article in 1981, the letters of smart stood for goals that were specific, measurable, assignable, realistic, and time-based.

In the years since, many have championed the idea, making it their own and adjusting it to suit their view of what makes a quality goal. As a result, there are now dozens of variations of the smart framework, each with very different meanings.

For example, I have seen the S stand for both specific, and simple, the M for measurable, and meaningful, and I would be willing to bet that 99% of the people reading this have never heard of the original “assignable” meaning behind smart’s A.

This can make collaboration a nightmare. If my idea of a good goal is one that’s specific, motivating, audacious, relevant, and time-based and yours is simple, maintainable, achievable, realistic, and trackable, we’re not likely to be prioritizing the same things.

Needless Redundancies

The most common current interpretation of smart goals is that they should be specific, measurable, achievable, realistic, and time-based.

Engineers are probably rolling their eyes with me right now.

Excuse me, but what is the difference between something that is specific and something that is measurable? If we can measure it, is that specific enough? Do we really need both reminders?

And what about achievable, and realistic? If something is achievable, doesn’t that also mean it’s literally realistic?

As a developer, I was trained to relentlessly trim the fat in systems.

Like George Carlin going to work on the ten commandments, I saw lots of waste in the smart framework and it irked me. Surely we could do better.

Dangerous Ideas

Aside from the redundancy, I found the terms achievable and realistic particularly problematic, especially when working with people who were new to goal setting.

Simply put, people tend to confuse the word realistic with small. In case after case, I watched as clients and teams talked their goals down in order to make them feel more realistic. On the surface, this makes sense. Smaller goals feel like a safe bet because they seem easy to achieve.

The problem with small goals is that they are also:

  1. Less inspiring – and therefore less likely to garner outside support, or spur massive, meaningful action.
  2. More common – and therefor open to more competition.

It seems counter-intuitive, but bigger goals are often actually easier to get off the ground just because they capture people’s imaginations and no one else is attempting them.

If people could continue to think big while remaining realistic, it wouldn’t be an issue. But that doesn’t seem to be in our nature.

Speaking of Human Nature

People who ascribe to Tim Ferriss’ Slow Carb Diet™ regularly achieve outstanding results, many of which were previously thought impossible within the fitness industry.


One of the primary reasons is that the diet has extremely high adherence rates. People stick to it. As I mentioned in the beginning, the most important factor in achieving any goal is sticking to a system that works. The problem with many other diets is not that they’re wrong. More often, they’re just very difficult to stick to.

The Slow Carb Diet works with human nature —  focusing on small changes, avoiding complex tracking, and allowing for regular binge-eating — rather than relying on developing multiple new habits and exercising will-power.

While it’s admirable to want to be disciplined, strong-willed, logical creatures, there’s an overwhelming abundance of evidence that says we’re just not. We can either struggle against this, or we can accept it and use it to our advantage.

The damn goal framework opts for the latter.

And Finally…

It’s just fun to talk about. The damn goal framework is the only system I know of which allows you to swear at your boss, at your client, or at your children while appearing to share actual helpful information.

“What’s your damn goal?” “That’s not a damn goal!” “Stick to the damn plan!”

Joking aside, it’s memorable. If you lead a team, one of the most important habits you can develop in your direct reports is that of regularly talking about goals.

One way to do that is to inject a dose of humor, and that’s exactly what the damn framework does.

So, is it better than smart goals? I certainly think so… But ultimately, I leave that judgement to the damn students, and to your own damn experience.

My Favorite Notebook

What movie had the biggest impact on your life?

If you’d asked me yesterday I probably would have told you something like Poltergeist. I watched that movie with my dad when I was seven and hardly slept again until I could legally drink. The last four places I’ve lived were completely without bedroom closets, and I’d be lying if I said there was no connection.

Or perhaps I’d have pointed to Man of the House with Chevy Chase and Jonathan Taylor Thomas. After watching that I spent the next ten years trying to pull off Jonathan Taylor Thomas’s cool-guy attitude and his haircut.

But the truth — which I didn’t realize until I sat down to write this — is that the movie which has had the most powerful impact on my life is one that I hardly remember anymore.

I was ten the first time I saw Indiana Jones and the Last Crusade, and now, nearly two decades later I recall just two things: The fight scene where Indie throws a man out of a zeppelin and tells onlookers it was because the guy had “No ticket”, and the grail diary. Dr. Henry Jones senior’s Grail Diary was a battered leather-bound book in which he’d recorded every clue gleaned from his lifelong quest to find the Holy Grail. Its pages were filled with notes and sketches from a hundred different adventures in places all around the world.

What is it about the leather-bound notebook that’s so powerfully linked to the life of the traveler? Even now when I see one on the shelf at a book store I’m transported to places yet unseen. Gypsied away to the heat and chatter of a bustling Turkish market square, or to an Amazonian lodge when the rains are about to come and electricity is in the air. Not unlike real books, notebooks have a special power all their own. From the moment I saw that book I wanted one of my own. Perhaps more importantly, I wanted to lead the kind of life that could fill those pages.

I must have talked about it endlessly because on the morning of my eleventh birthday I unwrapped a beautiful leather-bound sketchbook.

“Dear Ethan,” a note on the very first page read, “Thought you could use a place to record all your adventures! Love, Mom & Dad”.

That simple gift changed the direction of my life forever.

It’s not easy to lead a life of adventure. Going places means you have to leave other places behind, and when those other places are filled with the people you already know and love it’s hard to make the move. It’s much easier on the heart (and the wallet) to simply dream of faraway places.

But when someone hands you an empty notebook, they are in a way telling you “go”. They’re telling you to get out of your head and into the world. They’re telling you it’s okay to leave them, so long as you bring back a story from out there. And once you have an empty notebook, you can’t very well leave it empty. An empty notebook is a constant reminder of all that you haven’t done.

Your life changes when you have an adventure journal to fill, even if you’re just a kid — especially if you’re just a kid. At least a couple of times a day you find yourself pausing to think about whatever it is you’re doing, wondering does this count as an adventure? Can this go in the book? I began looking for adventure everywhere, if only to have something to write down.

And of course the secret, that only eleven-year-olds with empty adventure notebooks and even emptier bank accounts learn, is that adventure can be found anywhere. Even the most remote jungles are home to someone. Far-off mountains lie in someone else’s backyard, and somewhere there’s a little kid who’s bored of seeing that same Turkish market square every day. They dream of a far-away place that looks just like your backyard. And so it’s not the setting, but the mindset that makes for an adventure.

Those early experiences, scrounging for excitement in the bushes around my house, shaped me as a traveler. But I don’t think it’s necessary to start young. Just that you should have an empty notebook.

And if you’re in the market for a notebook of your own, you could hardly do better in my opinion than the Canson 180 artbook. I won’t pretend to be an expert on paper. I don’t know what acid-free really means. But there’s one thing I do understand and that’s writing in awkward places. In the years since my eleventh birthday I’ve been lucky enough to scrawl notes while holed up on the floor of a frozen mountain shelter while snow piled up outside, and in the back of a truck in the jungle. I’ve made do with the desks in a hundred hotels and motels, and with the balcony of the Queen Mary II as she made her way from New York to England. I’ve written by firelight, and head-light, in the rain, and after not seeing rain for a month.

Write in enough places and you begin to appreciate the little things. The Canson 180 is the first notebook I’ve ever found that will not only open but lie perfectly flat on every single page. There’s no awkward grappling with the binding or paper in order to keep it open. Simply lay it down, and put pen to paper. They accomplish this using a unique technology called a “coptic” binding and it’s truly remarkable. I’ve been carrying one every day since September of 2015, when I left for a month on the Appalachian Trail. That notebook lasted more than six months before I finally filled it, and went with me everywhere from the southern states to posh English country estates, rural France, Mexico, and many places in between.

After so long on the road, as you can imagine, the notebook had seen better days. The people at canson were nice enough to send me a brand new one so that I could photograph it. But lest you think this is just a product plug, you should know this — I was in France when my first notebook ran out. The replacement they sent me was six-thousand miles away in my home in the US. Rather than waiting a week to pick it up when I was home, I walked to the nearest art shop and spent $25 to replace it then and there. All told I’ve spent well over a hundred dollars on these notebooks, and plan to continue spending that money for as long as they continue to work, which based on my experience so far seems to be forever.

Ethical Selfishness and Systems Over Goals

The Write to Roam -- How to Fail at Almost Everything and Still Win BigOne of the reasons I love biographies is that they help you to see that successful people are riddled with problems too. Did you know that Scott Adams, best-selling author and the artist behind the Dilbert cartoon, once struggled with spasmodic dysphonia, and was mysteriously unable to talk to any other human being for more than three years?

It is just one of the struggles he talks about in his sort-of-biography How to Fail at Almost Everything and Still Win Big. The book was recommended to me by a mentor, and from it I got two interesting lessons.

The first is regarding generosity, and the need to take care of yourself. As a business owner, I enjoy talking about business, and helping other people to pursue their ideas. But every once in a while, I’ll get so excited that I commit to something I shouldn’t, and then get crushed under the workload. Whether it’s offering free help, or just taking on a long term project that I don’t have time for, I have to consciously restrain myself from saying yes to opportunities on a daily basis. Sometimes I feel bad about this. I’ve got specialized knowledge in a few areas. Why shouldn’t I share it?

Adams, who is a straight shooter almost to a fault, says that when it comes to generosity there are only three types of people in the world:

  1. Selfish
  2. Stupid
  3. Burden to Others

In order to help others, he says, you first need to take care of yourself. You need to take care of your health. You need to make a good living. You need to pursue “enlightened selfishness”.

“If you neglect your health, or your career you slip into the second category — stupid — which is a short slide from becoming a burden on society.”

People who look out for themselves have the resources to help others. Whereas someone who’s overcommitted, under-charging, or otherwise too “generous”, winds up with neither time nor money nor enthusiasm to contribute. They become a ball of stress — a broke ball of stress… I’ve been there.

The second, and much more profound lesson is perhaps best introduced with a question:

If you woke up tomorrow with the thing you currently dream of having — money, abs, love, etc — based on the way you lived today, how long would it last?

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