Career warfare rule 5

Kenny Rogers was right

If you’re gonna play the game boy

You gotta learn to play it right

Know when to hold em

Know when to fold em.

Know when to walk away

Know when to run

Of course, the song lyrics held truths and wisdom that went beyond the poker table. In the course of your career, there will be situations you will not be able to further your brand. Rather than choosing to die on this hill, you must know when to cut your losses and move on.

Nepotism means “not you”

Stay and learn what you can from family run companies, but leave when you are ready to become a leader in your own right. Understand that you are never going to be one truly in charge. At best you will be keeping the seat warm for the children. Do not think that because you are treated with love and as “one of the family” that you actually are family. The business will pass on to the children, regardless of their lack of qualifications or your abundance thereof.

Even if the children protest loudly that they have no interest in running the family business, chances they will still end up coming back once they realize how much easier it is in life to be the heir apparent. Even marrying in the family is not enough. There will always be a distinction by blood.

Worse, only 30% of family owned businesses survive into the second generation. This means that as the number of heirs increases, so does the likelihood of feuds and factions and infighting. You will eventually be forced to choose sides, and your career will be torpedoed if you end up backing the wrong horse.

If a gang controls the turf, set up shop elsewhere

D’Allesandro relates a story here about how he was working at a company when one of the senior managers took him aside and explained to him that the place was run by a Scandinavian tong. Unless he was a Midwesterner of Scandinavian origin, he would never be accepted and his career advancement halted. This book was published in 2004, and it mentioned that even then with all the laws against discrimination, that there still existed companies where you would be excluded from advancement on the basis of who you are.

The advice here is that you should recognize these situations, and not waste too many years in a situation where the existing people in power will be resistant to you. Besides race and gender, where you were born, what school you went to, whether or not you belong to old money, and other factors come into play here. It is an uphill battle to stay in such situations and try to be the pioneer that breaks through existing prejudice. If you do stay, don’t be in denial and recognize it as the gamble it is.

Don’t let the hazing go on too long

This is an issue with young people working at law firms, consulting firms, accounting firms, or architecture firms. The old make the young work difficult and brutal hours by dangling the hope of making partner as a carrot. The associates, eager to prove themselves, are forced to endure demeaning work and demeaning treatment from partners.

“Working for a partnership is longest hazing on record”.

This dynamic leads to young associates chasing older partners who are often not as smart. The old timer’s attitude is that since they put up with the hazing, the newcomers have to put up with it too.

Of course, there is a benefit of having worked at a prestigious firm and having it on your resume. Because these firms are prestigious, they also attract prestigious clients, and you will also learn a great deal there.

The problem is the young people are so focused on making partner that they become unrealistic in their expectations. Only 2-3 % of new hires ever make it to become partner. Existing partners don’t want you to make it, because that would mean giving up equity. The only way it would make sense for them is if you bring in a lot of new business. However, many people are not realistic about their own nature. Hunters make partner. People who skin the animals do not. So don’t fall into the trap of staying too long chasing a futile goal. At a certain point, you gain diminishing returns on the experience gained at these firms.

In fact, your brand will actually look suspect to many by the time you reach your mid thirties. You will be less willing to put in the long hours, as you have put in your dues at this point. You will have a family, so doing last minute travel all over the world becomes less appealing. Partners will want to replace you with someone younger and cheaper:

“People believe that the reason that middle aged men often look for trophy wives in their twenties has to do with looks. Actually, it is because young women are so much more pliable, wide-eyed and worshipping.

Parnterships, too, prefer pliable, wide-eyed, and worshipping.” Pg. 117

Don’t be the guy that stays too long at a firm hoping to make partner, only to get fired and replaced with someone younger. So be smart about it and give yourself a timeline. If people who came in around the same time as you make partner and you do not, make a note of it. If by next year you are still passed up, its time to leave. This advice is applicable to promotions at any company, not just at firms.

If you’re talented, expect to have your desk set on fire

Entrepreneurs are the ultimate narcissists. They tend to become paranoid under stress, constantly on the look out for enemies. As such, it is hard to remain in favor of such people. But don’t stay too long. To them everything is personal. They will do favors such as give you some time off or giving you a gift or a loan. But now you owe them. In addition, any sense of independence on your end is considered betrayal. Hence, at companies run by entrepreneurs, a cult of personality and worship grows around the leader. Employees will do anything for the CEO, including limit their own careers.

Entrepreneurs are insanely controlling. It is no coincidence that Elizabeth Holmes worshiped Steve Jobs. Both were incredibly controlling entrepreneurial assholes. Stories abound of Elon Musk terrorizing employees. While the best dictators like Steve Jobs and Elon Musk can get accomplish great things, the worst dictators are crackpots that ruin lives (check out the book, Bad Blood for a detailed look the horrors of Theranos). Entrepreneurs will be very picky about certain things and come up with arbitrary rules to enforce their obsessive compulsive whims.

Entrepreneurs do not like to share. They don’t want to share equity, and they don’t want to share credit for the company doing well and they don’t want to cede any decision making power. If you are good at your job and taking too much spotlight, your desk will be set on fire, such as John H Patterson of National Cash Register Company in 1884 was wont to do. Any power you gain at an entrepreneur run company can be taken away in an instant. The CEO giveth, and the CEO taketh away.

Entrepreneurs also tend to treat their employees like toy soldiers. Once they are done playing with you, you are abandoned. Worse in many cases they will attack your reputation or sue you and smear you. Again for a modern example, check out Bad Blood that documented Elizabeth Holmes and her reign of terror at Theranos.

So while working for an entrepreneur is a great way to learn, you will want to leave before you incur the entrepreneur’s wrath.

Regardless of whatever situation you find yourself in, if you no longer have a path forward for advancement in your career, it is time to leave and find someplace where you can continue to grow.

Career warfare Rule 4

Learn which one is the pickle fork

Manners matter. There are the type of manners that involve knowing which spoon to use at a formal diner, and the type of manners that demonstrate respect and compassion. Both types are important. The former type of manners are important because it is a part of the world in which the successful executives inhabit. Unfortunately, people will interpret cluelessness with respect to manners as cluelessness about your job. Hence why manners are important to brand. The latter type of manners are important because being able to demonstrate respect and compassion are the qualities of a leader, and as such will improve your brand, and come into consideration when it comes time for promotion.

Do not embarrass yourself

This is the most important rule above all. A single embarrassing moment is enough to torpedo your brand forever. The embarrassment may confirm something that has only been hinted at before – rumor may have it that you are are an alcoholic. Saying you’re going to a doctors appointment and being caught at the bar will torpedo your brand. The embarrassment may reveal hypocrisy and undo the reputation you’ve already built. If you’ve established a reputation for working hard and getting things done, but it turns out that all those WFH emails were really an excuse to go fishing, its not a good look. Finally, if you’re just starting out and establishing yourself, a single embarrassing moment may define you forever. Maybe you got drunk at the company party and vomitted everywhere and fled crying from the venue. This will cement your legacy, and not in a good way. So be extra careful and conscious of associating your personal brand with anything negative, negative, or embarrassing.

Don’t wash your face with a pancake

Dress appropriately for the job or you will not be taken seriously. This is more true in some industries than others. Learn proper table manners or you will lose credibility. There is an amusing anecdote provided in this section of the book about a woman wiping her face with a chinese pancake during a job interview. The rest of the interview went poorly because the interviewers had lost interest.

Making assumptions about people you don’t know can be fatal

While dressing well and having good manners is important to building a good brand, do not these same standards of criteria when judging others. Slow down and cautiously observe the people that you don’t know. There are countless stories of blunders – mistaking the wrong person as the CEO and ignoring the actual CEO, car salesman treating a customer poorly because the customer was dressed sloppily, only to find out they pissed off their biggest customer. The book provides a few amusing anecdotes. Also – keep any prejudices or bigotry to yourself. This particular piece of advice from the book has aged quite well. A quick glance at all the people who lost their jobs due to social media posts today should make that quite obvious.

Work with cocktail dresses and alcohol is still work

“Fun” time at the office is the most dangerous. Do not let your guard down. Even in offsite recreational events for fun, your behavior will be judged. Be incredibly cautious. Do not think that because there is alcohol, it doesn’t count as work. If anything, the presence of alcohol makes the danger to your brand that much more serious. People will remember and judge if you embarrass yourself. Be sure to avoid your boss. Spend too much time and you will look like a suck up. The longer you spend with your boss, the greater the risk of saying something inappropriate, especially with alcohol in your system. Say hi and move on.

Offsite meetings are the worst. Often run by training consultants, “the real snake oil salesmen of the business world”, these meetings are driven by an executive’s need to bring the org “family” together. But as mentioned before, work family is not “family”, and is always dysfunctional. Offsite meetings may be marketed as a time for relaxation and bonding, but they are anything but. Keep your guard up.

Keep your mystery

Keep your private life private. Avoid office romances. You have more leeway in the corporate world than in politics. Having an affair typically torpedoes your brand as a politician (Hi John Edwards), but typically won’t cause any issues at the workplace as long as you keep it to yourself. Do not bring dates to work events. You will be judged based on the company you keep. If you show up with too many different dates, you will be judged as a player, and someone not trustworthy. If you show up with the same person and they are well liked, you run the risk of pissing everyone off if you eventually break up.

This is especially why you should avoid dating at the workplace. Of course, office affairs and dating are a fact of life and happen all the time. But you would be wise to keep it on the down low. Breakups can lead to blowups.

Understand that marriage, unlike dating, is a public institution

Unlike dating, marriage does not remain private. Who you marry impacts your brand. “You are forgiven one divorce. You married too early, you grew apart, you spent too much time on your career. But if you blow the second marriage, its about you”. Someone who divorces too many times will be seen as someone who cannot keep their vows, whether work or marriage related.

Do not let your spouse speak for you. It will come off as weakness. Do not let your spouse nurture a grudge against your boss, and especially do not let them tell off your boss. That has never helped anybody’s career.

Treat your boss’s spouse as a proxy for your boss. Treat them with respect and as a human being. Not only is it the right thing to do, its the smart thing to do as well. If you manage to piss them off, they will find a way to ruin your brand. On the flip side, don’t be too friendly with them. There are conflicting loyalties at play here which can damage your career.

Patience is a virtue, maybe even the virtue

Be impatient for results, but patient in the way you handle people and situations. Listen to your colleagues with empathy before talking. Do not go for the second drink so you can remain in control. Do not brag about the affair. Take time to make your boss’s spouse feel at home. Having good manners means having the discipline and patience to stand back and take a deep breath before figuring out the right thing to say or do. Having good manners also means that you have the discipline and patience to become a great leader. Other smart leaders will recognize that, and it will benefit your brand.

Career Warefare Rule 3

Rule 3: Put your boss on the couch

Bosses all fall into a few generalized categories. Determine which one is your boss.

The Little League Parent

This type of boss acts as your parent. But do not fall under the mistaken impression that they are actually your parent. This is a dangerous way of thinking, because at the end of the day, parents love their children unconditionally (or at least they are supposed to). Your boss does not. To prove this to yourself, just do a bad job. Remember that any good work that you do will be a credit to your manager’s ability to hire and develop the best talent (Amazon leadership principle). If you look good, your boss looks good. The converse is also true. Do not forget that.

Now if you’re lucky, a little league parent boss acts as a mentor. Or they can be the bad kind of parent who makes you feel inadequate. Even in such a scenario, you can still learn much from them, as they may will teach you much, even if it is in a condescending manner. However, you can’t afford to have this type of boss beyond your 20s and early 30s, because you cannot develop a brand of your own under such a boss. If you don’t move on, you’ll be forced to regardless: At some point, as you presumably progress in your career and experience, you will start to question your boss more. Such a manager cannot stand this loss of authority.

The Mentor

This is the better version of the Little League parent. As mentioned before, work is not your family, and your boss is not your parent. A more apt analogy describing the bond at work would be military. A mentor will develop a “band of brothers” style team underneath him who will be fiercely loyal. This loyalty is earned by taking care of his subordinates. He is a rising tide, one that elevates the entire team. He protects you from the predators in the company, develops yours career, puts in a good word with the higher ups who matter, and when the time has come, helps you leave the nest and spread your wings.

The Wastrel

The mentor takes care of you, the wastrel wants you to take care of everything and do all the work. Yet even such a boss can be good. Because you’re doing all the work of someone one level above you, you’ll be given more responsibility. Leverage the tougher assignments as learning opportunities and a chance to meet powerful people, the people that your boss would normally interact with if he did his job.

The Pariah

This person is a hated enemy in the organization, but may have survived … so far. You will do well to keep your brand separate from your boss, as difficult as a balancing act as that may be. The key is to show that you are loyal to your boss, but also loyal to the company. Your brand should be that of someone who is useful not just to your boss but to the whole org. Make alliances with others. History is full of once popular bosses becoming pariahs, and his subordinates suffering the same fate.

This quote from the book stands out, and reads like something from the 48 laws of power: The most powerful king’s courtier is never given the same respect as someone who controls the smallest duchy.

Even if you have the best boss, and not a pariah, you will never gain as much respect as someone loyal to the company but also an independent power.

The One Way User

The one way user is the type of boss diminishes your contributions, claims them for himself, and doesn’t give you any recognition. These bosses are vain and concerned only building their own brand. They will use their employees, but forget that rewarding and acknowledging said employees is how to foster long term good will and loyalty. You will not be able to grow under such a boss. Recognize the situation, and find a new boss. Most people do. I’ve seen this before at work, and a tell tale sign is high turnover rate under such a manager, not to mention all the complaints on the rumor mill.

The Wimp

Indecisive and weak. Will not praise you for fear of losing you. Will require lots of hand holding, and reassurance on their decisions or emails, but won’t let you take initiative on any new ideas. In fact, the only time the wimp shows bravery, is in shooting down your ideas. Will tell you he has your back but then disappears at the first sign of trouble. He is the bureaucrat and dead weight of the organization. But of course will still try to claim all the credit. You will not get much done under such a boss.

The Know it All

This type of boss will never admit they are wrong, and will never listen. At least they won’t steal your ideas, but that’s because they think their ideas are the best. But when you implement their brilliant ideas and things don’t go well, you take the blame. Because after all, they are geniuses who know everything, so if something went wrong with their brilliant ideas, it can’t possibly be their fault. You won’t learn much from these type of bosses because they won’t let you think on your own. These types of people are terrible as bosses but even worse as subordinates. They can end up sinking the whole company with their brilliant ideas and inability to listen to feedback from others.

What can you do?

In the face of so much incompetence, arrogance, and abuse, what can you do? Your boss has all the power, but you are not completely helpless. Here’s a few things you can do.

Turn down passage on the Titantic

Don’t forget that when you go to an interview, you are also evaluating the company, team, and boss that you will be working for. Many bad bosses will have tells that give them away during the interview process. During the interview with the hiring manager, you might be criticized during the interview, or encounter overt hostility. A one way user boss will focus entirely on how you will benefit them. The boss might start criticizing people on the team. Guess what? You’ll eventually be a target of such criticism as well. Find out as much as you can about the boss, the team, and the company. Talk to other employees, ex employees, and read the news. Check resources like blind or glassdoor. If it doesn’t feel right, don’t take the job.

Get out of Dodge

As long as you are learning, the Faustian bargain of gaining experience and contacts in exchange for long brutal hours is worth it. However, if your boss sucks and your prospects are dim, go somewhere else. Staying too comfortable in a place after you’ve already learned everything you could at a position is going to lock you into mediocrity. Thinking that you can always change jobs and take on something more challenging in the distant future lulls you into complacency. Some day the distance future becomes the present and you’ll be wondering what went wrong. If you are no longer learning, adding to your brand, and if the company isn’t moving you up, its time to go somewhere else.

Make friends in high places

Even if you have a terrible boss, there’s a good chance other people higher up in the org have taken notice of you. For example, you are able to give a well thought out and detailed answer to a question from your boss’s boss, while your own boss cannot. Look for signs of sympathy, gratitude, and interest from higher ups.

Be careful though, and never talk bad about your boss. As stated previously, this is bad for your brand and makes you look untrustworthy. Furthermore, it is insulting to superiors, as it implies they’re unable to notice what’s going on. The exception to this rule is when a higher up directly asks you about the situation. In that case, be diplomatic but direct.

Finally, treat times of crisis as opportunity. Tough times and upheaval at a company will reveal who truly holds the power. In normal times, the hierarchy is observed, but in tough times, the people truly in power play their hands and step in to act. Those are the people you want to win over. You will also see just how much power your boss actually has. If they’re ineffective, it won’t be much. Crisis are also an opportunity for you to shine. Whenever there’s a fire, the people in charge will see who can get stuff done and who cannot. This is the best way to get out from under a bad boss.

You can enjoy a dish best served cold

Things may be bad now, but take comfort in the fact that someday you may end up in a position of power over a bad boss who once made life miserable for you.

Career Warfare – Rules 1 and 2

Career Warfare: 10 Rules for Building a Successful Personal Brand on the Business Battlefield is the follow up to the best seller Brand Warfare. This book is a pragmatic, if cynical guide, on how to manage yourself as a brand within the company you are working for. The book is self admittedly ghost written, but contains insights from CEO David F D’Alessandro, who gives a behind the scenes look at how things really work in the corporate world. The book contains many insightful and highly entertaining stories from his own rise to power; these notes outline some of the key ideas. The main idea of this novel is that working hard and hitting deliverables is a given. This is the minimum requirement for success. However, people on the management chain spend very little time thinking about you and your accomplishments. All your thousands of hours of hard work are condensed down to a few general impressions and opinions of you. A few casual offhand remarks made about you in a promotion meeting may decide your future. It is in these few and far between brief moments where your brand and reputation are the deciding factor. This ties in to law 5 in the The 48 Laws of Power, “So much depends on reputation, guard it with your life”.

Rule 1: Try to look beyond your own navel

Instead of looking through everything through the lens of self interest, add another layer of abstraction and view your actions in the same way everyone else will view them.

  • Instead of looking through everything through the lens of self interest, add another layer of abstraction and view your actions in the same way everyone else will view them.
  • Don’t flatter yourself and view yourself as better than you really are rather than how you actually are. Don’t make excuses for your behavior.
  • Get noticed by offering something to higher ups. Perhaps everyone wants the high profile tasks, but you can compete by taking on a more humble, yet equally essential task.
  • Halo effect – associate your brand with something good. Gain access to powerful people early on.
  • Think of yourself as a product. You cost the company a lot of money. Be sure to deliver the kind of high performance and reliability that is expected from a high end product: Earn money for the company, tell the truth, be discrete, keep your word, and make people want to work for you.
  • In a tribe, the hunter is the most respected. Likewise, not all jobs are created equal. The jobs or orgs that directly increase the company’s bottom line are the best ones to be in. Consider a hypothetical job at google where you are working on some internal software used by the teams, versus a job where you are directly working on google ad words.
  • Have a reputation for telling the truth.
  • Be discrete. Don’t blab. Leaks are common place. Do not write down anything that you would not want to have published to the whole world to see. Have a reputation as someone who can actually keep a secret and have the discretion to know when to share and when not to.
  • Always deliver. If you say you will meet this goal, then do it.
  • Be someone that people want to work for. Be able to manage down as well as manage up. Forget management theories, treat people as individuals who are motivated in different ways. Don’t pretend to be an expert at everything. Know what you don’t know, and hire people with diverse skills who can advise you on matters in which you are not the expert.

    My own thoughts: Some people I have seen are good at managing up, but bad at managing down. It gets noticed. There is high turnover and nobody wants to work for this person. This is in stark contrast to a manager whose team members will follow him across teams and even across companies.

Rule 2: Like it or not, your boss is the coauthor of your brand

  • The elders of the tribe eat first. Which means you’ll do the lions share of the work, and the upper management will take the credit and reap most of the benefits. You have to pay your dues first. If you can’t accept this, start your own company.
  • Your boss has the most control over your life. More so than your spouse even. You spend at least 40 hours a week at work, your boss commands your attention, your salary, what you work on, and more importantly your brand. Corporations are caste systems. Sadly, your brand is more at the mercy of subjective comments your boss says to his peers than objective measures of success. Recognize and acknowledge this power and act accordingly.
  • Bosses want loyalty. Don’t go above him or behind him. Snitching to a higher up is not a good look.
  • Bosses want good advice. Here you will want a balanced approach. Don’t go to either extreme of being a sycophant or a contrarian.

    “Other corporate people are sycophants not because they are actively terrified, but because they are naturally conservative and risk adverse. Their quest is to remain unnoticed, for the most part. So long as they are reasonably proficient at their jobs and keep their heads down, they are less likely to be called out of class then someone who speaks his or her mind.
    Their quest is to remain unnoticed, for the most part. So long as they are reasonably proficient at their jobs and keep their heads down, they are less likely to be called out of class than someone who speaks his or her mind. They want the kind of career where t hey will be rewarded with a 3% pay increase each year, good benefits, and a pension plan that makes sense. These are absoutely not the people for whom I am writing this book”.

    They make take some offhand remark and overreact to it, such as one executive who commented that he enjoyed some harp music at some event, and then got confused later when he saw harps at every event that followed.

    Don’t develop a reputation for being a suck up. Don’t be afraid to speak your mind and disagree with the boss. Otherwise you will be branded as mediocre.

    The sycophant agrees for the sake of agreeing, while the contrarian is the exact opposite. The contrarian will develop a negative brand because every interaction is unpleasant. Bosses will spend time figuring out how to get rid of you. Contrarians think because they are smart and well educated, that this trumps all else. Not the case, as many people in a large S-tier company will be smart and well educated.

    These people are just right. It takes time to strike the right balance. Work for a lot of different bosses to see who is receptive to advice and who is not. Study your own boss to see how he handles his boss. Work long enough to understand your value and have confidence in your opinions. Timing is important too. Also, disagree and commit. This is one of the Amazon leadership principles. Let your boss know you disagree and why, but also let them know you will do as you’re told.

    If you’re asked to do something illegal, now is the time to go over your bosses head. You might lose your job, but better that than losing your career – your brand will forever be tainted.

    Finally, you have to differentiate yourself from the rest. Pick the key moment to do so, and it will help you stand out. Don’t overdo this, otherwise you become a contrarian.
  • Bosses want their brands polished. One thing that is especially helpful is to complement their weaknesses with your strengths. If boss is organized but lacks technical ability, bring technical expertise to the table. Your boss will use you, but can you use them in return? The reputation you want is as someone who is destined for greater things to come.
  • What do you want from a boss? To be trusted. You will start getting opportunities. Second, you want experience and learning early on. The money will come later. You want a boss you can learn from, even if its to learn how not to behave. Even having a problem boss is helpful, because it lets you easily identify such people in the future.

Getting things done

The main thesis of the book, Getting Things Done: The Art of Stress-Free Productivity, by David Allen, is that all the tasks that bombard us on a daily basis prevent us from gaining the clarity we need to tackle the important things. In this way, this book takes a different approach from books such as The 7 Habit Habits of Highly Effective People, which stress the need to Begin with the End in Mind.

The author is not arguing that the big picture is not important. Instead, he argues that it is difficult to focus on such big picture stuff, when there are hundreds of little picture things vying for attention. His system provides a simple approach to clear the mental clutter, allowing people to then focus on the bigger picture.

Here I will provide a summary of the author’s general workflow process of managing all your tasks, as well as his natural planning model for tackling non trivial projects.

Workflow Process

1. Collect all Input

In order to clear out the mental clutter, we must have a single inbox where we collect all possible inputs to our workflow system. The importance of capturing all possible important is that it gives us permission to then ignore it, knowing that it has safely been recorded and will eventually be processed by our system. Note that this does not have to be a physical inbox, but rather someplace where you know every possible input will be safely collected. I personally like using evernote since I can access it from my work laptop, home computer, and on my phone. I use the word “folder” in my summary below because it fits better with the author’s paradigm, but in Evernote that would correspond to a “notebook”. 

2. Process input

Is it actionable?

No is not not actionable

Determine what type of input this is:

  • Trash – discard it. Sometimes problems magically resolve themselves. Sometimes the circumstances change, and the original input is no longer valid or relevant. For example, maybe you had to write some code for a particular feature, but the product management decided it was no longer needed. 
  • Action needs to be taken at a later date – This should be moved to a Waiting folder or a Someday/Maybe folder. The waiting folder is for action items that are blocked. For example, perhaps your dog is ill and the veterinarian has run some tests. You are awaiting the test results before coming up with the next steps, so this would now be moved into Waiting.

    The Someday/Maybe folder should be used for lower priority items such as tertiary hobbies that you would like to do someday, but currently are unable to. For example, I always wanted to play Dwarf Fortress, the world’s most complex computer game, but held off on it until now. It sat in my Someday/Maybe folder, which I review regularly, until I decided now was the time to act. 

  • Contains information. This should be moved to the appropriate folder in Evernote, corresponding either to a specific project folder, or a specific subject. To continue from my previous example, I am learning how to play Dwarf Fortress, so any interesting articles or guides that I encounter online would go to my Dwarf Fortress folder. I also have various websites, with a folder for each one in Evernote. Reference information could be notes on how I set up the website in AWS and got SSL working, or computer science articles that I want to write a blog post about.

Yes it is actionable

  • Determine the outcome. This is a critical step. Too often, goals in our life is vague and nebulous. “Get in shape”. What does that even mean? By giving specific and objective/measurable criteria with some kind of a deadline, it makes an item more concrete, and more likely to be acted on. Bench 3 sets of 10 reps of 225 lbs by end of year. 
  • Determine the next action for this input. This is also critical. We are unlikely to move on goals that are vague and nebulous, as previously stated. The way to tackle large seemingly unsurmountable tasks is to break them down into smaller, and more manageable subtasks. As in the previous step, we want to move from some vague/nebulous notion of a task into something that’s actually concrete. This increases the chance that we’re actually going to accomplish it. To continue from previous example, the next action item could be to get a gym membership. The next action item is to find a training partner or personal trainer. The next item after that could be to purchase protein shakes. And so on and so forth. 
  • Now either do the action (if it takes less than a few minutes), delegate it to someone better suited to handling it, or defer it (file this under Next Actions folder).

3. Organize

Now that we have processed the input, we want to collect this information into various folders. 

  • Projects folder (with subbprojects) – author defines a project as anything that requires more than one action. 
  • Project Support Material – the author has these in a separate folder. With evernote, I just have each subproject as its own separate notebook, and then any relevant reference material needed for the project added as notes. For example, if the project is to sell an app on the windows marketplace, support material would be my Microsoft account information (don’t store your password in here in plaintext though!), links to the publisher dashboard, information about my LLC, and so on and so forth.
  • Next Actions – This likely be subdivided. For example, the author recommends a separate subfolder for “Phone calls” (scheduling vet visit, doctor, car insurance claim, etc). I have another one for errands (grocery shopping, replacing light bulbs, assembling baby crib and so on).
    Reminders for actions should be categorized into time specific actions, day specific actions (no time component), and day specific information. Time specific would be an appointment and would go on the calendar such as outlook. Day specific could be that you promised Joe you would touch base with him regarding the financial planning report this Friday. Day specific information on the other hand, might be information that’s relevant on a given day (appointment confirmation info, activities that occur on that day such as plays, concerts, comedy shows and so on). 
  • Someday Maybe – as touched upon above, these are things you can’t tackle right now, but don’t want to forget about either. For me it was learning how to play Dwarf Fortress. Still on my Someday/Maybe folder are playing Dungeons and Dragons and learning how to play Arkham Horror, a board game I purchased but still haven’t gotten around to playing.

    This can be further subdivided into books you want to read, TV shows to watch, music to listen to, and so on. 

4. Review

In order to keep your head free of mental clutter so you can actually focus on a day to day basis, you must review the system. By consistently reviewing it, your frazzled brain can relax, knowing that any of the dozens of things you are juggling in your head can wait because they will be processed accordingly.  A weekly review is important to come up for an immediate tactical plan of action. The main point of the author is this – only once your house is in order can you then have the mental clarity to then do higher level reviews for current projects, areas of responsibility, 1-2 year plans, 5  year plans, and life goals. Trying to review life goals without first having categorized all your to do items in an organized and systematic fashion won’t work. 

Finally the author offers some general guidelines for deciding what to do at any point but doesn’t give any hard and fast rules. Context, time available, energy available, and priority should all be considered. One useful tip I got was to look for pockets of “weird” time. Such as if you have 20 minutes in between meetings, this is a good time to go through your next actions and look for simple tasks such as looking up how to renew a passport, or making a quick phone call to schedule a vet visit for your dog. You could batch certain tasks such as phone calls so they’re handled all at once, and similarly you can treat errands the same way. But by having all the actions items captured and organized, you gain the flexibility to review them at your leisure and decide what best to do at any given moment.

The Natural Planning Model

The Progression of the Unnatural Planning Model

The author first starts off by describing what a typical (and unnatural) planning model looks like:

  • Action – Due to a failure to plan up front, there is now a crises in the project. People are scrambling and working overtime to try to fix it and hit the deadline. Oops
  • Organized – Throwing more manpower and hours at the problem doesn’t help. Now someone clever suggests getting organized, by drawing some diagrams and labeling all the moving parts.
  • Brainstorm – Of course, drawing all these labels and putting them on a powerpoint won’t solve the actual problems. So now someone clever suggests brainstorming. The boss asks for some good ideas. When not much happens, now he brings in consultants.
  • Vision/Purpose – These highly paid individuals will now ask: “What are you actually trying to accomplish?” People will be blown away by these insightful consultants and then begin to figure out what the actual goal and scope of the project is. 

The natural planning model with example

  • Define purpose and principles. The purpose is what you are trying to accomplish. Your principles determine the scope. For example, if I wanted to go on a trip to Spain, the purpose might be to become enriched by the local culture – art, music, sculpture, and so on. My principles might not be explicitly called out during this, but it would implicitly determine things such as food and lodging. For example, do I want to stay in a fancy hotel, at an air b&b with a local, or do a hostel and party with other travelers? Do I want to do all the tourist style sight seeing? Do I want to go party where the expats are? Or do I want to see if someone in my social network can connect me with a local for an authentic experience? How much money am I willing to spend for comfort, luxury and convenience, versus how much of that am I willing to sacrifice for affordability? This step concerns the why.
  • Outcome visioning – What do I envision this trip to be like? I might think about viewing modern art at the Prado museum, or perhaps walking amongst the massive arches holding up Gaudi’s Sagrada Familia. This step concerns the what.
  • Brainstorming – This step concerns the how, and begins in a very informal and ad hoc manner. Questions are asked such as: where are we going to stay? How many cities are we going to visit? What forms of transportation will we use while we are there? Which exhibits will we see? This will generate a large number of ideas.
  • Organize – Now that there is a large number of ideas produced by brainstorming, we want to organize them. Ideas might be arranged in a hierarchy. For example, think of the following folder structure: Spain/Barcelona/Gaudi/Sagrada Familia. The Gaudi folder would contain additional subfolders for each of his famous architectural triumphs. We might also look to organize by priority and sequence of events. Priority might be the must see exhibits for a Spain trip, while the sequence would be the travel itinerary. 
  • Identifying next actions. Now that the why, what, and how have been covered, the final part of the planning process is the execution. Plane and train tickets need to be bought, hotels need to be booked, and so on. 

The author calls this the natural planning model (contrast to the unnatural planning model mentioned above used in most workplaces), and uses the example of going out to dinner with friends. You want to hang out with someone you haven’t seen in a long time (purpose), decide to go to a new Thai restaurant because you are both curious (principle), think about what kind of food you’re going to order (outcome visioning), start asking many questions such as what time to go and how you will get there (brainstorm), organize them into a plan of action (call friend to confirm, get reservation, look up directions on google maps, etc), and then executing the next action. The idea is to default to this everyday natural mode of planning for all your projects, not just figuring out dinner plans.