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The Mastermind: an overview of my planning process

Time is a humbling thing.

You can start something with beautiful intentions, all-consuming drive, and laser focus,

Only to find yourself suddenly abandoned by those virtues and completely out of steam.

Maybe it was a late night that broke your morning routine the next day.

Maybe it was an argument that never quite got resolved.

Maybe you suddenly found yourself without any gas in the tank, emotionally unable to continue pressing on.

All of a sudden, you’ve fallen off of whatever it was you resolved to do differently, and you’re feeling demoralized.

Maybe even ashamed.

You feel as though this better version of yourself that you were becoming was just an outer garment that’s now been removed, and the real, unremarkable you that’s not quite up to it, not really a born winner, is all that’s left.

This was my experience with yoga and meditation. For years, I had what you might call a “strong practice.” Up before dawn, dedicating hours every day to techniques that I believed had the power to transform myself into someone more evolved. I was involved in a community of other practitioners, and was remarkably consistent. You might say that people looked up to me.

But all of a sudden, it dropped off. A series of “life circumstances” happened, and my practice, and my community involvement, was derailed. It was an awful feeling, but somehow I felt powerless to stop it. Some mysterious something had simply vanished without a trace, never to return.

It feels strange to say this, but the world of yoga and meditation was never my plan. It was something in which I became swept up, and by which I was carried for a long time. About seven years, to be precise. When “life happened,” specifically my divorce from a woman I’d met through my yoga practice, and with whom I built a life centered around it, it was like a kite was released into the wind: gone.

When I said just now that it was never my plan, you might be wondering, well, what was your plan, then?

There was no plan. There were just habits. Habits, and the rigid persona of a “spiritual seeker” constructed around those habits in order to avoid much deeper questions of identity, purpose, and personal integration.

Since that time, it’s been a long journey to get to the bottom of what really happened, and how to proceed. For today, however, my autobiography of a former yogi ends here. Because, like I mentioned two weeks ago, I’m not really here to talk about me. It feels weird. People find it relatable, but I happen to be a very private person. But I want to get my point across as best I can, and that point is:

Vision trumps habit.

But wait, you say. Vision, or a goal, is powerless without the necessary supportive habits. Yes. You’re right. And the reverse is also true: activity, no matter how consistent, no matter how picture-perfect, is not sufficient without an overarching vision, a unifying plan.

And, why not?

Without vision, habits reduce life to a series of episodic days: a list of boxes to check, that are then magically unchecked while sleeping, awaiting completion yet again the next day.

Without vision, habit makes you the master of minutiae: impressive within a niche, but ultimately trivial.

Without vision, habit does not know when to shift, ease up, increase, or even cease in the face of new information. You may be writing a very intense scene, but there is, ultimately, no story.

A vision, a plan, is a story. It is the attempt of your future self to give directions to your present self.

(You might say habits are the attempts of the present self to reform the previous self…again, an undoubtedly noble endeavor, but not enough).

Become the man with a plan.

Done the right way, planning serves as the basis for selecting the right habits to cultivate, the right habits to break, and, perhaps most importantly,

Provides an overarching structure that can absorb the inevitable lapses in performance.

Nobody is perfect. Nobody is a machine. People have bad days, people lose hope, people fuck up.

The right plan, the right approach to planning the plan, has the power to radically alter, for the better, what those bad days, crises of faith, and fuckups actually look like.

The right plan will systematically make you less likely to fall off, and you will fall less far.

The reason behind this is simple: the right plan is a plan that systematically closes the gap between your actual self and ideal self.

Every step in this direction raises your self worth. Every increase in self worth makes you more proactive, meaning you are quicker to correct course, and less likely to throw up your hands and abandon your goals simply because you made a mistake, or even if your life experiences a major unexpected change.

With the right plan, you will increasingly become better at sticking to things.

This is the virtuous cycle we all hope to become swept up in: the actions that improve the quality, consistency, and efficiency of our actions.

So, where to begin?

To borrow a great title, start with why.

Open a Google doc (or equivalent) that will become the digital home for your vision.

1. Begin with a letter from your future self.

Talk to yourself like you’d talk to a close friend who is finally ready to listen to reason. This will vary quite a bit from person to person, but this is the place to brain-dump your frustrations with yourself.

It’s here that you’ll air out:

Your regrets
The advice you know you should have taken
The things you know you have to stop
The things you know you’ll have to face eventually
The excuses you’ve made in the past
Everything else that’s stopped you until now

Again, this varies. You may not be bouncing back from rock bottom. You may be in a good place looking to maintain momentum, accomplish more, or simply make your life more interesting. Either way, step one is to say whatever it is that you need to say to yourself. It’s time for the real talk. This should feel difficult. Prompts like “what am I avoiding” or “what am I doing to make my life more difficult than it needs to be?” You start here.

2. Define the big picture themes for the coming year

What is it you wish to cultivate in yourself? What do you really value in life? Who do you want to see when you look in the mirror? Maybe you want to be in better shape, maybe you’ve lost touch with something or someone important to you and you want to rebuild a connection. Maybe you want to take a skill to a new level, or get back into the habit of reading, or beautify your home, or clean up your diet, or feel less financial stress.

Whatever it is for you, get clear about it. You know what these things are, and, if someone else has to tell you, you’re not ready for this.

3. Behaviors

The person you want to be: what do they do all day? And what is it they don’t do?

Make a list of 12 habits to make, and 12 habits to break. Assign one of each to all 12 months. Start easy, and build in difficulty.

Pro tip: the habits you adopt should coincide with the habits you’re breaking. For example if 8 hours of sleep per night is a habit, adopt that at the same time that you break the habit of snacking after dinner. One supports the other.

Because you’ve already thought through what you don’t want to repeat, and what you want to move toward, or reclaim, these habits will already represent something more than mere activities to you: they represent keeping promises to yourself, honoring yourself, and treating your self and your life with the appropriate love and care.

For this reason, some of these habits should include the way you show up in the lives of others. I decided, for example, to be better about birthdays in my family. Making those improvements, and doing so through fairly foolproof systems, has absolutely made me feel like a better person, and it’s brought real happiness to people I care about as well.

Self improvement is meant to make you into a force for good in the world, and that means making a positive difference in the lives of others. Include these kinds of goals into your plan, and you will be doing a great deal to secure your progress in other areas.

4. Year-long goals

Set targets toward which your habits will carry you, one day at a time. A daily habit of reading should correspond to a reading list for the whole year you select in advance. I did this and it changed my life. I coordinated my reading goals with projects to beautify my living space with art that I purchased after reading books on various artistic and cultural movements in Paris and Vienna, for example. I set goals for weight lifting, goals for learning songs by having the habit of reading sheet music every day. I could go on.

The point is, direct your habits toward the completion of year-long projects. I memorized the Tao Te Ching, quit drugs and alcohol, resolved debts with the IRS, totally rebuilt my physique in the gym, turned my home into a sanctuary of luscious green plants and beautiful paintings, and became a serious reader again, all in one year.

This is the power of the ideas I’m discussing here.

You are becoming, essentially, someone you are inspired to care for. Someone with a future you care about. Someone you would never abandon or let down.

There are more details, but this is a lot for one sitting.

In future letters, I can discuss each of these phases in more depth, and go into the psychology of it all, but for today, I wanted to show how habits function better when placed downstream of answering larger questions about your life, and are subordinated to specific goals.

In closing, I want to let you know I’m at the beginning stages of building a consulting practice around this kind of big picture, year long planning.

If you’re interested, or have questions, just reach out to me by whatever channels this article came to you.

Thanks for your time, talk to you soon.

Jas

Fulfill Your Destiny Or Suffer Your Fate

Are you a fan of Led Zeppelin? I am. I don’t know all their songs inside and out, but I’ve always loved their sound. And, they’re truly one of the great rock bands of all time. But the downside of being as famous as they are is that society becomes “parent deaf” to their messages. Their wisdom and brilliance becomes hidden in plain sight after years, decades now, of repetition.

So, let’s take my favorite line from Stairway to Heaven, a song so famous that many guitar stores unironically prohibit you from practicing it while trying out gear:

“There are two roads that you can go by, but in the long run/you’ve still got time to change the road you’re on.”

Simple, yet, in many ways, profound: ultimately you will go one of two ways in this life, but it’s not too late to make a change.

I believe that, deep down, we all know this to be true. We all know that there’s a right way, and a wrong way. And, for us to live good lives, we have to know that the way we’re going is right.

Let’s call the right way “the path of destiny” and the wrong way “the path of fate.” As I say in the title of this week’s article, “fulfill your destiny, or suffer your fate.”

Today, I’m going to spend a little time clarifying that statement. Mostly, I want to give an exposition on “the mentality of reclaiming.” It’s one thing to know right from wrong, destiny from fate, but it’s another to really understand how to change from wrong to right. How to recognize the longing for that kind of change, and what the beginnings of that change look and feel like.

So, why do I use the word “reclaim?” Because the good life is about more than just progress. It’s about more than just moving forward, expanding, evolving, taking on more, doing more, becoming something more. To be clear, that is part of it. But, not all of it.

The good life is often framed as a process of expanding one’s territory to encompass new, better land, so to speak. A land filled with more money, better possessions, more influence, better friends, more control over your time, better things to spend your time on.

And, this is not wrong. The positive changes in my life can certainly be described, accurately, in these terms. But as I’ve said, there’s more to it. And, I’ll show you why there has to be something deeper and something different for the external improvements to come to pass in a meaningful and lasting way.

This “something deeper” is about the reclamation of what is inherently good in you. The reclamation of your dignity, and, dare I say, your nobility.

What I am fundamentally saying, and I will say it now as bluntly as possible, is that

You already had the thing that mattered, and you misplaced it. There’s nothing new for you to go and get that could possibly be better, or more valuable, or more useful, more rewarding, more special and meaningful, than what you came into this life holding, and which you now cannot find.

Do you feel deep existential dread as you read that? If so, good. Feel it, see it, claim it, own it. And, I will teach you to use it for good.

What is it that you already had when you got here?

Your purity and innocence. Your inherent goodness, virtue, dignity and nobility.

There was a time when your joy was total and irrepressible, when you delighted in exploration and discovery, when it was fun to be challenged, fun to engage fully, fun to be daring and imaginative and expressive. It was effortless to say what you really thought, effortless to be yourself. You knew what you wanted, and pursued it. This is what is meant by “purity and innocence.”

This is, of course, something that is experienced in early childhood and quickly fades away. Society is organized in such a way that it turns us into adults who seek status, stability, approval, conformity, and success on terms laid out by others. We learn that we cannot simply say and do whatever we want. Little by little, we are saddled with responsibilities, pressures, and expectations.

Essentially, we become adults at the expense of the children we used to be. This is everyone’s fate, and no one’s destiny.

“There are two roads that you can go by, but in the long run,
You’ve still got time to change the road you’re on.”

Now stay with me, and dip back into that feeling of existential dread. The dread of seeing that life is passing you by, the dread of wasted time, of “too late,” the dread of ultimate failure. Feel it, hold it, own it.

How do you know? How do you know which path you’re on?

The short answer is that, if you’re not sure which one you’re on, you’re suffering your fate. Everyone who walks the path of destiny knows that they are doing so.

Because destiny is the reward of agency,
The reward of honoring your conscience,
The reward of living wilfully,
The reward of using your strength and power to take back what was yours all along, that you yourself misplaced as the result of your own ignorance.

The path of destiny is illuminated by the light of a fire lit within yourself.

And, I say “fire” because there is something like anger in it. It is the anger of Dylan Thomas’s famous injunction to “rage against the dying of the light.”

It is the jolting awake of someone who suddenly sees that time is limited, that it is running out, and that now is the time to become good, whole, happy, sane, wise, and in control of one’s life.

It is the anger of someone who realizes he’s fallen asleep on the train, missed the stop, and is now far from home, far off track, and who’s entire organism has now quickly and decisively organized around the necessary corrective measures.

This is the initial shock that sets the rest in motion. It isn’t all about the angered jolt, but it has to start there.

It has to start with a full throated, defiant “NO” to the sleepwalking episodic torpor of mediocrity.

If you honor that anger, it will set you on the path, and then the anger will leave you. It is that deep terrifying existential dread that wants, desperately, to flare up into the “rage against the dying of the light.”

Do it. Use it.

Friedrich Nietzsche wrote that “the struggle of maturity is to regain the seriousness of a child at play.”

Someone who has learned the impulse control of an adult, has spent his or her adult life learning and refining skills, who can function in society, and bear the burden of responsibilities, is unstoppable when reunited with the childlike spirit of wonder, play, discovery, and vigorous activity.

I spoke of innocence and purity. I did not speak idly.

The child at play knows right from wrong, honesty from dishonesty, beauty from ugliness, desirable from undesirable. A child knows how to give and receive love and forgiveness. And, a child takes its conscience seriously.

When you reclaim that part of yourself, your purity and your innocence are returned to you.

This is the prize. The rest, everything good that flows therefrom, is to be shared with others. Only you are truly yours.

Thank you for your time, talk to you soon.

Jas

The Right Way To Plan: an introduction

I noticed something strange:

In the movies, it’s always the bad guy who has a plan. The responsibility of the good guys is to thwart it.

If you’re scratching your head, just think of the Chris Nolan Batman movies: even if The Joker asked, rhetorically, “do I seem like a guy with a plan to you,” the answer is yes, yes you do. Everything The Joker did was a masterpiece of planning. Bane says it outright: “it doesn’t matter who we are. What matters is our plan.” We’ll come back to this.

Sauron? Had a plan. Every Bond villain? Plans within plans. Game of Thrones? A show about conflicting plans. I could go on, but you get the point. The good guys are minding their own business until the bad guys show up with their well laid plans, and everyone’s gotta scramble to overcome it.

What I’ve discovered is that, in real life, the exact opposite is true: bad things happen when there is no plan. Do people plan on being late to work, or failing to complete assignments, or drinking too much, or quitting a relationship when it gets hard, or mishandling money, burning bridges, and never amounting to anything?

No. These are things that happen to people who don’t plan. To people who aren’t prepared.

If we’re using movies as an analogy, it’s more like you get to the middle, look around, and realize it’s been going nowhere, and worse. Nothing great is happening, and you can neither avoid nor properly recover from the bad things. Life is just happening to you.

But, why does that not include the good things? Why does “life happens” never mean a lasting, loving relationship, a fulfilling career, physical strength and mental clarity, and both a public and private life you can be proud of?

This was exactly my experience. Somewhere in the middle of my life, I looked around and saw that “the movie” was not progressing as I had hoped. Things were not falling into place. I was not doing well, and I was not happy. It didn’t feel like I was living a real life at all. A life of challenges, accomplishments, and big smiles with people who I love and admire. It wasn’t there, and it wasn’t heading there.

This isn’t going to be a “tell-all” about my life. Maybe later, when that truly has meaning and inspirational value for others, but not today. Because, today, as the man said, “what matters is our plan.”

In keeping with the little movie analogy, here’s a good old Hollywood cliche for you: I became the hero of my own story when I started making and executing plans.

And, these weren’t just any plans. These plans were totally distinct in their method, their quality, and my level of investment in their creation. These were not the new year’s resolutions doomed to failure. These were not the vows to never drink again made in the depths of a head splitting hangover that are broken the moment you recover and your friends hit you up again.

These plans were different. These plans were made to stick. And they did. And my life has never been the same.

However, just as I’m not necessarily here to discuss the negative elements of my personal past today, I’m also not really here to discuss details about my own private life in the present. Again, that’s not the point.

For now, let me just say that the plans are working. The things that were not working are working. Every area of my life,

Health,
Habits,
Fitness,
Finances,
Job,
Relationships,
Creativity,
Overall happiness,

These things are on track. I could walk you through every one of these areas and feel good about you seeing under the hood, so to speak, at a granular level. That is priceless: to be able to look around and see good things, in a good place, moving in a good direction. More on that later, when it matters more to you.

What I want to talk about, and what I had to lay all that out in order to then talk about, is this business of planning.

In time, I’ll get into all the details, but let me give you a kind of prologue here today.

If you’re into time management you might know the name Brian Tracy. Or possibly Cal Newport. But the time management idea that really changed my life comes from John C. Maxwell.

In his book, Thinking for a Change (good title), he has a chapter on long term thinking. In it, he lays out the “thinking schedule” of a successful CEO. Essentially, you set aside longer and longer blocks of time for thinking and planning for each increment of time:

A few minutes at the end of the day,
A half hour at the end of the week,
A half day at the end of the month,
Longer blocks at the 3, 6, and 9 month markers,
And, ultimately, a month’s worth of planning at the end of the year.

Long story short:

I’ve done this two years consecutively now, and will be doing it again this coming year.

Yes, I spend time every single day, for the entire month of December, planning the entirety of the following year.

This has dramatically changed my life for the better. This is what I want to get across to you. The seemingly radical and extreme act of trying to exert more control over my life than I ever had, more than I ever thought possible, was exactly what I needed.

Thinking about how you want the next year to go is one thing if you do it for a few minutes. Or an hour, or even a day. I’d beg almost nobody even spends a full day. I spent, at a minimum, thirty minutes a day, with a Google doc in front of me,

For thirty days.

As they say, let that sink in.

Let the gravity of that dawn on you.

I worked on a yearly plan every single day for a month. In that time I surveyed my life from top to bottom, gained clarity on where I was truly at, and searched for the roads that would reliably lead me in the right direction.

The difference between thinking out loud and living with a concrete document for an entire month is the refinement of thought. You drop the truly pie in the sky stuff. You permit yourself a small handful of longshots that are worth the risk.

You stratify the different areas in your life and start to see little ways they can be improved, and, even more importantly, you see that the big, serious improvements are actually made up of many small components.

And, because you are spending an entire month on formulating this plan, you don’t turn back in discouragement when you see that it’s actually many small steps and cannot be done quickly.

You simply assign each other those benchmarks to a reasonable increment of time.

Pretty soon, you realize just how much can be accomplished over the span of 365 days without any particular day becoming any more cluttered. Just spent differently.

Not just differently: more easily.

When I gave myself a month to plan a year, I was approaching time luxuriously. Not scarcely. Not frantically. As a result, I’ve been able to accomplish a tremendous amount of the goals I laid out for myself, two years in a row.

We’re out of time for today, but I’ve accomplished my mission:

To introduce you to the idea of long term planning, and to lay the ground work for more informative conversations in the future. I want to get into the weeds with you on this. And, more importantly, I want to teach you to do this.

But this is where it has to start.

Thanks for your time, talk to you soon.

Jas