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