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The Lever #043 - Planning (pt. 1/3)

All of your time, no matter what activity you are doing, is spent doing one of three things.

1. Planning

2. Performing

3. Problem Solving

To be effective you should work to master each of these skills.

You plan the thing, are present when doing the thing, and have to problem solve on the fly when the thing goes wrong.

Lets look at each:


But first:

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When a ship leaves port how does the crew know what route to take towards their destination?

They have a plan. And it’s the same in your life.

You plan a vacation, your wedding, a work project. You plan what you are going to eat tonight, and what you are going to do tomorrow.

It is possible to over plan and leave no room for spontaneity or happy little surprises. You become rigid in your thinking and easily upset when things don't go to plan.

You can also have a total lack of planning. This leaves you totally unprepared and subject to the whims of fate. You are robbed of control and autonomy.

So what then is the right amount of planning?

At least enough to get you to the next step, but not so much that you ever take action.

While nothing goes exactly to plan you will always be better off with one than without one. You can even develop a contingency plan for likely hazards so that when it DOES go wrong you already have a plan about how to deal with it.

But while planning is important it is also entirely wasted without effective action. Spend enough time on it, but not too much.

How to Plan Effectively:

Ship's officers receive detailed training on how to create voyage plans. This gives them the safest, most favorable for the conditions, and economical route to their destination.

It is a four step system:

  1. Appraisal

  2. Planning

  3. Execute

  4. Monitor

Turns out this is a great framework for planning anything. Here is how it can be applied in your personal and professional life:


The first step in creating an effective plan is to gather up information.

You probably already have a rough idea about how you want to get to your destination, but before you leave is a good time to consider the risk, critical waypoints, and potential hazards along the way.

Having the right information can also make the voyage much easier. To sail from Miami to Los Angeles you could sail down past Cuba to Brazil, all the way down to Argentina, around Cape Horn - where the Atlantic and Pacific meet, creating massive waves and high winds - back up past Chile, Peru, Ecuador, and Mexico before finally reaching California.

Or you could sail down to Panama, transit through the Panama Canal which connects the Atlantic to the Pacific, and bypass that pesky South America entirely.

Gather up the information that will help you create an effective plan. Look at the risks and consider how you can control or offset them. Know what you are getting yourself into.

And don't get caught up in paralysis by analysis.

Personal Story - A lack of preparation cost me $35k in a property deal. We sold a property at a loss and because I didn't fully assess the risks and requirements of the deal, also became liable for taxes on the sale at the end.

Because the sale was at a loss there was obviously no money earned to pay these taxes. We had to take the money from our retirement accounts.

The deal cleaned us out and took years to recover from. All because we didn't fully appraise the situation.

Lesson learned.


First you get the info then you make the plan.

With all of the information you need ready to hand it is time to make your plan.

The first step in planning is to know where you are now, and where you want to go. It's trite, but if you don't know your destination any route will take you there.

Planning a voyage at sea starts out on a small scale chart. If you were sailing from New York to London you would start by looking at chart where you could see both your current location and destination. Then you can (almost) draw a straight line connecting the two. Think 10,000 foot view.

While this is a great start the trouble with it is that you just can't see much detail from that high up. The reefs, rocks, and risks need a closer look. So you zoom in and start to adjust your plan accordingly.

Now you can add waypoints to your plan; specific points you need to hit before adjusting course and moving to the next one. By shortening the distance between waypoints you keep a close eye on your overall progress and can easily gauge how far you've come.

Finally you will assess the risks along your route.

If your course takes you through a narrow straight you might mark that on your chart. Then as you approach the area you'll remember to post an extra lookout and maintain a heightened sense of vigilance while going through.

You could also come up with alternate routes to take, or impose conditions that must be met before going attempting the passage.

Coming back to 'rounding the Horn, the best time of year to do so is between November and March when the waves are not as angry. You could plan your voyage then.

Having a well charted course will get you where you want to go. And having a fallback plan for when trouble arises will make sure you are ready for whatever may come.


With a plan in place its time to cast off the lines and set sail.

Because a plan without action is only a dream. It will never take you where you are trying to go.

More on doing the work in the next issue.


With the ship underway you now need to monitor your progress in real time.

There are no roads at sea. No lines to stay between or signposts to let you know how far you've come. Instead, you need to continually monitor your location using GPS, dead reckoning, or by the stars.

Constant awareness of where you are on the chart vs where you are in the ocean is critical to ensuring you reach your destination.

Plan For Your Future Self

Proper prior planning prevents piss poor performance -Unknown

A good plan is a gift to your future self. It allows you to show up in the moment prepared and ready.

Conversely, a lack of proper planning means that when the time comes you struggle to make one on the fly. You may succeed or you may flounder.

But time spent in preparation will always pay dividends.



When you are ready, here are a few ways I can help:

1. Subscribe to The Lever (if you haven't already)

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This short course will teach you the fundamentals of a powerful timeblocking system to make sure you never miss an obligation and always show up prepared. Give yourself the space you need to create the life you deserve.

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