in Success Algorithms

How to ensure you’re moving in the right direction with your plan


One of the things I hate most about productivity advice is that people tell you what to do without going into how to do it.

Take planning for instance… there’s a lot of info out there on how you should start with a plan, but few share their process in detail. And to make matters worse, when you seek out instructions on how to plan, you end up with a default method that leaves quite a bit to be desired.

The guessing-game plan approach

A key issue with most instructions on how to plan is that it prompts you to brainstorm and look forward into your future in order to guess your next steps. What this means, though, is that as you progress there are more and more possible steps.

This poses is a problem for 2 reasons. First, if your plan is new or big enough, you’ve never been where you’re going you’re uncertain of the right choices (step 1 – do this, step 2 – now what?). Second, having an increasing amount of options for next steps as you progress invites indecision. 
 So how then does one solve this problem of facing the paradox of choice at every turn?

The answer is to plan backwards.

This is a solution that stemmed from academia (to the best of my knowledge). It’s a practice where teachers plan lessons by looking at what the student should know by the end of the class.

So how do you plan backwards?

Here are the bullet points.
 The way that I do it is with a mind map:

  1. On a blank piece of paper, write out your final outcome and draw a circle around it. (E.g. Launch a newsletter).
  2. Then ask yourself: What do I need to have in place before I can reach this final step? (E.g. a list of interested people, a subject Area and topics, and a way to deliver the newsletter to them).
  3. Draw out lines from the main outcome to these intermediate outcomes.
  4. Circle them and repeat the process as you did with the first outcome
  5. Continue in that same manner, working backwards till you reach your clear first steps.

A few things to watch for:

Make sure you clarify at each step what you have to do to make that outcome demonstrable. You should be able to say in a sentence or two how your intermediate step contributes to the final result. And, having steps that you could show in a demo keeps you honest so you don’t create busy work.

Also, take the time to differentiate between one-time outcomes and repeatable tasks. (E.g. Setting up my mailing system versus writing new issues weekly).

Then, add deadlines where applicable and that’s it you’re done.
 Actually, not quite.
 To ensure that you carry out the tasks, you also need a system to manage those tasks. And this is where to-do lists come into play.

Use your to-do list to focus your efforts

The mistake we make with to-do lists is that we use them in an undirected way. We generate them without putting enough thought into how they’re going to get us to where we’d like to go.
 If you tried the steps above, you now have a plan in place. Your to-do list can serve more as a GPS to guide you towards your results.
 But you need to use a system. It doesn’t matter what system you use as long as you have one. It could be pen and paper, a check-list app, or a full-fledged task manager.

As an example, I use an app called OmniFocus. It’s a personal task manager in the apple ecosystem. (Comparable apps would be “things” or “Todo-ist”, or any other to-do list manager). It allows me to create projects, nested sub-projects, tasks, and subtasks. I can also put in repeating tasks, deadlines, and alerts to let me know when to start. It also allows for easy editing so that I can adjust my plans when life happens.

In short, I can recreate my mind map in my task management tool just as I captured it. And that’s why those are features worth looking for in whatever tool you consider. You don’t want to waste time trying to force your plans to conform to a tool or manage a separate calendar.

You want to go to one place, and at a glance, know what you have to do and how it leads you toward your outcome.


The beauty of a backwards plan is that it’s shaped like a pyramid. You start at the end goal at the top and work your way down. In this way, at your first level, you might have a bunch of tasks but the list only reduces from that point on.

Paired with a good system, you can be confident that you’re moving in the right direction at all times.

If you’re not planning and using a task management system, you should consider it. We tend to procrastinate, get distracted, and lose motivation when we’re unsure of our next steps. That uncertainty increases the chance that we might get derailed or sidetracked before we reach our outcomes.

So to ensure that you’re moving in the right direction with your plan, map your way backwards from the outcome you’re after to where you are and work your way forward and adjust your plan as necessary till you get to your goal. And that’s all there is to it.

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