Why Is Planning So Challenging?

Plan ahead; be prepared. Apart from that magical time around New year’s, planning is often forgotten.

The problems surrounding planning are:

  • Presence – how can you remain ‘in the moment’ when your thoughts are occupied by the future?
  • Foresight – hindsight is twenty-twenty but there are no certainties in the future so how can you prepare for what it has in store?
  • Keep track – you’ve planned ahead but how do you stay on the right path?

You need to strike a balance. Most of your time should be occupied by the present, though failing to plan is like a ship with no destination; aimlessly floating about the seven seas.

Also, reassess often and adjust as things change. Regular reminders, like mobile apps, can help with accountability.

Like a captain uses a map and a compass to find land, planning helps to guide you toward your goals.


4 thoughts on “Why Is Planning So Challenging?

  1. There are various ‘frameworks’ or methods out there to help people with planning. One I’m an advocate for (where appropriate and where it works for people) is using Scrum. At a high level, you plan out large things you intend to do further out in the future with little focus on detail. For things you plan on doing sooner you break those down into small chunks. Like you mentioned, on a regular cadence (like once a week) the , Todo list is reviewed (the backlog) making sure the next items are the highest priority and of an ideal size that’s able to be completed before the next backlog review. Let me know if you’re interested in more.


    • Thanks for your comment, Coach Nate.

      Do you find this system holds you to account? Also, how do you approach the length of a goal? I.e how far in advance should/could you plan?


      • Funny you ask. Ever heard that saying “those who can’t, coach…” Yeah, something like that. I’ve learned over time that i need external motivators -just how I operate. Need to clean the house? Schedule friends to come over. Car needs work? Plan a road trip. Sounds ridiculous, but that’s what seems to work.
        When I’m helping other folks arrange and organize their work, though… I can break it down no problem and help them find tactics to stick with it.
        When I’m helping others out I try to keep things that are likely to be finished further out more vague, because plans change. As time gets increasingly closer, you regularly look at the horizon and refine the details. I wouldn’t try to plan out more than say about two weeks worth of details.


      • Yes, I’ve heard about this. Gretchin Rubin talks about how there are people who rely on internal motivation while others need external things to keep them to account.

        Interesting. Two weeks is quite a short time frame. But like you say, the longer term plan is there it just hasn’t been fleshed out yet.


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