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10 Steps To Better Planning


I soon got to go pick up my car after its first oil change since we got it. This definitely changed the rhythm of my morning since I had to get my car there between 7-9 AM. Early. 


How you manage your time is a big indicator of success to me. The more disciplined I am, the better results I get out of life. Especially as each project gets more complex. I’m in the process of learning how to use Notion to manage my life. 


Anyway, once upon a time I stole some ideas and worked out 10 rules to planning/time management. So here they are. I hope they help you get a handle on time. If you want a one on one coaching session and have a budget, holla. 


1 - Use digital tools


For some of you this is a no brainer. For others it’s an argument. End of the day, you can start with a pen and paper. I know some people refuse the digital world when it comes to organizing and I’m not here to stop you. I am here to say that if you really want to be efficient, you need something that syncs to all of your devices.


As much as an old school agenda is fire. If you were to take a pic of it, OCR the text out of the image and import it into something digital, you’ll be winning. In all cases search beats browsing through pages of a notebook. Once you set up your digital tool (which may take time) you will be super on point. 


You’ll use this tool to prioritze tasks and projects and this tool needs to link to a calendar in some way. Without a calendar you get no reminders. 


2 - Understand your regular commitments


This is where the work starts. You need to be honest with yourself and map out, in detail, all the tasks you do. In your chores category this may include dishes and laundry. For work, it may be a regular report you must deliver each week. In my case I can add exercise, reading and daily blogging. 


This work represents your “whirlwind” (Read The Four Disciplines of Execution). Basically this is not work that advances your ambitions or goals. It’s all the other stuff you have to do on an ongoing basis. Spoiler alert, you are trying to see how much time you actually have for projects. 


Since this giant pile of tedium is here either way, understanding how much time it takes gives you a lot of power. A lot of our planning failures come from underestimating the whirlwind. 


3 - Add plan/schedule maintenance to your whirlwind.


You have to take time every week to review your list of work. You will have accomplished some of it. New tasks will appear. Ideally you can retroactively map out how your week really went versus how it was planned. Then take time to decide, during your dedicated planning time, what you are going to accomplish in the upcoming week. 


The rest of the tasks you get throughout the week, add them to a “parking lot” (a list of to be organized work) of sorts. These items will be managed in your next planning session. Obviously some things that pop up are top priority.  You are likely wise enough to recognize what’s urgent and what can wait until next week. 


I did not maintain my plans for a year. Now it’s a giant mess of ideas that may take me 2 months to sort out. The last time took me seven 2-hour sessions. Once the mess is cleaned, it takes like an hour.


4 - Define the roles you play in your life


When you come up with your various lists of tasks, each one will correspond to a role you play in life. This blog thing is part of my entertainer life. When I sell promo, the work associated with that is under the role of “salesperson”. Ultimately there are a few main categories that all of us are part of:

  • Work 

  • Home

  • Side hustle

  • Romantic partner

  • Parent

  • Community member

  • Etc


When you look at your life through the lens of roles, you can start to make sure that when you plan out your week, nothing gets neglected. You can see if you made any time to watch a movie with your girlfriend or left any time for recording music. When it’s just the whirlwind, certain things may be ignored.


5- Determine your priorities


This one is pretty straightforward. Think about your goals. Look at the roles you play. Decide what the main three things you are trying to accomplish are. As an example for me:


  1. Make more money

  2. Share Knowledge

  3. Get Healthier


As I go through my work, and proceed to step 6, I will have to keep those 3 goals in mind. If what I am doing is not related to those 3 things, it’s a waste of time. Your priorities can be whatever you want. Once you pick them, they should govern over your decisions to work on different tasks. 


6 - Now is the time for “To-Do” lists


At this point, you have a sense of what your life looks like at the top level. You know what you are trying to do. You need to still come up with the projects, and tasks that make those projects, that will bring you closer to your goal. 


Instead of worrying about projects for now, literally just make a bunch of general “To-Do” lists. You can plan for extra planning time to organize your lists as you go. You should manage these at one shot in your weekly planning session. 


A lot of the time when we make these lists we get distracted. It’s better to spend a solid 30-60 minutes focused on listing all the work. Then deciding what work needs to be done. All those little distractions make it take way longer to plan accordingly. Focus on making complete lists that track the minutiae of your life. Then dedicate time to getting the work done. 


7 - Live, review and improve those lists


Chances are, all your initial time estimates were trash. As you live life, you need to map out how long it takes you to do things. Track how successful your planning efforts were. It may feel like nothing moves forward for a while, but you are still building your efficiency foundation. 


One of the main things you need to look for as you live regularly is which tasks should be delegated. Determine what work you actually have to do and what work can be moved off your shoulders. Chances are you hated that work anyway and can make more money by paying someone else to do it (once the ball is in motion). This is a key part of scaling up. 


Also be honest with yourself about what work is not getting done now. We far too often clutter our lists with tasks we never had intentions of doing in the first place. Learning to identify the difference between wishlist items, items to delegate and items you will work on now is going to make you more successful. 


8- Structure your work into specific projects


Once you understand what work you are going to do, and what work is going to be delegated, you can create real ass projects. It probably takes a few weeks to get to this point. However if you really are in tune with yourself, step 7 is pretty fast.


Projects help your lists of tasks take shape into something bigger. Here you have real KPIs in place to measure success and are now pursuing success in a more meaningful way. Project management is definitely worth looking into. While project mapping takes some time, it will help you bring any idea to life. 


Projects will also involve other people most of the time. Since at this point you know what work needs to be done, and you know which parts you won’t do, you can actually recruit team members that bring value. Still you need to know where to focus your efforts. 


9 - Determine the level of effort 


Every task on your list has a level of effort associated with it. This is split between how long it will take to complete and how hard it will be to complete. You need to make sure to give everything a grade on a scale like from (1-5). Then do the same thing with the reward for each task. How much are you actually getting back from completing it, and how long will you receive it? 


Once you have completed that exercise you will be able to see which of your projects will return the most reward for the least effort. It’s pretty visual and helps provide clarity in group settings. Especially when this is decided as a team.


If a group of people make these determinations, the group ends up deciding what to work on first with far less argument. 


10 - Thin out your weekly To-Do list


Chances are you have been assigning yourself more work than you can complete. As time goes on you get better at understanding how much work you will really do when life hits and the planning session is done.


You should organize your tasks into two main categories. Stuff that you do now (Your whirlwind and highest priority items) and stuff you will do later. Any non-critical new item on your task list goes into later and is dealt with when you do your weekly planning.


Your goal is to be honest and think out that list so that you can actually achieve the perfect balance of assigning work to achieving it all. Without guilt.


Basically if you focus on building your plan/calendar over time you will find more time for recreation. In fact don’t forget to plan recreational time. 

Well that’s my first draft at a quick 10 steps to planning. Let me know what you think.


Live Long and Prosper Everyone

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