The Ultimate Guide to Your Planning Mental Game

By Alicia Cohen

Yes.  Just yes.  A planning mental game?  What??  Yes.  Just trust me on this one.


Have you ever even considered that planning has a mental game aspect to it?  It may sound strange, but it’s totally true and totally important!  In this ultimate guide, I am going to take you through an in-depth look at how to approach your mental game, when it comes to planning, to take your planning to a whole new level.  There is so much “mindset stuff” that goes into planning, and if you’re not accounting for it (or even aware of it!) then you are missing out because your planning simply isn’t going to be as powerful as it could be!  Powerful planning leads to powerful results -- like reduced stress, increased time, and more!  So, let’s get some of that, shall we?  Oh yes, please!  After reading this ultimate guide, you’ll be ready to elevate your planning to a whole new level of awesomeness, with your sharpened planning mental game, so that you get the best planning results possible for creating your intentional life of meaning, peace, focus, and calm!  Ready?  Let’s go!


Real quick…..before we dive in, if you’re just ready to get started ASAP, then click below for my FREE step-by-step roadmap that takes you through the six steps that you need to consider to go from living a chaotic life to living a calm life!

To keep things organized, I’m going to break your mental game for planning into three areas: doing your planning, living out your planning, and reflecting on your planning.  We’ll go in order!


Area #1: Doing Your Planning


This phase of doing your planning is just what it sounds like -- sitting down to actually plan out your day, week, etc.  When it comes to your mental game (which I’ll also refer to as “mindset”) for planning, there are a bunch of different elements to take into consideration.


Git’er done with your planning because your future self will thank you.

Let’s face it.  There are days that we just don’t feel like planning, right?  Maybe we’re tired.  Maybe there’s a lot going on.  Maybe we lack motivation.  Whatever the reason, sometimes putting in the time and effort to get our planning done is hard.  It takes work.  However, we’re starting with this piece of the mental game because if we don’t do the planning, then there’s nothing else to talk about!


Personally, I like to plan the night before, but being a “morning-of” planner works just fine, too!  Whatever the case, I know that 100% of the time, I feel better when I have my plan ready to go.  On the days that I didn’t do my plan ahead of time, the first thing I’m doing in the morning is scrambling to get my day planned.  With two little ones, this is rather challenging and stressful.  On these days that I haven’t planned, really, my day starts me instead of me starting my day.  I really don’t like this feeling.  I feel unclear, foggy, and just chaotic.  On the flip side, on the days when I have my plan ready to go such that I just open my planner book and see what the day holds, I feel a million times better!  So, this being the case, I am naturally very motivated to have my day planned ahead of time so that I can go into my day feeling confident, calm, and focused.


As such, for this first mindset piece of doing your planning, it’s quite crucial that you set yourself up for success to just “git’er done.”  Remind yourself that your future self will thank you for preparing yourself for your day by planning.  Be ready to combat any excuses that your brain may come up with to prevent you from planning.  I’m tired...I don’t feel like it...etc.  Again, remind yourself how much better you’ll feel and how much better your day will run with your plan in place.  Some days, you may need to just drag yourself kicking and screaming to your planner and force yourself to do it.  On those days, remember to thank yourself for being good to yourself by getting your planning done, even when you didn't want to.  It’s a big deal to get your plan done, especially when any and every excuse is popping up to prevent you.  


Practically speaking, though, figure out what you need to do to get your planning time in place.  We don’t want it to be so hard everyday.  That’s just not sustainable.  We want planning to just be part of the flow of daily life.  If you’re a “night-before” planner, maybe you need to start earlier in the evening before you get so tired.  If you’re a “morning-of” planner, maybe you need to wake up a few minutes earlier so you get a few minutes of quiet in order to get your plan done.  However it is for you, be sure that you’re taking a look at what you need so that you can have the time and energy to plan each day without needing to expend that much extra effort.


By the way, do you plan in time in your planner to PLAN??  If you are not doing this, do yourself a big favor and start today!  Literally, as one of your items to do on your planner each day, write “plan.”  Again, your future self will thank you! 


The grass is always greener where you water it.

Another piece of the mental game to check ourselves on is if the commentary and such running through our heads is serving us or hindering us while we plan.  Do you have any self-defeating thought patterns, comparison games, guilt, etc. that creep in while you’re planning?  If so, time to start making some mental thought swaps!  You probably have heard the expression “the grass is always greener on the other side.”  Well, I prefer the expression that gives a twist on this expression that says “the grass is always greener where you water it.”  And, it’s so true!  Forget about the grass being greener on the other side!  Focus on watering the grass around you, and it will become greener!  


For example, as you’re planning, you may be thinking, “Oh man.  Jane next door just took up underwater basket weaving.  Why am I not doing cool things like Jane?  And Sarah across the street always has sparkling countertops and floors.  Why is my house not sparkling like Sarah’s?”  But what good is it watering the “grass” of Jane and Sarah?  You do you.  Water your own grass with affirming thoughts.  Maybe it would look something like, “I like reading.  I managed to read that new book I’d been eyeing last month.  I enjoyed that.  Hm.  Let me see where I can plan in some reading time for myself.”  Or, maybe it would look something like this, “I really didn’t want to tackle the huge stack of papers that needed to be gone through, but I did it!  I sat down, went through them, and now the task is done.  And, honestly, it wasn’t quite as bad as I’d worked it up to be in my mind!”


So, water your own grass.  Don’t concern yourself with what other people are doing, especially when it comes to creating your own personal plan in your planner.  You plan you.  That’s what counts.  When you make the mindset shift to just focus on your own plan and not get wrapped up in the plans of others, you are watering the grass around you, which will pay off.   


Replace “have to, have to, have to” with “choose to, choose to, choose to.”

This next part of your mental game strategy is intended to really empower you.  Have you ever noticed if you are stuck in the "have tos"?  Do you find yourself saying to yourself or others, “I have to do this.  And, I have to do that.  Then, I have to do this other thing.”?  My challenge to you here is to catch yourself stuck in the “have tos” and upgrade the way you talk about your life to “choose tos.”  Even if it's something that you don't want to do, can you STILL choose it?  How does this shift feel? Personally, I feel like I have much more power and control when I switch from the "have tos" to the "choose tos."


For example, if I say, "I have to change my baby's diaper." -- that just feels like “ugh.”  And, technically, I don't HAVE to do anything, including changing his diaper.  However, I want him to have healthy skin and minimize any diaper rashes.  I want him to smell clean.  I want to take good care of him in this way.  So, I actually CHOOSE to change his diaper (even though I don't really want to!!!) -- and, when I approach it from this angle, it makes a world of difference to me in how I feel about the less pleasant tasks of daily life!


So, for this piece of your planning mindset, try on literally switching your vocabulary to talk about choosing to do something.  My guess is that you will feel way more empowered about your day, especially when it comes to doing tasks that you don't really want to do.


Choose between good and good.

Do you ever find that there are so many fun and interesting things to do in life? Volunteer with your local moms' group, volunteer to run the Girl Scout troop, volunteer to be on the PTA board, volunteer to coach your kid's soccer team, volunteer to be on your neighborhood's HOA board….the list goes on and on!  Then there are hobbies -- take the dance class you've been thinking about, read the next book on your booklist, try that new artisan bread recipe that your friend recommended, train for the half marathon that you’ve been wanting to do.  And ideas -- renovate the bathroom, start a book club for your neighborhood, participate in your local CSA.  And social events with family, friends, and otherwise.  And activities for the kids.  And vacations. And...and...and!  Sure, there are things on your calendar and to-do list that you don't want to do, but for this next piece of cultivating a helpful mindset, we need to think about choosing between good and good. 


As we all know, when we have too much that we're trying to accomplish in a day, it's just stressful and really rather impossible.  We end the day feeling defeated.  So, as part of our planning mindset, we need to keep tabs on all of the things that we are saying yes to, and along these same lines, we need to be mindful of saying "no" to good things.  As much as we may want to do all of the good things, there just isn't enough time in the day.  So, we have to make the hard choices sometimes between good and good. It's important that we do this because It will keep us from getting overwhelmed.  Overwhelm and stress don't keep score as to whether or not something is good or bad.  Overwhelm and stress just operate in the relationship between the amount of time you have and the amount of commitments you have.  While having things as part of your life that are undesirable or unpleasant certainly contribute to your stress level more, you can end up just as stressed by having committed yourself to too many good things.


Take a look at your commitments.  Have you said yes to too many good things?  Are there any good things that you are able to cut out of your life either immediately or sometime soon?  Then, moving forward, be aware of how many good things you are saying yes to.


Harness the power of weeding and deferring.

This element is similar to our last mindset piece.  In addition to monitoring what we’re committing ourselves to, we also need to monitor what we have on our to-do list that needs to be done now.  The truth is there are items on your to-do list that don’t need to be done now….or maybe at all!  Everything on our to-do list can tend to feel urgent, or at least important, right?  Here is a new mindset to cultivate: it’s not all the same priority.  I know that this might sound obvious, but we land ourselves in the stress lane when we live rushing from urgent thing to urgent thing because we’re just trying to get it all done.  Don’t try to get it all done today or even this week.  Start the habit of weeding through your list -- what is on your list that you can just cross off right now because it either doesn’t really need to be done or is just really not worth your time and effort?  Then, with the tasks left on your list, what can you defer?  Map it out!  Plan tasks for next week, next month, next year, etc.  Even plan some tasks for “someday.”  Again, developing this mindset that not everything is of the same priority level is important to decreasing your stress level.  As you’re doing this, only weed and defer what you feel good about doing so today.  No need to be drastic (unless you want to), but find some relief in deferring tasks.  They won’t be forgotten.  You will get to them in their due time, but that time isn’t right now.



So now that we have made choices between the good and the good, we have weeded through our to-do list to remove what we can, and deferred what is not important for us to be taking on now, let's talk about underplanning!  Underplanning is a toughie but goodie.  I will tell you now, you are most likely going to not want to underplan.  If you're anything like me, you will want to squeeze in what you think is just the right amount for your day.  I challenge you, however, to try on the mindset of underplanning.  And really, what do you have to lose?  Let's say that you underplan, and you accomplish everything that you wanted to in your day.  Now, you feel accomplished, productive, and successful.  How amazing is that?!?  And then, you get to choose -- you can just rest and bask in the wonderfulness of a well-planned and well-executed day, or there is nothing stopping you from taking on another item or two that you had left for a different day.


I mean, really, is there a reason NOT to underplan?  I can't think of one.  But I will warn you again, it is a tricky skill to master.  Think of underplanning as a muscle.  Each day that you work at it, you will be building that muscle and making it stronger, and overtime the hard task of underplanning will become easier and like second nature. However, at first, it can be a real bear to take on.


So, try this.  Pick a certain number of tasks that you will allow yourself to take on in a day.  Then, try out that number.  Was it too much?  If so, the next time that you plan, decrease the number.  Again, was it too much?  Keep doing this until you seem to reach your underplanning threshold.  Then hold there for a week or so and see how it feels.  What do you notice in your life?  What do you notice about how you're feeling?  My guess is that you will find that you feel really great for what you are getting done and have none of the pressure and stress like when you plan too much for your day.  And, my guess is that you are probably still being really productive, while also focusing on what matters, even though you are underplanning.


See, the thing about underplanning is that it helps us to actually achieve the Goldilocks "just right" amount of planning.  However, for us planner-mamas, we oftentimes need to shoot for underplanning in order to achieve "just right."


This might just feel like a bit of mental trickery, but again, it’s an important one.  When you find your rhythm of underplanning, you will be set!


Area #2: Living Out Your Planning


Now we’re going to get into the mental game areas that impact how we actually show up in our day-to-day lives when we’re carrying out our plans. 


Plan your work, work your plan.

So, you’ve gone to the trouble of planning your day, right?  You’ve “planned your work.”  Don’t self-sabotage by then not following your plan!  Sure, “stuff” may come up, but for the most part, commit to actually doing what you have planned for the day and not deviating much.  Commit to “working your plan.”  This takes intentionality, for sure.  As much as you possibly can, stick to your plan, and don't let yourself get derailed.  Get in the mindset that you have made your plan for the day, and that's what there is to do.  Anything else can wait and be planned for another day.  Use your plan to help you.  Don't get sucked into the trap of "putting out fires."  Use your plan to keep you focused and remind yourself that whatever else comes up can wait for another day.


Unpleasant tasks don’t age well.

By definition, unpleasant tasks are….well….unpleasant!  And, if you’re anything like me, you probably don’t particularly enjoy doing unpleasant tasks, right?  So, here’s a mental game challenge for you to take on: when you don’t want to complete a particular task or find yourself procrastinating, remind yourself “unpleasant tasks don’t age well.”  In other words, if you don’t want to take out the trash at 7:00pm, are you really going to want to do it at 10:00pm?  Probably not.  The earlier in our day that we complete the unpleasant stuff, the more likely we will be to actually carry out and finish these types of tasks.  So, again, whenever you find yourself stalling, remember: “Unpleasant tasks don’t age well.”  Then, go accomplish whatever that task is because you’ll feel great for getting it done and out of the way.  And, really, that’s what we’re going for here in our planning mental game -- mindset shifts that lead us to approach planning differently such that we’re more effective and calmer.  This mental game shift will bring you one step closer to that more effective and calmer existence!


Do a midday refresh.

This piece of your mental game is intended as a sanity-saver.  If you don’t already, make sure you’re checking in with your planner throughout the day to stay on track.  If you’re finding that part of the way through your day that things are just not what you hoped, for whatever reason, cut yourself a break and then take five to ten minutes to refresh your plan.  Move items to another day that juuuust aren’t going to get done today.  Figure out what’s realistic for you to still take on for the rest of your day, and then, just do that.  Forget the rest.  Again, move it to another day and move on.  You will feel much more peace when you’re not racing to accomplish all of the originally planned things in a day where there just isn’t enough time remaining to calmly do what you had originally hoped.  Allow yourself to do this midday refresh so that you can squash any overwhelm that’s cropping up and finish your day strong!  


Stop using your brain as a container.

This next piece of your planning mental game is part mindset and part habit.  Our brains are not meant to be containers.  Our brains are designed to create, problem solve, come up with ideas, analyze, etc.  But, be a container?  Nope!  Not a good use of our precious brains!  When we fill our brains with clutter -- reminders, to-dos, appointments, etc. -- there isn’t space for doing all of those other important functions that our brains are designed for!  So, adjust your mindset (and your habits) so that you stop using your brain as a container. When we try to hold too much in our brains, our brains can't rest, and this is stressful and overwhelming.  It is best to allow our brains to be the empty containers that they were designed to be.  When we do this, we will feel better in our day-to-day lives.  Start a practice where you write down whatever is swirling around in your head so you're not having to track it.  Your mental peace and clarity will thank you!


Replace busy with full.

This is another mindset piece that involves a word swap.  As you are going throughout your day, do you have a mental tape running that’s chattering about how busy you are?  I want you to stop thinking of yourself as “busy” and start thinking about having a “full life.”  Is it just semantics?  Eh, not really.  The words we use matter!  To explain this further, here’s a very relevant excerpt from a blog post I wrote that takes a deeper dive into this topic, and I think it’s worth sharing the excerpt here for the purposes of this ultimate guide.  (By the way, the blog post is called “Are You Really THAT Busy?”).



When was the last time you began (or ended) a sentence with "I'm so busy" and then immediately felt empowered? Never, right?!? Maybe you felt somehow justified in your declaration of busyness. Maybe you felt like you had a "competitive edge" of sorts over someone else because you perceived that you were busier than she was, but empowered? I'm just not seeing it. I wager that if you're TRULY honest that you have never said "I'm so busy" and then felt empowered, strong, and ready to take on the world.  But this isn’t a surprise because "busy” is a word that disempowers us consciously and unconsciously!  Here’s why...


Busy is an indirect, non-specific word we use -- and please note that your use of the word “busy” is likely unintentional and something that you’re probably not even aware that you’re doing! -- to describe the state of our lives while conveniently being able to avoid taking responsibility for our choices.  Really, busy is a euphemism -- a “nice” little word we say to cover up taking ownership over the state of our lives because taking responsibility would be unpleasant or embarrassing!  But remember, in many cases, I’m guessing a lot of you reading this aren’t even aware that you’ve been doing this!


It’s important that we put “busy” in its place and change how we approach busyness so that it stops sucking our joy and sapping our energy.  


And, it’s important that we stop using “busy” to condone our stress levels because this just isn’t healthy for us!



Take a big leap forward in your planning mental game here.  Make the word swap.  Empower yourself!


Area #3: Reflecting On Your Planning


Phew! Congratulations on making it to the third and final area of our planning mental game! Fortunately, for this area, there is only one element to our planning mindset.


Continual reevaluation of your system/process.

The best way to be successful at optimizing your planning system is to engage in continual reevaluation of the system and processes that you’re using.  Start cultivating the mindset that ongoing reflection is a good and necessary thing.  Make plans to tweak, try things out, reflect, tweak some more, try things out some more, and so on and so on.  Even once you’re in a groove and happy with your planning system, still engage in this ongoing reevaluation (perhaps less frequently) just to keep things in proper working condition -- kind of like an oil change for your car.


So, there it all is! All the pieces that you need for a top-notch planning mental game! When you incorporate the mindset shifts needed in doing your planning, living out your planning, and reflecting on your planning, you are naturally going to be well on your way to a significant shift in your planning system for the better. Now that you are rocking the planning mental game, hop on over to my free download which will take you through the other crucial elements for crafting how you plan to rockstar level. My Chaos to Calm Roadmap will lay out the steps that you need to continue your journey! Click below to get on it! See you on the flip side!


Heeeey, Sweet Sister!  I'm Alicia, and I'm so excited that you're here!  I love a lot of things in life, but at the top of my list are my wonderful husband, my two precious kids, and helping other planner-mamas get back their joy and peace in life through intentional, functional planning!


Are you feeling frazzled?  Stuck?  Overwhelmed?  Exhausted?  I get it.  I've been there.  It would be my privilege to help you create a new reality for yourself!


​Click below to get started with my step-by-step guide!