Struggling to meet your goals and deadlines?  Learn 6 powerful strategies for becoming more effective at planning.




Doing planning on a regular basis may not sound sexy, but it definitely increases your odds of getting what you want in life and making things go a whole lot smoother.

Hey Everyone, it’s Dr. Karen Kendrick, and welcome back to Mastery Now. 

I know as I record this, we’re actually already mid-way through the year, and so I think this is always a good time to take a step back and take a look at where we are and how we’re doing against perhaps whatever intentions or goals that we may have set up back in January. 

And I also know with things moving and changing so rapidly all around us right now, it can really be easy to feel less in control about what’s going on in your life and whatever it is that you wanted to accomplish this year. 

So I thought it would be useful to do an episode on planning. 

Now, planning may not sound that sexy, but when done right, it really can give us a huge sense of confidence and much more control over many aspects of our lives, including our finances, personal goals, social life, time and so on. 

And yet I know that for many people, that’s not really something that many of us enjoy.  It can feel tedious and boring.  It requires thought and discipline and focus.   And it also requires time, which I know many of us feel time crunched, and so it isn’t always easy to fit it in.  And so although we may plan for parties or weddings or vacations or funerals or our kids college expenses, we often don’t get really good at planning our days and our weeks and our years because we just don’t find it enjoyable or because we just don’t have a good feel for how to really do it well. 

So what I want to do is walk you through some principles and tactics for getting good at planning on a daily, weekly, monthly, and annual basis.  Now, the strategies for each of these timeframes is going to be slightly different, but we’ll talk about that as we go along. 

Now, I also want to point out that we’re primarily talking about planning in your personal life.  I’m not talking about in the context of a job where you might be doing planning for a team or a department or a business or a brand rollout or something.  So although a lot of these same basic principles apply, I’m really focused here on the personal rather than the professional. 

Now, I also want to point out that planning is really only one piece of the entire achievement cycle.  You know, when you think about achieving, it starts out with good goal setting.  You have to set up metrics.  You have to think about time management.  You have to think about resource management.  You have to monitor what results you’re getting, and you have to make adjustments.  You have to think about what productivity habits that you’re implementing and so on.  And so planning is really an integral part of that entire cycle. 

Now the first step to being more effective at planning is to set up your planning space.  So this is the physical area where you’re going to be able to sit quietly, spread out, get comfortable, and have access to the tools that you need.  So this could be a portion of your office.  This could be your kitchen table or dining room table.  This could be maybe even outside on a porch somewhere if maybe that works better for you. 

Wherever it is that you’re going to be comfortable, and you can spread out.  You can have things like your calendar, some blank paper, maybe a whiteboard, or a computer or laptop if you’re going to need to research or type things up or whatever.  But you’re needing to set this up in such a way that it’s going to be your “go to” space that you visit regularly for planning purposes, and you’re going to make it a habit and a routine. 

So, the goal here is you’re really making something that you’re not going to dread going to each week.  You’re not going to associate it with drudgery and boredom and discomfort.  But instead, you’ve got a comfortable chair.  You’ve got room to spread out.   It’s quiet.  It’s functional.   You have everything you need right there.  You don’t have to dig for things.  And that you’re going to be ready to go when you get there to start doing your planning.

Now one thing that could help with this, this is just a little tip, sometimes if you need more motivation to go to that space each week.  One little trick that I use sometimes is just to add in some other pleasant element like maybe having a nice cup of tea or some certain snacks that you only bring out when you’re doing the planning.  In other words, it’s almost like a reward for getting into your planning space on a regular basis. 

And so you start to associate this time and this space with something pleasant, something that you look forward to, like the tea or the snack, or maybe it’s certain music that you put on or whatever.  But it’s really something good that you associate with this space.  And it also creates the sense that you’re doing something for yourself that’s good and/or for your family.  And it’s something that gives you that greater sense of control and confidence. 

So the second strategy then, to do more effective planning, is to start with the big picture of what you want your year to be about and work down into the details from there.  So we’re really talking about setting some goals here.  So what I really want you to do is just ask yourself, “What is it that I want to happen this year and what do I want to get done?”

And so I recommend just sticking to about one to three big ideas or big goals here.  So examples of this might be things like finish paying off my student loan, finding a long-term relationship, launching a business, or finding a new job.

Now, you really need that big picture as a primary guide so that you can keep coming back to it as you go throughout the year.  That’s really going to help focus your attention and also keep you motivated. 

Now, I should point out that if it’s not the beginning of the year when you do this, it’s okay.  If you just have five months left or nine months left in the year, then just frame it as what you want to get done between now and the end of December.   

Next then, once you have those big goals, I want you to start looking at quarterly goals.  In other words, what you’re going to do within about a 90-day period.  And I would shoot for about three to five goals here per quarter at the most.  Sometimes it might only be one or two goals, and if so, that’s fine as well.  But the idea is you’ve got to be more specific than at the annual level and get down to what you can really do in a measurable 90-day period. 

Now, there’s a lot of different ways to phrase these quarterly goals.  You might consider them to be specific projects that you’re only going to do one time.  In other circumstances, it may be you’re expressing the quarterly goal as an ongoing part of your job that you do or an ongoing deliverable that you have to do every 90 days. 

Either way is fine, but I find that one of the most effective ways to do it is to frame it in terms of some deliverable, like complete XYZ project, finalized college tuition loan applications, sign up for three online dating sites, etc.  So it’s kind of tangible and there is a specific output or deliverable that you’ve got to complete. 

So next, after you have both these quarterly goals articulated as well as the annual goals, then you want to start to lay these out visually so you can see it all in one place.  So I recommend either a calendar grid if that works for you, or some single page of paper just in an outlined format.  So either way can work.  But bottom line is you want to see all of these goals in one place at a glance. 

Now again, some of these goals may be part of your work that you do every year and you’re just putting them on the calendar grid or the outline as reminders or placeholders of the main areas of work that you do on a quarter.  But just remember, whatever quarterly goals that you have, they do need to link back to those bigger ideas and goals that you have because otherwise what’s the point? If you’re doing a bunch of tasks and work and setting up all these quarterly objectives, but they don’t really link back to what you said at the annual level, then there’s a disconnect.  So you’ve got to make sure that in some way all of those 90-day goals link back to the bigger picture.   

Once you have those quarterly goals and the idea is then you’re going to want to start to review them about once a month.  Now, we’ll talk more about reviewing a little bit later, but I just wanted to make sure that you had that perspective. 

Now the next strategy is to look at your calendar for the entire year and fill in all the key dates.  So your goal here is to better understand when during the year you won’t be available as much to work on your goals, such as during a planned vacation, or when you’re traveling, or when you’re hosting guests at your house or anything else that may impact your normal focus on these goals. 

Now this doesn’t mean that nothing is getting done during this period at all, but it just means that you need to take into account the other things that are going on in your life.  And so by adding in all these planned events, you’re really going to start to see when you might start to have less time to work towards a specific goal and then plan accordingly to either step up your efforts before or after, and then possibly even move some goals farther out.  It really is incredibly helpful to see this entire year laid out before you and see the big picture. 

Now I realize that you may not know all your key dates yet, and so I would just fill in what you know and then add to it as you go.  And that’s really another key reason for why you want to keep coming back to your planning space regularly to review and add to and adjust your plans and dates as needed. 

Now, how granular you get here in terms of how many events you add is really going to depend on how much you think the event or activity impacts your ability to work on your goals.  So some people here might like to put every single person’s birthday, especially if they’re going to be having big parties or something.  Other people may just choose to put entire weeks when they’re going to be out of the office or when they’re traveling or whatever. 

But the main thing here, whichever way you choose to do it, is just to not put so much on there, not be so down in the weeds that you really start to get overwhelmed.  So if this starts to feel like you, I would try to think about removing some of those smaller items or events or at least possibly using some kind of color coding scheme to help you distinguish between major and minor events that can impact your time. 

Bottom line is that you really just have to be looking farther out in the future.  Most of us just aren’t doing planning far enough out.  We’re just looking at the 30 or 90-day period.  Or maybe we just do annual goals, but we’re not really doing quarterly goals.  So goal setting really works hand in hand.  You got to do them both annually and quarterly because the big goals, the annual goals, give you that big picture and inspiration.  And the quarterly goals break things down into manageable and tangible projects. 

Now, I should mention again that some people may find it helpful to look beyond 12 months, maybe even up to 24 or 36 months.  And if so, that’s great.  But again, for our purposes today, we’re just looking at that twelve month cycle. 



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So the next strategy, strategy number four, is to develop a habit of weekly and daily planning.  So once you have those annual and quarterly goals, you want to start disciplining yourself to plan your weeks and days.  Now, the weekly planning helps you get down to specific tactics and forces you to start focusing on prioritization.  And then daily goals breaks things down even further and reinforces that need to prioritize. 

Now, you may or may not have weekly goals themselves.  Some people just describe it as a list of stuff that has to get done that week.  Now others may define it as specific targets to meet.  So for example, sales people might have weekly sales numbers or weekly sales calls to make.  Or people working on a weight-loss program may have pounds that they need to lose for a specific week. 

So whether or not you define these weekly goals, so to speak, as targets or just a project list, I think it’s really up to you.  But the key with this level of planning is that you have to start looking at what you’re doing in a seven-day period and then tie that back to, again, the bigger picture of what you’re doing quarterly. 

If you don’t have the weekly and you just try to go specific to the daily planning, I think you’re missing too big a gap.  Trying to go from a quarterly 90-day set of objectives and really whittle it down to what you’re doing on a day-to-day basis I think can be pretty hard.  So that seven-day weekly look and plan can really be that bridge between what you’re doing quarterly and what you’re doing every day.  So I highly recommend that no matter how you define those weekly goals, whether it’s as a specific target or just a list, just do it and you will find that that’s helpful in your overall planning. 

Now, I think if many of you just fall into that pattern of only having weekly goals, but they don’t really tie back to what you’re doing or wanting to get done on the quarterly basis, then you really have to re-examine that.  You really have to go back and look at that.  Because if all your weekly and daily goals have nothing to do with what you said was important to get done by the end of the quarter or by December 31st, it’s going to be incredibly hard to expect that you’ll get those bigger goals accomplished. 

Now the other reason to do weekly and daily level planning, as I mentioned, is to force you to focus on prioritization.   Because there’s always going to be so many more tasks that we identify than we can typically get done, and it’s just too tempting to just go down the list without any real planning or prioritization or discipline to stick to doing the things that are really going to help you the most. 

So how do you do this? How do you do the prioritization? Well, there’s a lot of different frameworks out there, but the one that I like is simply this it’s either “critical” to do, you “need” to do, or you “want” to do.  Now it doesn’t mean that you have to personally do all these tasks yourself.  You may still delegate something, but it just means that this is what needs to get done. 

So again, the “critical” means that there are real consequences if you don’t do things that week or that day, like missing a payment or something, or falling behind on a goal, or these are really the most essential to helping you meet your goals.  The “need” to do category is also highly important, but it could slip a day or two if needed, or slip a week if needed.  And then the “want” to do is really more discretionary.  It really is something that if push comes to shove, they’re third on the list.  You really want to do them, but they may get pushed to the following day or week or whatever, and there’s not going to be as many significant consequences.  So this could be something like returning an non-urgent phone call or doing your exercise routine for that specific day or whatever. 

But either way, you’ve got to use some sort of prioritization framework, whether it’s this one that I’ve just described or something else.  But you do need to have a way to sort through all this laundry list of stuff that’s going to come at you every single day and do that prioritization. 

Now the next step is to do contingency and resource planning.  Now so far we’ve just talked about goals, and projects, and tasks, etc.  And prioritizing and sequencing those out against a calendar, while taking into account other events and activities that impact your time. 

Now we need to look at other elements of planning in terms of what else we need to plan for.  So two things in particular come to mind here.  We need to plan for contingencies and we need to plan for resources. 

So let’s take a look at contingencies.  Now, it’s always good to expect that things aren’t going to go as planned.  We all know that whatever our best intentions are, sometimes things go sideways, and we have to come up with either a plan B or a C or a workaround for something that happened.  Common contingencies include things like a missed deadline, or maybe you run out of money, or people don’t show up, or equipment or software breaks down, or the scope or complexity of your project goes up, or you get new information or changes happen that are beyond your control. 

So the goal is to try to anticipate as much as possible to the extent that you can here, in terms of what else you can do.  So what can you prepare to do in case X happens or just if things don’t go as planned.  So in terms of common contingency plans, those are things like having a backup reserve of money.  Padding the time on your goals so that you have a buffer.  Maybe having an alternative person that you can call for help.  Having some other equipment or software that you can use as a backup.   Maybe making sure your documents are backed up in the cloud.  Or buying insurance or something else.  So those are just a few examples.  There’s actually many, many more. 

Now, we may not need contingencies for everything, but it’s really for the most critical things that you need to accomplish.  And obviously the more consequences there are for something going wrong, the more planning that you really should do here. 

In the same vein then, resource planning is also important.  So again, this is just thinking through what people or money, equipment, software, tools, advice, learning, or whatever that you’re going to need.  Again, depending on the complexity of what you’re working on, the more you’re going to need to really think through these things and write them down and plan for what resources you’re going to need. 

So for example, if you’re planning a 3-month remodel of your house, that’s a pretty big project, right? Because there’s a lot of money involved with that.  There’s a fairly long time frame.  There’s a lot of moving parts.  So obviously you want to do more planning.  You’re going to need a budget.  You’re going to need a list of contractors and possibly some alternative contractors in case somebody doesn’t work out.  You’re going to need places to shop for materials and so on and so on. 

So this element of planning is so critical.   Think about your contingencies.  Think about what resources you need.  And build that into your planning routine. 

Now the 6th and final strategy for doing good planning is to review your plans and make adjustments.  Plans are only as good as if you stick to them as well as review them and make changes based on how you’re doing.  Now we’ve talked about reviewing annual goals at least once a quarter, and quarterly goals at least once a month.  And then we also said that you need to review your weekly goals at least once a week, and your daily goals at the beginning or end of every day. 

So how do you actually do that reviewing? Well, I suggest that you do a couple of things.  First, is just to look at the overall status against that goal or against that project.  Just in general, are you behind or ahead or on target?

Now, for larger goals I recommend that you use some kind of color-coded method.  You can get down to basics of just using green for on or ahead of target, yellow for slightly behind, and then maybe red for really far or completely off track.  Now just a simple coloring is going to help you see the big picture here.  It really helps serve as kind of a dashboard for the overall sense of how well you are on track or how far behind you are.  If you have a whole list of dots of red for every single one of your goals, that’s a pretty good indicator.  That’s a pretty good sense that you need to step things up, or just decide you’re going to have to push back some deadlines on some of your projects or goals that you’re behind on. 

Now one thing I should say is, I may have not clarified how many weekly or daily goals you should have.  Now this is really kind of hard to gauge.  I said one to three annual goals and I said three to five quarterly goals for each quarter.  But when you get down to the weekly level, my sense is probably one to two is plenty or maybe three at max.  And then when you’re getting down into the daily level, because it’s at a more granular level, you may have more.  You may have three to seven to ten little things. 

In terms of using this color-coding scheme, I think it’s probably going to get a little bit too detailed if you really try to have a green, yellow, red code for every single task that you’re working on, or maybe even for all of your weekly goals or projects.  So I really recommend the color-coding primarily at the quarterly or the annual level, because otherwise I think it’s just going to overwhelm you and it becomes counter-productive. 

So again, start with the status in terms of reviewing things.  But then also, secondly, look at, besides the actual targets and deadlines, is whether you’re really making progress.  Are you moving in the right direction? Sometimes progress is the most important metric just for keeping you motivated.  And motivation is such an important part of goal attainment and project completion.  Even if you’re behind on a goal, if you’re making progress, that can really ease your mind a bit and then help you refocus your efforts to step things up if you need. 

Now the third thing to look at, the third thing to review, is how are your resources doing? Do I need more time on this? Do I need more people involved? Do I need more or better advice? Do I need more cash, or whatever, to boost my chances of success? So this is really where your contingency planning pays off.  And your resource planning.   Knowing what other things you can really do or access or get back on track to fix a project that’s stuck or off track, is really going to help you here. 

Now, the fourth thing to review or ask yourself is, “Am I still happy with my overall goals and plan? Or do I need to drop or add certain goals or projects?”  “Or do I need to postpone any goals to the following month or quarter or year?”  “Have there been things that have been coming up in my life that may have changed my priorities or plans?”

So, this is really kind of a catchall fourth level review, is just to step back and say, you know, “How am I feeling about all this? Is it too much?” “Do I need to cut it back?” “Do I need to add more?” “Am I feeling great about things? Are things on track?”

But it’s just kind of that fourth and final review, about your level of satisfaction and what you might need to take into account in other parts of your life, that may be impacting your plan.  And this is really because things can come up that require you to revisit things, and so that’s why this whole review thing is so critical. 

I love that quote from John Lennon here.  He is famous for having said, “Life is what happens when you’re busy making plans.” And that’s so true.  But that doesn’t mean that you shouldn’t plan at all.  It just means that you need to keep checking in on things and be flexible and be nimble to making adjustments as you need. 

So I hope this has been helpful.  You know, planning is really an important discipline to practice if you want to have the best chance of getting what you want in life, especially with a smoother path and fewer bumps.  But you’ll need to decide how much you really want to dedicate yourself to doing this work.  But always keep in mind that with some practice, it does get easier, and you’re more likely to feel that sense of confidence and control of your days, weeks, and years. 

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