Great at Planning, Terrible at Executing: 10 Strategies for Becoming a Doer

Most people are pretty good at coming up with ideas for the future, and many of us are pretty good at developing plans to achieve those things.

I know I certainly am. If you were to take a look at my pocket notebook, many of the things in there are ideas for things I want to do followed by a page or two of details on how I could do it.

In just the last 10 or 12 pages of my pocket notebook, I have plans for a novel, a nonfiction book, a video series about board games, a complete revamp of my home beer making process, an exercise routine, and an improved DIY home security system.

Will I ever do those things? Most likely, I won’t.

Yet when I step back and look at the big projects I’ve actually executed in my life, the number is relatively small. I built The Simple Dollar out of nothing. I paid off all of our debts – a total that added up well into the six figures. I completed a few additional large-scale professional projects, each taking a year or more of my professional life. I’ve also completed several quite large but comparatively smaller projects, both personally and professionally. And… that’s it.

Like almost everyone else on Earth, I’m good at planning and relatively awful at actually executing those things.

Over the last few years, though, I’ve spent a lot of time reflecting on the big projects that I have achieved in my life and what set them apart. How did I take those great plans and execute on them then and then fail to execute on plans now?

Along the way, I came to realize several things about the most successful plans in my life. And, recently, I’ve been trying to use these steps to accomplish a goal I’ve had for a long time. I’m essentially self-educating myself through a college major, using all of the same books and readings and lectures one would need to go through to major in philosophy (using a pastiche of materials from different universities available online). It’s going slowly, as it’s a very big project, but it is moving forward with a progression that makes me very happy.

These 10 strategies seem to be working in my own life. Hopefully, they’ll work in yours.

Strategy #1: Commit to at Most Two Central and Important Goals at a Time

We all have busy lives, with lots of responsibilities and interests of various sizes. Those things pull us in a lot of different directions at once, keeping us from bearing down on anything with a strong central focus.

Often, whether we notice it or not, we are working on several big projects at once in life. Whether it’s maintaining our job, being a good spouse, being a good parent, executing a community responsibility, or even something as simple as watching through the entirety of a lauded television series or reading a book series, we often have several projects going on at the same time in our lives.

It is that splitting of our focus that keeps us from hitting a home run with whatever additional projects we add to the mix. It’s like adding yet another scoop of ice cream to an overflowing bowl. Eventually, you’re going drop one of those scoops and it’s going to be messy.

Instead, I encourage you to take a much different approach to the problem. Choose at most two of the big projects in your life and make them the central focus of your time and energy. Yes, you have other responsibilities you’re going to have to take care of. That’s fine. View those other responsibilities as supporting your main goals.

So, let me give you an example from my own life. Right now, I have two major projects that are central in my life. One is my immediate family – my wife and kids – and ensuring that they are truly happy and taken care of and have good relationships with everyone else. The other one is my aforementioned study of philosophy, which I’m engaging in because it is improving how I think.

The other responsibilities I have in my life are all subservient to those two main projects. I take my writing responsibilities with great seriousness because they provide income to support my family and they sometimes let me put some of those philosophical ideas into my own contexts and writings. I take care of our home and possessions and make meals — but, again, those are all connected to taking care of my family. I have a few community responsibilities, but they’re related to my family, too. I try to keep myself in good health so that I have energy and lasting health for my family and for what I’m learning.

What have I thrown away? Aside from a few minor hobbies that simply provide a “release valve” for me – home beer making, board games, and reading things besides philosophy – I don’t really do anything else with my spare time. I don’t watch television other than a rare family program or something I watch late in the evening with Sarah. I don’t play computer games or video games with the exception of ones I play with my children (which is a huge turnaround from my substantial play of League of Legends a few years ago).

Those two projects really are the focus of my life at this point. Almost everything I do is related to one or the other of them.

Strategy #2: Break Down Your Plan Into Tiny Tasks

So, what’s my plan with each of those goals?

With my family, it’s simply to ensure that they are happy, they have a strong relationship with me that they can rely on, and that my children are raised to be thoughtful, intellectually curious, and independent people.

With my studies, it’s simply to study enough philosophy to be roughly equivalent to a college degree in the area.

From there, I can start breaking down those big goals into plans. The philosophy study is easy – I’m just following a degree plan that I synthesized by looking at the course catalogs of several universities. The family plan is a bit trickier as much of it involves around consistently doing a bunch of things like keeping care of the house, providing an income, spending time with everyone, engaging in educational activities with them, encouraging personal growth, having fun with them by doing simple things like playing kickball, and so on.

The thing is, those tenets are still far too big and nebulous. They don’t really mean anything at that level.

They need to be broken down into tiny, tiny actions that I can take on right now. We’re talking pieces that are half an hour or less in length.

For the study goal, I can break it down into a single reading and add that to my to-do list. I figure out what class I’m taking, what session of that class I’m on, and what readings and other materials are required, and then I just bite off that chunk. If the reading is big, I break it down even further.

With my family, it involves things like basic housework tasks, but it also involves things like doing something with each family member one-on-one each day (like reading my youngest child a book or playing a game with my oldest child). It also involves getting some exercise.

Those are specific next steps that I can take to move forward on these goals. I try to keep them very small so that I can knock them off of my to-do list with ease.

You can essentially do this with any goal. How can you move forward today in terms of paying off your debts? Well, you can take on a frugal project, you could negotiate with your credit card company, and so on. Almost any big goal or project you have can be broken down like that.

Strategy #3: Eliminate Distractions

Life is full of distractions, from cell phone games to interesting websites, from enjoyable television programs to idle conversations with friends, from the best restaurants and snacks to simple daydreaming.

Every time we allow ourselves to get caught in a distraction, we take away from the things we really want to accomplish in life.

I struggle with this myself. I often get caught up in interesting websites and online discussions that really aren’t very productive at all. I often catch myself playing with my cell phone when I shouldn’t be, taking my focus away from whatever is going on in front of me. Those distractions – and many others – take me away from my goals.

The best response I’ve found? Cut out any and all distractions from whatever it is you’re focusing on.

I often turn my cell phone completely off when I’m trying to focus on something. Yeah, I might miss a notification or a text. So what? I can check them later.

I often close my office door to focus on things. This reduces the sounds that might distract me and keeps people from coming in when I’m trying to blow through a particular task.

I have a program that blocks time-wasting websites so that I don’t get sucked into a black hole of Facebook or discussion forums (I find the “nuclear option” to be really, really useful).

I’ve deleted virtually all computer games from my computer.

You get the idea. I’ve simply cut out a lot of the things that distract me. That enables me to put my focus on the things that actually matter, and it makes a tremendous difference. I get things done much faster and actually have time and focus for the important things in my life.

Strategy #4: Set Up “Triggers” for Positive Behaviors

At the end of each day, I spend a bit of time thinking about some of the stuff I want to do the next day to move forward on my projects and the specific tasks I want to execute (as discussed in Strategy #1).

For each of those, I try to find a way to “trigger” those things.

For example, let’s say I need to read a section in Plato’s Republic and take notes on it. I’ll set out the book, bookmark the places I need to start and finish, and put my notebook and a pen out next to it.

Let’s say I want to play a particular board game with my oldest son. I’ll set that game out on the table right now.

That way, during the next day, those pieces are already in place, making it really easy to just jump into those things.

In fact, this whole process has been really useful for me in terms of moving forward with my two big central projects. I just sit down the evening before, come up with the things I want to complete the next day, and set things up to make those tasks easy to start (and thus complete).

Let’s say your task for tomorrow is to make four pans of homemade lasagna and stick three of them in the freezer. One way you can “trigger” this is by setting out all of the non-refrigerated ingredients and equipment you’ll need on the table and stovetop right now so that it is ready to go in the morning. You’ll see it and already feel like some of the effort is done, so you’re much more likely to dive right into it and get it done.

Strategy #5: Block Off Time for Your Project

If you’re focused on one or two singular goals in your life, it shouldn’t be too much of a stretch to block off significant parts of your day for each of those singular goals.

Make it happen. Go to your calendar and literally block off some of your day for direct progress on those goals.

I block off two hours a day right now for philosophy reading and study. It’s what I do during those hours. I shut off distractions as much as humanly possible and either watch a lecture, do some reading, or do some thinking and formulating responses to what I’ve read or heard.

I block off two to three hours a day in the evening for family time each and every day, and some days I devote most of the day to it.

Those types of devoted time blocks might be difficult for you, but if they are, it’s a sign that you have a bunch of other things in your life that you’re assigning a higher priority to than your supposed “priority” projects. If you’re finding it difficult to devote real time each day to the one or two things you really want to succeed at, then you’re not really interested in succeeding at those things.

Find the time. Cut out other distractions and other things that aren’t related to those things. Yes, this might mean eliminating other things you find “fun.” It’s worth it. Few things are more “fun” than nailing it at something you’ve really wanted out of life.

Want to really get in shape fast? Block off two hours for exercise each day and maybe one hour for healthy meal preparation. If you do that and actually follow through for a while, you’re going to be an animal. Why don’t people follow through? They don’t block off the time.

Strategy #6: Set One Specific Micro-Task to Complete Each Day

Here’s the thing: I can block off all the time in the world, but that still doesn’t guarantee that I’ll actually do the thing I want to do. Simply devoting time doesn’t guarantee success.

Another problem: Sometimes life just throws things at you that you don’t expect. Those new challenges can sometimes throw all of your plans for a loop, cutting right into the time you’ve set aside and disrupting everything you want to do.

Yet another problem: It’s often hard to really determine whether a block of time has been successful or not. Did you really achieve something there? Or did you just waste time?

For me, I’ve found a lot of success in addressing all of these things at once by defining one small thing that’s the key criteria for success. Usually, that small thing puts me in a position where it is incredibly easy to do more than that – and usually I do far more – but it’s that tiny thing that really defines success.

For my philosophy study, the one thing that defines success each day is whether I spent time reading and taking notes on one single page of a book or one single minute of a lecture. That’s it. If I managed to do that, then today is a success. Naturally, if I’m already in position to do those things, it’s really easy to do more – and I often do a lot more.

For my family, it’s as simple as this: Did I spend one minute one-on-one focused with each other member of my family and one minute focused on a family need? That totals five minutes – one for my wife, one for each child, and one for some sort of household or family care task. Naturally, it’s really easy to do much more than that once I’m already doing it.

Maybe your goal is different. Maybe your micro-goal is to simply choose not to spend money once today during a time when you would normally have spent that money. Maybe it’s something as simple as setting foot in that gym where you have a membership.

Whatever it is, make that your threshold of success for today. Then, try to build a chain of those successes. I actually use a wall calendar for this, marking each day I succeed at one goal with a purple X on that day and a red X for the other goal. Once I start building a long chain of X’s, I don’t want to break that chain. That motivates me to at least achieve the minimal amount each day, and that minimum amount virtually always encourages me to do more.

Strategy #7: Be Extremely Clear on the Reasons for the Project – and Keep Those Reasons in Focus

Why do I want to do this?

That’s my question that I think about with my big projects. What is my reason for even wanting this.

The family goal is easy to articulate. I want very strong relationships with each person there. I want my wife to have a wonderful life. I want my children to grow into thoughtful, independent, intellectually curious, and self-reliant individuals.

The study goal is a bit different and more difficult to articulate, but it mostly comes down to clarity of thought. I want to be able to understand the world a little better and have better approaches for thinking through the problems of life.

Those reasons remain front and center all the time when I think about those goals.

With my family, I think about the people I hope my children become. I think about the strong moments in my relationship with Sarah. And I also reflect on potential bad outcomes if I don’t follow through.

With my study, I think about those big moments of insight and discovery I’ve had, and I also think about those moments of frustration where some idea is almost within my grasp but it slips away.

I try to keep those thoughts in my mind as much as possible. I reflect on them each day as I’m thinking about what I achieved today and what I hope to achieve tomorrow.

Strategy #8: Couch Your Efforts in Positivity

Whenever I succeed at whatever threshold I’ve set for success for myself, I intentionally pat myself on the back for it. I intentionally think positively about it.

I often look back at how far I’ve come and what I’ve achieved in my goals. I look at the good side of the relationship I have with my family members (and it is almost entirely good). I look at the progress I’ve made in my studies and the things I’ve learned.

And I’m proud of it. I let myself feel very proud of it, and that feels good.

I relish that good feeling. I don’t want it to go away at all, and I know that the best way to keep it going is to keep moving forward on the projects at hand.

I dig into those positive feelings whenever I cross that minimum threshold for the day. I dig into those positive feelings whenever I finish a block of time devoted to a project. I dig into those positive feelings at the end of the day when I reflect on what I did that day and what I’ll do tomorrow.

It makes the whole project feel much more positive and uplifting and often helps carry me through when it becomes a struggle.

Strategy #9: Allow Yourself to Plan Other Goals, But Set Those Plans Aside Without Execution

Like many people, I often make plans for big goals and ideas I might have. I’ll draw up a great plan for redoing my home brewing system, or sketch out ideas for a board game design project, or come up with an exercise plan, or so on. I’ll often sketch these out in my pocket notebook.

However, once I’ve done that a little, I intentionally set them aside as “someday” projects. I don’t even really allow myself to move forward into execution, even a little bit (unless it’s a very small project).

Why? It’s going to end in failure. I know that it is.

That new project would simply mean that I’m splitting my time more than before and trying to squeeze more into what amounts to an already full day. That’s not going to add up to success over the long haul.

So, I commit these things to a “someday/maybe” notebook that I have. It includes sketches for many, many different projects that I’ve thought about but not really committed to.

At some point, my focus might change. My children will grow up, after all, and at some point I will either finish out the philosophy studies or decide a different direction is more urgent.

At that point, I may then take up one of those “someday/maybe” plans and do my best to run with it. I’ll flesh it out using many of the strategies described here and elevate it to one of my major focuses in life.

Until then, I’ll make plans, enjoy the process of planning, and then intentionally put them aside. After all, it’s really the doing that matters, not the planning.

Strategy #10: Share Your Plans with a Trusted Circle and Ask for Suggestions and Reinforcement

Once you’ve committed to a major life project, share that project plan with a trusted circle of family, friends, mentors, and advisors.

Before you do that, think it through. If you’re going to devote a couple of hours a day to something, what are you giving up to make that happen? Where is the time coming from? Why is this goal important to you? How exactly will you execute it? Write all of that stuff out before you share your plan.

There are two big reasons for sharing your plans with this trusted circle.

One, they will help you see holes in that plan. Some of the criticisms might be strange and not worthwhile, but many of the criticisms will be. They’re worth thinking about and they will help you strengthen whatever it is you’re trying to pull off.

Two, they can become a source of inspiration and forward motivation. Lots of people you value and care about now know about your goal. This simple fact alone can be a motivator, but it can go beyond that, too. You have people to talk to when you need advice or suggestions or when you simply need encouragement. They know the struggle you’ve chosen to take on. Plus, you’ll know which ones are positive about it and those are the ones that are likely to offer positive support.

My family provides a lot of encouragement for almost any goal I work on. Beyond that, I have several friends who are very positive about both of my goals. In particular, I have a friend of mine who is a philosophy professor who has been incredibly positive and encouraging about my self-study of philosophy. Those people make my goals achievable and exciting.

Final Thoughts

I use these strategies together on the big projects I’m facing right now in life, but I can also see them at work in my own past on the projects I’ve succeeded on before. All of these things were present to some degree in my professional successes, my success in starting The Simple Dollar, and my personal finance turnaround.

On the other hand, when it comes to the things I’ve failed at, many of the pieces above were missing from the picture. I didn’t think positively or set daily goals for myself or block off devoted time or set triggers or have people to motivate and encourage me.

If there’s something you want to achieve in your life, whether it’s a big professional success, turning around your personal finances, getting in better physical shape, or whatever it may be, use these strategies. In fact, use as many of them as you can, all at once. Make it happen for yourself.

You’ll be glad you did, both today and in the future.

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