The Definitive Guide to Planning Your Life

The Definitive Guide to Planning Your Life


Why Did I Write This Guide?
You have dreams. I know this because I have dreams, we all do. But unfortunately, for a lot of us achieving these dreams is easier said than done. In order to get things done, we need an actionable plan for doing so. I wrote this guide to help you build that plan and take action on it every day.

Who Is This Guide For?
This is a guide for two people: (1) someone with huge aspirations but little plan for getting there; and (2) someone who is still struggling to determine their life purpose.

How to Use This Guide
While you can still get a lot out of this guide by skimming through, I encourage you to download the worksheets and actually work through each step. You’ll use this guide to build a real, tangible plan with which to base your life on.

What Does This Guide Cover?
This guide is divided into five chapters, with each chapter focusing on a different stage of your journey. Here’s a quick look at each:

Number-OneWhy Plan?
This chapter will explain why planning is so important and set expectations for the rest of the guide. This is an essential read for anyone who has yet to define their life’s purpose or build a five-year plan.

Number-TwoLifelong Goals
This chapter explores the process behind discovering your lifelong goals. We’ll also look at what makes a good goal, and how to set these SMARTR goals as part of your plan.

Number-ThreeMaking Big Plans
With your lifelong goals defined and written down, we’ll look out how to translate those goals into a five-year, one-year, and month-by-month plans.

Number-FourMaking Each Day Count
In this chapter, we’ll look at what you can do to make daily progress towards your goals. The objective of this chapter is to have you build the habits and routines that will drive your success.

Tools and Resources for SuccessNumber-Five
Finally, I’ll share some of the productivity tools you can use to keep yourself on track. This won’t be an exhaustive list, so if you don’t see your favorite tool here, be sure to write in and let me know.

After each chapter I’ll list a few resources you can visit to learn more. I highly encourage you check these out when you have time. Now, let’s get started and head over to Chapter One, Why Plan?





We all have some idea of the kind of person we’d like to be. Even if it’s a hazy, ill-defined image, I’d say it’s safe to assume we’re all on some kind of journey towards self-improvement. Some of us want to be world leaders on the cover of TIME magazine, others just want to be seen as a decent person, someone worth getting to know.

But whatever your vision of your ideal self looks like, I can promise you one thing: without planning your progress towards this ideal… your chances of arriving there are slim to none.


By allowing yourself to simply wander through life without a clear end goal, you’ll find yourself wasting a lot of time on activities inessential to your progress. That’s why a life plan is so important— without it, your energy is unfocused and can leave you spinning your wheels for years on end.

You’ll also find that by clearly defining the kind of life you want to live, the people around you will actively help you get there. Devote yourself to your dream, and your friends and family will become part of that journey. They’ll be inspired by your passion and will connect you with the right people, resources, and opportunities.

However, to make the most out of your life plan, it’s important that it’s built with three essential components in mind: direction, accountability, and measurability. These are the building blocks of long-term change. Let’s look at each in turn.

A well-defined life plan begins by painting a clear picture of who you want to be and what you want to accomplish. With clear direction, you can quickly determine what needs to happen next in your journey. This helps you narrow your focus and devote your full attention to living your dreams. We’ll talk more about direction as we set lifelong goals in the next chapter.

A life plan also adds accountability to your pursuit of the ideal you. Instead of making vague goals that you lose interest in as quick as you state them, a life plan will help you establish and check in with your goals to ensure you’re making progress towards them. This accountability is an essential piece of the self-development puzzle.

With anything you set out to change, if you can’t measure it, it won’t improve. That’s why your life plan provides the essential function of giving you a measurable framework to track your success. It’s not enough to state that you want to, “become successful,” if you haven’t defined a way to measure and track what “success” means. Over the course of this guide, we’ll work on setting goals and milestones that quantifiable and easy to measure.

More Resources





Think about the last time you said, “I have no idea what I want to do with my life”? Maybe you said it a week before you graduated high school. Maybe you said it last week. Or maybe you’ve never had the thought cross your mind, maybe you’ve always known what you wanted to do and you’ve been working towards that end since birth.

If so, you’re in the minority. For most of us, knowing what we want to do with our life is a luxury we simply don’t have. If that’s a better description of you, let’s change that right now.

Starting with SWOT

A SWOT Analysis is a tool used in business to help a company to discover new opportunities and develop strategies. However, I find it can be powerful tool if used on a personal level. Use it to identify what you want to achieve, and where you might have difficulty or opportunity doing so.

The tool works like this. Take a sheet of paper and divide it into four quadrants (or download this free worksheet). Label the quadrants Strengths, Weaknesses, Opportunities, and Threats (SWOT). You’ll now fill out each of these sections in order to get a better of picture of what kind of things you can (and should) achieve.


I’d encourage you to go a little crazy here. This is the foundation that you’re about to guide your life with, the more things you have in this section the better. Need some ideas? Here are some prompts to get you started:

  • What are you better than others at?
  • Enjoying an activity is a strength in itself. What’s something you enjoy doing where others often do not?
  • What have you accomplished that makes you proud?
  • What passions do you have that you devote yourself to?
  • What personal characteristics do you have that others frequently commend you on?

Try to be objective here and don’t hold back. If you’re having serious trouble listing your strengths, try taking a personality test to determine what you’re best at.


Often, our lifelong goals include a journey to overcome a certain weakness. For example, I used to be pretty seriously introverted. However, I recognized this early, decided it was something I would spend my life reversing and have made some serious progress. If I’d never reflected on it, I may never have made changes. As you’re developing your own lifelong goals, it’s important to have an accurate picture of what might hold you back. For example:

  • What do you hate doing? What would you pay large sums of money to have someone else do for you?
  • What tasks or activities are extremely challenging for you?
  • What personal qualities are you sometimes reprimanded for?
  • Where do you lack confidence?
  • Would you consider yourself a well-rounded person? If not, why?

As before, it’s important to be extremely objective here. You’re the only person who will read this, so don’t hold back. Be fair to yourself and ensure you’re painting an accurate picture of your capabilities.


This is where you examine your strengths not from a personal standpoint, but from your current position in the world. You’ll want to examine your current relationships, your network, and how your interests line up with new trends and technology.

  • What activities do you enjoy that are becoming more popular worldwide?
  • Are you particularly well-connected in a specific area or industry?
  • Is there anyone in your life who shares similar strengths to those you listed above? How might you connect with them?
  • Are you uniquely positioned to help someone achieve their own goals?


Different than weaknesses, this quadrant is where you list areas of your life that might detract from your success. As with opportunities, examine your relationships and competition. Try some of these prompts to get started:

  • Do you have any enemies? Who would love to see you fail?
  • Are there any new technologies or trends that might amplify your weaknesses?
  • Is there an increasing or decreasing demand for your strengths?

Putting Your SWOT Analysis to Work

After spending some time fleshing out your SWOT analysis, look to see if there’s any area where your passions seem to align. For example…

Say you listed yourself as a creative individual who enjoys writing (strengths). You also feel you have troubles being vulnerable, something you’d like to overcome (weaknesses). You’ve noticed that self-publishing is becoming easier and you happen to know someone who’s self-published several books (opportunities). But you also know that to get a self-published book out in today’s world is beginning to require a better grasp of social media marketing (threats), something you’re unfamiliar with.

From this analysis, you might decide to write a novel. You’ll overcome your issue with vulnerability by blogging about the process, which will simultaneously help you adapt to the threat of a more socially connected world. Your first action step would be to contact your friend ask what it takes to succeed as a self-published author.

This is just one example, but notice how it’s a very different process than arbitrarily deciding you’d “like to write a book someday”. By performing this analysis you’re able to figure out what kind of dream your strengths and opportunities support, and what kind of challenges you can overcome through the process.

Of course, even with a well-defined dream, you can’t hope to get there without setting clear milestones. In the next few chapters we’ll talk about setting goals as part of your overall life plan. But before we do, it’s important to understand what makes a good goal.

Setting SMARTR Goals

We’ve already briefly touched on the danger of ambiguous goals. Simply deciding to “be more successful” or “have others look up to me” is a vague goal that you’ll find difficult to track and measure. In order to make serious progress towards your goals, it’s important that you start with goals that are quantifiable. To help you out, let’s look at the SMART framework and how you can use it to set better goals. We’ll also look at how you can apply the SMART system to your life goals using a small tweak.

Using this system, you’ll build goals that are:

  • Specific;
  • Measurable;
  • Attainable;
  • Realistic;
  • Timely; and
  • Rich.

When setting your goals, you’ll want to ensure they’re very specific. Try answering the four “W” questions: Who is involved? What do you want to accomplish? Where will this goal take place? Why is it important?

What does success mean? How will you measure it? Make sure that you establish at least one specific metric that will help you track your progress.

This is where it’s helpful to have already completed your SWOT analysis. Ensure that whatever life goal you set, it’s within reason that you’d be able to achieve it. However, don’t allow this to limit you. Even if something seems out of reach right now, remember that you can accomplish almost anything you truly set your mind to. Just make sure it’s within the laws of physics.

Similar to the above qualification, but here you’ll want ensure it’s a goal you’re happy working towards. Don’t set a goal that you know you’ll get bored with after only a few days. A realistic goal is one that you can see yourself pursuing.

Set yourself a timeframe to complete the goal by. Without some kind of deadline, you’ll find it difficult to keep yourself accountable to your goal. However, when setting this deadline make sure that it abides by the attainable and realistic guidelines. You can’t change the world in a day, give yourself a reasonable amount of time to succeed.

On their own, SMART goals work great for small to medium achievements. For most of the goals you’ll set over the course of this guide, a SMART goal is fine. However, when setting your life goals, using the SMART system can pose some problems. Namely, the system can be a little too focused on metrics. For your over-arching, purpose-driven goals, you need to ensure your goals are what I call Rich.

That is, when setting your goals, be sure to paint a very vivid, tangible picture of success. This is key for accomplishing big goals. Make sure your goal includes what it will look and feel like when you’ve accomplished it. By doing this, you can give yourself a taste of the success you’re craving. It’s only by adding this final step that you’ll provide the intrinsic motivation needed to keep yourself pursuing your goals long after you’ve set them.

More Resources





Now that we’ve looked at why plans are important, and the goals you want to accomplish, let’s put together a framework towards achieving them. We’ll start big with a five-year plan, then narrow down and look at some of the day-to-day tasks you’ll need to accomplish.

Building a Five-Year Plan 

Your five-year plan is your chance to define exactly what needs to happen in the next five years in order to accomplish your life goals. You’ll use this plan to guide your efforts as you pursue your dreams. How you build this plan is entirely up to you, but I have a few guidelines that will make the process easier:

Work backwards
Right now it’s 2015. So start at 2020 and determine what you will have accomplished. This is easier than planning each year chronologically, as it gives you a chance to break down each year’s goals into a logical progression. For example, if your goal is to have built your own house by 2020, perhaps you would be finishing the house in 2019, you’d have bought the property in 2018, and until then you’d be saving money and learning the necessary skills.

For each year’s goals, use the SMART framework you used to set your life goals in the previous chapter. This will keep your goals quantifiable and achievable.

Dream Big
Five years is a long time. If you want to become a best-selling author, don’t spend four years writing and one year getting the book published. While still being realistic, use the final fifth year as huge milestone like having had your sixth book published, or having brought your startup to $2.5M in revenue.

Write Quickly, Edit Slowly
Don’t get too caught up in calculating exactly how much you need to buy your dream home in year three. Get everything out on paper, everything you plan to do and then go back and edit.

The Further, the Fuzzier
Your final three years should allow a certain amount of room for error. Five years isn’t an overly long time, but it’s still plenty of time to make mistakes or meet with misfortune. There’s no point planning each month of year four as everything will have changed by the time you get there. Instead, spend that time bring next year into sharp focus— something we’ll talk about next.

Making Next Year Count

Now that you have a general outline for the next five years, let’s get ultra-specific and make a plan for the next year. This is a process you’ll want to get familiar with and is something to revisit each year.

STOPSTOP Before we go any further, I’d just like to confirm that you’re writing some of this down. Specifically, your over-arching goals. If you haven’t written down who you want to be or what you want to accomplish in the next five years— DO THIS NOW. Studies have shown that just the act of physically writing down your goals can vastly improve the chance that you’ll achieve them.

With your goals for the year written down and in front of you, think about what steps will be required to accomplish them. As before, try working backwards in order to determine what needs to happen at each stage. Figure out where you need to be six, three, and one month from now. Then figure out the first thing you need to do in order to make those dreams reality, and the metrics you’ll be using to track success.

To make this work, you’ll also need to establish how often you’ll be measuring your progress. I suggest finding some time to regularly check in, say once a week in order to evaluate your efforts. Set yourself reminders to ensure you don’t miss these critical appointments.

Additionally, I recommend spending a little more time at the beginning of each month to look at your bigger picture and reexamine your goals for the year. If you find yourself behind in any area, what could you do to get back on track? What might be holding you back?

Planning Months and Weeks

Now that you have a clear vision for the next year, what needs to happen this month in order to get there? I suggest breaking your monthly plan into four weeks and working from there. You’ll need a calendar app and a to-do list app, have a look at the list of tools at the end of this guide.

Narrow Your Focus
To start out, let’s look at your priorities. Of all the things you need to accomplish this month, which is most essential to the pursuit of your lifelong goals? Make it priority one and ensure you have enough time to guarantee its completion. For example, if your lifelong goal is to become a world-famous public speaker, perhaps you first task is to join Toastmasters and write your icebreaker speech. This goal should take priority over everything else, leaving you plenty of room to accomplish with perfection. If you have to drop one of your less-important priorities to make room, so be it. You don’t really need to take those tap-dancing classes do you?

Using your calendar app, plan all your major milestones for the month. If you’re writing the next great American novel, how many pages do you need completed by week one? On which days will you sit down to write? Are they all in your calendar? They should be.

Reflection Time
As I mentioned in the previous section, it’s important to set aside days where you’ll be measuring your progress. I like Sunday, as it’s generally a day where we don’t have much going on. Be sure to plan for this and set reminders, otherwise you may never get around to it.

This is a good time to look at areas of your life that might be better handled by someone else. If you’re currently spending considerable time and effort on something that isn’t building towards your lifelong goal, why not delegate it? Plan your month so that you’re spending as much time as possible chasing your dreams. If you don’t have the time to spare because you’re spending your weekends maintaining the house, maybe it’s worth paying a professional to do it instead.

This should be more than enough to get you started. Remember that while planning your month you should be leaving a little wiggle room. Life has a funny way of derailing your plans a generally being a bit of a nuisance. Don’t plan too meticulously, or you may find yourself feeling trapped by your plan.

More Resources





Until now, we’ve been talking about big picture stuff: setting your over-arching goals, planning years and months in advance, and tracking progress towards your dreams. However, the only way for you to actually make any progress is to take constant, continuous action towards your goals every single day. To make this process easier, let’s go over a few tips to help you make the most out of your days.

Step One: Starting With a Plan
As mentioned in the first chapter, it’s impossible to be successful without direction. You need some kind of definition of success otherwise your efforts remain unfocused and ineffective. So as you start your day, sit down and write down what needs to happen in order for this to be a successful day. This simple action will tie together your simple daily actions with your big, lifelong goals.

Step Two: Schedule Your Success
Once you’ve determined what it will take to call today a success, pull up your calendar and establish when and where you’ll make those things happen. If at all possible, try to get these things done early. By accomplishing your biggest tasks first, you can give yourself the momentum necessary to fuel the rest of your day.

Step Three: Track Your Efforts
There is a wealth of productivity tools out there to help you stay on track. But I’d like to emphasize the importance of using habit-building tools rather than simple reminder apps or alarms. One great tool to check out is This is a fantastic tool for building long-term habits. Use it to force yourself to work on your novel, go to the gym, or practice your public speaking. Of course, this is just one tool. How you choose to track your progress is not nearly as important as ensuring that you do. Find something that works for you and stick to it.

Step Four: Use Productivity Hacks to Get More Done
Contrary to popular belief, multi-tasking is actually terrible for your productivity and can lead to poor results. In order to reach your goals faster, it’s important that you learn to manage your time more productively. If you aren’t already, get familiar with the idea of batching. This technique will allow you to get more done during the day by getting hyper-focused on one task at a time.

Step Five: Reflect
Just like you did at the beginning of your day, take five minutes at the end of your day for a moment of quiet reflection. Was today successful? Why or why not? Are you closer to your weekly and monthly goals than you were yesterday? This reflection time is critical for long-term success as it allows you to spend a moment measuring your progress and keeping yourself accountable to your goals.

That’s it!

If you Google, “how to be more productive” you’ll bump into massive lists that promise to help you get more done. But if you think about it, it really boils down to the above five points. Which can be simplified further into four core statements:

  • Plan and schedule
  • Finish big tasks early
  • Focus on one thing at a time
  • Track, reflect, repeat.

That’s really all there is to it. If you follow this plan and align it with your monthly, yearly, and lifelong goals, you’ll be miles ahead of the majority. Most peple fail to live life on their terms and instead let life live them. Take action today and put together a plan to achieve your life goals. Even the simple act of discovering what you want to do with your life will take you further than most.

More Resources





Building beautiful things is easier with the right tools. This is true for building your dreams, too. Here are just a few of the tools available to help you plan your life.

Throughout this whole guide, anywhere I’ve suggested writing something down, you should probably be doing in Evernote. I use Evernote daily, to stay on top of important projects, store important information, and well… so many things it would take a long, long time to list them all out. If you’ve never given the app a shot, I suggest downloading it today. The free version is likely more than you need already.

While I personally don’t use this app, I’ve had it recommended enough that it warrants a mention here. Todoist is a very simple todo list manager but comes with an interesting rewards system for accomplishing tasks. This can help offset human inertia and motivate you to get more done.

Google Calendar
I’m a huge fan of the Google apps and Calendar is no exception. Use this app to schedule your life and stay on top of your goals.
Chains is a habit-building app that helps you turn new habits into established routines. The app let’s you build long chains to track how often you accomplish a specific task. Even though there’s no negative consequence for breaking these chains, you may find that simply seeing how well you’ve been doing is enough to keep you on the right track. (Previously Lift)
Lift adds accountability to your goals by connecting you and your goals to a larger community. This way, instead of simply stating your goals to yourself, you can release your goals publicly and receive motivation, advice, and reminders to keep you on task.



I’m a serial entrepreneur and I write about things I have learned along the way. I’m passionate about helping entrepreneurs and executives to find success and harmony in business and in life.

2 comments On The Definitive Guide to Planning Your Life

  • Hi David,

    Great post! I especially like your use of SWOT. I’ve never considered Opportunities and Threats as tools for goal setting.

    I’ve found that quality goals really comes down to the quality of the questions you ask, and you have definitely given me a fresh perspective.

Leave a reply:

Your email address will not be published.

This site uses Akismet to reduce spam. Learn how your comment data is processed.