Chapter 4

After you decide what New Year’s resolutions you want to make, your next step is to create a concrete plan to keep them.

This part of the guidebook contains everything that should be in your plan, and it is divided into three chapters.

  • The first chapter will force you to dive deeper into your actual goals, and will show you how to clearly define what you want to accomplish
  • The second chapter will talk about how you form habits, and how you can convert your resolutions into habits you can adopt
  • The third chapter goes over five more elements you should seriously consider putting in your New Year’s plan, including peer pressure, some structure, and a way to avoid the “progress trap”

First thing’s first

But before we jump into creating a plan, I have to call you out on something. It’s a trap I fall into almost every day because I read and write about becoming more productive so much.

I often fall into a trap of reading about some cool changes I should make to my life, but then I completely forget about them a few days later because I didn’t act on what I learned.

This guide may be interesting to read, but it will also be completely useless to you unless you act on what you learn. Without actually acting on what you read, you’re basically just looking at productivity porn. I think that’s a trap that’s easy to fall into; after all, reading about changes you can make to your life is way more fun than actually acting to make your life better.

So if you haven’t already, I highly recommend you take out a pen and paper (or fire up Word in another window) before you read on.

Alright, let’s get planning!

Make your goals SMART, small, and challenging

When you create a plan to achieve your New Year’s resolutions, it’s critically important that you make your goals SMART, small, and relatively challenging. Doing so will force you think about what accomplishing your goal will actually be like, and it will also help you define exactly what you want to accomplish.

Make your goals SMART

The “SMART” model to setting goals is very simple and very powerful, and it’s so powerful that I use it every week or two. It’s a very simple framework for creating goals, and unfortunately for that reason it can be easy to gloss over. In practice, though, the framework is one of the most powerful techniques available to you to convert your vague New Year’s resolutions into goals that you can create a plan for. Now is a good time to take out a pen and paper if you don’t have them out already.

The SMART model says that for a goal to be a good one, it has to be specific, measurable, attainable, relevant, and time-based.


Your goal should be as specific as possible. That means your plan should include:

  • What you want to accomplish, in as much detail as possible, as well as what the end result will look like
  • Who needs to be involved for you to reach your goal
  • Where you will accomplish the goal
  • Why you want to accomplish the goal, and what costs will be associated with the goal

The more specific you make your goal, the more powerful your plan will be, since you will know exactly what you want to accomplish.

For example, instead of making a New Year’s resolution to lose weight, make your goal as specific as possible. For instance: “I’m going to lose 15 pounds, with a personal trainer, at the gym after work every Monday, Wednesday, and Friday, and I want to accomplish the goal so I can look amazing in my sexy man-speedo when I go to Cuba in February. It will cost me four hours a week, and some willpower until I make a habit of going to the gym, but it will be worth it.”)


Next, define exactly how you will measure your progress in reaching your goal, and make sure the criteria you use to measure your goal’s progress are quantifiable. For example, if you plan to lose weight, know exactly how many pounds you will lose, and exactly how you will measure your progress.

If you don’t measure your progress toward your goal, it will be impossible for you to figure out if you’re on track to achieve it. In your plan, make sure you include exactly how you will measure your progress, as well as how often you will measure your progress (e.g. “by weighing myself before breakfast every morning”).


This is a biggie, and determining how attainable your goals are might require a bit of processing on your part. Is the resolution you’ve defined up to this point realistically attainable by you? What do you not have that you will need to accomplish your resolution? Will you have the energy/focus/time to achieve it?

The “attainability” of a goal is centered around you, and whether you have the focus, energy, time, and drive to achieve it.


A goal that is relevant is deeply connected to your values and priorities (both of which you defined back in Part One).

Relevance can also refer to whether it is the right time to follow through on a goal. Some resolutions might be worth following through on later in the year (e.g. training for a marathon later in the year after the weather is warmer).


Time creates urgency, and your goals should be time-based. For example, instead of making a goal to lose 10 pounds, make a goal to lose 2.5 pounds a month for four months.

It is also important to define the milestones you will reach along the way to reaching your big goal, and when exactly you plan to reach those milestones. Since you have already defined your goals to be measurable and attainable, you will be able to make realistic, real progress toward your milestones after you create your plan.

It’s often not an easy process to define milestones for a goal, but I guarantee that when you define measurable milestones along the way, your New Year’s resolutions will become a lot less vague and a lot more understandable and relatable.

Creating goals that are specific, measurable, attainable, realistic, and time-based is one of the most powerful strategies I know of to define and stick to your goals. I’ll be honest, defining SMART goals can be a tedious process, but if you’re serious about sticking to your resolutions, you absolutely have to include a SMART definition of your goals in your New Year’s plan.

Make your goals small

One of the biggest lessons I learned from a productivity experiment where I was a complete slob for a week was that the best way to make positive, lasting changes to your life is to start small. Very small.

That may sound like counterintuitive advice, but the reasoning behind it is simple: the smaller the changes you try to make to your life, the more likely you’ll actually make them.

Interestingly, the more of a slob I became during the experiment, the more resolved I became to become more productive, but ironically the less energy, willpower, and focus I had to actually make changes to my life. The deeper I fell into the experiment (as much as I could over a week, that is, which ended up being surprisingly quite a bit), the more I wanted to make huge changes to my life, and the more unreasonable I became with what I wanted to accomplish.

I think the key to making successful changes to your habits, behaviour, and routines is to start small–very small, because that way the changes will actually stick. I’ve been playing around with making changes to my habits and routines for the better part of eight months with AYOP, and when I make changes to my habits I still try to make them as small as possible so they’ll actually stick. Small resolutions take less time, willpower, and motivation, which means you will actually keep them, and become more confident in your ability to change.

Smaller resolutions will also make you delightfully anxious. For example, if you make a New Year’s resolution to lose one pound a month for four months, create a plan to reach your goal and then only visit the gym once a week to start. If you care about making the resolution (that is, it’s aligned to your values), you will be incredibly anxious to ramp up how many times you hit the gym a week as the year rolls on.

It’s counterintuitive. But when you only have so much willpower, time, and energy to make changes to your habits, if you want your New Year’s resolutions to actually stick, make them as small as possible.

One of the biggest ideas we’ll talk about in Part Three is that you should go easy on yourself when you make resolutions. There is no sense being overly hard on yourself when you make your New Year’s resolutions, and when you respect yourself when you make them, I believe you’re a lot likelier to actually achieve them. Making smaller resolutions is a great way to show more respect for yourself in the new year.

Make your goals challenging

Just because your New Year’s resolutions should be small doesn’t mean that they should be easy. Especially if your resolution is to learn a new skill (or you need a specific skill to achieve your goal), activities that pose a challenge roughly equal to your skill level will allow you to experience “flow”, and according to research, will make you a lot happier.

Flow is that magical place where you’re completely absorbed in what you’re doing, where time seems to pass so fast it’s like it doesn’t exist at all.

The book Flow by Mihaly Csikszentmihalyi is somewhat dry and academic, but it contains several golden nuggets, my favorite of which is the chart below:

If you have no idea what’s going on in the chart, I don’t blame you. Here’s what the chart is about, in a nut:

  • Every activity that you do falls somewhere on this chart, depending on how challenging it is (to you), and how many of your skills it utilizes.
  • The ideal place to be is, you guessed it, in the “Flow Channel”. In the Flow Channel, the challenge of what you’re doing is roughly equal to the skills you have to do that thing. Especially when you’re motivated to get something done, according to Csikszentmihalyi, this is where you’ll experience flow, and be the happiest. For example, spelling ‘Csikszentmihalyi’ is a task that is pretty challenging, but it doesn’t require a lot of skill, which places the activity in the “Anxiety” corner of the graph.

Let’s say you make a New Year’s resolution to learn how to play tennis. In Flow, Csikszentmihalyi uses learning tennis an example to illustrate how you can experience flow. I’ve added four numbered circles to the chart to illustrate his example.

Here’s what the numbers mean.


Your starting point. Here, you’re playing tennis for the very first time. You’re practicing serving the ball over the net (which is tricky, but manageable at first), and trying to hit the other side of the court from your side (or something–I’ll admit, I have no idea how to play tennis). At this point, you’re experiencing flow, because the challenge of what you’re doing is roughly equal to your skill level, and you’re having fun.

From this starting point, one of two things can happen:


You move to “2”. You improve your skills to the point where you get bored of just hitting the ball over the net. The challenge of playing is now lower than your skill level, and you no longer experience flow.


You move to “3”. You challenge yourself at a level that stresses you out – for example, you decide to play a tennis-loving friend of yours, and she kicks your ass. Here, the challenge of playing is greater than your skill level, and you no longer experience flow.

Depending on where you’re at, there are two ways to get back to the Flow Channel.


If you’re bored (“2”), you will need to find a way to increase the challenge of playing, like by finding a opponent whose skill level is roughly equal to yours.
If you’re anxious (“3”), you will need to work on improving your tennis skills to get back in the Flow Channel. (You could also decrease the challenge, but that’s more difficult in practice.)

According to Csikszentmihalyi, this “explains why flow activities lead to growth and discovery. One cannot enjoy doing the same thing at the same level for long. We grow either bored or frustrated; and then the desire to enjoy ourselves again pushes us to stretch our skills, or to discover new opportunities for using them.”1

I think one of the reasons people fail to keep their New Year’s resolutions is they become either bored with them because they’re not challenging or interesting enough, or they become anxious because their resolutions feel out of their reach. Though you have already made your New Year’s goals measurable and attainable, when it comes time to hunker down and actually do your New Year’s resolution, continually reflect on whether your efforts are in the “flow channel”.

Every single activity you perform falls somewhere on this diagram, and according to Csikszentmihalyi’s research, the activities that let you experience flow are the ones that will make you the happiest. If you make a New Year’s resolution that requires skill on your part, make sure you balance the skill required to do it with about the same amount of challenge so you can be the most motivated. Just make sure you’re kind to yourself in the process, by setting smaller goals, and by clearly defining your goals in the first place.

  1. Source: Flow book 

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