The Complete Guide to Setting and Achieving Goals: Turning Your Ambitions into Accomplishments

My favorite tools, mental models, and advice on setting and achieving goals. A guide for people who keep failing but don’t stop trying anyway.

The New Year’s Resolution

New year’s resolutions tend to get a bad rap. Maybe you avoid making them because you’re afraid you’ll fail. Maybe you think new year’s resolutions are silly. Maybe you think that people who make such resolutions are silly.

It’s easy to mock resolutionists as naïve or lazy; frequent gym-goers will often mock the “amateurs” entering the gym every January with some variant of “if you were really serious about training, you would have started yesterday, bro.” This kind of attitude is easy to maintain when you’re already doing something other people are trying hard to get into, like going to the gym frequently.

It would indeed have been better to have gotten started yesterday, and many people who set new year’s resolutions don’t follow through with them. But as it turns out, success rates of new year’s resolutions are much better than most of us would suppose. One reason for this could be that the new year is a temporal landmark, a transition between the past and what comes next, just like a new week or a new day. Maybe there really is something to the old saying, “new year, new you”.

In any case, even if you don’t make it all the way, trying and failing are often much better than not trying at all.

Setting goals

Everyone has goals. Whether it’s a new year’s resolution or a yearly goal, whether it’s time-bound or not, whether it’s a deliberate goal or just a vague idea. They’re all goals.

Some people write them down and track them in a spreadsheet. Some people just imagine a thing they want and go after it. Some people give up before they’ve even started to take their goals seriously. But everyone has goals. A goal doesn’t have to be grandiose, or something everyone else will consider impressive. A goal is simply something that you want to achieve but that you wouldn’t accomplish just by going about your days as normal.

From personal experience, I’ve spent many years setting goals and designing projects to achieve them, often failing but learning a lot along the way. Through trial and error, I’ve discovered that when I actually write things down, think about what success means, and keep things top of mind, I’m much more likely to achieve something, even if it’s not the perfect outcome I was hoping for.

In this article, I’ll share some key insights, ideas, and best practices for successfully setting goals and achieving your ambitions. Whether you’re looking to hit the gym more, start a new career, or improve your daily habits, you’ll learn the tools and strategies you need to make your goals a reality. As with a lot of my writing, it’s as much a therapeutic intervention for myself as it’s a guide to help others.

Wisdom is nothing more profound than being able to follow one’s own advice.
- Sam Harris

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I. Laying the groundwork: mental models and tools

Process vs. outcome

One of the most foundational mental models for goal setting is the input/output distinction.

When we imagine what we want to achieve, we often start with the outcome, an imagined output of a process that reflects our desired end state. This is obviously important — you should have an idea of where you’re trying to go — but it’s rarely enough. It’s more helpful to define a process-oriented goal: the process most likely to lead to the desired outcome (or at least one conceivable path toward the ultimate goal).

Another way to frame this is that it’s easier to start with the investment needed, the effort you put in, rather than the result you want to achieve. You can easily grasp and commit to a plan of putting in X hours per week, for example, but it’s harder to commit to achieving target Y by the end of a given period. The results will follow the investment, and if the investment or effort is insufficient to reach the result, you will be able to adjust your plan as long as you track your progress.

A goal of “losing 10kgs by June 31st” may be better than “get fit by summer,” but neither is very actionable. I think this is where the advice to set “SMART” goals is misguided. You’re more likely to make progress if you define a metric that is inherently within your control, such as “workout 4x per week” or a rule like “fast for 24 hours 2x per week.” Of course, you might still fail any of these goals, but at least it’s largely within your control. Whereas “getting fit” is not something you can notice or track on a daily basis.

Yet another framing of this is that of leading and lagging measures. I wrote previously on this topic, saying that:

“…lagging indicators describe the past. They are high-level metrics that describe results (or lack thereof). They are typically not actionable because they describe the consequences and only provide generic feedback, which means that they afford you less control.

Leading indicators, on the other hand, describe the future. They are actionable, give you more control and provide specific feedback since they describe the causes of the outcome.”

A good goal helps you define the direction of your desired outcome, and the process helps you make progress in that direction.

The takeaway here is to define the inputs that are the most likely to lead to your wanted output and work on achieving that kind of process-oriented goal (what I often call a Project) rather than an outcome that is largely outside your control.

Mastery vs. performance

A different but related approach to the above is thinking of mastery vs. performance. Research has shown that you are often more likely to achieve goals when you focus on mastering a skill or method rather than only judging yourself according to performative outcomes.

Let’s say you have the high-level goal of building an online business that gives you enough passive income to sustain your desired lifestyle. It’ll be a long time until you can declare this goal accomplished, and there many different paths you can take. One intermediate goal might be to learn how to code and design a website. While doing that, you’ll focus more on mastering the craft itself; how much better are you at remembering syntax or writing functions, for example, compared to the week before? A mastery focus is often more rewarding and practical because when you’re of the mindset that you’re trying to improve a skill or learn something new, you’re expecting to fail a bit, so mistakes aren’t really a problem, just a part of the process.

Judging yourself only based on your performance against some internal or external standard, like how much money you’ve made in sales this year, reduces the speed of your feedback loop and removes your sense of satisfaction when making progress (mastery). This decreases your chances of getting to where you want to be.

The takeaway is to set goals based on where you are. In other words, you’ve gotta consider what you know, your experiences, and how well you understand the causality between actions and outcomes.

If you’re just getting started with dieting, and your goal is to get fit and build a strong physique, you’re unlikely to get where you want to be by chasing arbitrary performance metrics (like a 100kg bench press). Instead, you should focus on learning and building habits. You need to get the reps in. You need to set goals where success has to do more with mastering straightforward actions like going to the gym 4x per week or learning to cook rather than specific strength goals that may be months or years into the future.

You also need to make room for error and expect to fail. A mastery mindset makes this much easier. It lets you get more small wins and start to build confidence in your own ability. When you accomplish your goals, even simple ones, you’ll start to trust your ability to get things done. A sense of mastery begets confidence. As I’ve written before, confidence is nothing more than having the experience to trust in your own ability.

The pyramid of feedback

Understanding the causality between actions and outcomes can be done by connecting leading and lagging success metrics or mastery and performance metrics in a hierarchy, a so-called “pyramid of feedback.”

Say you’re trying to become (or are) a professional football/soccer player, and you want to score more goals. A good coach will help you focus on practicing your technique, stamina, and other inputs that make you a better striker. Scoring goals is what’s really important in the end, but you need to understand and practice the behaviors that increase your chances of scoring more goals. That’s the thing to measure and improve when you’re training, rather than the number of goals scored to get accurate feedback on whether or not you are, in fact, getting better.

Practice improving on the Target, or the middle layer, rather than just focusing on the top layer, the Goal. Introduce as many layers as needed to understand the feedback loops accurately.

The pyramid of feedback is a framework to guide our improvement, learning, and communication efforts when working towards our goals, personally or in an organization. It connects the lagging indicators, the outcomes you want to achieve, with the leading indicators, the inputs, in a hierarchy of feedback. Every level supports the level above. Crucially, it is the lower-level actions and underlying behaviors that fundamentally determine the final results, “several levels” above. Every level provides feedback on the level above or below in a kind of feedback loop.

The pyramid is another way of looking at the connection between efforts vs. outcomes. In particular, it emphasizes that you have much more control over the lower-level actions and much less control over the top-level outcomes.

First steps and final destination

To focus on the behaviors, actions, and processes that will drive the desired outcomes is to plan your goal-achievement efforts by breaking them down into various smaller steps.

What’s the first step for you? Don’t just consider the obvious starting point with regard to the final destination but also your personal preparedness, psychologically and behaviorally. What are your strengths and weaknesses, and how can you use that knowledge to your advantage when mapping out the rest of the milestones? You always need to start where you are now.

What does the final destination look like? When have you reached your goal? You need to know where you want to go, so you know you’re on the right way. This could be a very high-level goal or a closer, more intermediate goal.

What are the intermediate milestones and steps along the way to the final destination? How will you space out the milestones or break the goal down into interstitial steps, logical and achievable on their own? Another way of putting this is that you need a strategy and strategic goals representing the milestones for navigating toward the goal. A plan, in other words.

I find it’s often quite easy to come up with a few possible first steps, but that later milestones are harder imagine. Backcasting is a useful technique to broaden your horizon: Imagine that you’ve already achieved your goal and work backward from that ideal future/outcome you’re aiming for. Working backward from the goal helps you clarify the steps that led you to that end state. It’s essentially a creative exercise that can unlock new ideas about what needs to be done or help you make a hard decision.

Efficiency vs. effectiveness

A foundational mental model that applies to both personal and organizational productivity is the dichotomy between efficiency — doing things right — and effectiveness — doing the right thing. In other words, being efficient is concerned with the process used to achieve a result, and being effective is about the degree to which you achieved the result you actually wanted. I’ve written about this in the past as well:

“For example, say you’re taking your car on a road trip across the country and you’ve planned to be on the road for 7 days; your goal is to see as many interesting places as possible. In this case, being efficient would mean taking the optimal path and getting to each city or place as fast as possible. Being effective is about whether or not you saw as many places as you wanted and then — perhaps retrospectively — whether or not those were the most fun places to visit. An inefficient route would be one that is needlessly long or requires many stops, whilst an ineffective route would be one that takes you to the wrong places or misses some places you’d have wanted to see.”

As you can probably tell by now, both of these aspects are important for goal achievement. But if you need to choose, you’re probably better off trying to be effective rather than efficient, as that is what enables you actually to reach your goals. Of course, if you can be both, that’s always more desirable, but sometimes there are tradeoffs you need to make. Knowing the difference between efficiency and effectiveness is useful to ensure you’re optimizing for the right thing.

Different modes of thought; near-mode and far-mode

A useful technique for goal setting is to contrast far-mode thinking with near-mode thinking, that is, planning vs. doing.

Planning, fantasizing and thinking big are good but can lead to inaction and a lack of progress. You should complement this by trying out the thing you’re dreaming about in practice. Far-mode puts you into the motivational and visionary frame of mind, and near-mode brings you back into the reality of how you can work towards that today or this week.

A good way to do this is to apply so-called mental contrasting, a science-backed technique where you imagine various successful or unsuccessful outcomes and contrast that with where you are now. The act of doing that will usually make you figure out potential hurdles in your way, which helps to make you feel more motivated and confident about your plans. It’s similar, but not exactly the same as backcasting.

A problem with goal setting, at least for some people, is that they become a little overzealous in their forecasts of future achievements. Just wishing for something to happen will not make it so. This is why it’s a good idea to set ambitious goals but make pessimistic plans. Pessimism is a feature when you’re planning but not when you’re dreaming. Optimism is a feature when you’re dreaming but not when you’re planning.

This helps us resolve the dilemma between an idealized future we want to reach and the practical hurdles in our way. Set aspirational and lofty goals but bring yourself down to earth when it’s time to plan.

Positive vs. negative framings

Some goals are positive and action-oriented, while others are negative or avoidance-oriented. A positive goal is a goal that describes what you want to do or achieve, like “become a millionaire” or “run a marathon.” A negative goal describes something you shouldn’t do or avoid, like “don’t eat ice cream” or “only drink alcohol two times per week.”

It’s been shown that positive, approach-oriented goals can often improve not just your emotional well-being but also increase your chances of successful goal attainment. Although, as I’ve written previously, simple rules, dos and don’ts are often very helpful to avoid decision fatigue and slipups when working towards your goals. But it may be a good idea to formulate the rules in a positive rather than a negative manner. In other words, rather than having the rule to “Don’t drink alcohol after 10 pm and never on a weekday”, you can say, “I can drink alcohol on Thursdays to Saturdays before 10 pm”. The latter feels a little better.

Goal difficulty and motivation

What’s the right level of difficulty for goals? As with much else, you wanna hit a sort of Goldilocks zone — hard enough to be motivating but easy enough to be attainable — goals that are just right. Or, as we say in Sweden, “lagom.”

The problem, of course, is that your goals and projects will necessarily be hard because most of the things we want to achieve are non-trivial and require major changes to our behaviors. Nevertheless, a hard goal by itself may feel overwhelming and hard to progress towards (if the results are far into the future) because you don’t notice the progress you may be making. That’s why we break goals down into smaller goals and projects that are more actionable and achievable; process-oriented goals. But here, too, you want to hit the right level of difficulty. If you make them too easy, they won’t feel very motivating, and you’ll not feel any different about achieving them. Completing a project should feel like an accomplishment. You can’t bullshit yourself for long. You’ll know in your gut whether or not something is way too easy or too hard.

Related to aiming for the right level of difficulty is making things as enjoyable as possible. If every aspect of your work towards achieving a goal feels makes you feel miserable, you’re very unlikely to stick with it for the long term. While it’s true that you will need to push through some sticking points and do boring things, this can’t be everything you do. People that consistently achieve their goals and do hard things are able to do them because they get rewarded for their actions at various levels.

The larger point here is that good goals have drawing power. Good goals have an emotional pull on us that makes us want to take action on them. When goals are used to try to predict the future, which is unknown, we inevitably set ourselves up for failure or disappointment.

The real purpose of a goal is to make us take action in the present. If it fails to do that, it doesn’t matter how well-written the goal is; we won’t move on it.

You need to a) trust your ability to make progress (you can’t bullshit yourself) and b) feel motivated by the goal itself, so you take action. By setting the goal at the right level of difficulty within a hierarchy of higher-level goals that are inherently motivating to you, you’re much more likely to succeed.

Designing your environment to support desired behaviors

Most self-help literature starts with the assumption that “you are the master of your own life” and that if you want something enough and can muster the requisite amount of willpower, you’ll overcome all obstacles and achieve any goal.

Although it’s important to have an internal locus of control, decades of research in economics, psychology, and biology clearly show that the surrounding environment largely determines our behavior. This includes both internal and external environmental stimuli. Consider for a moment where most of your habits — good or bad — come from? The automaticity with which you are reminded to brush your teeth or walk over and open the fridge every time you come home from work is entirely a result of internal or external cues that trigger such behaviors.

With this in mind, you can greatly increase your chances of success by “designing” your environment to support productive actions and reduce unproductive ones. Do you have a hard time staying away from unhealthy snacks or candy? Don’t have them at home or put them in a place that’s hard to reach. If you have to surmount a herculean amount of effort not to eat that candy bar every time you open the cupboard, you’re fighting a losing battle.

Do you procrastinate work or studies by browsing social media or watching YouTube videos all evening? Leave your phone out of sight or install a website blocker in your browser to reduce the cues that trigger unwanted behaviors. People who maintain a lot of healthy behaviors typically do so because they avoid environments that detract from that lifestyle and live in an environment that supports it. They don’t have more willpower than anyone else.

Visual cues are a powerful guiding mechanism. They can be used strategically as reminders or as visual representations of progress. Things like the Paper Clip Strategy and “streaks” are used to stay accountable and motivated. In software development, teams use physical Kanban boards to visualize both progress and impediments to progress, which is both motivating and useful.

Another kind of environmental support is social support and accountability. You’re often more likely to stick to a desired behavior if you are surrounded by people that behave in similar ways or that call you out when you’re about to slip up. This is why it may be useful to announce your goals to friends and family. You’ll be more likely to keep at it when you have a sense of external accountability. We’re social animals and do anything we can to avoid the feeling of shame.

Identity & relatedness

Your identity, the kind of person you consider yourself to be, and the groups or cultures you identify with have a major impact on your behaviors.

It’s much easier to stick to a diet if you see yourself as a “fit person” that lives a healthy lifestyle rather than someone who is “on a diet right now” but doesn’t feel at all connected to the kind of lifestyle healthy people have. It’s been well-documented that, e.g., formerly obese people who lost a lot of weight and subsequently manage to keep it off have also redefined who they are in the process and have been able to adopt a better lifestyle as a result of that shift in identity. Whereas people that regain some or all of the weight they lost still retain their regular identity and the associated lifestyle.

Your identity is also closely connected to your relationships with others — the feeling of relatedness. Relatedness is about your sense of belonging and your connection to other people. Your identity is shaped by your interactions with others and by the groups you belong to in a sort of feedback loop. In other words, your identity is created in concert with others you feel related to as much as it “comes from the inside”. Within self-determination theory, relatedness is one of three key components that drive your intrinsic motivation. Along with a sense of competence and autonomy, it’s what makes you feel empowered to make choices and manage your life.

In the context of your goals, you can consider how relatedness or a lack thereof is connected to driving the desired behaviors. For example, many people get motivated to work out largely because they train with others or do activities with a group of like-minded people. Crossfit is a great example of a type of training that successfully harnessed the concept of relatedness to drive training adherence. It’s no wonder some people call Crossfit a cult.

Personally, I identify as someone that works out, and I feel like I “fit in” with the kind of crowd that also trains a lot. Going to the gym frequently is entirely coherent with this identity, and not doing so is completely out of character for me. As hard as going to the gym can be on some days, it feels even worse not to do that because I am the kind of person who works out regularly. In the context of working out, relatedness isn’t as important to me because I prefer training alone. Still, I do feel like part of that group, and it reinforces my identity.

So how do you “change your identity”? Certainly easier said than done, but in so far as you can think of your identity as a coherent concept at all, every little habit or action you take in support of a certain kind of lifestyle is a vote for that identity. I’ve built my gym-goer identity over more than a decade of training, and it’s a deeply ingrained part of who I consider myself to be. Nurturing a sense of relatedness to a group of people where the desired behavior is normal and encouraged can also help reinforce the identity you are trying to adopt (like buying a membership at a Crossfit box rather than training solo at a gym).

The takeaway is that your identity and your relationships, much like your social environment, tell you something about what you should or shouldn’t do and makes it more or less likely that you’ll take goal-directed actions.

A note on priorities

Many people make a big deal about how to prioritize goals, projects, or tasks. There exist a lot of different frameworks and models for coming up with what is the most important out of a set of choices. And while they can be helpful in many cases, it’s easy to get paralyzed by all the options. In most cases, I find that going with your gut (as long as you have most of the information) goes a long way.

For companies or organizations, prioritizing and committing to goals or projects require a bit more effort, and “just going with your gut” is not something that works when you have dozens of stakeholders with a lot of data points providing crucial input to a decision. But for an individual setting new year’s resolutions or prioritizing their daily todos, going with some version of “what do I want to do next/what do I want to accomplish today” is a very useful heuristic. (By want, I mean a complete picture of what’s important, what’s required, and what you feel pulled towards, which isn’t necessarily what you desire to do in the hedonic sense.)

Via negativa

Nevertheless, rather than focusing on what to prioritize over something else, focus on what not to do. What you don’t do and what you say no to is just as important as what you say yes to. Being able to eliminate options is a productivity superpower. The stuff you avoid, the stuff you don’t spend time on, the people you avoid. All of it creates space for the truly important and interesting.

The same applies to your goals. It’s easy to get carried away by many exciting opportunities and overcommit to too many goals at once. If you have too many things pulling your attention or just too many ongoing projects, it can be hard to make real progress, and your motivation will fizzle out. Of course, there are circumstances where it makes sense to have a few different projects ongoing simultaneously. Perhaps they are complementary to each other (subordinate to the same goal). Or perhaps pausing a project for a while to work on something else makes sense so you can keep making progress overall. But let it be a deliberate choice, not something you fall into because you can’t make hard choices upfront.

I’m not saying you should never take the time to dream or make a list of all the things you’d want to do or achieve in the future, but when it comes to what you’re gonna do next; this year, this month, or this week, say no to almost everything else and focus on one or two goals at a time.

II. Driving change: a system that leads to goal achievement

The goal hierarchy

When it comes to setting and achieving your goals, there’s more to it than just identifying what you want to accomplish. In fact, the key to success lies in understanding that goals exist in a hierarchy of high-level, intermediate, and subordinate goals connected to one another.

At the highest level, you have your ultimate outcome or “why”. For example, if your goal is to “lose 10kg”, this is not the ultimate outcome you’re after, but rather an intermediate goal on the path to a higher-level goal such as “get fit.” And even that may not be the utmost outcome, but rather another intermediate goal in support of a higher-level goal or personal value, such as “being healthy,” “being independent” or “being more attractive to women.”

Below the intermediate goal of losing 10kg, you have practical and effort-based goals. These are things like “going to the gym 3 times per week” or “fasting 2 days per week”, and are supported by even more specific plans, routines, and daily habits.

Good goals exist at the intersection between being too big to be practically achievable and too small to be interesting.

I have formalized this goal hierarchy into a system with a few levels that tie together your personal values and ambitions all the way down to your daily habits and actions. I refer to this as my “productivity system” in the sense that it helps me to be both effective and efficient.

The goal hierarchy is your productivity system.

1. Ambitions — The first level starts with your high-level, emotionally driven goals that are hard to define but that you feel pulled towards. These are your long-term aspirations, such as wanting a big family, being a successful entrepreneur, being famous, or having traveled the world. These ambitions may be hard to quantify and daunting to approach, but they are the driving force behind your goals.
2. Goals — The second level is where you have more concrete, measurable goals that support your ambitions. At this level, you can set specific targets to track and measure progress. For example, “lose 10kgs of bodyweight by June 10th” is a measurable goal that supports a broader ambition of getting fit.
3. Projects — The third level contains projects which are essentially effort-based goals that focus on actions rather than outcomes. Projects are a collection of tasks or actions coordinated within a plan. They are subordinate to the intermediary goals and focus on the inputs that drive the desired outcomes. For example, “Complete a fasting regimen” with a description of “Fast 2 days per week for 15 weeks” is a project that supports the goal of losing weight.
4. Routines — The fourth level concerns the habits that support accomplishing your goals and projects. These are the small daily actions that you take to achieve your goals. They may require a high degree of effort and tracking at first, but over time, some habits can become more automatic. For example, setting an implementation intention, such as “I will go to the gym at 6 am every morning,” is a habit that supports the goal of losing weight within the project of going to the gym every week.
5. Tasks — Finally, the fifth level captures your routine tasks, the next actions related to projects undertaken, your to-do lists, and so on. These are typically subordinate to the projects you have, are work-related, or connected to your broader areas of responsibility or “life maintenance” (take out the trash, call mom, file taxes, etc.). This is where the rubber meets the road.

Hacking your routines and habits

Use Implementation Intentions to turn your goals into actions

Implementation intentions are a powerful tool for turning your goals into actions. They are specific plans that outline when, where, and how you will implement a behavior associated with your goals. Research shows that you are 2x to 3x more likely to follow through with a habit if you make a specific plan for when, where, and how you will implement it.

An example of an implementation intention is “Right after waking up, when I get into the kitchen, I will drink a big glass of water,” which promotes the overall goal of being healthier. The idea is to make it easier to take the predefined action by defining a specific time and place, increasing the chance that you’ll remember and do the thing.

It’s important to target specific, low-level (atomic) behaviors that are uncomplicated to do because if you don’t, you’re unlikely to remember or take the action when the trigger occurs. A common failure mode is trying to force actions that are not obvious or that you don’t want to do. For example, the implementation intention: “every time I get up from my desk, I will do 10 pushups,” isn’t that hard to remember, but there are also a hundred other things you could do every time you get up from your desk.

A better example would be, “every time I see the stairs, I will take the stairs (rather than the elevator)” this is better because the trigger is more likely to occur, and the action is connected to the trigger in an obvious way. An even better version could be to make the action ridiculously easy such that it’s practically impossible not to occur: “every time I approach the stairs, I will LOOK the stairs.” This works because the act of looking at the stairs will prompt you to want to take the stairs too, and it’s so simple that you will always experience the trigger and take the action of looking, which has the benefit of turning this more readily into a habit since habits require repetition.

Use habit stacking to add a new habit on top of an existing habit

A variant of implementation intentions is habit stacking, popularized by B.J. Fogg and James Clear. With habit stacking, you pair a new habit you’re trying to introduce with a habit you already have. It can be written in the form: “After/Before [CURRENT HABIT], I will [NEW HABIT].“ An obvious example is to pair flossing with brushing your teeth or taking vitamins with drinking a glass of water in the morning before breakfast.

This tends to work because the trigger is an action you’re used to doing without much forethought or mental effort (a current habit). Stacking the new habit on top of that is like piggybacking on the prior behavior to make a new one more likely to occur.

Use temptation bundling to do something you don’t like together with something you like

Another related technique is temptation bundling which is a method for habit formation where we “bundle” something we enjoy doing with something we don’t.

The classic example is to listen to a podcast or stream your favorite tv-show when you’re on the treadmill or cardio machine.

A personal example is how I’ve connected eating with training. I have trained consistently 5–6 times per week for many years. This isn’t something that requires a lot of willpower for me to do anymore because I have several other supporting habits around the training. For example, I always look forward to eating a nice lunch or dinner after the workout, giving myself a tangible reward. I also genuinely enjoy the feeling of being tired and having achy muscles. If there was no tangible emotional or physical reward right after a workout, I doubt I’d be able to stick to the training for so many years, as the act of doing the exercises is rarely very enjoyable by itself.

Applying the tools and models

There is any number of ways to create and structure your goals, break them down into sub-goals, and make actionable plans for how to achieve them. Nevertheless, using the tools and the hierarchy I’ve suggested above is a great way to start mapping out your goals and plans.

At the simplest level, this could be as trivial as just spending a bit of time considering what you want, why you want it, what the next steps would be as well as what hurdles might get in your way. This is the 80/20 approach. If you want to get a bit more structured, you can start writing things down. A bulleted list, a spreadsheet, pen and paper, and diagrams. All of these tools work well and what to use depends on your preferences.

To get a bit more concrete, let’s use the example goal of losing 10kgs by summer. The first step would be to place this goal within a hierarchy of other goals to understand your motivations and reasons:

Why do you want to lose weight? “I want to look better and feel healthy.” Why is that important? “Because looking fit at the beach will make me feel more confident among others, and being healthy will increase my physical well-being over the long term.” Ok, we can see that losing weight is about appearance and social status, as well as general health and well-being over the long term. So it’s about your higher-level life goals or purpose.

Why 10kgs? Maybe you know that’s what you used to weigh when you were younger. In any case, pick a good target that’s achievable yet not trivial. So we have:

What are the subordinate goals, and how can you achieve those? We know that to lose weight, you have to create a calorie deficit. You can do that by expending more energy or consuming less energy, or both. Eat less, move more, in other words. There are many ways to achieve this, but from here, we can start creating a plan — one or more Projects — for how to achieve this goal:

What starts to take form here is a plan that considers your preferences, duties, and other requirements. There are some first steps in place to get started; you’ve considered what new routines or habits will have to take shape and tried to think of ways you might slip up and how to avoid that (designing your environment to support behaviors). If there are specific tasks (like “set up a spreadsheet”) that need remembering and prioritizing as part of the project(s), those should go on your todo-list for later.

Starting with a time-bound and measurable goal of wanting to lose weight and having connected it to your broader ambitions, you can now start to see the shape of what working on this goal will actually look like and what sacrifices you will have to make. The Project turns the outcome you want into a collection of effort-based subgoals (fasting 2 times per week) that are achievable and rewarding in and of themselves.

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III. Troubleshooting

Self-reflection

Self-reflection is crucial for continuous improvement. Goals, especially rigid goals, have the tendency to get stale. You may lose the motivation to pursue them, or your reasons for wanting to achieve the goal may have changed. So it’s wise to pause every now and then, like during a monthly or quarterly review, and think about the progress you’re making or not making. If you’ve failed to reach a goal many times, is it really something you want — really? Maybe you’re mistaking what you want for something else? What problem are you trying to solve?

Another kind of self-reflection is to consider when or during what circumstances you have successfully achieved your goals and when you haven’t. Have you failed because of lacking motivation, lacking organization, not sticking to it long enough, etc.? Similarly, what strengths have you leveraged when you succeeded? Did you lean into your identity? Did you design your environment in a good way? Did you make good plans, and did you follow them? Did you adapt to changing circumstances?

Personally, I’ve often failed at making steady progress toward goals when they have been too vague or have lacked achievable plans of action. Having good process-oriented metrics in place, instead, has helped me focus and feel a sense of accomplishment. The metric must not just be a clear indicator of success but also a mechanism for sticking to the goal, a yardstick. This makes it motivating in itself to push on. Don’t get to hung up on the word “metric” here; it doesn’t have to be super formalized. All I’m saying is to have a way to measure your actions.

When I started writing my Skepsis Newsletter, I set a goal to write and publish 25 newsletters in 25 weeks, something I achieved with only a minor slip-up, like sending out one edition a day or two too late. Had I just said to myself that “I’m gonna start writing every week,” or worse, “I’m gonna write more this year,” it’s unlikely I would have followed through. Indeed over the past few months to a year, the number of newsletters I’ve written has dropped significantly (as you may have noticed as a long-time reader). I’ve prioritized other things recently, which is fine but had I continued with measurable, achievable process-oriented goals for my writing, along with a writing routine I can stick to, I would have probably published 3x as many newsletters over the past year. Maybe it’s time I take my own advice.

At the same time, the metrics you put in place can become constraining if you forget about the bigger picture. Measuring progress on goals is really not about the goal itself; it’s about learning how to reach the goal or maybe even learning that the goal was not that interesting to begin with. Measuring what you do in some way is important because what gets measured gets managed. On the other hand, “when a measure becomes a target, it ceases to be a good measure”. This is often referred to as Goodhart’s Law, which cautions against making the metric your main goal when it’s only something to help you track your progress.

Getting unstuck

Suppose you’re not making progress or are slipping back into old behaviors. In that case, it usually comes down to one or more of the following: not having the requisite capabilities or competence, an environment lacking the right opportunities to achieve your goals or a lack of motivation. According to the COM-B model of behavior change, these three inputs are all needed to modify your behavior successfully.

Competence

Are you physically or mentally capable to perform the activity or actions required? If not, you might need to learn something new, adjust the difficulty of your goal (as mentioned above), or create an intermediate goal you can achieve and start from there. If your goal is to launch an app and build your own startup, but your app isn’t getting any traction, you might need to take a step back and work on your design skills to improve the quality of the app or learn about marketing to make sure your app can reach its intended audience.

Environment

Is your day-to-day environment supporting your goals or not? What changes can you make, and what can you add or avoid to improve your surroundings in accordance with your goals? As mentioned above, if your goal is to lose weight, but easily accessible snacks and junk food surround you at work and at home, it’s no surprise you’re falling back into old habits. Avoid having junk food at home or at least put it where it’s harder to grab and eat.

There are plenty of opportunities every day to take the right or wrong actions, given your goals. Do what you can to ensure the opportunities are working in your favor.

Motivation

When setting a goal, it’s important to consider the combination of intrinsic and extrinsic factors that motivate you to take action. Are you setting goals that align with your intrinsic motivations? Are you working with or against your own inclinations?

Reflecting on the deeper motivations behind your goals can help you stay on track and avoid halting progress. If you haven’t adequately considered why you wanted to achieve a particular goal, you may find that it isn’t connected to a higher purpose or ambition. As a result, you may lose motivation and struggle to make progress.

It’s also important to recognize that motivation can come from both intrinsic and extrinsic factors. Intrinsic motivation comes from within and is driven by internal factors such as personal interests and values. Extrinsic motivation comes from outside and is driven by external factors such as money, social status, or avoiding pain.

Additionally, motivation is impacted by your level of perceived competence and having the right opportunities to complete the task. If the goal is too difficult and you don’t believe in your own ability to accomplish it, your motivation will take a hit.

In any case, the point is to look at your (lack of ) progress from the perspective of your motivational resources, whether they come from within or outside, and adjust your plans accordingly.

Clear goals, loosely held

In a past edition of Skepsis, I wrote about the pros and cons of goal-setting and suggest that we should have clear goals, loosely held.

Goals have the ability to direct your attention in a productive direction and can help you achieve hard things. But long-term goals can feel vague or even daunting, and goals may also cause you to focus too narrowly (that’s a feature, not a bug!) and get stuck on a local optimum. Nevertheless, you can see goals as stepping-stones to personal development and self-discovery rather than as a rigid thing you have to achieve as prescribed;

“Since you discover what you want in practice, not in theory, goals are always under constant negotiation. You think you wanted X, but once you worked on A, B, or C for a while you realize that you actually wanted Y, or maybe Z. So while it’s good to have a target to aim towards, you should think of goals as an emergent property of your experiences in combination with your values and overall ambitions. One informs the other in a never-ending cycle. Clear goals, loosely held.”

This ties into the whole aspect of motivation and your higher-order goals — the why. Yes, work hard to achieve your goals, but don’t be surprised when you achieve them and still feel like something’s missing. That’s part of the process; you’re learning what’s really important to you and what you don’t want.

The meta-game

This brings us to the big picture. When you think about your goals long enough, you’ll eventually start asking the existential questions. I call this the meta-game of goal setting. What are you really doing? What is it that you want out of life? Why do you want the things you want?

At some level, it’s important to realize that we’ll probably never feel fully satisfied; we’re always on a journey, and we never truly arrive; happiness is but a fleeting emotion; we move the goalposts of what satisfaction means to us. Life is a paradox in this way. We must learn to be content with our current predicament in every moment, whatever our circumstances. Yet, at the same time, we should recognize that we will always want to strive for more and work towards something better.

Even so, achieving goals and doing hard things are still valuable. Goal attainment leads to a better sense of achievement and self-efficacy, all of which make you feel better about yourself and able to accomplish harder things. It’s a positive, self-reinforcing feedback loop.

Good luck out there!

* A note on claims: Throughout the article, I’ve referred to various methods, ideas, and claims, some of which are backed directly by scientific research, but I haven’t provided sources for all of them. Below I’ll list a few articles, books, and other sources that I’ve found useful and from where I’ve learned much of what I write here.

• The Goal — A Process of Ongoing Improvement — a book about change management, processes, and organizational productivity
• Scott Young — blog, courses, book on learning and self-improvement
• Menno Henselmans — podcast and book on training and nutrition, creating better habits
• Atomic Habits by James Clear — one of the best books and blog about habits
• Stronger by Science and Macrofactor — blog and podcasts that heavily inspired this piece
• Peter Drucker — The effective executive — the classic management book
• Essentialism: The Disciplined Pursuit of Less — a book about getting your one thing right
• OKRs framework — the classic goal-setting framework
• Luca Dellanna — from which I’ve taken the pyramid of feedback
• Shane Parrish — blog on decision-making, mental models and more
• Secrets of Productive People: 50 Techniques To Get Things Done: Teach Yourself — todo lists
• Thinking in Bets — decision-making and probabilistic thinking
• Tiago Forte — blog about productivity and projects
• Getting Things Done (GTD) — the classic productivity framework

Should you doubt any of these claims, feel free to reach out — or use your Googling skills to find the relevant sources or studies. :)

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