PDF Summary:Intentional, by Chris Bailey

Productivity expert Chris Bailey says that what keeps you from your goals may be a lack of intentionality—choosing goals that reflect your values, followed by deliberate, purposeful action. In Intentional, Bailey offers a productivity system that emphasizes deliberate, focused work on your most important tasks while leaving space for refinement as you go. This balanced approach will give you the guidance and support you need to turn your intentions into reality.

This guide organizes Bailey’s principles into four sections: how to set achievable goals that align with your values, how to keep yourself on track, why it’s crucial to update your goals and methods, and what to do after you’ve achieved a major goal.

To deepen your understanding of Bailey’s principles, we’ll compare them with other influential productivity books such as Grit and Indistractible. We’ll also provide scientific research that supports Bailey’s ideas and offer practical advice to help you start acting with intention.

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(Shortform note: Neuroscience supports Bailey’s suggestion that you stick to three intentions for each time period: Research on working memory suggests that the average person can only hold three to five items in their minds at once. So, by limiting yourself to three goals, you make it much more likely that you’ll remember what you decided was most important for that day, week, or month. This is especially helpful in light of the endless barrage of demands and distractions that will try to occupy your working memory and push out the intentions you set for yourself.)

An additional benefit is that this strategy helps you align your short-term and long-term goals. When you’re setting clear and concrete goals, you can ensure that your daily intentions contribute to your weekly goals. Those weekly objectives, in turn, contribute to your monthly goals, which build up toward your long-term ambitions. Finally, all of those goals help you live in alignment with your values.

Short-term Goals Can Guide You Toward Long-term Goals

Bailey describes how you can set smaller goals to build toward your long-term goals, but this process assumes you’ve already identified your major life goals. Conversely, in Grit, psychologist Angela Duckworth says you can use your short-term goals to figure out what your long-term goals are. Her method is to examine your current goals and ask why you set those specific goals.

Start with something small that you want to accomplish today or this week, and ask yourself why you want to do that. Your answer will point toward a larger goal—for instance, you might want to go to bed early because you want to develop better sleep habits in general. Now ask why you want that; perhaps it’s because you want to have more energy. You’d then ask why you want to have more energy, and so on, until you reach a goal that doesn’t seem to have another “why” behind it. Duckworth says when you reach that point—when you identify something you want to do for its own sake, rather than as part of some greater agenda—you’ll have found a major life goal that aligns with your real desires.

Two Ways to Schedule Your Day

Beyond choosing what to work on, you also need to manage how you move through your day. Bailey offers two complementary approaches: time blocking and task sequencing.

Method 1: Time Blocking

Bailey explains that time blocking involves scheduling specific periods for specific types of work. To accomplish this, divide your available hours into clearly defined windows of time, dedicating each to a particular type of work. These blocks provide an external structure that removes the need to constantly decide which tasks you’ll handle next. They also make your commitments clear, both to yourself and to others who might otherwise interrupt you with their own requests.

For example, you might give yourself an hour in the morning to check emails and handle any prep work for the day, followed by two hours for your most mentally intensive work. You could then plan a shorter window of personal time to rest and recharge, and dedicate the remainder of your workday to meetings and collaborative work.

(Shortform note: Time blocking—also known as “timeboxing”—has many other benefits. In Indistractable, Nir Eyal contends that creating timeboxes prevents you from focusing too much on one responsibility to the detriment of others, since you’ve already set an end time for each activity. Meanwhile, in Deep Work, Cal Newport argues that time blocking reduces your chances of becoming unfocused and switching between tasks, since you’ll have a goal for each block.)

Method 2: Ordered Productivity

Bailey’s second method for managing your day is to bear two things in mind: what you’re supposed to do now and what you intend to do next. This approach works well on less structured days—times when you need to stay flexible without getting overwhelmed by too many options.

Bailey recommends that you keep a visible list (perhaps on a whiteboard or index card) showing your current focus along with your upcoming tasks in the order you plan to tackle them. When you inevitably get distracted, glancing at this list reminds you of what you intend to do. It also prompts a decision: Either return to what you’re doing, or consciously update your plans if something more important comes up.

(Shortform note: You can expand on this method by using what Jim Benson and Tonianne DeMaria call a Personal Kanban. Simply take the list of tasks you need to do and add two more columns: “doing” and “done.” To incorporate this into Bailey’s strategy of ordered productivity, you’d move one task at a time from “to do” into “doing,” and not move on to the next thing until you’re able to move that task to “done.” To go one step further, you might add a “do next” column so that you can always clearly see what your next intention is, as Bailey suggests.)

Continually Improve Your Goals and Methods

No matter how carefully you choose goals and make schedules, you’ll inevitably need to revise your plans along the way. That’s why a key part of Bailey’s system is to regularly examine what’s working for you and what isn’t, and make intentional improvements where you can.

We’ll begin with an explanation of why you should frequently review your goals and how to do so. We’ll then go over some of Bailey’s suggestions for improving your daily work practices—ways for you to overcome mental barriers and keep yourself motivated during the daily grind toward your goals.

Revise Your Outcome and Process Goals

Bailey urges you to view your goals as educated guesses about what you want, rather than absolute commitments to yourself. You’ll need to revise your goals as you learn more about what works for you. Some of your goals will need to be tweaked, others will need to be reworked—occasionally, you’ll even realize that a goal isn’t right for you, and you need to abandon it.

The ideal time to update your goals is during the planning sessions we discussed before. Bailey suggests that you examine your progress toward each of your goals, your processes for working toward those goals, and the outcomes of the previous period (day, week, month, or whatever timeframe is relevant to your current planning session).

(Shortform note: Bailey’s revision process is similar to what Ryder Carroll describes in The Bullet Journal Method. However, Carroll’s method requires you to record your daily, weekly, and monthly goals in a journal (like the title suggests) and to regularly rewrite things in different sections of your journal. Carroll argues that transferring the journal’s content from one section to another forces you to re-engage with what you’ve written, which naturally leads you to reflect on your goals and the reasons behind them. This codified process of rewrites and reflection helps ensure that you use your time and energy deliberately, rather than just autopiloting toward the goals you’d previously set—or, worse, forgetting about those goals entirely.)

Bailey also emphasizes that goal attainment is rarely smooth or straightforward: Tasks will take more or less time than you expect, you’ll learn more about what you really want (and don’t want), and external circumstances will change unpredictably. Therefore, make sure to review and update your process goals as well as your outcome goals during your revision sessions.

(Shortform note: Bailey points out that your life won’t improve as quickly or completely as you might hope, but that lack of immediate progress can be impactful. In Reset, Dan Heath says one of the most common reasons people give up on making improvements is that the changes are too slow and too widely dispersed to see—the lack of immediate, visible progress discourages people, so they stop trying. His solution is to start any attempt at major changes with a brief period of intense effort. Then, once you’re able to clearly see how your life is improving, you can slow down and keep pursuing your goals at a more sustainable pace.)

Revise Your Practices

No matter what goals you set, you’ll have to push through the day-to-day work of achieving them. To help you do so, Bailey offers a variety of ways to overcome the mental barriers holding you back and to stay motivated even when the work starts to feel like drudgery.

Overcome Mental Barriers

Sometimes you’ll find that you simply don’t want to work toward one of your goals. Even when you genuinely want the outcome—when the goal is truly in line with your values—your mind seems to resist the tasks you have to do to reach that outcome. Bailey identifies what makes work unappealing, and he suggests methods to overcome each obstacle:

1) The work is boring. When a task is too easy or routine, you’re likely to become disinterested with it. In such cases, you could make that task more engaging by adding constraints such as using only your nondominant hand, or an additional challenge like a time limit.

(Shortform note: In Atomic Habits, James Clear also notes this issue of routine or otherwise simple activities becoming boring, and he concurs with finding ways to make them more difficult so they hold your attention. Specifically, Clear says the ideal level of challenge is one where you succeed approximately half of the time. This makes every attempt at the task feel fresh and exciting, because you can never be sure whether you’ll succeed or fail.)

2) The work is frustrating. This is the opposite of the previous characteristic: When a task is too difficult, you’re likely to become frustrated with it. Bailey recommends that you reframe such tasks as learning opportunities rather than as things you need to finish. This strategy shifts your focus to developing your skills, and it makes setbacks feel like valuable lessons rather than personal failures.

(Shortform note: In Right Kind of Wrong, organizational learning expert Amy Edmondson suggests developing specific skills that will help you accept your failures and learn from them. These skills include resilience to endure failures and keep trying, accountability to recognize and accept your mistakes, and reflection to learn from those mistakes and do better in the future.)

3) The work is unpleasant. When you dislike a certain task, Bailey suggests a practice he calls aversion journaling: writing down specifically what makes it unpleasant. It may seem counterintuitive to devote more attention to what you dislike about something, but identifying and articulating those issues lessens their emotional impact. This will help your rational mind overcome your emotionally driven urge to avoid that task.

(Shortform note: This strategy works because, neurologically speaking, task avoidance is the result of a conflict between two parts of the brain: the limbic system’s emotional drive to avoid discomfort and the prefrontal cortex’s rational drive to finish a task. Journaling helps you understand and address the feelings behind your procrastination, which soothes your limbic system. In essence, your brain recognizes that your discomfort isn’t a sign of a real threat, and therefore you don’t need to avoid the task.)

4) The goal is distant. Even an outcome that you truly want can fail to motivate you if it’s too far away. For instance, the thought of reaching your desired weight six months from now is often less tempting than the thought of eating junk food today. Bailey says you can make a goal feel more immediate by tracking your progress and setting intermediate milestones. In this case, if your ultimate goal is to lose 40 pounds, you might track your progress by weighing yourself at the same time each week, then give yourself a small reward for every 10 pounds lost.

(Shortform note: This strategy takes advantage of what Mark Manson (The Subtle Art of Not Giving a F∗ck) calls the motivation loop. Manson says many people misunderstand how motivation works—they think motivation has to come first, and then it leads to action. However, motivation and action are a cycle: Motivation can lead to action, but taking action also creates more motivation to keep going. Therefore, by achieving a small milestone, you can motivate yourself to keep working toward a more distant goal.)

Boost Motivation

In addition to qualities that lower your motivation to finish a task, Bailey identifies factors that increase it, including:

1) Social norms: The people around you shape your behavior in significant ways. You absorb the habits, attitudes, and intentions of the people you spend the most time with, often without noticing you’ve done so. You can intentionally leverage this by seeking out people and groups who support your goals, such as finding a gym buddy or an addiction support group.

(Shortform note: Author and entrepreneur Jim Rohn famously said, “You are the average of the five people you spend the most time with.” In other words, the people around us exert a large influence on who we become. And in fact, it’s not just the closest five: Research has found that second-degree (friend of a friend) and third-degree (friend of a friend of a friend) social connections influence the spread of obesity, though the strength of that influence diminishes the more distant the connection is. Other studies suggest this “network effect” also affects behavior related to work, health, and educational choices.)

2) Sense of control: Your confidence that you can actually achieve a goal matters as much as wanting to achieve it. This means believing that you have the time, resources, and ability to achieve something will greatly boost your willingness to try. Maintaining a sense of control also includes anticipating problems you might run into and remaining confident that you can overcome them.

(Shortform note: In Stop Self-Sabotage, psychologist Judy Ho offers one reason a sense of control makes you feel more motivated: Evolution has hardwired us to avoid threats, and we perceive feelings like frustration and embarrassment as actual threats to our safety. When you feel like you’re in control of a situation, there’s no sense of danger—you’re confident that you can handle any issues that arise, and therefore that instinctive drive to avoid the situation disappears.)

3) Anticipated emotions: The feelings you think you’ll experience influence how much you want to pursue a goal. Imagining the pride, relief, or satisfaction you’ll have after reaching a goal pushes you toward it. On the other hand, anticipating the shame, disappointment, or regret of failure can paralyze you into inaction, so it’s important to stay focused on the positives.

(Shortform note: As a counterpoint to Bailey, Jeff Haden (The Motivation Myth) warns against imagining your success before you’ve achieved it or telling others what you intend to achieve. He says you might trick yourself into feeling like you’ve already accomplished your goal, which will make you less likely to follow through and actually accomplish it.)

Next Steps: Celebration, Review, and Upkeep

So far we’ve discussed Bailey’s methods for setting and reaching goals, but what happens once you actually achieve one? According to Bailey, you need to do three things after a major accomplishment: Celebrate your success, do one final review of the goals and methods you used, and (if relevant) determine how you’ll maintain the progress you’ve made.

Celebrate What You’ve Achieved

Bailey argues that celebrating your successes is one of the most important—and most overlooked—parts of personal achievement. Celebration rewards your efforts, which helps you feel like the work was worthwhile and makes you more likely to maintain your progress. It also connects positive feelings with the general concept of pursuing goals, thereby making future goals seem more attractive. Finally, celebrations can mark key transition points in your life where you can recognize and appreciate your own growth.

(Shortform note: In The Molecule of More, Daniel Z. Lieberman and Michael E. Long offer one explanation for why celebrating successes is such an effective practice: Making progress toward a goal causes your brain to produce a chemical called dopamine, which causes intense feelings of pleasure. Because the dopamine high is so enjoyable, it naturally motivates you to keep working toward your goals in order to recapture those good feelings.)

With that said, Bailey adds that it’s important for your celebrations to align with your values. For example, if you value pleasure, a good celebration might be a sensory indulgence like ordering your favorite meal or treating yourself to a spa day. If you value benevolence, a celebration might involve a party to share your success with loved ones, or finding a way to give back to the people who supported you.

(Shortform note: It’s important to celebrate in ways that you’ll truly enjoy, but it’s equally important that your celebrations don’t undermine your goals. For example, buying yourself an expensive gift wouldn’t be an appropriate celebration for reaching a savings goal—spending money to reward yourself for saving money doesn’t really make sense.)

Review Your Process Goals and Practices

Just like you continually examined and updated your plans while working toward a goal, Bailey says you should do one final review after achieving it. Look back on the process of reaching your goal, from when you first set it to when you finally accomplished it. Think about which process goals and methods worked for you, what didn’t work, and what you’d do differently next time.

This review session will help you reach future goals, and it will also teach you important lessons about yourself. Every goal you pursue will help you learn more about your values, preferences, and capabilities. Over time, these lessons compound into greater self-knowledge and more effective self-direction.

Self-reflection can take many forms, so once again, you’ll need to find what works best for you. Bailey says the most important thing is to give yourself time to process and learn from your experiences. For instance, some people like to write about their experiences, while others prefer to discuss what they’ve done with a trusted friend or partner. Even something as simple as walking and thinking can be an effective way to conduct this final review.

Try an After-Action Review

In Start Finishing, entrepreneur Charlie Gilkey suggests that you conduct your final reviews in the style of a military After-Action Review (AAR). In contrast to Bailey’s “whatever works” approach to self-reflection, this pseudo-AAR requires you to prepare a list of specific questions about your goal, the process of achieving it, and what lessons you can take away from the experience.

For instance, your list might include questions like:

What was my goal?

What was my plan for reaching that goal?

What parts of my plan went well?

What changes did I need to make, and why?

What new skills have I learned, or what new knowledge have I gained from this?

You’ll then go through the list and provide clear, detailed answers for each question. This process will help you recognize and solidify what you learned throughout the process of achieving a major goal. As a result, you’ll be better prepared to tackle other big projects in the future.

Maintain Your Progress

Finally, Bailey points out that many goals require ongoing upkeep even after you’ve achieved them. Therefore, he recommends that you explicitly identify which of your completed goals should become maintenance goals, and allocate time and effort accordingly. For instance, most skills fall into this category: Whether you’ve learned a new instrument or developed a working knowledge of calculus, you have to practice regularly so that skill doesn’t deteriorate.

Bailey adds that people often overlook maintenance goals because they aren’t as novel or exciting as new pursuits. However, they’re necessary to turn temporary improvements into lasting accomplishments.

(Shortform note: Research suggests that people often struggle with maintenance goals because, as far as the brain is concerned, they’re completely different from outcome and process goals. Specifically, maintenance relies on your satisfaction with your current situation—and therefore your desire to keep things as they are—while other types of goals rely on your anticipation of what might happen in the future. As a result, the skills and strategies you developed to accomplish something new may not carry over when you start working to sustain what you’ve accomplished.)