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Lesson 0: Pilot your plane
Think about the last time you set a goal. What are three things you could have done differently in the planning process for that goal, that would have been aligned with the pilot’s mindset?
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Lesson 1: Seeing the world through far-colored glasses
For this first exercise, I want you to see how you can shift between the far and near modes of thinking with your own goals.
Let’s start with a goal you’re working on. To shift further into far-mode, you can think about:
- Things you’d like to accomplish in the very long-term
- Imagine what it would be like to have achieved your goal already
- Ask yourself how achieving this goal lines up with your values in life
Now, consider shifting into near-mode:
- Take one concrete step towards the goal right now
- Look through your calendar this week and plan out exactly how you’re going to work on the goal
- Try to vividly imagine working on the goal, this week. What does it feel like?
These are just rough exercises, but getting an intuition about the differences between them is helpful to figuring out how they impact the goals you set!
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Lesson 2: Mike Tyson’s bathtub
Spend a moment to write out what the biggest weaknesses you’ve had in achieving goals in the past. Lack of organization? Low motivation? Switching goals too often?
Now, ask yourself what your strengths are in goal-setting. In what situations have you tended to succeed in the past?
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Lesson 3: The busyness trap
Write down at least three things that you have to do right now, which you might be able to find ways to eliminate, automate, outsource or reduce. These could be parts of your work, household errands, commitments to groups, friends or teams.
What’s one way you could take action to reduce your commitment burden today?
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Lesson 4: One rabbit
What is your one rabbit? Write down what your number one priority is for right now.
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Lesson 5: Achievable goals
Look at the plan you have in place to achieve your goal right now. Given this input, what is an outcome that you think is quite likely to be achieved as a result? Is your stated target higher/more difficult than this? If so, what would be a reasonable outcome you could put as your “minimum” benchmark to try to attain?
If your goal is highly-variable (meaning it has a large variety of possible outcomes) what would be the minimum success target that would be under your control to achieve?
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Lesson 6: Idea journal
Do you have a to-do list software or a place you keep your files? Open up a new document and put “IDEA JOURNAL” as the title.
Whenever you get an idea for a new project or goal, write it down there. Set up the document now and you can fill it in and review it in the future.
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Lesson 7: The positive and negative confidence spirals
What is one example of a negative-confidence spiral you’ve experienced in your life? What is a step you could have taken to pull out of that spiral?
Write down one example of a positive-confidence spiral you’ve experienced in your life.
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Lesson 8: Lying to yourself to look good for others
Write down a list of the top five goals you have for your life. For each of those, ask yourself which you’d prefer:
- You’ve accomplished the goal. BUT, you can’t tell anyone and nobody around you would know you did it. (i.e. you lost weight, but nobody around you realizes it and still thinks you’re the same as before)
- You didn’t reach the goal. BUT, everyone around you acts as if you did. (i.e. you didn’t lose weight, but everyone thinks you’ve slimmed down and gotten into great shape.)
If you’re not sure, you might want to put a weight on the value of each of these goals (i.e. 50% actually doing it, vs 50% appearing like I did). Goals done for appearances risk social desirability bias.
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Lesson 9: Tacoma narrows bridge failure
Pick a goal you set recently where you didn’t achieve as much as you had hoped. Now list five things that you could have done differently to have avoided those problems.
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Lesson 10: Dangerous drugs and hard decisions
Pick an area of your life where you want to achieve something, but you’re not quite sure how. What are three different experiments you could run that could give you valuable information towards those goals?
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Lesson 11: The first-last-milestones technique
What is the starting point for your current goal?
What is the ending point you’d like to reach?
How could you break down the difference into discrete phases or milestones?
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Lesson 12: Marathon or sprint?
Try to think of the last five long-term projects (6+ months) you’ve started and write them down. Next, try to think of the last five short-term projects (<6 months) you’ve started and write those down.
Which were more successful? Should you make your goals, on average, shorter or longer? Could any of your longer projects have been broken into shorter ones? Could any of your shorter goals been extended into longer projects?
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Lesson 13: Prioritization life raft
What is the smallest action you could take to maintain progress and commitment to your current goal?
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Lesson 14: The problem with setting goals
Think back to the last three goals you’ve worked on. Did you have an action-oriented or results-oriented mindset for each of those? How successful were they?
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Lesson 15: But will you be any happier?
Write down your top five goals. For each of these goals, ask yourself how these goals will change your day-to-day experience of life for the better? Write down any ways that achieving these goals might make your day-to-day experience worse (say getting a promotion, but having to work more hours).
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Lesson 16: What’s your self-improvement debt?
Write down a list of all the existing commitments you have that take up at least twenty minutes per week. (Don’t worry if you can’t think of all of them, just try your best)
Now, try to brainstorm a list of things that might unexpectedly create new commitments (car repairs, overtime, extra child care, etc.):
How much time do you estimate is left over, per week, to work on your goals?
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Lesson 17: The California sunshine problem
Pick a goal you’re working on. For this goal:
- Who could you ask to see what it will be like after you achieve it?
- What changes would the goal create for your life that occur once and fade away, versus recur again and again?
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Lesson 18: The effort paradox
Choose a goal you’re working on currently. For that goal, write out a list of all the time you spend on the goal. Next, ask yourself how many times you need to make a decision while working on the goal (such as when to work on it, whether to work on it now, what to do to move forward).
What could you do to reduce the amount of decision-points needed to make progress?
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Lesson 19: Goals vs project metrics
Think about a current goal you are working on right now. What would be a goal metric and a project metric for it? What is the crucial difference between the two?
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Lesson 20: Spot disaster before it strikes
Pick a goal you’re currently working on. What are the biggest three sources of friction for that goal?
What are three ways you could reduce each point of friction (9 total)?
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Lesson 21: Can’t exercise today…
What are three things you tend to procrastinate on?
Write down what the consequences would be if you forced yourself to do them right away, instead of waiting.
How could you change your behavior to take action instead of delaying?
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Lesson 22: Alfred Hitchcock and the elephant
Think back to the last time you worked on a goal. Try to identify at least three different versions of “you” that you felt during that process, thinking back to specific incidents where you did things differently than you had originally planned.
Now imagine that, for your new goal, you need to create a plan so that all three versions of you would still be able to complete it. What would you need to change in the plan so it can still get done?
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Lesson 23: Untested convictions
Write down at least five beliefs you have that (a) impact the goal you’re working on now and (b) might not be true.
What is one thing you could do to test each of these beliefs?
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Lesson 24: Shortcut vs effort mindsets
Think back to the last five goals you’ve considered. For each, ask yourself whether you believed in more of an effort mindset or short-cut mindset for each of those goals?
Now, pause your thinking and ask yourself what you’d do differently if the *opposite* mindset was correct. For instance, if you believed a short-cut mindset mattered more (finding the most efficient methods) what would it look like if you believed an effort mindset was the real key to success (that putting in effort is all that matters, and methods don’t differ much).
What could you do to test which mindset is more useful for you?
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Lesson 25: 1-5-20 Method
Name a person for each of the following categories:
- Someone one year ahead of you in a goal.
- Someone five years ahead of you.
- Someone twenty years ahead of you.
If those people aren’t already in your life, how could you meet them?
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Lesson 26: Are you checking your stats too often?
What is one way you could “smooth out” the measurements for your goals, by focusing on averaging out over time, or over multiple measurements, to prevent overreacting to meaningless noise? How can you discipline yourself to check and adjust your strategy only on intervals long enough to make sense?
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Lesson 27: Thales fell in the well
Schedule an appointment with yourself, right now, to review your goals in the future. If you have a productivity system or digital calendar, you should make it a recurring event which can allow you to check in on your goals.
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Lesson 28: Overkill method
Pick a goal you’re working on that you haven’t been satisfied with the progress you’re making. Now, write down a level of effort/intensity where you would be certain you’d make progress.
Finally, write down a strategy you could use to test out that level of intensity/effort.
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Lesson 29: The horse is here to stay
Pick three areas of your life and ask yourself whether they more closely match a logarithmic (fast initial success, which slows down) or expontential (slow initial success, which speeds up) curve.
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Lesson 30: Accountability partners
If you had to pick one person to hold you accountable to this project, who would it be? How would this person hold you accountable and give you an incentive to stay committed?
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Lesson 31: Flexible versus Rigid Decisions
Consider a decision you’re attempting right now. Which direction do you think it should be adjusted? More rigid? More flexible? Or is it just right? How could you make this adjustment to ensure success?
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Lesson 32: A few minutes
Spend five minutes, *right now* to plan your upcoming day. What will be your biggest priority? What tasks are you going to do? When will they fit in your daily schedule?
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Lesson 33: What to do with your metrics?
Think about the current project you’re working on? Do you need to make strategic adjustments or stay the course? If you haven’t already set up specified review checkpoints, when should you put those in place?
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Lesson 34: Burnout
What is one action you could take to prevent physical burnouts in your current project?
What is one action you could take to prevent emotional burnouts in your current project?
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Lesson 35: Be unreasonable
Think about the last time you failed at a project, because of an unexpected obstacle. What would have been the biggest downside if you had pushed through instead?
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Lesson 36: 3-pointers from your bed
Visualize working on your goal during the upcoming week. For each of the following, try to vividly imagine what they would feel like:
- The best-case scenario
- The worst-case scenario
- The most-likely scenario
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Lesson 37: Project Post-Mortem
We have a full interactive worksheet dedicated to running a project post-mortem. For a shorter analysis, let’s look back at one project you recently attempted. For this project write down at least three things that you did right, and at least three things you did wrong. Writing these out can help you articulate some of the patterns you might be running subconsciously which are supporting your success or keeping you from it.
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Lesson 38: Perfectionism paradox
Consider the last time you felt pressures to do everything perfectly. Where were those pressures coming from: yourself or others?
Consider a goal you’re working on right now, do your high expectations prevent you from making progress? How could you convert a short-term perfectionism into a longer-term process?
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Lesson 39: Your personal assistant
What do you use to store your plans, appointments and action items? If you don’t have these right now, set them up on your phone for easy access. If you do have them, what is one step you could take to make them more efficient at offloading the mental burden of remembering all you need to remember?
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Lesson 40: What gets measured, gets improved
Pick one of the goals you’re working on. What is the best way to measure success towards that goal? What things are omitted by taking that measurement in that way?
(e.g. Weight -> Fitness, this misses that you may gain muscle. Revenue -> Business Success, this misses that you might be using up relationships with your customers)
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Lesson 41: Front-loading
What are the most difficult parts of your project. Are there any ways you could move them up to be earlier in the process?
Will your schedule for success in your project still work if the intensity lowers over time? Is there enough slack in your schedule to compensate?
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Lesson 42: Sprint to the finish line
How could you reassert your commitment and intensity to a goal you’re already working on? Write down three steps you could take to make sure you finish strong instead of slowing down.
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